Selling is a creative act

I was in Texas recently to help a client redefine their brand. My agency, Zander Media, was hired to learn about the client and help them distill a new organizing idea.

The team and I had done a lot of preparation, but I was still nervous. We had promised the client a new organizing principle by the end of the day-long workshop!

I facilitated the workshop, we covered most of what we’d planned to discuss, and then – as if by magic – we found a new tagline that perfectly captured the company and brand.

Zander Media had been paid to deliver an outcome, and we did. But describing that day so clinically doesn’t do justice to the magic of that moment.

How to do creative work

As prospective salespeople we don’t generally regard ourselves as artists.

There are a lot of mundane tactics requited to sell. You have to source leads, make cold calls, and get comfortable asking for what you want.

But, at its most elegant selling, is a creative act. To sell your ideas is to channel something bigger than yourself for a cause that is more important than money.

Preparation is essential

The more thought and care that you put into a project, the more likely that project is going to be successful.

I spent a hundred hours conducting interviews and researching my client in advance. Expect to spend ten times as much time preparing as you do executing.

But preparation alone doesn’t equate to creating something from nothing.

The moment of execution

None of the preparation I did for our client would have mattered had we not delivered the workshop.

Place the phone call.
Send that email.
Step out on stage.

Don’t use preparation as a way to avoid the work that needs to be done. The pitch – any moment of execution – matters more.

Have a cause that’s more important

Have a cause greater than your own self-interest.

The cause doesn’t have to be grandiose. The world wasn’t immediately going to be altered through our client finding a new organizing idea.

But by harnessing that purpose, applying all of your preparation, and coordinating the time and effort of others, you may be able to create something bigger than any one person.

Creativity in sales

I’m fascinated by moments of peak performance in sales – when we outperform our own expectations.

And transforming sales from work into a creative habit takes practice.

But with enough preparation, a clear purpose, and an openness to the unexpected, your outcomes can be greater than the sum of those parts.


Today’s homework is to look for creativity in your daily work.

Instead of attempting to make your current sales efforts creative or cultivating an entirely new creative habit, look for creativity within your current habits.

What is something that you do every day that you can turn into a creative practice?

By practicing a creative habit, no matter how small it is or in what domain, you’ll be better at recognizing creativity elsewhere and when it really matters.

Until next week,

Why you should focus on a single customer

You’ve probably heard that you should focus on a specific type of customer or prospect.

I’ve always found this to be a struggle because I don’t want to work with just one type of client! I like a lot of people and want my business to serve a variety, as well.

Today’s article is about organizational burnout and the consequences of not serving a single client.

The consequences of high growth

My creative agency, Zander Media, took off in 2020. With a lot of companies in need of video production, we grew from one full-time employee to ten in less than two years.

Being an enthusiastic salesman, I said “yes” to every piece of inbound work. Zander Media produced scripted commercials, testimonials, animated videos, entirely new brands, and even a documentary.

Building the plane while flying it

As a ten person company delivering a wide variety of services, we tried to be everything for everybody. As a consequence, the team and I were perpetually stressed.

We were building the plane while flying it.

The benefits of a singular focus

What would have happened if we had only provided a single service?

I’d have had to turn down a lot of work. But the team would also have had time to learn the specifics of the tasks required.

We’d have gotten better at doing the specific things required for that kind of deliverable.

Burning out my team

At Zander Media, we had enough sales to keep the business going. We had an abundance of skilled employees. But we didn’t have enough time to learn how to do each job from scratch, which then led to an unsustainable working environment.

Trying to adapt to the needs of each new project took a toll and we lost several valuable employees.

Dissatisfied customers

There are a lot of unknowns when you try something for the first time.

It takes a lot more work to deliver a novel offering. Things are likely to go wrong and there’s a high likelihood of poor communication.

We were fortunate at Zander Media that many of our clients from that stressful era continue to work with us today. But I worked consecutive 80 hour weeks for two years to make it happen.

Without a specific focus, you are much more likely to lose repeat business, or lose your business entirely.

An efficient way to think of business

Think about your business as a manufacturing plant that produces a very specific type of widget.

While you probably don’t want to work on an assembly line, it’s a useful metaphor.

What’s the one thing that you or your business want to do exceptionally well? Focus there.


Who do you serve? Describe a single, unique customer. (It is okay if that ideal client changes in the future.)

Think of a single person in your life – someone you actually know – and write a few details about that person.

Their demographics:

Their psycho-graphics:

Practice getting very specific about the person you are selling to. Doing so will help you sell more sustainably.

Until next week,


How to sell video production

I sat down with a Snafu reader recently who runs a one-man video production company.

In the five years I’ve been building my own agency, Zander Media, we’ve been in the fortunate position of handling inbound work, not cold calling prospects. I still have a lot to learn about selling video production.

Today’s newsletter is for solo professionals interested in doing bigger budget work for high quality clients.

Got Milk?

I watched a MasterClass with Jeff Goodby and Rich Silverstein, the legendary founders of Goodby, Silverstein, and Partners. That’s the advertising agency behind such icon marketing as “Got Milk?” and the Budweiser frogs.

Jeff and Rich discussed how they go about getting new work for their now 40-year-old ad agency. Jeff (or maybe it was Rich) describes pretending to be a journalist and talking his way into a fancy car convention in order to meet with a marketing executive at BMW to make a pitch.

Even having built and grown a 300+ person institution for decades, these two founders are not above entry-level tactics in order to meet the person they are trying to pitch.

Prior to this interview, I’d have believed that leaders as savvy and experienced as Jeff Goodby and Rich Silverstein wouldn’t need to sneak into an event in order to sell to a new client. But it turns out that nobody is above selling, no matter how fancy their title or company.

This approach – going out and finding new clients – I’ll call hunting. The other approach – cultivating existing clients; generating goodwill and referrals – I’ll call farming.

We’ll tackle each in turn.


In order to hunt, you have to first know who you are trying to reach.

It wouldn’t have worked for Jeff and Rich to show up at a flea market and pitch their company. (Though I’m certain they’d have enjoyed that, too.)

They chose a very specific event, and one very specific attendee whom they were trying to reach. In short, they knew who they wanted to work with.

Most of us probably aren’t going to target the Head of Marketing for BMW North America, but we can target specific people.

Choose a single, specific person you’d like to work with. Go hunting for them. You can always expand your audience later on.

Identify the work you want to do

When my ideal customer sees an example of our work, they should be able to say “That looks like a Zander video!”

A video production company that does this especially well is Sandwich Video. Sandwich explainer videos are recognizable on sight – the bright colors, lighthearted demeanor, and the presence of their founder and CEO in each video.

What do you and your work stand for?

That mission statement might evolve over time, but you need a singular focus in order to be recognized and to stand out to your preferred customers.

Where to find your customers

Once you know who you are trying to reach and the type of work you want to do, you need to find the customers who want that work done. There are infinite numbers of ways of doing this, so here are just a few of my favorites…

Asking for connections

Asking for help from connections has been the most impactful approach I’ve found to date for building any kind of business.

I wrote an article on “How to sell with no network or connections” about selling tickets to my annual Responsive Conference.. Also, watch this video about how I went from selling $1,000 scopes of work to $100,000 scopes of work in just a couple of years at Zander Media.

Asking for help goes a long way!


Since 2014, I’ve run more than a hundred events on behavior change and the future of work.

If I’m not organizing an event myself, I try to set myself up to be an authority – by speaking, working at the event, or otherwise coming into contact with as many people as possible under favorable conditions.

Consider even just organizing a dinner or an un-conference targeted at the people you are trying to reach.

LinkedIn Sales Navigator

There are a wide variety of digital tools that provide you easy access to people, including LinkedIn Sales Navigator.

Most of the people you cold email won’t want to hear from you, so you’ll have to get over your reticence for contacting people who might not be interested. But LinkedIn Sales Navigator, and tools like it, allow you to reach out directly to the people you’re trying to contact.

Cold calling

The most extreme version of this approach is cold calling people directly, or even knocking on doors.

While you are likely to get a lot of “No, thank yous” in response, cold calling prospects is also the avenue that most sales people avoid or use poorly.

Most of us are scared of rejection and will go to great lengths to avoid asking people for what we want – and those who do use this approach rarely do so with finesse.

If you’re going to cold call people or knock on doors, use it as practice honing and refining your pitch, instead of actively trying to close a deal with every call.


Farming is reminding your current and former clients that you exist, up-selling, and cultivating raving fans who will recommend you to their friends and colleagues.

Do great work

The first principle of farming is that you have to do great work. This is a good principle of business in general because without great work, the best marketing and sales in the world will just reveal that you have a terrible product all the quicker!

Promote your work

You should always be striving to improve the quality of your work – both in your delivery of the work and in how you communicate about it to your customer.

Doing great work that nobody knows about is doing a disservice to your potential future customers!

Ask for referrals

Anytime, you deliver work for a customer, asking for referrals.

When a client walks away satisfied with the work you have delivered, it isn’t enough to just anticipate or expect that they will recommend you in the future. As we know, most people are bad at selling, and referring work is a form of sales.

Towards the end of an engagement, schedule 30 minutes with your client and tell them that part of your business revolves around people – like them – referring clients to your business.

Keep in touch

The best referral system in the world doesn’t matter if you are not then top of mind for your customer. They need to be thinking about you at the appropriate time in order to hire you again or refer you to a likely connection.

My preferred mechanism for keeping in contact is an email newsletter, because everybody uses email. But this can also be through consistent social media, contact, videos, or even a text base platform.

The key is to remain top of mind, so that your clients think of you at the right moment.

Surprise and delight

Look for ways to surprise and delight your clients.

At the end of every year, I receive a handful of care packages from customers and clients, all with varying degrees of thoughtfulness and care. This is the same principle behind the ubiquitous startup branded hoodie and other swag.

But surprise and delight can be more nuanced. What’s a little thing at the right time that can encourage or delight your customer?

A get well card for a sick child. A sports jersey to their favorite team. Thoughtful gestures that take time and consideration can have an impact for years.


It’s easy to get overwhelmed by the number of things that can be done to improve your business.

The only recourse is to take one small step today every day towards one of the objectives, and focus on that goal every day until it has been improved.

Your homework is to pick a specific tactic from this list and write out the incremental steps towards its improvement.

What are a few small steps which will improve your client’s experience?

Until next week,

What is the Future of Work?

In 2016, I started a business conference about an obscure idea called “the future of work.”

Seven years ago, a lot of the tensions that we’ve seen accelerated in the last few years weren’t well known. AI wasn’t a ubiquitous tool. Most of us weren’t working on Zoom every day. Even the importance of connection and empathy at work weren’t well understood.

Today, our lives and our work are very different. But the importance of doing meaningful work is more significant than ever.

I write Snafu each week because I believe that we need more people who advocate for themselves. I think this is the best way to combat the helplessness and pessimism that are so ubiquitous.

The solution to divisiveness and disconnection is compassion, empathy, and a sincere desire to connect. And that’s as true in sales as it is in building high performance teams or raising great kids.

Thus, I’m thrilled to share that after a 4 year hiatus and together with two longtime collaborators, I’m bringing back my annual event Responsive Conference.

The conference will take place across two immersive days in Oakland, CA on September 18-19th.

Tickets are on sale now!

This is my one big event of the year. We’re going to have ~20 speakers from across industries and 250 attendees from around the world. This is your opportunity to learn and practice the principles that we discuss in Snafu with an incredible community.

Learn more and get your tickets here. I hope you’ll join us this September!


What’s in their best interest?

I recently started dating somebody new. She’s a fellow athlete, owns her own business and I’m quite excited. Unfortunately, it’s unclear if she’s available for the kind of relationship that I want.

The solution is to want what is best for the other person, even over what you want for yourself. And this is true whether you are selling a product, hiring an employee, or dating someone new!

It is hard to want what’s best for the other person while still advocating for your desired outcomes. Here are some things that can help…

Generate goodwill

I use the example of the Santa in the Miracle on 34th Street to depict the benefits of a well-executed sale.

In the movie, the department store Santa sends eager customers to a different department store because that store has exactly the right product for that customer.

The store manager is furious that Santa is sending people elsewhere – until he sees that customers are returning and buying more, because of the goodwill that Santa has generated.

In business, and in life, positive word of mouth can determine success. When you do the right thing, you’re more likely to succeed.

Don’t be too eager

I first learned to negotiate in the busy marketplaces of Oaxaca, Mexico as a child. I went back to Oaxaca with my family this winter and one thing I wanted to buy was a new leather belt.

I found a local market and one leather seller, who had a wide assortment of beautiful leather goods.

I began the process of negotiating for the belt I liked. The stall purveyor was polite, and completely unattached. When I returned hours or days later, she showed no sign of recognizing me.

She wasn’t pushy, but she had clear boundaries on price. And between the dozens of people passing her stall, she also didn’t have a lot of time to spare for one customer who wasn’t in a hurry to buy.

That stall owner didn’t have my best interest in mind. She wanted to make a sale! But she also wasn’t pushy.

And that freedom gave her a lot of flexibility when it came to making a successful sale.

As a result of her non-urgent attitude, I not only did buy a belt from her – I purchased two. I left satisfied and will refer other people to her in the future.

Maintain clear boundaries

One of the things that I loved about the leather goods seller is that she had clear boundaries. She did not need me to buy but was happy to entertain some amount of bargaining if I showed up in good faith. On an early visit, I proposed a price that was laughably low. She declined and moved on to another customer.

Know where your boundaries lie – the price of what you are selling; the amount of time you’re willing to spend.

It never helps to give more than you are comfortable with in the hope that the other person will come around. When you self-sacrifice, they won’t.

Invite, then leave it alone

Invite towards the outcome you want and then remain unattached to the outcome.

Invite someone on a date or ask them to buy what you are selling. Observe how they respond! And, if they don’t, that tells you everything you need to know.

It is too early yet to say where my new romance will go. But I’m reminded that when I don’t cling to a specific outcome, I’m more likely to get what I want.


What is an outcome that you are attached to?

It could be the specific outcome of a sale, but it might also be something much more personal.

Identify 1-2 real life examples where you are attached to things going a certain way. If you’d like, email me with your examples!

Then, practice, just for a minute, asking “What’s best for the other person?”

That simple question, asked with curiosity and not with a sense that you know better, will likely make things easier.

Until next week,

How to practice cold calling

Two friends of mine recently started a new business, which we’re affectionately calling BookBook.

It is a digital platform that allows users to display their favorite books.

The platform would display the spines of books, just like I do on my physical bookshelves. And the collections would only feature collections of books, like my favorite cookbooks or a list of what Tyler Cowen calls quake books.

Sourcing book spines turns out to be quite difficult. So I set out to phone book publishers in the attempt to find book spine designs for this project!

I took on this task of cold calling publishers because I love books, my friends are starting a company and I wanted to help. Really, though, I undertook this project to practice making cold calls.

Here are a few things I learned that will make your next cold calls easier.

Outline your pitch

The first step was to decide on my sales pitch.

I sat down with my friends and asked each of them to sell me on their startup. I recorded the audio of their sales pitches and took copious notes.

Then, I pitched my own version and asked for feedback.

We went back and forth like this until I had a rough script and was prepared to answer a variety of questions.

Outlining your pitch shouldn’t be complicated. Decide what you are going to ask for and write a rough script. Bullet points are fine! Consider getting some feedback

Then move on to the next step.

Set a deadline

Practice enough that you are ready to deliver your pitch, but don’t let practice get in the way of actually getting started.

Don’t use preparation as a form of resistance. And don’t forget Parkinson’s Law – work will expand to fill the time allotted for its completion.

I scheduled a day when I would start actually calling publishers. That deadline gave me a concrete window in which to practice.

Set a deadline and give yourself a limited amount of time to prepare.

Rehearse your pitch

My next step was to rehearse my pitch.

I booked time in my calendar, because, for me, if something isn’t in my calendar it doesn’t happen.

During those rehearsals, I reviewed my notes and recorded a voice memo of my new pitch. Then I listened back, took notes and tried it again.

Hard things often take less deliberate practice than we think. But you do have to show up and do the work!

Make some calls

The final, and most critical step, was to actually start calling publishers.

On the day I had set aside, I Googled book publisher phone numbers and called all six of the big book publishers.

It would have been more effective to locate phone numbers in advance, but fortunately book publishers are easily available online.

This is the most critical step, because without actually putting in this practice, outlining your pitch, deadlines, and rehearsal don’t have much impact!


In talking to representatives at all the big publishing houses, I learned that book spines are even harder to source than I’d thought!

So while I haven’t yet gotten access to book spines, I’m grateful to have taken on this small sales project as practice.

As people who have something to sell, we all want to be more comfortable talking to strangers. Likely the reason you don’t ask more often is that discomfort and your fear of rejection.

And the best way to overcome that discomfort is to practice.

Most of us are uncomfortable asking strangers for things. But through this project, I put in the practice and took an incremental step.


Cold calling is one of the scariest things most people do. But that’s because the steps are too big.

Get comfortable doing the uncomfortable thing when the stakes are low.

Today, pick up your phone and call one person spontaneously. Most people don’t use their phones for phone calls, so maybe that’s enough of a stretch.

If you do talk to people by phone, phone someone you don’t speak to regularly.

See if you can stretch beyond your comfort and phone when you’d ordinarily text, or to contact somebody you don’t normally talk to.

All the practice and rehearsal doesn’t matter if you never pick up the phone and call, so just get started.

Until next week,

How to get over rejection

I just read an interview in the New York Times about what it’s like to be a sociopath. The subject of the interview, Patric Gagne, is preparing to publish a book called Sociopath: A Memoir.

The article highlighted that I am not a sociopath because I care deeply — often too deeply — what other people think of me. Most of us do.

And caring too much about other people’s opinions limits us from doing scary things like asking for what we want.

Asking is hard

Asking for what you want can be really hard!

Let’s use a concrete example:

I would like to take you to lunch.
I know the best secret sandwich spot in Oakland.
And then finally the ask: Would you like to come with me?

Asking means risking being told “No.” Or worse yet, getting laughed at.

Asking is even harder when we’re trying to sell something $1000 tickets to my annual Responsive Conference.

I am confronted by insecurities like “What if they take offense to me asking?” or “What if they agree, but then hate the experience?”

Asking is scary because of the risk of rejection.

What is rejection?

When I compare myself to someone who actually doesn’t care what people think of her, like the author of Sociopath Patric Gagne, I have to define my terms.

What is rejection?

Rejection is caring about what people think, even if I shouldn’t. It means basing my decisions and actions on how I think someone else might respond.

Rejection is the fear that you are going to be judged, or worse yet, ostracized by your peers.

Throughout human evolution, getting ostracized meant likely death. Infants can’t survive without the support of their adult caregivers. Prehistoric humans couldn’t survive without the support of their community.

Today, we live in a world with eight billion people. Even if we were to get excommunicated (which isn’t likely to result from a single request), that probably wouldn’t mean the death that would for our prehistoric ancestors.

The world is a lot safer and more convenient than it was tens of thousands of years ago!

Motivated by the opinions of strangers

I can rationalize why I should care about the opinion of my best friend. If I acted in a way that a close friend found unacceptable, I’d like to know so that I could at least consider changing my behavior.

I’m also highly motivated by what my parents think of me. This is less appropriate, because, at 37-years-old, I’ve outgrown the need for their approval.

Worse, I’m motivated by the opinions of strangers. When I meet someone walking down the street, I wonder what they think about me.

Most of us are too busy judging ourselves through the eyes of strangers to pay close attention to what we want, recognize our fears and then ask for it.

I haven’t found a magic solution to not caring what people think of me, but here are some approaches to overcome the fear of rejection.

How to care just a bit less


We have a word for acting in the face of fear. That word is courage.

And most of us want to be more courageous.

A good way to practice being courageous is to practice asking for what you want. Incidentally, you’ll get better at asking!

Identify what you’re afraid of

The first step to overcoming your fear is to identify what it is that you are afraid of.

Fear is often an amorphous emotion that clouds even our ability to notice what it is that we’re afraid of.

First recognize that you are fearful and then identify the specific thing that you are afraid of.

The worst case scenario

When I opened up Robin’s Cafe in 2016, I did so with the knowledge that if it failed, I might end up $50,000 or more in debt.

The only way I was able to step into the unknown and open the cafe was to literally calculate how long it would take me at $15/hour (plus tips!) to earn back that $50,000.

Ask yourself “What’s the worst thing that could happen?” Write down a few of your answers.

Practice asking

Asking takes practice.

Just like anything else worth doing, learning to ask for what you want is a learned skill that you can improve with practice.

Unless you work on a sales team, you probably don’t have a lot of experience selling, asking or risking rejection.

Make facing rejection a deliberate skill you practice.


I’ve started a new practice this year of complimenting strangers on the street. Any time I walk by someone who’s clothing or style I admire, tell them so.

It seems like such a small thing – and it is – but I, for one, and most of us are hesitant even to pay a compliment.

For the next week, complement someone you see at least once a day on some element of their clothing or style. As you do so, notice your discomfort – and complement them anyway!

By the end of the week, you may find that you are less uncomfortable than initially.

The difference between marketing and sales

I taught a workshop a few weeks ago for a handful of entrepreneurs who wanted to get better at selling.

I asked attendees what they thought of when they heard the word “salesman.” I expected answers like used car salesmen and telemarketers, but instead attendees described the challenges of creating social media content.

I realized that most people don’t have a clear distinction between marketing and sales.

Marketing and sales both require:

Selling adds a few crucial steps including asking, “Would you like to buy my thing?”

What is marketing?

Marketing is storytelling. It is the stories we tell each other and about ourselves, which inspire toward a desired outcome.

When I was ten years old, my Dad and I read The Odyssey aloud together. The book was written two thousand years ago. Nonetheless, I vicariously experienced Odysseus’ ten-year journey home from the Trojan Way.

Marketing is using the story of Odysseus’ bravery, loyalty and pride to inspire the next generation to stand up for what they believe in and to lead.

Marketing consists of telling stories that are:

Marketing is the stories we tell about our work, or tell each other about the world around us.

What is sales?

The ask is the primary difference between marketing and sales.

Selling is attempting to persuade somebody to adopt a belief, asking to change their behavior, or inviting them to buy. Even the “Buy now” button at the end of an ad moves it into the category of sales.

Effective sales incorporates an ask after first delivering a story that is personal, relatable and inspiring.

After we finished reading The Odyssey together, my father asked if I’d like to run cross country. I’ve been an athlete, gymnast and runner ever since.

Good selling is about making an ask. Great selling is about making an ask that you’ve prepared for by telling a compelling story that pulls on emotions, aligns incentives, helps the other person become more of who they want to be.


What’s one thing you’re trying to sell?

Before you pitch, what’s a story that inspires the other person to become more of who they want to be?

Write out a couple of sentences about:

  1. What you have to sell.
  2. What you are selling will help your audience become more of who they want to be.
  3. A story that bridges that gap.

Send me an email with your answer to these questions!

Until next week,

The car salesman bias

Most consumers are leery of car salesmen. And that’s understandable because car sales usually means a lack of price transparency, a high price tag, and pressure.

As soon as I walk into a car dealership – and I’ve purchased more than my share of used cars! – my hackles rise up because I’m approached by salespeople looking for a fresh victim.

Attitude, first

Everything in sales comes down to the salesperson’s attitude.

Here are a few tips:

As a salesperson, your attitude matters more than anything else.

Be aware that the customer is likely to be skeptical and hold a “used car salesman” bias. Counter that narrative by being different from any other car salesperson the customer has met before.

Build community loyalty

Pressuring a customer to purchase can work in the short term. But it never results in long-term loyalty.

And since word of mouth referrals – people talking about you to their friends – is the ultimate mark of success in any business, a primary goal of your salespeople should be building loyalty within your local community.

This can mean the subcultures that each of your salespeople lives within – a neighborhood, the local recreation league, someone’s favorite coffee shop – and also your city itself.

People talk about their experiences. So it should be the job of each of your salespeople to create positive experiences and generate goodwill towards your business.

Become the mayor

You want your business to become the “mayor” of your city. When people think of your town, you are one of the first names that comes to mind.

This can either be you, as the owner of the business, or something that represents your business, like a mascot or the logo.

One way to approach this is to run for local office: city counsel, leader of the Parent’s Association, etc. But this can also be implied power.

Doing things that someone with deep ties to a community would do is a way to generate goodwill.

The value of cold call

Doubtless, you’ve already considered the benefit of having your salespeople make cold calls. But I think that the likelihood of actually selling cars by “dialing for dollars” is very low.

To do so a salesperson has to reach someone who is:

If any of these four aren’t true, then cold calling damages the reputation of your business.

Instead, I suggest cold calling for a completely different purpose. Teach your salespeople to make cold calls to collect information.

Here’s a script:

Hi there –

Do you mind if I take 3 minutes of your time?

I’m calling from your local BMW dealership 
but I am not calling you to try to sell a car. Instead, I’m just collecting some demographic information about local residents so that we can be a better part of this community.

Again, I’m not here to sell you a car. Do you mind if I ask you three brief questions?

If they respond in the affirmative, proceed:

Do you own a car? If so, what make and model?

What is your perception of BMW cars?

What is your perception of car dealerships?

End the call by asking if they would like to be added to your free monthly newsletter, which is about the goings-on in your region. Thank them for their time, appreciate them for the time you’ve spent together and encourage them to reach out if you can help them in the future.

This approach will help your salespeople get better, spread the brand of your business, and generate future leads. The last question, What is your perception of car dealerships? will highlight for your salespeople the perception that they are having to combat to build customer loyalty in the region.

The prospect will be pleasantly surprised when the salesperson doesn’t try to sell them a car at the end of the call, thus ending on a positive note.

Hire great people

It goes without saying that you want to hire great salespeople. But instead of focusing solely on people who always hit sales quotas, hire people who add to the reputation of your company through goodwill and long term customer loyalty.

A great salesperson who also alienates customers or employees does more harm to your business.

Define what a great salesperson brings to your company, and don’t settle for less.

Company culture

We often overlook the importance of company culture in sales. After all, the purpose is to close more deals and make more money!

The cohesion of your sales team matters. One overly pushy salesperson can model for the rest of the team an approach that will alienate customers.

When we put a smiling face on what is actually an unhappy working environment, our customers can tell the difference. Similarly, customers know when a member of your team really, sincerely enjoys their job, and is excited to be a part of the company.

A culture that derides the worst performing salesperson or hazes newly incoming team members creates an environment that will, invariably, trickle out to the customer’s experience.

I’ve written a book about the importance of team culture, so start here.

A culture of feedback

One important aspect of company culture, particularly in sales, is creating a culture of feedback.

Sales teams often only provide feedback during the onboarding process of a new salesperson. But every salesperson – and everybody! – can benefit from feedback. And in a thriving company culture, every employee should want to.

Here are a few ways to incorporate feedback into the daily cadence of your company:

Be generous

One of the phrases least likely to be uttered about a typical salesperson is that they are generous.

The common perception is that a salesperson wants to take advantage of the customer. It is your responsibility to contradict this narrative by being incredibly generous with your time and effort on behalf of each customer that you work with.

As often as possible go to the extra effort with each person you come into contact with to help them – even if that help has nothing to do with the sale you are aiming for.

By being unexpectedly generous you foster long-term relationships and make it more likely that a customer will come back in the future.

Until next week,

The three pillars of selling

What do you think of when you hear the word “salesman?”

I think of the Wolf of Wall Street, the movie Glengarry Glen Ross or a used car salesman. My first thought is of someone who will stop at nothing to get what they want.

That’s unfortunate because we are selling to each other all the time – our ideas, our beliefs, our products.

But what are the core characteristics of selling? There are three:

Connection – form an authentic connection with the other person.

Story – tell a story that is authentic to you and resonates with the person you are selling to.

Ask – Invite powerfully towards the outcome that you want.

Authentic Connection

When I was five years old, my father had me plant pumpkin seeds to grow pumpkins for Halloween.

Together with a couple of neighborhood boys, I stood in the street, waved down cars and asked them if they’d like to buy my pumpkins.

Because, even then, I was a bit ridiculous, often I dressed in a full body scarecrow costume – passers by would speculate if I was a motion-activated robot – and would then tear off my costume to chase down cars.

That childlike enthusiasm to sell something that I’d worked hard to grow is authentic for me. I’m excitable and playful. That exuberance allowed me to connect with my customers.

Whenever you are selling – a product or an idea – look to share yourself with the person you are selling to. Be yourself and you’ll be more likely to create a real relationship with your customer.

That authentically connection is why, when I visit my hometown, I still get asked if Robin’s Pumpkin Patch is coming back next Halloween.

Tell Them Stories

When I started Robin’s Cafe, I’d lived in the neighborhood for a decade.

That period was a time of transition in the Mission District in San Francisco. There were new companies moving into the neighborhood and a lot of local residents were feeling displaced. But that gentrification also came with benefits.

What had historically been an unsafe neighborhood was becoming a thoroughfare. What had been a parking lot across the street was turned into a playground.

As somebody who had lived and worked in the neighborhood for a decade, I bridged the gap between longtime residents and newly incoming tech. workers.

By relating my story, and listening to the stories of my neighbors, I was able to sell the idea of Robin’s Cafe as a community space that served the needs of the neighborhood.

By relating your own personal experiences, and listening thoughtfully to the personal experiences of others, you create the trust and connection which ultimately leads to sales.

The Ask

This final step is the part of a sale that salespeople call “closing.” The moment when you ask your prospective client, “Would you like to buy my thing?”

But I think closing is the wrong word because it gets the incentives backwards.

The goal isn’t to close a deal at any cost. Pressuring your customer to close a deal is more likely to result in a dissatisfied customer and long-term ill will.

Instead, invite them – powerfully – towards the outcome that you believe is best for them, while knowing that they are ultimately responsible for making their own decision.

Selling something can be as simple as forming an authentic connection, telling your story and listening to the other person, and then asking the other person if they would like to buy what you are selling.

Until next week,

How to sell without a network or connections

In 2016, I was given an amazing opportunity to take ownership of a global community called

After running my first ever business event early in the year, I decided to create my first business conference, Responsive Conference, 9 months later.

I’m a circus performer. I had never attended a business conference, not to mention produced one, so that first year of selling tickets to Responsive Conference was a madhouse.

That was also the same year that I started Robin’s Cafe, so any moments that were not spent behind the counter, or hiring and firing baristas, I was on the phone with everybody I could think of asking for advice.

This distinction is key: I wasn’t trying to sell tickets to the conference at first. Instead, I asked for advice.

Ask for advice

I brought 275 people to Responsive Conference 2016 by asking people for advice. It is really that simple. I turned to the founders of, everybody who had come to my free event earlier in the year, and everyone else I could think of.

When you ask for advice, you create the opportunity for excitement and support from people who might not otherwise be open to purchasing. People get enthusiastic about your cause, regardless of whether they’re interested in spending money – or attend my conference.

By asking for advice, you create advocates who want to see you succeed.

Practice telling your story

One of the things that making those hundreds, even thousands, of calls in the first months of Responsive Conference gave me was practice telling my story.

I was new to By luck and good timing, I was able to bring together 150 people for a free event at the start of the year and there was a lot of interest in our topics. But I was no expert!

By asking everyone I could think of for advice, I got a lot of practice telling the story of the ecosystem and why I wanted to create Responsive Conference.

Build a network

When you are beginning to sell something new, you probably don’t have a network or a reputation. But what you lack in network you can make up for in short calls with strangers.

Ask everyone you talk to refer you to three other people. Quite quickly, the size of your network grows!

It takes time and effort to take calls with so many people, but you’ll also go from no contacts to hundreds of potential prospects in a very short time.

The final step is to ask

The final phase of this saga, once you have enough experience telling your story and have built out a network, is to begin selling. Change your pitch from “Will you give me advice?” to “Would you be interested in purchasing a ticket?”

Several months into asking for advice, I’d talked with hundreds of people and generated a list of prospects in the thousands.

It takes courage to ask people to purchase. You can’t hide behind the “I’m just learning how to do this” anymore.

The final step is to muster up the courage and ask, “Would you like to buy?”

A word on authenticity

This approach to learning how to sell something new only works if you are sincerely interested in what people have to say.

If you go into an “advice call” with the desire to sell, the other party will know and be turned off by the experience.

Be humble, stay curious, and look to learn.


If you don’t need to, I don’t recommend spending hundreds of hours on the phone with strangers asking for advice. That said, the practice of building a network is incredibly valuable. This is the same process I use anytime I’m starting a new business or exploring a new opportunity.

Your homework is to call one person in the next two days and ask them for advice. The rules are simple:

And just like that, you’ve landed your first advocate.

Until next week,

How to tell a great story

I’ve told the story of starting Robin’s Cafe with no experience and selling it on Craigslist hundreds of times.

What’s funny is I’m actually most proud of the culture we built behind the counter, the amount of learning I went through in learning to operate the cafe, and the role the cafe played in creating community in that neighborhood.

But when I mention selling a restaurant on Craigslist, I invariably get a laugh. “Craigslist?” People ask, incredulous.

Stories are the reason people buy from us – our ideas, our services, even our avocado toast. In order to sell, you need to tell a great story.

Everything is storytelling

You are already telling stories all the time.

The stories we tell ourselves become how we think of ourselves and the stories we tell others define those relationships.

The first step to telling a good story is to recognize that you already are.


Take note of a story you’ve told recently. I like to do this during my morning journaling. Take two minutes to note down a story that you told someone yesterday.

See What Sticks

The parts of a story that matter the most to you aren’t necessarily the things that matter to your audience.

When it comes to Robin’s Cafe, I’m more proud of having opened up a restaurant in 3 weeks, but that tends to fall flat. I’m proud of the culture we had behind the counter, but without experiencing it, that’s not of great interest to the listener. The moment I get a chuckle is when I share that I sold the cafe on Craigslist.

You aren’t telling a story for yourself, but for the person you are talking to.


Look for reactions. Aspects of your story will land and other parts won’t. That’s useful information! Save the parts that illicit a reaction for your next telling.

Notice What Stories You Already Tell

In 2020, I moved into a house in the woods with my partner. Within a couple of weeks, my partner was parroting back to me a handful of stories that – apparently – I told all the time on Zoom. I hadn’t realized that I was repeating so many of the same stories on different calls!

Even if you aren’t aware of it yet, you are telling other people stories all the time. Pay attention to those stories, and use them as fodder as you refine your narrative.


When you are beginning to sell something new – as sophisticated as a new business or as simple as asking a friend to lunch – write down a list of possible stories that might help you accomplish your goal.

Refine and Hone Your Stories

We take for granted that a comic has to practice their jokes, or an athlete their sport, thousands of times for every single performance. It is less obvious that that storytelling, too, is a craft.

Every time you tell a story is a chance to iterate and improve your storytelling craft.


Try telling a story in a subtly different way. Add a new variation or detail, and notice how your audience reacts.

Emotion > Rationality

When we foster connection with another person, we create the opportunity for change.

Facts and figures are great, but they don’t accomplish much without the wrapper of a good story. To get someone even just to listen to your data, you have to form an emotional connection.

We like to tell ourselves that we are rational, but most of our behaviors come down to emotion.


As you head into your next meeting or difficult conversation with your spouse, ask yourself how you want them to feel.

We don’t get to control another person’s emotions, but just considering how you’d like for them to feel will influence how you show up and the course of the interaction.

A good story doesn’t guarantee in a successful sale, but without a good story your attempt to sell probably won’t work. Storytelling is necessary, but not sufficient.

Hone your storytelling skills, by noticing and improving the stories that you already tell, and you’ll be better able to move your audience – and your objectives – forward.

Why we’re afraid to ask

Last week, I wrapped up a two and a half million dollar fundraise!

That is, by far, the most money I have ever tried to raise. One of the issues I had to face was my fear of the close, of asking the question, “Would you like to invest?”

It is one thing to tell a good story, complete with compelling data. It is more difficult to ask someone to purchase what you are selling.

I can’t share the specifics of why, together with a few close friends, we were trying to raise the two and a half million dollars, but we were ultimately successful, even though the deal fell through.

As I went through the process, I wrote down reasons why I was afraid to make the final close and some strategies to address each of those fears.

Concern: Taking advantage of people

One of the most common concerns I hear about selling is the fear of taking advantage of your prospective customer.

Most people find coercive salesmen offensive. But there is a big difference between relying on pressure to close your deal, and never asking people to buy in the first place.

If I’d let my fear of taking advantage of someone stop me, I’d never have started Robin’s CafeResponsive Conference or Zander Media. More importantly, I wouldn’t have developed the courage that I’ve learned along the way.

Answer: They get to decide

Define what you mean by “taking advantage of people.”

Inherent in that phrase is the belief that you can force people to do things against their better judgment. And while I could, theoretically, use physical force or the threat of violence, the kind of gentle persuasion that I encourage is the furthest thing from that force.

Here’s my shortcut: If you are the kind of person worried about forcing or coercing someone, you don’t need to worry about taking advantage of your prospective customer.

The person you are talking to gets to decide what’s best for them. There is no such thing as “taking advantage of someone” when you don’t use force, believe that they are their own best expert and trust that they will decide for themselves.

Concern: Using force and pressure

Inexperienced sales people don’t close a deal or make their ask because they are afraid to pressure their prospects. And the experience of being pressured by a salesperson is unpleasant.

I have built up a robust immune response to that kind of pressure. If someone pressures me, I leave, even if the pitch was something I’d otherwise have agreed to.

But as unpleasant as being pressured is, being a pushy salesperson yourself is more so. The fear of pressuring someone else can be so intense that that we don’t even try to sell.

Answer: Know your emotional state

To ensure that you aren’t using force or pressure, learn to assess your own emotional state. If you’re not sure how you are feeling, check in.

Pressure usually comes from the significance we’re placing on a specific sale. I don’t sell unless the thing I’m selling really matters to me. And if it matters that much, I can get attached to the outcome.

Any single sale isn’t worth the feeling of having pressured someone else.

Use that knowledge to let go of your own pressure. Know yourself and what you are feeling. Ensure that you aren’t feeling pressure. Then show up with your customer with the desire to help.

Concern: Rejection

I learned to juggle in high school, and eventually became quite good. Inherent in juggling is dropping balls, which we could call failing to juggle.

Inherent in asking people for things is being rejected, being told “no.” That’s a part of selling.

Getting turned down when something matters can be unpleasant, absolutely, but it can also be just another data point. As with dropped balls while juggling, get rejected is part of the process.

Answer: Rejection is less scary than you think

Oftentimes, our fear of rejection is the thing we’re actually scared of, even more than the declination itself.

In selling, a rejection means nothing about you. It is actually great because it provides you data about how to improve and the simple clarity to move on to your next prospect.

Since clear answers in life are pretty uncommon, a rejection is cause to thank your prospect for their clarity. They were able to give you a clear answer, which is a compliment to everyone involved.

Concern: Danger to your reputation

Another common fear is that asking people to buy your thing will endanger your reputation.

Sorry to break it to you, but people will judge you based on what you ask for, what you promise and what you deliver.

Answer: Sell things you are very confident in

The answer is to have the utmost confidence in what you are selling and then to be very honest about the the risks and benefits involved.


Next time you are on a sales call or ask a friend to lunch, notice what concerns come up for you. (I keep a pen and paper nearby to take notes.)

Take a few notes about how you are feeling. Afterward, come back to the specifics of the sale and evaluate your feelings.

Assess how you felt and why you felt that way. What were you believing about yourself and the other person?

The more practiced you become at identifying your concerns, and the more you explore them, the better you’ll be at addressing and avoiding those fears in the future.

How to raise money

In 2016, I started a cafe with no prior experience in less than a month.

Robin’s Cafe is still in San Francisco today. And though I no longer get discounts, we should meet for coffee there sometime!

I had to raise $50,000 to purchase the assets I needed to start the business – espresso machine, ovens, tables and chairs. It was the first time I ever raised capital and I had to raise the money in less than three weeks.

Over that manic 20 days, I pitched more than a hundred people – and learned a lot. These are the tactics I wish I’d known then.

Know your business

I had lived blocks from Robin’s Cafe for almost a decade. The neighborhood was long considered “the wrong side of the tracks,” but in 2016 it was about to undergo a transformation.

When I opened the cafe there was a parking lot across the street. Today that parking lot is a children’s playground. Startups were beginning to move into the neighborhood. 17th Street is now a thoroughfare for walking and biking traffic.

Starting the business amidst a growing neighborhood gave Robin’s Cafe the momentum that it needed to succeed. Though I had never worked in the restaurant industry before, I had a competitive edge in knowing what the neighborhood was about to become.


Know your business. That doesn’t mean that you are an expert on the entire industry (I certainly wasn’t!) but you do need a competitive advantage.

What’s yours? What is the thing that you see that other people don’t? As you prepare to ask for money, focus on that.

Have a clear vision

My vision was simple: create a place where dancers, parents, local employees, and neighbors could eat and meet.

It helped that I was a member of many of the different communities that I wanted to serve: I was a community member and dancer of the building owner ODC. I was friends with employees of tech companies in the neighborhood. And I was a long time resident of the neighborhood.

In order to sell someone on your idea, you have to know the specifics of the vision.

As a member of these different groups, I was better able to communicate that vision and serve those groups.


What’s your vision – the reason you are trying to raise money? Write it out as plainly as possible in two or three sentences.

Sell your idea

As I started to ask for money, I talked to people about the decade I’d lived in the neighborhood and how I’d seen it change.

I walked people across the street to Mission Bowling Club, which is now a staple in the neighborhood, and shared the story of meeting the owners years before inside their gutted, abandoned warehouse.

I helped people see my vision for what this cafe could ultimately become – if only they’d be willing to loan me the money to buy the equipment I needed.

In order to raise money, you have to first get buy-in for your idea, which means you have to sell your idea.


Why should someone be interested in your idea? What’s in it for them? Answer this question by listing out at least ten reasons why someone might be interested in the idea you are selling.

Share your emotions

I was determined to open Robin’s Cafe within a very narrow window of three weeks because I was running a conference for 150 people in the same building and needed to feed my attendees. The entire idea for the restaurant came because I had the conference coming up and wanted to get coffee and lunch for my participants.

During those three weeks, I lived on caffeine and five hours of sleep – and I didn’t try to hide my intensity from my prospective investors. Instead, I channeled that intensity into furor for what this business could grow into.

That excitement and optimism, combined with a sober assessment of the business opportunity, gave me the conviction to pitch the restaurant.


Share your emotions with your prospective funders – your excitement, optimism, and hope for what you are selling.

What are you excited and hopeful about? Tap into their eagerness to be a part of something bigger.

Show them, and don’t just tell them

At Robin’s Cafe, I was able to walk people through the neighborhood and give them a taste of what the cafe could be – if only they would help with funding!

I shared my vision for what the cafe could be: a gathering space for dancers, for parents of kids, local employees and neighborhood residents. I walked my prospective funders through my landlord’s building. (Fortunately, the landlord owns two very beautiful buildings!)

I made them samples of our menu and poured them free wine (conveniently ignoring the fact that I didn’t yet have a liquor license).

Show your funders what the opportunity looks like. Help them to see the future that they are going to help you create.


Show your prospective funders the things they will experience. Give them the ability to put their hands on a product. Allow them to experience what you are selling.

Tailor your story to the person

Fundraising is highly personal. Everyone, whether a professional investor or a personal friend, invests for their own reasons.

I showed off cafe spaces available for meetings and co-working to a friend who took meetings with clients throughout San Francisco, and mentioned that we could also cater their company’s lunches.

There is an art gallery attached to Robin’s Cafe, which I showcased to a local artist who was considering funding the business.


Learn why each prospective funder is most likely to invest before you pitch them. The more discovery you do, the more likely you are to succeed.

In the end, I successfully raised $50,000 from five people in under 20 days and successfully ran the cafe for three years before selling it.

I attribute that successful fundraise to three things:luck, determination and the decade of preparation I’d inadvertently put in while living and working in the neighborhood.

I don’t know how to control luck, but incredibly hard work and a lot of research can make the impossible happen.

Until next time,

The importance of feedback

During the years that I danced classical ballet, I was always surprised that video recording was discouraged – or even outright forbidden.

When I studied Brazilian jiu-jitsu, which is at the cutting edge of functional martial arts, we were encouraged to film during class. Unsurprisingly, Brazilian jiu-jitsu continues to evolve faster than almost any other sport.

Feedback dramatical accelerates learning.

Incorporating feedback

The profession of sales has a history of incorporating feedback. Pick up any book written for salespeople and you’ll find a chapter dedicated to feedback.

Unfortunately, for the rest of us who don’t work full time in sales, it is less clear how to use feedback to improve.


The simplest way to get feedback is to record a phone or Zoom call, and then watch it back afterwards.

Important note: Know your local laws! It is often illegal to record calls without consent. That’s why there are the “This call may be recorded for quality assurance purposes” messages on custom service help lines.

You’ll learn a lot about how you can improve by listening back to one call for every ten you make.

Internal feedback

You are your own best source of feedback.

As you watch back a sales call, take note of what you said and did. Note your prospect’s reaction. Over time, you’ll see patterns and areas for improvement.

Do try to avoid berating yourself for your mistakes. Just observe and save your assessment for later.

External feedback

Anytime I’m teaching someone how to sell, I watch some of their sales calls and give a lot of feedback.

Ask a friend to watch back with you and give you feedback in real time. Pick your most detail-oriented friend and trade 30 minutes of their time for a coffee.

They’ll help you see things that you don’t by yourself.

Notice what you say

The most obvious area to critique is what you say. Where did what you said work well and where did it fall flat? Are there patterns of speech that you use that work well or that you could improve?

Body language

Notice your body language. How does your posture, facial expression, and body language complement or interfere with what you are saying? Are there ways that you can improve your body language to improve how your sales pitch is received?

Notice how you felt

Prospective customers pick up on how you’re feeling.

During your review, analyze how you feel during a sale. Look for specific moments where you felt especially good and bad. Query those moments to understand the emotions and states behind them.


Look for the small successes during your sales call – moments when you felt great – and celebrate them!

Practice feeling appreciative of what went well for you and those moments will be more likely to recur in the future.

(Read this article for a more thorough discussion of the benefits of celebration.)

The impact of feedback in learning to sell – or in any discipline – is profound.

These days, I record a few moments of every workout, not just for posting on social media, but so I can observe myself from the outside and look for areas of improvement.

Next time you’re going into a sales pitch or even just making a mundane ask of a friend, record yourself, review it, and let me know what you learn!

Until next time,

My family and other animals

My family read together each night throughout my childhood. We’d sit on our faded blue living room couch and listen to my father read aloud.

One of the books we discovered together was My Family and Other Animals by famed naturalist Gerald Durrell. Gerald relates stories from living on the Green island of Corfu with his fractious siblings and widowed mother between 1935 and 1939 and the beginning of his naturalist adventures.

One story stands out in my memory. Gerald, a precocious 10 year old, asks for birthday presents. Very carefully, from family member he requests a gift which that family member is well suited to gifting.

From his brother Larry (who became noted author Lawrence Durrell), Gerald requests a pair of binoculars because he knows his intellectual brother appreciates the importance of observation and detail. Gerald’s brother Leslie is the most practical member of the family, so Gerald requests a sensible Ersatz alpine hat. The list also includes exotic items like an airgun and a scorpion encased in amber.

I’ve always been impressed with the poise and forethought Gerald showed in assessing the personality of each person and requesting the appropriate gifts.

As I’m traveling in Mexico this week with my own family, that forethought seems even more useful. It is hard to play to the strengths of another person, but worth the effort.

Help people do things they already want to do

Years ago, my old professor BJ Fogg advised me that the best way to help people was to enable them do things that they already wanted to do.

You are going to be more successful if the idea you are selling is one the other person is already inclined to believe.

Develop the empathy to know what they want

Gerald Durrell accurately assessed the strengths of each member of his family. To do so required a lot of empathy, an understanding of each person.

Practice this kind of empathy through curiosity. As I discussed in Everything is Sales selling is rooted in discovery and a deep curiosity about your customer.

In order to sell, you must first develop the curiosity to understand who the other person is and what they need.

Spend time with people doing their thing

My good friend David and I live 30 minutes apart and would enjoy seeing each other more than we do. But we only get together only a few times a year.

We share a love of weight lifting and recently went to the gym together for the first time. Now we’re scheduled to spend time weight lifting together once a month.

Identify the person or group that you want to spend time with. Adopt their activity or find something that you both enjoy that you can do together.

I only go on dates that I’d be happy to do solo

First dates have a low probability of success, whether due to cancelation or a lack of chemistry. Years ago, back at the dawn of online dating, I decided to only go on first dates that I would be equally happy to do solo.

Prioritize things that you’ll enjoy, even if the company or outcome is uncertain.

Maintain flexible goals

In my early 20s, I built a company helping kids with autism and their families.

With children with autism, progress is often so gradual that most people wouldn’t notice any change. And because progress can be so unpredictable, it helps to maintain flexible goals.

The more you cling to a specific outcome, the less likely it is to happen!

In selling, too, not getting attached to a specific outcome results in better learning and more growth.

Gerald Durrell took enormous delight in carefully requesting the exact thing of each family member that they would be most inclined to gift him.

Even if the rest of us aren’t quite so meticulously, there are some lessons to be learned about selling and persuasion from his example.

Until next time,

How to ask for what you want

I’m traveling in Mexico with my family this week. It is really special: the first time in decades that my family has traveled internationally together and the first time we’re doing so with my two nephews. And operating in such close proximity reveals some habits that I don’t love.

We don’t use the word please, for example. Growing up, please was mostly used as a demand in moments of peak frustration. “Will you please do what I asked!” More generally, we (and I am very much included in this assessment) are not very good at asking directly for what we want.

Except for pushy telemarketers, most of us don’t ask for things directly. And almost nobody asks without some amount of demand or expectation.

But asking is really important – whether in closing a sale or voicing an opinion. Without a clear expression of what you want, it’s hard to get anywhere quickly.

Here are some habits that I’m practicing with my family – and will be exploring in more depth in a workshop on selling I’m planning for the New Year.

Recognize what you want

It is pretty hard to ask clearly for something that you aren’t clear about wanting, yourself.

Identify what you want. If you don’t know, write a list of things you might want and pick the ones that seem the best.

Know why

After you’ve recognized what you wantconsider why. For a primer on finding your why, check out last week’s article on the topic.

Brainstorm a list of reasons why. Choose several! The more reasons, the stronger your desire will be.

Let fear be a guide

Fear is an excellent guide. When you’re afraid of selling your idea, your product, or voicing your opinion, that’s a great reason to move towards that fear, not away from it.

Start small

Starting small is a secret to unlocking any sort of behavior change.

Don’t compare yourself to anyone else’s ability to persuade, ask or close a deal. Just take the next small step from where you are currently.

Practice in advance

Asking for what you want requires rehearsal, just like athletic performance and everything else in life.

If you aren’t good at selling your idea, that’s probably because you haven’t practiced!

Start by writing out your pitch. I suggest writing out a pitch in three formats – one sentence, one paragraph, and one page.

Iterate as you go

Great salespeople – greats in any domain – don’t just get good at their thing and then stop progressing. They continue to iterate.

Learn from every pitch, notice what works and iterate as you go.

Ask for what you want

Ask for what you want!

When you are talking to someone, writing to someone, speaking to them on the phone, or promoting your thing on social media, end with a clear ask.

“Would you like to buy?”
“Would you like to go to dinner?”
“Do you agree with my opinion?”

Get feedback

A day or a week after you’ve tried to sell someone or pitch your idea, ask them about their experience. How was it received? Is there anything they think you could have done better?

There’s a lot about my family that I’m grateful for. And we come with quirks and challenges.

I’m not proud of the extent to which I don’t comfortably use the word “please” and hesitate to make my opinion known. But when I see those dynamics within the broader context of my family, I have a bit more empathy and understanding.

The only way to get better at asking for what you want is by observing where you are now and taking the next steps from there.

Enjoy your holidays and see you next week,


The importance of knowing your why

Two years ago, my best friend was diagnosed with Stage 3 cancer. They are among the most optimistic people I’ve ever met and it has been incredible to watch them assess why they are undergoing the difficult surgeries, procedures, and daily efforts that have made up their treatment.

The thing that I’ve watched them do – more intentionally than I’ve ever seen someone practice before – is come up with specific reasons why they are going through those difficult procedures.

In order to change your own or someone else’s behavior you have to have a reason why you or they should change. The stronger the reason, the easier it is to do things that are otherwise out of reach.

Here are some habits to discover and reinforce your reasons why, whether in persuading someone else or trying to change your own behavior. 

Who is it for?

One of the simplest ways to strengthen your rationale for tackling any other audacious goal is to understand who you serve. 

When I started my old restaurant, Robin’s Cafe, I did so because I was very clear about the variety of reasons I had for building the business.

I was only able to take on such an audacious undertaking by having lot of clear reasons why.

Habit: List out the different individual people or groups of people that would benefit from your things being successful.

Brainstorm a list of reasons

Since my friend’s cancer diagnosis, they have gone through two major surgeries and uncountable treatments. Many of those treatments, in turn, have caused additional problems, which require their own treatments.

Every few months, we sit down together and list out the reasons why they are spending all of their time and tens of thousands of dollars on treatments. We list out lots of things: their children, their spouse, serving as a role model, teaching others and staying alive until better testing and treatment becomes available.

Habit: Write out a list of reasons why you are trying to tackle this audacious undertaking.

Brainstorming isn’t the time for editing

I always have to remind myself that brainstorming isn’t the time to critique my ideas. I’m tempted to critique a list of brainstormed ideas even while I create them. But that negates the creative exercise.

Habit: When you are brainstorming, resist the temptation to censor or judge your ideas. List out reasons why, without considering if they are good or bad, or how true they might be.

Revisit your reasons regularly

After you’ve written out reasons why, come back to that list regularly. My friend, for example, found that celebrating their life in Puerto Rico and the beautiful views they wake up to each morning was a powerful reason for them to go through tough treatments. 

As they delved into this reason, in particular, they recognized both their joy during tough times and also their excitement for life post-cancer, when they could enjoy these things even more. Double bonus!

Habit: Revisit your reasons and rationales. When you find one that is particularly juicy, explore it further to strengthen your resolve.

Ask other people for creative ideas why

When I was at my lowest points building Robin’s Cafe – and there were many of them! – I would turn to other people for help. Restaurateurs who’d been through it before, entrepreneurs in other industries, family and friends. Even books, like famed restaurateur Danny Meyer’s Setting the Table, which I gifted to each new employee. 

Each of these conversations would remind me of some aspect of the business I appreciated. Of a great employee or a great experience. To this day, my mother talks fondly of the avocado toast and gallery space at Robin’s Cafe! 

Habit: Ask for help with your reasons why. Listen to what people say, write down their suggestions.

Don’t Ask “Why Not”

Once I’ve settled on a course of action – for example, starting a new business – I purposefully don’t ask myself the question “why not.” Doing so – querying myself why I should not do something that I’ve already decided to do – leads to stagnation.

If the goal is to continue moving forward, then explore your reasons for that course of action, not against it.

Habit: Ask yourself why; don’t ask yourself “why not?” If you do feel the need to explore “why not,” do so deliberately and separately from your explorations of the reasons for the behavior you are wanting to take.

We found out this week that my friend is NED, or there is no evidence of disease. This is great news! And while there’s no causal proof, I’d bet anything that my friend’s optimism contributed. 

Whether your desire is to persuade someone you love, sell your services, or change your own behavior, the more clearly you have your reasons why, the easier it will be.

What I’ve learned about human behavior from dating

I’m recently back on the dating market and, to my chagrin, a lot of friends who are in committed relationships want to know about my dating life. They live vicariously through my dating exploits even while I envy the placid stability of their domestic lives.

I’m pretty good at dating; to win a bet I once went on 13 dates in less than 3 days! And from internet celebrities complaining to Bumble profiles asking “Can we please get off this app together?” the consensus seems to be that online dating is difficult. 

We are more digitally connected than ever. And have never been more lonely or divided.

I counted: I receive communication via several email addresses, iMessage, WhatsApp, Signal, Instagram, Facebook, LinkedIn – and that’s not counting dating app DMs. This is a variety of communication that my grandparents, who literally met on a dance floor, couldn’t conceive of.

I think there’s a broader solution to be had to the dating dilemma – though I’m not sure what it is.

When everybody agrees with an opinion, I’m reminded of the Mark Twain quote that, “When you find yourself on the side of the majority, it is time to pause and reflect.” Like Bernard D. Sadow, who first put wheels on luggage in the 1970s, there is a solution that we just haven’t thought of yet.

I’m not sure what the solution is, but here are some thoughts I’ve found helpful, whether applied to my dating life or human behavior, more broadly.

The impact of small changes

I have no conclusive evidence as to why, but my dating profile is much more popular than it was a year ago. I have made very few substantial changes – in fact the only thing that’s much different is my age. And with that small change I’m receiving 5-10x more connection requests than I was one year ago.

This is a good reminder that sometimes all it takes is one tweak – one small adjustment – to go from nothing to something. 

A single word choice can be the difference between closing a deal and a rejection. The same is true in dating. 

Habit: Nearly everything we do in life allows for iteration and improvement. Don’t settle for good enough if you want a spectacular outcome. Look for small things to improve.

Everyone is looking for something

I get a lot of dating app connection requests from a wide variety of people – all shapes, sizes, ages and genders. But the one thing that I see in common is that everyone is looking for someone. 

Whether they know clearly what they are looking for or not, each person on the dating apps – and everyone I’ve ever met – is looking. 

As I wrote last week about the importance of knowing your “why,” it helps to know what you’re looking for!

Habit: If we let go of self-judgment, what are you actually pursuing – in any domain in life? The more clear you can be on that, the more likely you are to find it.

Listen to what they say. Watch what they do.

I like to listen to people. Ask questions and see how people respond. 

More than listening, though, it is helpful to watch what they do.

When I connect with someone on a dating app or in a business transaction, I notice:

Watch what people do privately and when there’s very little on the line.  That will tell you a lot more than what they say.

Habit: In business and in your personal life, hold to your standards. Write out what you are willing to tolerate and what you’re not willing to accept.

A little bit every day

It can feel daunting to attempt something big. There’s a lot of work that needs to be done!

But dating is a lot like learning anything: it takes a little bit of practice every day. 

Take one little action every day towards your desired outcome. Action builds what BJ Fogg calls “success momentum” – the momentum that comes as a result of making progress.

Habit: Focus on the next little step. That might be learning a new skill, joining a new app, finding a new community. Even just listing out one thing – right now – can help.

There are days I agree with the dating profiles that say “Persuade me that I’m wrong about online dating.” I still get overwhelmed when I don’t break a task down into incremental steps. I still don’t love opening my mail.

But I also find that it’s helpful to remember that human behavior hasn’t changed all that much.

While we’ve seen astounding technological advances in the last few decades, as humans – with all of our brilliance and foibles –  we’re still about the same as in my grandfather’s day. 

Jedi Mind Tricks – How to Travel with Family

I’m traveling with my family to Mexico for two weeks this winter. The trip is a throwback to holidays from my childhood. Every other year, my family avoided the holidays altogether and traveled to Latin America. As a kid, I was sad to miss the holidays, but in retrospect those international trips were formative. This will be the first family trip in a decade and the first time with my nephews (7 and 10).

Know why

When I took a month-long trip with my mother to Ghana, I had to get very clear in the months leading up to the trip why I was going. And my purpose for taking the trip wasn’t to have a great experience.

Visiting Ghana was a lifelong dream of my mother’s and a trip she wouldn’t have attempted alone.  My primary reason for going to Africa was to support her; to facilitate her having a positive experience. 

As you are heading into an experience with family, ask yourself why you are prioritizing spending time in this way:

The more clearly you know why, the better you will be at boundaries and making productive use of the time.

Habit: Write down 10 different reasons “why” you are taking the action that you are. They won’t all feel true, but you’ll find something new through the exercise.

There’s no problem so big you can’t walk away

I use this phrase, which is oft repeated by a close friend, to remind myself that I have agency. We always have the ability to leave – even when it feels like we don’t.

It is something of a cardinal sin in my family to leave a conversation or issue unresolved. And yet I’m always calmer for stepping away for ten minutes and coming back to the issue later.

Any of us is free to take a break or walk away at any time.

Habit: Remind yourself, maybe even aloud, that “There’s no problem so big I can’t walk away.”  Repeating that serves as a reminder that you are not stuck in a difficult situation.

Take a pee break

Years ago, a friend taught me the trick of taking a “pee break.” Maybe you actually need to use the toilet, but that’s beside the point. 

The goal is that when you are upset you take a couple of minutes to reorient yourself and come back refreshed.

Under very few circumstances is it considered socially inappropriate  to take a couple of minutes out of a conversation “because I have to use the restroom.” And often you come back better able to handle whatever challenge has been going on.

Habit: Practice “taking a pee break” when the stakes are low. During an otherwise unheated conversation say, “I’ll be back in 2 minutes. I need to use the restroom.” The better you get at taking a break, the better you’ll be able to when things get heated.

Therapy with your parent/child

I’m a proponent of facilitated conversation: therapy, coaching or anything else that works for you.

In advance of our trip to Ghana, my mother and I went to therapy together. The objective was to create some guidelines about what we might expect while we were traveling in Africa, and how to collaborate better.

My mother and I walked out of therapy with a new willingness to listen to each other, which led to a gentler trip in Ghana then might have happened otherwise. (It was still an intense experience!)

Habit: Organize a facilitated conversation. It might not change anything, but it might also result in less drama.

Family meetings

We had regular family meetings growing up. Once every few weeks, our family of four would sit down and discuss challenges that had come up recently.  

I don’t remember what got discussed, but “let’s have a family meeting” remains my family’s shorthand when communication is getting tough.

Habit: Schedule a brief “family meeting.” The goal isn’t to change anybody’s behavior, but to create space for airing of grievances – so they don’t bubble over at inopportune times.

As I get ready to spend two weeks in close quarters with my family in Mexico, I know that I am going to need to practice a lot of these habits and tools. I hope that one of these habits is useful for you as you head into your own holiday plans.

Habits for Gratitude and Celebration

Throughout my life, I’ve believed that in order to acknowledge what’s going well in my life, I have to first solve any difficult emotional situations. Over the last several years, I’ve realized that it is often more effective to focus on the positive, instead of first trying to solve the negative. 

Instead of waiting for things to go just right, it’s a lot more effective – and more fun – to focus on the things that are already going well. Here are some tools that can help… 

Celebrate the small things

By celebrating the small things that are going well – no matter how small they are – we get more practice with celebrating. Don’t wait for things to go well in order to celebrate. Practice and you’ll be surprised at how much more quickly you are able to feel good about seemingly mundane things in your life.

Habit: First thing in the morning, write down one small thing that went well from the day before..

Flip the negative

I have daily practice with my best friend: we phone each other and inquire “Is there a judgment that you would like to flip?” 

We choose a negative judgment – that we’re holding about ourselves or in the world around us – and look for the positive.

If I’m berating myself for a misunderstanding with my mother, I’ll look for ways in which that misunderstanding could be beneficial. If I’m judging myself for pushing through an injury, I’ll examine how that pain could actually be helpful and result in recovery.

By taking something that you are judging as bad and looking for the positive in that same example, you are ” flipping the negative” and practicing gratitude.

Habit: Flipping judgements requires a lot of mental dexterity, so start small. Select something small about yourself or something else that you are judging as bad. Write a few sentences about how that situation could, hypothetically, be beneficial. 

Worst case scenario

Tim Ferriss popularized the idea of “fear setting” through this TED talk and the article “Why You Should Define Your Fears”. The purpose is to identify the worst case scenarios, which usually turns out to not be quite so bad.

My worst case scenario usually ends up with me shitting my pants in public and leaving the country in humiliation. But even in my hypothetical worst case scenarios, I usually survive and learn from the experience.

For extra credit, you can also explore the Best case scenario!

Habit: When you’re considering something you are scared of, ask yourself “What’s the worst thing that could happen?” Write down a few of your answers. You might be surprised by some of your answers.

What went well exercise

What Went Well is my favorite among the many exercises Martin Seligman, teaches in his book Flourish.

Traditionally, psychology research focused on “abnormal” psychology or problems to be solved. More than 30 years ago, Seligman began researching and teaching tools that help everyone improve.

One exercise that Seligman teaches is “What Went Well.” Very simply, the practice is to list out three things every day that have gone well. 

This practice forces you to focus on the specifics of what has gone well. By bringing attention to them, you recognize them, reinforce them and make them bigger.

Habit: Write down three things that went well for you in the last day.

Feel shine

In Tiny Habits, BJ Fogg coined the word “Shine” to describe the internal positive emotion we give ourselves when we’ve done something well. When we reward ourselves with that internal feeling of celebration, we create a positive feedback loop. For more on Shine, here’s an article on the topic from TED.

Habit: Take 2 minutes and deliberately feel good about something you’ve done today. Pat yourself on the back, pump your fist or smile in the mirror.

Look for awe

I was sitting in the sauna a few weeks ago and struck up a conversation with UC Berkeley Professor Dacher Keltne, who has spent his career studying awe. 

As we began to talk about his research I was reminded of the life changing moment when I first saw the circus. My parents took me to see Cirque du Soleil’s Alegria, shortly after I began studying gymnastics at 17 years old. Watching the acrobats opened my eyes to what the human body is capable of and led to the last few decades of my movement career.

Awe has the capacity to fundamentally change our perspective or widen our world view. 

(I’m also going to attend the professor’s last class of the year next week and will report back!)

Habit: Seek out awe. Whether through a beautiful view, over a meal with family or in listening to great music, look for an experience of awe. When you open yourself to the feeling of awe, you’re more likely to experience it.

As you spend time with friends and family this holiday weekend, or go about your life, I hope one of these tools is helpful.

Habits for Grief

Two years ago, my best friend was diagnosed with Stage 3 breast cancer. Two months ago, I went through a breakup. Whether personally or globally, challenges arise.

Grief is complicated. We aren’t taught much about it or how to deal with it.

It is important to take time to mourn a loss.

Here are some habits and practices that might help.

The role of emotions

Sometimes emotions are almost too much to handle. You’ll criticize yourself, or other people. You are less happy or healthy than you want to be. But, it turns out, without emotions, we are unable to function in the world.

There are some interesting studies done on the role of emotions. When someone suffers brain damage such that they can’t experience emotion, they are also unable to make decisions.

While you sometimes might prefer to do without emotions, the alternative is much worse. You can’t enjoy the beautiful things in life if you don’t also experience some of the challenges.

Habit: When you are grieving, find something in the same situation, however small, to be grateful for.

Take time to grieve

Grief sneaks up at random times. When you least expect it, you may see something that reminds you of someone who’s died and the upswell of emotion can be hard to handle.

It doesn’t have to be an actual death, either. The loss of a relationship, or even a missed opportunity can be something we need to grieve.

It helps to take time to grieve. Difficult emotions will still come up, but setting aside time does help.

Habit: During a difficult time, carve out at least one minute a day to be present to your emotions. I like to set an alarm on my phone as my cue. I prefer to write during this pause, but any reflective activity can help.

Don’t judge your process

Everyone’s process for getting over a challenging situation is different. It might mean going to therapy or bitching to a friend. I process emotions by waking up at 5 a.m. full of adrenaline and going for a hard run.

The key is not to judge yourself for the fact that you are grieving. Then you’re not only feeling bad, but you are beating yourself up about it, too.

Don’t judge your process.

Habit: Recognize what helps you. Take 10 minutes and write down a list of things that help you take care of yourself.

Grief takes the time that it takes

I was in a serious car accident last year. I knew that it would take some time to heal and I was gentle with myself for the first couple of weeks.

But a few weeks in, I started getting anxious to get back to my movement practice and the rest of my life. I wasn’t in pain, but I was still very shaken up and the added pressure didn’t help.

In all, it took more than six months to get back to baseline.

Just like healing from physical injury, grief can’t be rushed. Healing happens on its own time.

Habit: If you find yourself pressuring yourself to “get over it,” decide on a timeline. Give yourself one day, one week, or one month where you won’t pressure yourself to “be there” already.

Don’t use force

The Morningstar Company, which I wrote about in my book Responsive: What It Takes To Create A Thriving Organization, is one of the largest tomato manufacturers in the world. What makes the company unique is that it is self-managed by the employees.

One of the company’s two core tenets is “Don’t use force” in working with each other.

We’re accustomed to using anger, pressure, and blame at work – but at what cost? To the detriment of relationships, our own health, and building the habit of doing more in the future.

Instead of trying to force yourself to feel better, acknowledge your grief. Take time to feel what you are feeling.

Habit: You wouldn’t use force – physically or emotionally – with a young child or in an intimate moment with a partner. Treat yourself that same way, even if only for a moment.

We don’t get to control what happens to us or to the people we love.

(I can’t. If you’ve figured out how – please email me!)

But we do get to control how we respond.

Grief is a natural part of life. It is how we make sense of what’s happened and move forward.

When you’re going through a challenge, take the time to acknowledge your grief. I hope some of these habits help.

Do Hard Things. Move to the Caribbean!

My best friends are crazy.

I just returned home from a month living with some of my best friends on Vieques, a tiny island off of Puerto Rico.

They don’t live on “mainland” Puerto Rico. Instead, they’re on a tiny island, only accessible by an irregular ferry or an eight-seater airplane.

They are building a bed and breakfast overlooking a stunning 270-degree view of the Caribbean Ocean and the world’s most luminous bioluminescent bay. They are building out of concrete because anything not made of concrete gets destroyed by hurricanes. But getting concrete, or simply groceries, is a full-day journey that requires careful preparation and timing.

All the difficulties are exactly why my friends moved to Vieques. For the love of a challenge.

Do More Scary Things

I appreciate the irony. Do hard things, move to the Caribbean!

And while most of us probably aren’t going to move to a tiny island in order to make our lives more difficult, there are a lot of simple habits that can help.

Identify One Thing Every Day That Scares You

Identify something that scares you.

You don’t need to take action – not yet! Just bring attention to one uncomfortable moment.

Start with awareness.

A Daily Movement Practice

There is a lot to be said for daily exercise.

Exercise is hard. When you push your physical limits, you get better at pushing the boundaries of what’s possible everywhere else in your life, too.

Unfortunately, more than two thirds of Americans are overweight or obese, so clearly pressuring people to exercise doesn’t work.

My approach to movement is different. Having broken my neck on a trampoline, I also know the negative consequences of pressure. Instead, I make a habit of moving every day to build the confidence that I can learn new things.

If you’re interested, here’s a short video about my movement practice.

Coffee Shop Challenge (h/t Tim Ferriss)

Try this challenge: go to your local coffee shop and ask for a 20% discount.

The rules are that you are not allowed to give any explanation for why you are requesting a discount or any additional details alongside your request. If asked why, just say that you would like a discount and that is why you are asking.

The point of this exercise is that you are going to be uncomfortable. It will take you outside of your comfort zone.

Notice how it feels to make this request. Notice the tension in your body and your voice. It doesn’t ultimately matter if you get a discount or not, so long as you try.

(As a former coffee shop owner, please give that 20% back to your barista as a tip!)

Do Something Difficult Every Day

Do one thing today that is out of your comfort zone. It could be as small as a short exchange with a stranger, a much-needed conversation, or advocating for your opinion.

When my friends first moved to Vieques, I was skeptical. I’m all for beautiful ocean views, but it was so remote and isolated. (And the hurricanes!)

Now that I’ve spent a month living in that remote paradise, I understand their motivation a little better. Living there is difficult. Every day is a stretch. And that’s the point.

In a world where I – and probably you – enjoy every other modern convenience, it is easy to get complacent.

Perhaps we could all use a bit more discomfort in our lives.

The Line Between Habit & Addiction

My grandfather and uncle died of alcoholism. I’m predisposed to addiction.

As I write this, I’m in the midst of my fourth 5-day water-only fast. When I began fasting, my friend Michelle warned me, “You be careful. You be safe!” knowing that my addictive tendencies might lead to extremes.

Given a predisposition and love of intensity, it has taken me decades to develop an appreciation of the fine line between habit and addiction.

What Is Addiction?

The DSM-5 defines addiction as a chronic, relapsing disorder characterized by seeking and use despite adverse consequences. In other words, compulsive engagement in naturally rewarding behavior.

What’s complicated, though, is that what we call addictions aren’t necessarily problematic in moderation. There aren’t a lot of downsides to having two drinks a week. Short of sexual addiction, sex is great!

But to get the same positive experience and dopamine reward over time, we have to increase the stimulus. We need more alcohol, more drugs, more sex, or more exercise to get the same – or even a lesser – outcome.

There is nothing wrong with chasing naturally rewarding behavior. It is just important to choose the right ones!

A Little Escapism

Some years ago, I spent a night at Lake Titicaca in Peru. The locals were celebrating their annual harvest, which entailed getting black-out drunk for days – and nights – on end.

Growing up around alcoholism, I’d always judgmentally deemed alcohol as problematic. What I learned in Peru is that the locals were practicing a form of once-a-year escapism in the form of celebration and a significant cultural ritual.

We all need escapism, whether that is a die-hard devotion to a sports team, binge-watching Netflix, reading science fiction, or my own study of movement.

Altered States of Consciousness

We all enjoy altered states of consciousness.

Few things feel better than getting out of my 39 degree cold plunge after 3 minutes. As I’ve written about in Habits for Fasting, I enjoy the altered state that comes with fasting. Whether through a physical accomplishment or an emotional victory, winning feels good. (And can be made even better by Deliberate Celebration.)

It has taken me years to realize that the pursuit of an altered state – whether a slight alcohol buzz or exercise endorphins – isn’t harmful. And to identify two characteristics which help me steer clear of habits that could too easily spiral out of control.

How I Differentiate Between Habits & Addictions

The keys I’ve found to differentiate positive habits from addiction are in these two questions:

Is it difficult to do? – The habits that I let myself pursue today are hard to do. Exercising is never easy. Cold plunging can be miserable. Fasting is the single hardest discipline I’ve ever attempted.

By contrast, drinking alcohol is easy. There’s very little barrier to entry, and the second drink is even easier than the first!

When something is difficult to do during the practice of that habit, you are much less likely (to be able to) abuse it.

How do you feel afterwards? – The second criteria is how you feel afterwards. Alcohol feels great immediately, but you can be sluggish or hungover the next day. Cold plunging is uncomfortable, but the endorphin high afterwards is exhilarating.

Fasting is the most difficult delayed gratification I know. But even more than the altered state of consciousness that comes during a long fast, I like how I feel afterwardsWith exercise, cold plunge, and many other pursuits, the reward comes after the effort.

This newsletter aims to be a tactical guide to good habits. As someone who has long been afraid of my own predisposition towards addiction, I’ve found it useful to recognize that when a habit is difficult to do and leaves me feeling good long after, I’m probably on a good path.

Until next time,

P.S. I’m not a medical doctor and nothing here should be construed as medical advice! If you are struggling with addiction, please consult with a professional.

Do What Matters

An Obscure Blood Test in India

I’m spending the month living with my best friend on the island of Vieques, Puerto Rico. My friend was diagnosed with Stage 3 breast cancer, so one of my goals this month is to get them access to a promising cancer detection blood test. Unfortunately, the blood test is currently only available in India.

There’s something absurd about attempting to get access to an obscure blood test that is only available from a single lab in India while living on a tiny Caribbean island. It’s is a big project with a lot of unknowns.

Whenever you are tackling a new project – starting a business, adopting a habit, or supporting a friend – there are a myriad of to-dos. The key is to pick the right one.

What’s Your Objective?

I have a clear objective. I want to get the patent holder of this blood test to test blood samples from the United States or to license their technology to a lab in the US.

There are ancillary goals, too. With several family members in remission from cancer, I’d like to get each of them access to this test. And, because I’m ridiculous, I’m considering turning this into a new business.

Knowing why you are tackling any new endeavor helps you to stay focused.

The Next Most Important Thing

When you are tackling any new project it helps to identify the single thing that most needs to be done. And in a world full of bright and shiny distractions (or is that just my ADHD?), it is easy to focus on everything but the most important task.

As I learn more about this obscure blood test, there are a hundred small tasks that I could spend time on:

  • How to get blood samples to India
  • US export and India import policy
  • How much dry ice is needed to transport blood vials
  • The cost of flights to India
  • How to set up a testing laboratory in the US

The list is endless, but there is always just one or two important things that need to be done to move a project forward. And, with a little introspection, we often know what those things are.

The question I ask myself is “What’s the one thing that if I do will move this project forward?”

Is it absolutely necessary that I learn about country-specific import and export policies or begin to build a website right now? No.

Today, there was only one thing that had the potential to make a big impact: connect with the Indian laboratory – in other words, a sales call.

The Hard Thing Is Often The Most Important

The first thing I did this morning was phone the laboratory in India that provides the blood test and speak to a representative. I didn’t know if anyone would answer, but that was the single most important task that needed to be done.

I was nervous phoning India this morning. Will anyone answer? Do they speak English? What do I say if they do? But phoning the laboratory was my next most important step. Since the laboratory is the only group that has answers about this blood test, that phone call was the single linchpin that has the potential to move the project forward.

The hardest thing to do is often the thing that most needs to be done.

The First Small Step

By working backwards from the end goal, you’re more likely to be able to do the single most important thing. And while I love attempting to do hard things, I prefer making those hard things accessible, first.

My call to India this morning was, in essence, a cold call. And to make that international sales call small enough to attempt, I did a lot of things to prepare.

  • I scheduled the call at an appropriate time – First thing in my morning is afternoon in India, which gives me the best chance of reaching someone directly.
  • I planned out what I would say ahead of time – I wrote out what I would say in advance, including my questions and potential questions they might ask me.
  • Then, pivotally, I took that step – Because the only way forward is by taking a single next step.

Today my most important thing was a sales call to a laboratory in India. Fortunately, I reached someone and I got a few of my questions answered.

Tomorrow, my most important thing may be totally different. But whatever it is, my most important task will be a linchpin that moves a project forward.

Until next time, Robin

Beyond Fear

Earlier this week I signed up for an Ultra Marathon. I’ve never run a marathon before, or anything more than ten miles. And while I’m a strong runner, 50 kilometers is a big step. I’m afraid. And I’ve been reflecting that when I’ve been afraid, and taken action anyway, are the times I’ve experienced the most growth and joy in my life.

Beginning something new never gets easy. But most good things come on the other side of fear.

Fear is an Indicator

My car indicates if there is something in my blind spot. It also indicates if my tire pressure is low or I’m out of gas. Fear should be treated like the indicator: neither good nor bad, but warranting further attention. 

Fear is always an indicator that something merits further consideration. It can be a good guide of the direction you want to go. 

Notice What You Are Avoiding

Pay attention to what you are avoiding.

There are always things in business that I would just as soon ignore and opening my mail is high among them. As I discussed in How to Reframe Failure, the reason behind my reluctance to open mail was fear of failure. By noticing the avoidance, I was able to identify the fear.

There’s often a hint of something that you are not wanting to start, or that you are afraid of in the tasks that you are putting off.

Get Curious

We treat fear as something to be avoided.

Whether the thing you are afraid of is asking for a promotion, starting a new business, a first date, or running an ultramarathon – get curious. That is a form of courage.

Curiosity is a way to channel your attention and take a small step. Though it doesn’t feel like action, bringing your attention to focus on what you are afraid of moving towards your fear. 

“Fear Setting” Exercise

Tim Ferriss popularized the idea of “fear setting” through this TED talk and the article Why You Should Define Your Fears. The purpose is to identify the worst case scenarios, which usually turns out to not be quite so bad.

The simplest version of this exercise is to repeatedly ask the question “What am I afraid of?” 

What are you afraid of?
Not being able to do an ultramarathon

What about this are you afraid of?
That I’ll try to run the ultra and get injured.

What about this are you afraid of?
That I’ll feel like a fool.

What about this are you afraid of?
Even if I don’t run it or don’t finish, signing up gives me an objective and six months to train.

And I recognize that my fear isn’t as big as I’d made it out to be.

Take a small action today

The final step towards accomplishing a big audacious goal is to take one incremental step. 

No one who has done something you admire got there in one big step. Unfortunately, we usually see the endpoint and not the journey along the way. 

Notice what you are afraid of, get curious, and then take some tiny action towards your fear.

Signing up for an ultramarathon when I’ve never run more than 10 miles might sound crazy. It is, as they say, “jumping into the deep end.” But I like to run. I’ve wanted to run a marathon. And the worst case scenario isn’t that bad. I’m excited to discover who I am as I go towards this thing that I am afraid of.

Do the thing you are afraid of. Take action. Fear is a good indication that there’s something there for you to learn.

My System for Emotional Self-Management

I spoke with an entrepreneur recently who described founding her startup as the loneliest of jobs. Elon Musk, somewhat more dramatically, said that “starting a company is like staring into the abyss and eating glass.” Running Robin’s Cafe was the loneliest job I’ve held. It taught me a lot about my own emotional management, which has made running companies since somewhat less difficult. 

Regardless of whether you are building a business, trying to get better at managing a tough situation, or starting something new, I approach emotional management in two stages: avoid the spiral and incremental growth. 

What is the Emotional Spiral?

Throughout the first few months of running Robin’s Cafe, I lived in a state of overwhelm. With everything that needed to be done, there were nights that I’d finish cleaning the cafe after midnight and then sit alone in the dark, too tired to go home.

That’s the emotional state I call the spiral. A state of overwhelm, of being upset about being upset, where it is impossible to make forward progress or to plan ahead.

How to Get Out of an Emotional Spiral

Recognize the spiral

During the worst moments of Robin’s Cafe, I often called my best friend and complained that I wanted to close the business. She would remind me that I could, in fact, walk away at any time. 

The reminder that I wasn’t stuck – that I had the ability to shutter the business –  allowed me to step outside of my emotional spiral and move forward slightly less overwhelmed.

I’ve described bystander apathy, the cognitive bias in which we assume someone else is going to take action. Just as the solution to bystander apathy is to remember that it exists, the path out of an emotional spiral is to recognize it. Simply identifying a spiral can serve as a heuristic to take action.

Take Incremental Action

One block from Robin’s Cafe is another cafe called Stable Cafe, which has been around for a decade and functions seamlessly. On my bad days at Robin’s Cafe, I would compare my business to Stable – and berate everything about my own small operation.

It is tempting to focus on goals and aspirations that are far out of reach, but the consequence is feeling bad about where we are. We amplify that which is at the center of our attention. Being stressed about being stressed results in even more stress! Take some small positive action to build momentum.

Begin by taking one small step in the direction you want to go. 

Take Any Small Step

Sometimes you don’t know what the right next step is. I didn’t know how to start a cafe! As I’ve written about in How to Conduct an Effective Interview, I had to interview a lot of professionals and then take some action. When you are in a spiral, take some action. 

Don’t attempt to solve everything in a single moment. Put one foot in front of the other. Make each step as small as possible. If you try to do something dramatic, you are more likely to fail and resume your spiral. 

Adjust Course As You Go

Think of a sailboat leaving San Francisco for Hawai’i. You don’t leave the coast, point the ship towards the Hawiian islands, and then stop navigating. You’ll get off course. 

The best way to navigate is to adjust course as you go. The best time to adjust your trajectory is while in motion. 

There were a lot of difficult days building Robin’s Cafe – moments of panic, overwhelm, and loneliness. The businesses I’ve built since then have gotten progressively easier. There are still incredibly hard moments, of course, but I don’t stay stuck.

I have more mental and emotional fortitude, better habits to avoid the spiral and to get out quickly. I hope this framework will help you do the same.

Habits for Combatting Resistance

As I discussed in last week’s article, “Resistance” was coined by Steven Pressfield to describe the inertia that gets in the way of our most important work. If you missed last week’s article on recognizing Resistance, read it here.

My own personal story: I’ve long had a writing habit. I like how I feel when I write regularly. Writing clarifies my thinking and makes the rest of my work better. And yet I haven’t written anything publicly since my last book in 2017. Why not? Because of Resistance. Here are some habits that can help.

Ask yourself “why”

Ask yourself why you are resisting. Despite writing on the Internet since 2007, I don’t create nearly as much as I want to. Among other things, I have a handful of books that have never been published. 

One reason I don’t share more is shame. I’m avoiding the shame I’ll feel when I publish this newsletter and find a typo immediately after, or when I declare something that, looking back a decade later, I’ll cringe upon re-reading. For me, examining that shame has been a key to unlocking Resistance. 

Another reason I don’t create more is that I frequently compare myself to other people. My father is a better writer than I am. My friend Todd is more even-tempered.  Ryan Holiday reads more than me. These comparisons put me down, without motivating me towards a path towards greater efficacy or change. 

What are the reasons that you aren’t doing your most important work?  The underlying reasons will be different for you, but the better you can get to understanding those emotions or motivations, the closer you’ll be to overcoming Resistance.

Make it tiny

I’m currently writing 2 hours every day, but I didn’t start there. A few months ago, I challenged myself to write for 10 minutes each day. That escalated pretty quickly to 20 minutes, and then eventually into an hour, then two. 

The key, throughout this process, though, is that my baseline has remained the same: 10 minutes a day counts as success. Otherwise, it is too easy to fall out of the habit and not come back again tomorrow.

For more on this idea, watch BJ Fogg’s Tedx talk on flossing one tooth.

Make the tiny habit inevitable

As my friend Michelle says, the goal is to make a habit so small, so tiny, that you can’t help but to achieve it.

I’ve been journaling for 30 minutes each morning for years. To start writing for a wider audience again, I substituted 10 minutes of journaling for 10 minutes of writing instead.

Make the small habit so small that accomplishing it is practically inevitable.

Stack your habits

To start a new habit, especially one you’ve been avoiding, add the new habit you just after something you already do regularly.  This is “habit stacking.”

For me, my writing habit comes just after journaling. I journal each morning, so it wasn’t all that difficult to add 10 minutes of writing immediately after my journaling habits. By stacking the new habit immediately after a pre-established habit you are better able to do it.

Decide what you are going to give up

I learned during my 30 days of mediation that to add something substantial into your life requires that you also give something up. 

To begin writing every day, I removed 10 minutes of journaling, so as to carve out the time. What are you going to give up in order to take on something new?

Whether you call it Resistance, writer’s block, or inertia, we all have habits we want to pursue and that we’ll go to great lengths to avoid. Identify those obstacles and then take small steps to combat Resistance, and maybe you’ll finally be able to begin. Thanks for following along! 

See you next week,

How to Create an Ideal Environment for Learning

In the fall of 2003 I broke my neck on a trampoline. (That sounds dramatic, I know, but isn’t uncommon in gymnastics). To heal, I began to study with a woman who specialized in working with kids with autism.

While her work focused on helping parents help their special needs children, I found it also helped me with my injury. Pretty soon, I too began working with autistic kids and traveling around the world to teach parents how to help their children flourish. In the process, I became a student of how different variables create a supportive learning environment for these children and families.

Even more than the rest of us, kids with autism respond to their environment – to the emotions of the people around them and the situations they are in. They don’t respond to pressure.

Learning is a vulnerable process that requires that we try new and uncomfortable things. But just like any other skill, you can get better at learning with practice. Today I want to share how to create an ideal learning environment. While most of us don’t require ideal conditions for learning, these tools are applicable everywhere.

Attention – paying attention to what is happening while it is going on

I found that kids’ attention was the deciding factor in their ability to learn. What we attend to, we make bigger, and this single notion is the bedrock for learning.

We live in a world where everyone, and everything, is vying for our time and attention. Advertisements, social media, push notifications all interrupt our focus for their own agendas.

Practice channeling your attention – whether for a few minutes or a few hours. Direct your attention to the things you are most interested in improving. The more concentrated attention you can bring, the faster you’ll be able to learn.

Slow – “Slow is Smooth and Smooth is Fast”

Moshe Feldenkrais, founder of the somatic discipline the Feldenkrais Method, said, “Fast, we can only do what we already know.” Learning demands that we stretch outside our comfort zones, and that is much harder under pressure, urgency, or force. Learning benefits from spaciousness and safety.

While it is counter-intuitive in today’s fast-moving world, slowing down is the best way to get faster. A similar idea comes from the Navy SEALS: “Slow is Smooth and Smooth is Fast.” Moving slowly means moving with intention and attention; it reduces the risk of making the kinds of mistakes that then would take more time to undo and correct.

Consider how you’d approach a skittish horse or a nervous child. The best way isn’t with force or aggression, it’s instead to approach gently and from the side. To move your hand slowly towards the horse’s muzzle or ask the child, in a quiet tone, how their day has gone.

In slowing down you are better able to absorb and make sense of novel information. You’ll create better conditions for learning and deeper integration.

Variation – playing with the variety of options available

When I was in university, I studied the impacts of variable practice. Here’s how it works:

You and I are on a basketball court, taking turns shooting hoops. You shoot from the free throw line while I shoot from all over the court. In effect, you are learning to shoot free throws – and only free throws – while I’m learning to shoot baskets.

Assuming we are starting from a similar baseline, your free throws will outperform mine during this practice period. You are shooting from a single location while I am shooting from all over, so you get more practice at the specific task.

But when we test at the end of the trial period – even as little as 30 minutes later – I have better performance. My performance is still better several days later, and from a variety of conditions around the court. Practicing with variation results in more learning.

This concept extends beyond the basketball court. When you are feeling stuck, try variations around the edges of what you can currently do to learn more thoroughly. Approaching the problem from a different angle offers the opportunity for more connections and perspectives.

Enthusiasm – enjoy the process

During the years I worked with autistic kids, I often attended training programs for parents of special needs children.

One day at a workshop, I walked into the dinning hall to see my friend Stan in the center of a circle of attentive parents. As I walked up, Stan paused what he was talking about and asked: “Robin, why did you come up?” I responded that I was curious what was going on.

Stan explained that he was being enthusiastic deliberately, so that the parents in the room would be excited to learn from him. He went on to share that this was what each of us needed to do to create the conditions for success and learning for the children in our lives.

It worked: when I was engaged, excited, and energetic, the kids I worked with were more engaged with me and our shared activities.

Even when you aren’t trying to teach or inspire someone else, you can be deliberately enthusiastic about what you’re learning. Excitement reinforces positive feelings about the process, which, as I’ve discussed in this essay about celebration, is a great way to incentivize behavior change.

Flexible Goals – be flexible in how you define “success,” especially during the learning process

Goals are great. They give you direction and motivation. But your goals need to be reevaluated regularly because every step you take provides more information about whether that goal is realistic or even worth your effort.

Most often, you are learning something new with a clear objective in mind. I worked with kids with autism to help them function more effectively. You practice shooting basketball with the goal of making baskets. We practice for the outcomes that practice gets us.

But if the metric of success is too narrow, it sets us up for a win/lose binary. Instead, working towards a goal is ultimately about practicing the skill of learning.

Growth is a vulnerable process. Take the pressure off and you’re better able to absorb new information!

I’ve long since recovered from my trampoline injury, and the years of working with autistic kids are also behind me. But when I’m feeling stuck or not learning as fast as I want, I incorporate more enthusiasm, flexible goals or variation into my daily practice. I invite you to do the same.

Everything Is Sales & You’re Doing It Wrong

Everything in life is sales. From inviting your child to do her homework, to deciding where to go for dinner, to encouraging a colleague at work, the situations we encounter daily are filled with the dynamic of sales and persuasion. And, unfortunately, most of what you know about sales is wrong.

What is Sales?

My favorite example of sales comes from a scene from the classic Christmas movie Miracle on 34th Street.

In Miracle, the Macy’s department store Santa asks each child who sits on his lap what they want for Christmas. Santa then tells the family where they can purchase that toy at the best price, even if it means at a competing department store. At first, the store manager is outraged that Santa is supporting his competitors – until he sees enthusiastic customers returning to Macy’s because of the excellent customer service. The value to Macy’s of Santa’s recommendations is greater than the sale of a single children’s toy; it’s customer loyalty.

Sales is having a clear solution – a service, opportunity or opinion – that can help to solve somebody’s problem. Like Santa, good sales means aligning yourself with the interests of the person you are talking to, to discover if your solution is a good fit for them. If it is, invite them toward your solution, and if not, move on. 

How to Do It Wrong

Sales and persuasion are most often practiced with pressure and urgency.

Think of the reputation of a car salesman – pushy, fast-talking, deceptive. They aren’t considering what is best for the customer. They only want to sell a specific car at the best possible price. The result: nobody enjoys the experience and the customer won’t recommend that product or service in the future.

Pressure and urgency can work, but only in the short-term. They don’t increase trust or loyalty.

How to Do It Right

A Process of Discovery

Done well, sales and persuasion should be a process of discovery. Instead of using force, inquire about what your friend wants to eat for dinner. Get curious about why your colleague doesn’t want to do the work assigned to them.

When you start by asking questions about what someone is looking to solve – for themselves, their business, or their family – you’ll discover if what you are selling is a good fit for the other person.

People relate through the stories that you tell them, so share your experience, too. As I discussed in “Everything is Storytelling,” your story should be brief, personal and relatable. 

Useful Beliefs About Sales

Abundance – If the person you are talking to doesn’t want the solution you are offering, somebody else will. There are between 7 and 8 billion people in the world today. If the person you are talking to is not a good fit, move on.

Believe it – Believe in what you are selling. That doesn’t mean that it is valuable to every single prospective buyer, only they can tell you that. But believing that it is valuable in the world makes closing easier, genuine, and fun.

Decrease the stakes – There are very few game changing moments in life, and this specific sale isn’t likely to be one of them. Whether or not you make this sale today isn’t likely to matter over the course of your or your customer’s life.

Autonomy – Foster the belief that everybody knows what’s best for themselves. You aren’t trying to convince anyone, but rather inviting them to entertain if what you’re offering is a good fit for them.

Look for “What I’ve learned” – It is useful to hold that even if you don’t close a sale, you will have learned a lot along the way. This practice of iteration and repeated repetitions will make you better at closing future sales.

Put in the Reps

Improving at sales is a matter of practice and incremental improvement. Many of the most successful salespeople and deal makers in the world have practiced tens of thousands of times. Sales is as much a performance as trying out for a sport or auditioning for a play, and practice makes for consistency.

Your Attitude Closes Deals

Who you are and how you show up with a prospective customer is what will determine whether they buy. Who you are closes deals.

Maintain an attitude of enthusiasm and want what is best for the other person. You’ll have a better chance of having things go your way.

Next time you are debating with your spouse about the dishes, trying to get your child to do their homework, or asking an employee to fill out their hours, think of Santa, sitting in Macy’s department store, referring customers to the competition.

Until next time, Robin