A few weeks ago, I spent several hours with my friend Michael, a ghostwriter who helps authors clarify their ideas. One of the fun tasks he gave me out of our time together was to list my Commandments for Reluctant Sales.

The argument behind Snafu is that the very things that make us reluctant salespeople are actually superpowers that make us great. What, then, are those attributes?

Thou shalt not use force

I first heard the phrase “Don’t use force” from Doug Kirkpatrick, who I wrote about in Responsive: What it Takes to Create a Thriving Organization. It is one of the two principles of the Morning Star Company, an entirely self-managed tomato manufacturing company.

“Don’t use force” describes my approach to learning. I’ve learned the best – and accomplished the most – when I don’t use force. (Incidentally, all my best personal relationships embody this principle.)

Stereotypical salespeople are pushy. They use pressure to prioritize what they want even over what’s best for prospective customers. When we don’t use pressure, we are embodying the first and most important commandment of a reluctant salesperson.

Thou shalt be of service

I have been enamored of Danny Meyer, the famous restaurateur behind Union Square Café, Eleven Madison Park, and the Shake Shack empire for more than a decade. He coined the term “enlightened hospitality” in the 1980s to describe businesses that prioritize their employees, even over their customers.

I tried to apply this principle at Robin’s Café by showing up in service to my employees. By creating a culture of service for my employees, my hope was that they would then show up in service to our customers.

When we show up in service of something greater than ourselves, sales happen naturally as a result.

Thou shalt lead with curiosity

For many years, I ran a business helping children with autism.

Autistic children often lack the social standards that we take for granted. The only way to work with those kids was by being completely curious about their experience – even when you don’t know what their experience is.

When you are even more interested in the best interests of another person than you are in getting what you want, you are more likely to get what you want.

Thou shalt have boundaries

One of the reasons many of us are reluctant salespeople is an absence of boundaries.

Boundaries can be as simple as time-boxing meetings, arriving on time, or discussing what you are going to discuss in advance. Boundaries can also be as nuanced as not negotiating past your comfort or saying “no” to a sale when you don’t think your offer is a good fit.

When you know what you’re willing to do – and what you’re not willing to do – it is much easier to be curious, show up in service, avoid force, and make clear asks.

Thou shalt ask boldly and without apology

Asking is the most difficult part of selling for reluctant salespeople. In our nervousness to do well or not cause offense, we ask hesitantly, apologize, or just don’t ask at all.

The simplest way to ask boldly without hesitation is to believe that the other person can – and will – decide what’s best for them. The person you are talking to is their own best expert.

There is no such thing as “taking advantage” of someone else when you don’t use force, try to help them, and trust that they will decide for themselves.

Thou shalt tell them stories

Humans are constantly telling stories. The stories we tell ourselves become how we think of ourselves and the stories we tell others shape those relationships. The first step to telling a good story is to recognize that you already are.

The best stories have four parts: a beginning, middle, and end, and something unexpected. This “turning” or moment of surprise helps make the story memorable.

Finally, practice the stories you frequently tell. Notice what lands, improve your delivery, timing, and affect.

Everyone likes a good story, so get better at telling them.

Thou shalt practice incrementally

Bruce Lee said: “I fear not the man who has practiced 10,000 kicks once, but I fear the man who has practiced one kick 10,000 times.”

Selling is a craft. Like great athletes and artists, salespeople improve through practice, reflection, and feedback. It is the small refinements, consistent practice, and feedback that create mastery.

Improving at sales is a matter of practice and incremental improvement. The key isn’t to be perfect at each iteration but to put in the repetitions which will help you to improve.

Thou shalt celebrate small wins

Acknowledging wins isn’t self-indulgent; it’s essential to creating lasting change.

BJ Fogg argues that there are two necessary steps to adopt a new habit: making the habit tiny and celebration. When we celebrate our successes, we create a positive association with the behavior, and when we make those behaviors so small that they feel almost inevitable, they are easier to do.

The same holds true for selling.

Celebrate any success; not just a closed sale, but the tiny steps along the way. Thus, you become better at the habit of selling.

Thou shalt accept rejection (and move on quickly)

For most reluctant salespeople, it is the fear of rejection – even more than rejection itself – that limits success.

Get to know your prospect and their needs as quickly as possible. There are eight billion people in the world. If the person you are talking to is not a good fit, somebody else will be!

Great selling means getting rejected and knowing when to move on.

Thou shalt maintain flexible goals

When I worked with autistic kids, I found that most parents would see incremental progress and then get fixated on that issue continuing to improve. The more fixated these parents would become on their child’s speech clarifying or digestion improving, the less creative they’d become.

People who want something, who are very driven toward an outcome that they are seeking, often get fixated on the specific outcome.

You can want a specific sale or objective a lot, but never lose sight of other beneficial outcomes.

Thou shalt know thy purpose

Purpose is at the core of sales and persuasion.

Whether launching a product, pitching an investor, or trying to be taken seriously at work, having a clear purpose helps you get over rejection and continue to improve.

The most influential people have a clear sense of purpose.

In last week’s How To Sell Yourself workshop, one participant admitted he sometimes asks too many questions. He gets so caught in curiosity that he “gives away all his marbles” before ever making the ask. Another participant shared the opposite pattern: she avoids asking questions because she’s afraid of what the answers might reveal – especially when she’s afraid the prospect isn’t a fit.

Both patterns are a form of resistance. Whether we over-ask or under-ask, we’re avoiding the discomfort of discovering the truth.

The conversation inspired me to write an article about questions – why they matter, the different types of questions, and which to use when.

Why Questions Matter

There are several different kinds of questions, and the kind you choose determines the outcome — in sales, in conflict, and in life.

Asking questions demonstrates authentic curiosity about the customer, which allows you to build rapport and an emotional connection. And in asking questions you’re able to get to the heart of the customer’s issue.

Ask Questions as Training for Real Life

One of the most important interpersonal skills anyone can practice is the ability to ask questions. Whether you’re gathering information, selling, coaching, interviewing, or navigating a hard conversation, asking questions trains many other essential human skills.

How Questions Sharpen Your Thinking

There are no inherently right or wrong questions – only questions that are more or less useful depending on the outcome you want. Asking better questions improves your ability to listen, connect, persuade, and think clearly.

High-Pressure Conversations

Any situation that matters – a first date, sales call, job interview, or giving feedback to a colleague – brings uncertainty. Important moments require the ability to think while under pressure.

Most people become passive in high-stakes situations. They respond reactively or expect the other party to lead. But if you can stay curious and ask thoughtful questions, you change the dynamic. You become an active participant instead of someone being carried along by circumstances.

Thinking on Your Feet

High-stress conversations are unpredictable. Someone says something surprising and emotions get involved.

You have to respond in real time.

The only way to train for this is to practice before the stakes are high. Asking questions builds the habit of staying calm when it matters.

Practice Before the Moment

We all face pivotal conversations. Instead of waiting for the critical moment to arrive, you can practice the skill of asking questions every day. This might mean:

• asking a friend one more follow-up question
• pausing to clarify someone’s intention
• checking in during a difficult conversation
• being curious instead of defensive

These small practices prepare you for the moments when the pressure is real.

The Different Kinds of Questions

There are several different types of questions, and each serves a different purpose.

Blaming questions

These are the most common — usually asked in frustration: “Why did you do that!?” When used intentionally, blame can motivate action, but more often these questions land as an attack and create distance.

Manipulative questions

These are the pushy, sales-adjacent questions everyone dislikes. They steer someone toward a predetermined answer and usually feel transactional.

Research questions

These are questions that accelerate learning. By asking an expert specific questions about their discipline, you dramatically increase your speed of learning.

Consulting questions

These assume you’re the expert and help the other person see the problem the way you see it. They’re directive and designed to move someone toward your conclusion.

Leading questions

These guide someone toward an insight, a storyline, or an emotional shift. They’re useful for teaching, storytelling, and persuasion — especially when they contain an unexpected twist.

Connecting questions

These presume the other person is their own expert. They create space for introspection and help someone articulate what they think or feel. They’re the least common, and the most powerful for building trust.

Each of these types of questions has an appropriate context. Even blaming and manipulative questions can be useful. But each type shapes the relationship differently – and some build connection while others break it.

Know Your Intentions

It’s important to know your intentions before beginning to ask questions, and to leverage your intention to ask the right kinds. All too often, we are attached to a specific outcome – closing a sale, getting what we want from a family member, achieving our desired ends. That desperation is perceived as pushy and a lack of consideration.

If you are feeling urgency, stop. That urgency, which comes across as pressure, will ultimately not serve you or your desired outcome.

Regardless of what you are selling, or the knowledge that you have, your intention should be to help the person you’re talking to. If, through the course of discovery, you find yourself thinking that what you are selling is not a good fit for the person you are talking to, explain “I don’t think this is a good fit for you.”

Thank them for their time and move on.

Being clear about your intentions means that people are more likely to come back later and the goodwill you generate by being so straightforward outweighs the loss of a sale.

Putting It All Together

In order to sell anything – an idea, a changed behavior, or a product – you must first understand the other person’s challenge. But you also have to know your own intentions.

I once heard Tony Robbins say thinking is the process of asking and answering questions. As we learn to ask more refined questions, our thinking improves. By asking more questions, you train yourself to think more clearly, understand your intention, and get better at asking the right questions.

I’ve never compiled a gift guide before, but with the holidays around the corner and two years of “3 Things I’ve Loved” in the Snafu newsletter, I thought I’d give it a try!

Best Mechanical Pencil: Pentel GraphGear 500 Mechanical Drafting Pencil​

I’ve been using the same mechanical pencil since high school. They used to cost $40, but have substantially decreased in price in recent years. Now that my fiancée has begun borrowing (read: stealing) mine, I find myself ordering more and keeping them stashed around the house.

Best Marker: Paper Mate Flair Pen, 0.7 mm Medium Tip​

I take a lot of physical notes. Even though my Zoom calls are recorded with Fathom, and I keep my To-Dos in Asana, I think better when jotting down ideas on note cards. For that purpose, I love these markers and keep a box on my desk.

Voice Dictation: ​Wispr Flow​

I’ve tested voice-to-text dictation apps since Dragon Dictate came out in the late 1990s. None have worked well enough for daily writing until a friend recommended Wispr Flow. After a week of testing, it’s easily the best voice-to-text app I’ve ever tried.

Best Green Tea: Numi Organic Gunpowder Green Tea​

Sadly, I’ve stopped drinking my beloved pu-erh in favor of green tea. I’m sure I’ll return to it, but the unknown quality of the tea (there are concerns about buying tea from unknown origins in China) combined with a deep dive into my gut health has led me to drink only green tea for my daily caffeine. For that, I love this bulk gunpowder green tea from Numi.

Best Gut Aid: Seed​

Speaking of gut health, I’ve continued to enjoy Seed DS-01, since first starting to use it daily early this year. I’m intrigued by the science behind their product, and have also heard a lot of good reports from friends who’ve tried the supplement.

Best email tool: ​Superhuman​

I don’t love paying for email, but Superhuman is an email app that I can’t live without. It really does save me a lot of time managing my inbox – their promise – and continually reminds me that there are a lot of behavioral cues that can (and probably should) be built into any technology.

Best newsletters (besides Snafu, obviously)

• ​5-Bullet Friday – I’ve never been disappointed by Tim Ferriss’ five recommendations each week. His weekly 5 inspired me to include my “Three Things I’ve Loved” in each Snafu newsletter.
• ​Ryan Holiday’s Reading List – I’ve been on Ryan’s reading list since 2010, and read hundreds of books he’s recommended. He’s never steered me wrong.

Best Gym Tool: Timebirds Timer – I’ve recommended the Timebirds Mini magnetic timer before. I use one anytime I’m working out, and keep another on my desk as a writing timer. They’re nearly indestructible, magnetic, rechargeable and keep you from using your phone as a timer at the gym.

Best multi-tool: Leatherman Wave​

I’ve owned and loved a Leatherman Wave for more than two decades. Now that I own a house, there are a lot of household projects that call for a multi-tool, and I keep my Leatherman handy.

Best knife: Kershaw Leek​

My everyday carry knife is the Kershaw Leek. It is small enough to be unobtrusive, handsome, and sturdy. I own several, and have used them for everything from opening mail to gutting fish.

Best Kitchen Knife: Victorinox Swiss Classic 8-Inch Chef’s Knife​
​This is the kitchen knife everyone should own. Don’t take my word for it. Just search “Victorinox Swiss Classic Chef’s Knife” and you’ll come to see why normal people love it and most chefs have it in their kit.

Best Finishing Salt: Maldon Sea Salt​

Everyone needs Maldon sea salt. It is the default sprinkling salt in fine dining, and I consider it a kitchen staple. Pro tip: buy the 20 oz. tub, and not the 8.5 oz. box.

Best Specialized Salt: Beautiful Briny Sea​

If you want something a bit more unusual, I discovered Beautiful Briny Sea back during the pandemic, and have used their salts regularly since. Based in Atlanta, Georgia, this little company makes a variety of salt blends. Their Sultan Papadopoulos Sea Salt remains my favorite – I use it on air fried chicken, in stir fry, on eggs, and just about anywhere else that occurs to me.

Best Supplements

Fish Oil: Nordic Naturals ProOmega, Lemon Flavor​

When I’m asked my favorite supplement, it’d be a hard choice between fish oil and magnesium. Most people are deficient in both! For fish oil, I like Nordic Naturals as a well-sourced, single-source fish oil that has the Omega-3s we need.

Magnesium: Doctor’s Best High Absorption Magnesium Glycinate Lysinate​

Humans used to get a lot more magnesium through our food, but there isn’t as much in the soil as there was pre-Industrial Revolution, and so we all need more magnesium. While a lot of people recommend magnesium citrate for sleep, I find this magnesium is excellent for the blend of recovery, sleep, and mood stabilization.

Best flashlight: ​Fenix PD36R Pro High Lumen Tactical Flashlight​

Whether I’m running in the dark or trying to find something in the closet, my iPhone light just doesn’t suffice. This tactical flashlight – highly recommended by a variety of reviewers – has been the best flashlight I’ve ever used.

Best Barefoot Shoes: Whitin​

Back in the early 2000s, I was one of those weirdos sporting toe shoes. These days, I prefer my barefoot shoes less ostentatious. The Whitin brand of barefoot shoes looks perfectly ordinary, cost $40, and last longer than many of the more expensive brands. I currently own three pairs.

​
​Best Cold Plunge: The Plunge​

This is the one item on my gift guide that’s more than $100. It is, in fact, in the range of $6000. But cold plunge is as hard to do as it is worth doing. While it is possible to make your own, anything that makes this already difficult task harder means that you’re less likely to do it.

I started the How to Sell Yourself cohort series when, independently and within weeks of each other, two friends asked me for advice and mentorship on self-promotion. I’m not an extraordinary salesman or self-promoter, so I declined “mentorship” but suggested we get on a Zoom call to discuss and share ideas about selling.

That single Zoom call led to more, and eventually to me compiling the curriculum for How to Sell Yourself. Since the beginning of the year, I’ve run two 10-week cohorts through the program.

We’re a few weeks into the current How to Sell Yourself cohort, and last week I changed the curriculum on the fly.

I start the workshop with a segment on “Sales as Service,” drawing on Danny Meyer’s reinvention of restaurant service with Setting the Table, Will Guidara’s recent sensation Unreasonable Hospitality, and my own restaurant experience.

I start with redefining sales as service because it’s an unusual place to start a discussion about selling. Service is the opposite of stereotypical selling and one of the big differentiators in how I approach sales.

The second week is about the attitude of a great salesperson, which I encourage everyone to define for themselves, but for me includes love, presence, and acceptance. Instead, we spent the second week of this cohort discussing habits and behavior change!

Behavior change applies to sales in two ways:

• Our own behavior – if we can develop better habits and change our behavior, we’ll learn faster and thus sell more.
• Others’ behavior – when we understand behavior change, we’re more likely to sell in ways conducive to getting what we want.

Every sale is an effort to change behavior – whether your customer’s or your own. Predominantly, though, I focused on habits and behavior change in order to help my students become better learners. As reluctant salespeople, we learn more quickly and are more likely to keep improving.

I asked cohort members to watch this TEDx talk by Stanford behavior designer BJ Fogg. BJ articulates the two things necessary to adopt a new habit:

• Make the habit tiny
• Celebrate your successes

(Now, if only change were as easy as that sounds…)

Make It Tiny

Common advice about habits is that if you want to run more, leave your running shoes out ahead of time. That makes it easier to start by changing the environment around the desired behavior, but it doesn’t make the success of the habit smaller. What if we called success just stepping outside the door? Or running just the length of the block? What if success was sending one email?

There are always ways to set your objectives smaller. This isn’t a lack of ambition. Doing so makes success easier, and thus easier to repeat.

Celebrate Your Successes

I’ve written previously on the unexpected benefits of celebration. BJ describes a handful of different celebrations like doing a little dance or pumping your fist in the air. Celebration is uncomfortable; we have a cultural bias towards self-critique.

As with dog clicker training, the key is that your celebration has to immediately follow your behavior. You don’t trigger the dopamine of positive reinforcement if you wait a few hours and reward yourself with a nice dessert.

Tiny Habits of a Great Salesperson

I left it to my cohort members to apply these two principles of behavior change to their own work in sales, but here are a few suggestions:

Make It Tiny:

Most reluctant salespeople don’t sell because they make their metric of success too big. While selling rewards persistence, most people define success to mean something so far from where they are that they never get started.

Instead, tiny selling can mean:

• Make one clean ask per week.
• Write one short email.
• Send one “thank-you” note or follow-up after a conversation.

Celebrate:

Traditional salespeople are actually quite good at celebrating. At Zander Media, we have a Slack channel that notifies my team when we sell a ticket to Responsive Conference.

The problem is that most sales teams celebrate only a successful sale or meeting their quotas – not the small steps along the way.

Instead, celebrate the little things:

• Physically celebrate (smile, exhale, fist pump) after every phone call.
• Pat yourself on the back after a single difficult client conversation.
• Say out loud, “That was a good ask!” every time you ask for anything.

One of my students, an HR executive-turned-coach, shared that she’s begun celebrating herself after meetings where her only focus is on helping the person she’s with – even if they don’t turn out to be a good fit for her practice. She found herself enjoying meetings, as a result.

As an added benefit to the practice of celebrating, the group now sweetly celebrates others throughout our Zoom with fist pumps and rocketship emojis.

Behavior Change – and Sales

Across the 100 or so books I’ve read about sales and persuasion, there isn’t much about about habits and behavior change. That’s an oversight.

I’m coming to believe that anytime anyone is teaching anything, they ought to start with a segment or two about learning. When we can help people become better learners, they’ll learn more of what they’re there to practice.

This last week was the first time I’ve applied two principles of behavior change to the topic of sales, and this article just scratches the surface. But, at a minimum, anytime we make our habits smaller and celebrate successes, we’re more likely to succeed.

A few months ago, I started collecting Snafu articles into categories, and was surprised by how many taught the tactics of doing something very specific: fasting, buying a used car, raising a puppy, or buying a house.

None of these experiments was a sure thing. In fact, nearly all of them began with the same phrase: “This might work.”

That phrase is the title of my new book. It’s an invitation.

We’re living in a dichotomous era – of unprecedented change and uncertainty. Of leaders promising guaranteed outcomes and “ten steps to anything.”

This Might Work is a record of experiments – of trying things without knowing how they’ll turn out, and what I’ve learned along the way.

Each essay began as an attempt to figure something out: how to tell a great story, how to curate a conference, how to change someone you love.

The through line isn’t expertise – it’s curiosity.

If there’s one thing I’ve learned from them, it’s that progress begins when we stop waiting for certainty. This Might Work is my attempt to compile those lessons in one place – and to invite you to try your own. Because the only way to know if something will work is to start.

Download “This Might Work” here for free:

https://download.filekitcdn.com/d/c7gqh8rbyNUQGR6tynkbna/nYxsYdXjpap6yAD8osSsPb

I went on a fly fishing trip last weekend in Montana with several work colleagues.

When it comes to fishing, I’m a bit out of my element. A trail run through the mountains, a mountain to climb, snowshoeing, or a ski resort – these are all outdoor adventures I know well. But fishing is entirely new to me. Fortunately, two of our party were avid fly fishermen and eager to teach me.

I ended up catching one fish (it was two feet long, I promise), but that’s scarcely relevant. I do understand why people fall in love with fishing. It’s quiet, peaceful, meditative – and a really deep rabbit hole.

Where in the river the fish are. The time of day and year; so many factors determine whether the fish are biting. How you throw the line matters, as well as where it is in the water. Whether your bait is underwater or floats on the surface. I could write an article on “A Beginner’s Guide to Fly fishing” just from the single day I spent on the river.

On the first day in Montana we took a boat down the Madison River and my friends gave me pointers. It helped, of course, that our guide was endlessly patient, rowed our boat, and replaced my flies anytime I got my line tangled in the trees! (As with learning anything, it helps to have someone else take care of the more tedious parts.)

Sitting on a boat on the river, casting and recasting my line – while trying not to get distracted by the bald eagle overhead and the snow-capped mountains in the background – was not a bad way to spend the day.

Even Great Salespeople

Everyone in our party was in sales. Whether an entrepreneur like me who sells to clients, someone managing a startup’s sales team, or as a relationship-driven salesman for an enterprise company, all of us are in sales.

As we were waiting to board our plane, I got to chatting about the Snafu Conference. One of our party said that the best salespeople don’t think of themselves as salespeople. He went on: “We are relationship builders, community builders. What we do is provide value. But we don’t consider ourselves salesmen.”

The best salespeople don’t call themselves salespeople because the word doesn’t describe the way they operate. It turns out that even salesmen don’t care much for salesmen!

Why We Avoid The Label “Salesman”

As I discussed in The Taboo of Sales, just the term “selling” feels manipulative or self-serving. We associate sales with greed, pressure, and rejection.

No one wants to be perceived as a persistent telemarketer among their friends!

There’s cultural shame around sales, even among people who are good at building a network and at persuasion. And understandably so: humans are hardwired to avoid rejection because rejection from the tribe meant death to prehistoric humans. As a species, we crave the approval and support of our peers.

But this results in the ironic twist that while everyone is selling something – ideas, trust, reputation or their love of fly fishing – even the best salespeople resist the identity.

Great Sales Isn’t About Force

As my friend pointed out at the airport, great salespeople bring value to other people. My friends who brought me fly fishing shared with me their love of the sport. I went to Montana! I saw a bald eagle! I caught a fish!

Those friends invited me to join them, encouraged me to try. They provided enough support that I learned something new.

They weren’t trying to win. They didn’t waste breath on why I should enjoy fishing. They just gave me an experience that would – they hoped – show me why they love it.

Great sales is voluntary. It respects the other person’s agency. Had my friends kept saying “See! See! This is why fishing is great!” or had they used pressure, I would have walked away.

Great sales replaces force with service and connection.

What Great Sales Looks Like

My friend didn’t have time to elaborate on what great salespeople do because we were boarding the plane. But I thought about it a lot on the plane ride home. Here are a few of my ideas.

Great Salespeople Are Empathetic

Empathy means the ability to understand the feelings of another. I always think it’s useful to define empathy in contrast to sympathy, which means to feel pity or sorrow for someone else’s misfortune.

Great salespeople pay enough attention that they can relate to or understand what another person is feeling.

Great Salespeople Provide Value

The trip to Montana was orchestrated by my friend Jesse. He planned out where we would fish, where we would stay, and even some local live music on our last night in town.

Providing value is a much-overused concept – especially when you listen to Internet marketers. Everyone’s advice is “provide more value.”

What does that mean, especially when it comes to selling?

I think providing value means trying to help people. We never get to control if we are actually being helpful, but the effort of trying is often enough.

Great Salespeople Connect

I recently got engaged, and two men in our party have been married for years. Throughout the trip, they shared specifics from their marriages that related to my own inexperience.

There’s a delicate balance between offering advice without being condescending. They did an excellent job and only offered feedback when I asked.

When we walked by a jewelry store, and I mentioned the challenges of sourcing an engagement ring, they shared their experiences. When I mentioned that my partner would like a gift from the trip, they offered sage advice on what to bring home.

Great salespeople connect with where someone else is.

Great Salespeople Listen

Jesse spoke at Responsive Conference 2025, and is excited for the Snafu Conference in 2026. While we waited for the rest of our party one morning, he asked questions and listened closely to my thoughts about who the Snafu Conference is for, why I’ve gone to the trouble to start an entirely new conference, and what I’m hoping to accomplish as a result.

At the end of the conversation, we had several new ideas for Snafu and how the conference might benefit his community, which could benefit us both.

He listened carefully and thoughtfully to what I had to say. Great salespeople listen before anything else.

Great Salespeople Have Good Timing

One of our party had taken the entire week in Montana, and I asked him how that influenced his day job and client relationships. He shared that closing clients on a project came down to timing, and that he’s learned over twenty years in the industry that timing is everything.

In a two-minute discussion, he outlined how clients will always take the time they need to make a purchasing decision. They can’t be rushed. I’ve experienced the same with selling tickets to Responsive Conference. No matter what I do, 50% of attendees always want to purchase in the last few weeks.

In taking time off, my friend wasn’t sacrificing relationships with those clients. Instead, he was giving his clients the space they needed to make their purchasing decision.

Great salespeople have good timing. They know when to follow up. They also know when to give space and let someone take time to make a final decision.

Great Salespeople Say No

One member of our party does a lot of paid sponsorship, and sponsored Responsive Conference 2024. They didn’t sponsor Responsive Conference 2025 because they didn’t find the return on investment sufficient. In short, they said “No” to sponsoring the conference for a second year.

Great salespeople know when to say no – to opportunities and to clients who aren’t a good fit. They can be relentless chasing the right opportunities, but only by first saying no to things that aren’t good for their business.

Great Salespeople Help People

There was a pool table at our Airbnb, and while I’ve played pool before, I’m a long way from being a pool shark. After dinner, the four of us teamed up and played five games of pool. (Of course, my team won.)

My partner owns a pool table, and spent much of the games giving me pointers. He saw that I was interested and offered to help.

Great salespeople help people do more of what they already want to do!

You’re Not Alone In Avoiding The Label

I had a great time in Montana, and am tempted to make a very regular habit of fly fishing in the future. But more than the joys of spending several days in the mountains, or even in learning something new that I’d previously known nothing about, I learned something new about selling.

If you don’t think of yourself as a salesperson, you’re in good company! Most of the best salespeople don’t, either. They just do things that help people, and sometimes collect money in return.

The title doesn’t matter; the behavior does.

Whenever I curate a conference, I think about how people are feeling when they arrive and how they are feeling when they walk away.

When it came to Responsive Conference 2025, most people – regardless of political ideology – were coming in with some degree of apprehension. Whether anxious about politics, AI, or the accelerating rate of change in the world, most people I talked to throughout 2025 were nervous. The next question was to decide how I wanted them to feel at the end.

My word was “excited.” I wanted them to feel excited for their ability to contribute. Hopeful. Ready to roll up their sleeves. My work was to curate an experience that helped people move from apprehensive to excited through the course of the 2-day conference.

I wrote a few weeks ago about my concerns that people were having too good an experience, and the accompanying need to let go of the outcome. The outcome that I curated – almost without knowing it – revolved around purpose.

Simone Stolzoff debuted a new talk based on his forthcoming book How to Not Know. Many attendees came up to me afterwards and talked about how much his talk on uncertainty shaped their experience of the conference. I loved the stories he told about choreographer Twyla Tharp, whose book The Creative Habit is a must-read.

On Day 1, I facilitated A Funder’s Fishbowl with three venture capitalists about investing in startups amidst uncertainty. Perhaps the highest praise I received about that session was each of the VCs approaching me afterwards to share that they intend to use the fishbowl format in the future.

My former boss Vivienne Ming opened on Day 2 with a talk about How to Robot-Proof Your Kids – about how technology can make us better humans (and not replace us). As always happens, Vivienne’s talk ended with a long line of people who want to ask her questions and share ideas. Vivienne’s got “riz.“

I got on stage alongside Suzy Welch, author of Becoming You, and entrepreneur Shelby Wolpa, for a session on values and purpose in an age of AI. Suzy said that most people don’t even know what their values are. As a professor of management practice at NYU Stern School of Business who has studied values for decades, Suzy pointed out that values determine much of our lives, but aren’t taught, or well understood.

To close the conference, Eldra Jackson III brought the audience to tears with a talk about the importance of maintaining our humanity amidst constant change. Eldra was incarcerated for two decades and has dedicated his life to helping people inside the penitentiary system get and stay out. He brought gravitas and provided a perfect end to the show.

As we’ve collected feedback from attendees over the month since, conducted our internal After-Action Review, and considered what we want to do differently at Responsive Conference 2026, I’ve had no regrets. That was new to me.

Ten years ago, producing Responsive Conference was about logistics, ambition, and survival. This year’s conference was fundamentally different. I was calmer and well-resourced. The shift I experienced mirrors my attendees’ experience: moving from apprehension to excitement.

I wasn’t just running a conference. This year, I knew why it existed. That clarity wasn’t only professional – it came from the alignment in my personal life (I’m newly engaged. I bought a house. I’m happier than I’ve ever been.) And when purpose aligns across personal and professional work, execution is much easier. I’ve gone through the same transformation – from apprehension to clarity of purpose.

Attendees arrived at Responsive Conference anxious about politics, AI, and the pace of change. Through talks, workshops, un-conferences, and plenty of time to reflect (and play with animals), they rediscovered what they care about and what they can control. The conference itself was a live demonstration of moving from uncertainty to purpose.

The experience of Responsive Conference – or any great event – isn’t just about content. It’s about remembering why we do what we do, and how to do it better. Without purpose, everything is difficult. With purpose, everything gets easier. The antidote to chaos is purpose.

My mother has been a practicing artist for fifty years. She makes mezzotints, which are something of a lost art. Her curriculum vitae is impressive and her work has been presented in some of the most famous museums in the world.

But my mother lacks salesmanship: the ability to promote herself, share her story, and get people to buy her work.

She is a reluctant salesperson – and she isn’t alone. Most of us have some fear of self-promotion.

We fear rejection, or what people will say about us when we promote our work. We don’t want to be seen as selfish or self-serving.

Part of this is cultural. We’re taught to value generosity and service. Most of us are not raised with an emphasis on self-advocacy. We associate selling with the threat to belonging within our community, to being authentically known, even to being loved.

The cultural taboo

There are only a few cultural taboos – of which sex, death, and money are the most significant. Our boundaries around taboo topics have shifted and the Overton window continues to expand. Once-private, shame-filled topics are now more openly discussed, but sales still carries a charge.

The taboo of sales exists for good reason. From LinkedIn cold pitches to multi-level marketing schemes, there are lots of examples of sales gone wrong. Given the choice, most of us would rather discuss death over dinner than ask someone to buy our work.

The paradox

The irony is that the taboo of sales blinds us to how deeply human persuasion really is. Even though we stigmatize selling, everyone does it daily.

Daniel Pink argues in To Sell Is Human that most people aren’t in direct sales. Instead, Pink describes “non-sales selling” as any activity that requires persuasion and influence. When you convince your team to try a new process, or ask your partner where to go for dinner, you’re selling.

We pretend selling is something only other people do – even while we are all constantly selling.

The cost of a taboo

When we avoid selling, we also avoid clarity. We don’t acknowledge what we want and don’t ask for it.

Meanwhile, a small subset of people do the opposite. These are the salespeople who ask – obnoxiously, incessantly, and without apology.

When we avoid sales, we avoid the clean embodiment of an inherently human behavior.

Redefining the act

The solution isn’t to sell harder but to redefine what selling means. Done well, selling isn’t about convincing. It’s about being clear what’s true for you and inviting others to see that, too.

As my mother begins to tell her story — to share why she fell in love with mezzotints and what they reveal about the world — people won’t just buy her art. They’ll buy into her love for it, as well.
​
Sales isn’t something we avoid by pretending it doesn’t exist. When we refuse to speak up, we’re just leaving room for someone else to fill the silence – someone louder, less careful, and perhaps even less honest.

Homework

The sales taboo dissolves the moment we treat sales as service. Sales is a way of being honest about what we want to give and what we need in return.

Make one offer this week. Not a pitch. Not a plea. Just one clean, explicit offer for something you believe in. Say what it is. Name your price. And then stop talking.

The night before Day 2 of Responsive Conference, I spent an hour agonizing over how enthusiastic everyone was. I was worried the conference hadn’t struck the right balance of existential dread and optimism for the future – given that I feel a fair bit of existential dread myself!

But after stressing over my attendees’ experience for an hour, I looked back at the agenda I’d curated for Day 2 – starting with my old boss Vivienne Ming and ending with Eldra Jackson III – and realized that the program I’d created would provide attendees the experience I wanted them to have: real, raw, but not pessimistic.

One of the things I like most about live events – whether as an MC, speaker, or athlete – is that once the show begins, we have to let go of the outcome. As much as we’ve practiced our lines, rehearsed our talks, or reviewed our notes, once the show begins, there’s nothing to do but continue.

One of my early teachers, Feldenkrais-disciple Anat Baniel, described this idea as “flexible goals.” In the subsequent eight years I spent working with autistic kids, maintaining flexible goals was the only path forward! A myopic focus on hypothetical outcomes, like “I want my child to be neurotypical,” would impede progress.

Maintaining flexible goals, or letting go of the outcome, doesn’t mean that you don’t have an outcome in mind. When I am trying to sell tickets to Responsive Conference or a client on behalf of Zander Media, I want them to buy! But that’s only one of a handful of goals I hold simultaneously – including to be of service. Maybe there is someone I can introduce, a book I’ve read, or something else that would make a difference in their lives.

Let go of the outcome

Anytime I find myself feeling urgency or anxiety, I remind myself “Let go of the outcome.”

In the case of my attendees’ experience of Responsive Conference Day 2, the solution was simple. I’d already curated an excellent experience that didn’t shy away from difficult topics. From our opening and closing keynotes to topics ranging from AI to politics to the Safari animals who joined us at lunch, the experience of Day 2 provided my attendees with a rich and varied experience. I’d already done the hundreds of hours of preparation necessary. All I had to do was let them enjoy the experience.

Letting go of the outcome is a mental act. It is more about coming up with a half dozen ways in which other outcomes – in addition to your goal – could be just as good.

In the case of Responsive Conference 2025, if my attendees have too good an experience, is that a bad thing? So, they feel optimistic leaving the conference – and only afterwards are confronted by the realities of our rapidly changing world. There’s nothing wrong with providing a bit of escapism.

But if I’m trying to sell something specific or my mortgage depends on a certain level of earnings, it can be difficult to stay flexible. I have to deliberately make a list of alternative outcomes:

• If someone doesn’t buy from me, they’re looking out for their best interests.
• Maybe I haven’t done enough preparation? Maybe I’m not telling a compelling story?
• Or perhaps what I’m selling doesn’t fill a pre-existing need.

In the months leading up to Responsive Conference 2025, one reminder I had to give myself was to “Be less entitled.” As salespeople, we are not entitled to someone else’s attention – not to mention their money! If I was asking for help from colleagues to promote the conference, it was my responsibility to make it easy for them to promote. And when someone bought a ticket, take a moment to celebrate that small victory – instead of immediately calculating how much farther I still had to go.

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Homework

What are you trying to accomplish? List out 5 alternatives, beyond your primary objective.

Even with your primary objective in mind, can you make one of these secondary goals as big or bigger than the first? Can you want more for the person you’re talking to than for yourself?

It helps to write out then goals, and then write an explanation for each.

Last month, I bought a house.

Buying a house is more complicated than nearly anything else I’ve done – besides, perhaps, running a business.

Over the last few weeks, I’ve highlighted some of my most popular articles from the last two years. In doing so, I realized that many of my personal favorites are those I reference repeatedly; they’re evergreen.

But over the course of the eight months leading up to the purchase, I learned a lot. So today I’m sharing the article I wish I’d been able to read when I started.

This is not an argument for or against buying a house. If you want to be talked out of buying a house, read Ramit Sethi. If you want to hear reasons to buy a house, ask a Boomer.

Instead, this is what I wish I’d known about house buying when we got started back in February.

I’ve seen a lot of backward industries:

• I’ve worked in large non-profit arts organizations.
• I’ve worked within family-owned SMBs.
• I had a chef throw a plate at my head in a restaurant.
• I’ve worked in fast-paced, drama-filled tech companies.
• I’ve obtained a myriad of impossible-to-get permits at Robin’s Cafe. San Francisco doesn’t make brick-and-mortar permits easy.

So believe me when I say that I’ve never met as backward, corrupt, and intentionally complicated an industry as real estate. First, let’s define some terms.

The people you’ll meet:

• Buyer – That’s you!
• Seller – The current owner of a property.
• Agent – Agents work for either the seller or the buyer – but actually they work for themselves. Their goal is to get you to buy or sell a house, and serve as a liaison between you (the buyer), the seller’s agent, and the seller. Agents aren’t financially motivated to help you get the best deal because their commission is a percentage of the price of your house. A small price reduction barely affects their fee, even though it matters a lot to you. You are not legally required to have an agent in most states.
• Mortgage broker – These folks help find your mortgage – assuming you aren’t paying all cash. They’re very salesy and eventually sell your mortgage to someone else. The benefit is that they’re available all hours and can get you information very quickly.

The companies you’ll work with:

• Real estate brokerage – Agents work within brokerages, and split income, usually 50/50, with an agent. Brokerages also list houses for sale. There are small, boutique brokerages and also national chains like Compass and Coldwell Banker.
• Mortgage company – The company that ultimately holds your mortgage. If you get a mortgage with a specific bank or credit union, they’re not likely to sell your mortgage to a third party.
• Title company – The company that ensures successful transfer of ownership between the buyer and seller.

The terms you’ll hear:

• Buyer’s agent vs. listing agent – Typically, the Buyer and Seller each have an agent, and agents discourage you from communicating directly with the other party because it keeps them as the middleman.
• Pre-approval vs. pre-qualification – These are terms you’ll hear from your mortgage broker, and represent whether you are qualified for a mortgage. Pre-qual is a soft estimate of how much you’ll be able to borrow. Pre-approval is documented and stronger.
• Foreclosure – When a bank is selling the property, instead of a person. Not for the faint of heart.
• In contract – An agreement between buyer and seller that the buyer will purchase the real estate, assuming specific conditions are met
• Earnest money – Money you put down (usually 3%) to show proof that you are serious about buying a specific property
• Contingencies – The requirements that need to be met before you buy.

Our adventure started in February of 2025. My then-girlfriend and I were planning on renting, when – seemingly out of the blue – she texted me a house for sale. A house we saw that weekend – a dilapidated mansion with spectacular views – became the focus for my learning for the next five months.

The mansion had a lot going for it – great views, extremely quiet, an abundance of indoor and outdoor space, pool, garden, easy rental opportunities, and more.

It was also a completely ridiculous project. It had been a party house, built in the 1970s and then illegally rebuilt, which, we later learned, triggered county requirements like seismic retrofitting and a sprinkler system. There were three levels of decks with incredible views, but they had been poorly built and were on the verge of collapsing. We discovered two nests of bees in the walls – so active in the spring that the buzzing could be heard inside the house!

After five months of research and seven offers on the property, we walked away. More than the repair and reconstruction required, we walked away because of the county requirements. The onus on a new owner to make up for the previous decades of illegal construction was too high.

We bought another house in the same city, which also has views, a pool, and rental opportunities. Our new house isn’t a mansion, and needs only modest repairs – and we’re very happy here. But I learned more about real estate during this months-long sprint than I ever thought possible.

These are some of my biggest takeaways.

Mindset

1. Don’t fall in love until after you buy

It’s really helpful if you don’t fall in love with a single property until after you own it. This is the single biggest purchase most people will ever make, and the decision is usually made emotionally. Instead, try not to get too excited until after you’ve purchased. Obviously, you don’t want regret. Make sure you like the house you’re about to buy! But too often people fall in love and then get into a bidding war out of the desire to win a deal.

2. An entrepreneur’s mindset

The thing that helped me the most through my real estate learning journey was what I’ll call an entrepreneur’s mindset.

We wanted a home, yes. But I also didn’t want to lose money on a project – if anything, I wanted to make money.

Know how to protect your downside and plan for contingencies in case things go wrong.

If your circumstances change and you can no longer afford your mortgage, what are you going to do? What are the ways this property could cash flow, even if you weren’t living in it? Are there cosmetic repairs you could make that would improve the value of your home?

3. They treat you like the product, but actually you have all the power

I’m fascinated by how different industries talk about their customers. At Robin’s Cafe, we had diners. At Zander Media, we have clients. At Responsive Conference, we have attendees. Facebook, OpenAI and most software companies have “users” – which is the same term that drug dealers use to describe their customers.

In real estate, agents call real estate “inventory” and us, the clients, are called “buyers.”

There’s a sense as you begin to get serious about a property that you are a cog in the machine. Agents will push you to bid on a specific property. Mortgage brokers request that you sign before you’re ready.

The most important thing to remember is that you hold all the power. As the buyer, you can walk away at any time. (Though if you wait too long and contingencies are past, you stand the risk of losing your earnest money.)

You always have the power to walk away.

Research

4. Know what you want

We had lots of criteria starting out:

• We wanted a house that was not too far from San Francisco
• That was safe
• And that we could afford
• We wanted within walking distance from an interesting town
• Ideally we wanted open space nearby
• The house should have rental opportunities
• And best case scenario for it to have a pool
• Weirdly, we both had a thing for double front doors just because that felt fancy

However big or small, list out the criteria you want in a house. You’ll have to settle on some of them, but the clearer you can be on what you want, the more likely you are to get it.

5. See lots of houses

The best way to learn about houses is to see lots of houses. Agents are great for this – but don’t commit to working with one agent for a long time, or maybe ever. You can call the listing agent – the person who is showing the house – and ask to see it. I prefer not going to Open Houses because there are other people and a (false) sense of urgency. Even driving by houses for sale is useful to get a sense of regions and neighborhoods

6. Do your research

In this industry more than anything else I’ve ever experienced, it’s essential to do the research. The more thoroughly you get to know a specific region, neighborhood, and even a specific street, before you decide which house to buy, the better off you’ll be. Use ChatGPT to do Deep Research on a variety of topics related to things you see in each house you visit. Ask real estate agents a lot of questions. Talk to people on the street.

7. Get lots of (free) quotes

I’m surprised that home buyers don’t visit homes they are seriously considering with an entourage of contractors, plumbers and electricians.

There are two different types of quotes – those you pay for and those you don’t. If you call a local HVAC company and request a pre-sale quote, they’ll charge you. But, instead, if you say that you are planning to buy this house and just want to plan for your future, they’ll likely come to the house, look around, and send you an estimate of costs.

A lot of the difference depends on whether they write up a multi-page summary of their findings or just a single page with a price. Either one works fine when it comes to negotiating down the price of the house.

But even if you did have to pay for every technician at every house you’re considering, those few hundred dollars would save you tens of thousands in having avoided bad decisions.

8. Talk to the city or county

One of the most under-leveraged aspects of real estate is talking to your local jurisdiction – the city or county within which your property falls. Even just the question “What’s this city/county like to work with?” which any agent or contractor should be able to answer, will help inform your decision about the amount of work you’re willing to tackle and the amount of bureaucracy you are willing to wade through.

The county where the mansion sits is quite a bit easier to work with than the city within which we now reside. But since our new house requires so much less renovation, we decided that trade-off was worth it.

Moreover, the city or county will have some amount of records about the property in their files and some people within the city/county may even be familiar with the property itself.

Talk to your local jurisdiction before you buy!

9. Read the fine print

I’m continually shocked that most people don’t read every bit of fine print in every document. The very first real estate agent who showed us a house requested that I sign an exclusive agreement with him even in order for him to show us the property. Had I not read the contract in advance, we would have been stuck with him without recourse.

The title company who transferred ownership of our new house from the previous owner to us was surprised that I requested the 250 pages of legal documentation in advance of the day of signing. And that we protested that they had only given us one hour to review the documents in person.

Is reading fine print and intentionally obscure legal language a difficult question? Yes, of course it is. And as you go into a hundred thousand dollar project, it is also a necessity.

Never, ever sign without reading the fine print.

Cautions

10. Everyone has something to teach you

Real estate, especially when you’re just starting out, is a matter of talking to a thousand people. And everybody has something to teach you.

In the last seven months, I’ve been on the roof of ten properties with at least a dozen different roofers. Every time I go up, I learn something new about roofs from a casual comment the roofer makes.

Talking to an abundance of people, even if you only learn one new thing from each, will enable you to make better decisions going forward.

11. A false sense of urgency

As with most forms of unethical selling, everyone will try to create for you a false sense of urgency. Agents will tell you to bid now. Mortgage bankers will tell you you have to sign today, or else deadlines won’t be met.

And it is true, especially in a competitive real estate market where time matters. But it rarely matters as much as the people you’re working with will have you believe.

Don’t get swept up in the adrenaline of the rush and lose sight that you are considering among the biggest purchases of your life.

12. Agents are out to get you

There are a lot of good people in the trades. But it has been my experience (and is widely agreed) that people who make their living in real estate – agents, brokers, mortgage brokers, etc. – are out to get you.

But of all of these, real estate agents are my least favorite.

I’m reminded of the Charlie Munger quote, “Show me the incentive and I’ll show you the outcome.” The money circulating around real estate is large. Most of us don’t otherwise handle transactions in the 100s of thousands of dollars. And when someone is compensated purely on a percentage basis of the cost of the home, their incentives are – at best – only loosely aligned with yours.

It’s hard, but not impossible, to buy houses in the United States without an agent. And how to choose an agent – or avoid getting one – is a longer topic than this article will allow. But know, going in, that “your agent” is not on your team.

13. Read How to Buy a Used Car (and then do that for houses)

Last week, I revisited my article, “How to Buy a Used Car.” There are a lot of similarities between buying a used car and buying a house.

14. Read Abundance (and know that’s not the world we live in)

Ezra Klein’s Abundance is a hopeful picture of what the world might look like if we were to build in the United States. And it isn’t the world we live in.

Instead we live in a world where the accelerated rate of change exists in stark contrast to the slow tedium of hundreds of years of bureaucratic process. Even as technology enables us to move and think faster than ever before in human history, the lethargy of governmental bureaucracy stagnates growth.

That’s how it is right now – unfortunately. Plan accordingly.

Conclusion

I’m thrilled with our new home, and the sensation of being a first-time home buyer. But perhaps even more importantly, I’m no longer overwhelmed by an industry that previously felt impenetrable, overwhelming, and ridiculously complex. Hopefully this article is a first step for you to achieve the same.

Last week’s Responsive Conference was the best event I’ve produced. Attendees have been raving about the experience, my team bonded in new ways, and I walked away without the post-conference crash that too often accompanies producing a big event.

One of the things we did especially well this year was to incorporate alternative event formats into the conference format. Specifically, there are three atypical formats that I think every event organizer should incorporate.

Fishbowl

A fishbowl is a panel with 1-3 additional seats on stage. Your audience is encouraged to sit in that seat and join the speakers in conversation.

Why this works:

Fishbowls challenge the audience to stay engaged. Every time there’s a new participant in the hot seat, the audience – even if they weren’t fully engaged before – has the opportunity to reengage with the conversation.

This format also adds variety for the speakers. Most panels fail because panelists talk to each other about pre-planned topics or things they know too well. Regularly adding new people to the conversation changes the dynamic with each new attendee.

Best-case scenarios:

A fishbowl can work with four seats on stage, where one seat is empty for participants. At its best, though, there are five or six seats available, of which two are available to participants or the facilitators.

This session can work in a fixed seating format, but it works even better when the audience is literally sitting around the speakers, while the speakers are facing each other in the middle. A literal fishbowl shape added to the intimacy of the experience for everyone involved.

Considerations:

You need a strong facilitator – The first consideration is that a strong facilitator has to set the context for this format and keep people moving in and out of the hot seat (or seats). This facilitator needs to describe how a fishbowl works and encourage attendees to join in. The facilitator can occupy one of the seats on stage throughout or facilitate from the side.

The audience needs to be engaged – a fishbowl only works if attendees participate. This requires the facilitator to encourage attendees to jump in. Some gentle facilitation may be required to make this happen.

The people on stage need to be engaged – this isn’t an issue for most speakers, but participant speakers should know that this won’t be a typical panel. Most speakers don’t want to phone in the experience – they want to enjoy the experience! But a fishbowl is not a panel, and some speakers may be hesitant.

Interview-in-the-Round

An interview-in-the-round is a session where each speaker interviews the next speaker. It works like this:

• Speaker 1 interviews Speaker 2
• Speaker 2 interviews Speaker 3
• Speaker 3 interviews Speaker 4
• Speaker 4 interviews Speaker 1

​Here’s an example from Responsive Conference 2019.

Why this works:

Attendees want to hear from the speakers. In this format, they get 15 minutes uninterrupted from each speaker (assuming a 60-minute session), with another 15 minutes where that speaker conducts an interview. Assuming good speakers, it is always a good experience for attendees.

Best case scenario:

Speakers have an intimate experience on stage, which then translates into the attendees’ experience of the session. Through intimate one-on-one interviews, they are able to go places that they wouldn’t in a larger group.

Considerations:

Unpredictable outcome – The “outcome” from an interview-in-the-round is unpredictable. There isn’t someone in charge of summarizing the experience for attendees, so event organizers might feel uncomfortable with the experience.

Speaker egos – The problem with this format comes down to speakers’ egos. It isn’t a common format compared to panels, and as a result, speakers feel like they won’t be able to get on stage as much as they expect to. This isn’t factual – in an interview-in-the-round, speakers generally get more stage time than in a typical 4-person panel. But from an appearance perspective, they often feel like they’ll get less limelight.

I’ve never seen attendees dislike this format, but speakers may have to be persuaded.

Unconferences

I define an unconference as any event where the attendees set the agenda. I’ve written a full article on how to run an unconference, so start there.

Why this works:

Unconferences work because there is always more collective intelligence in a group of attendees than in a single person on stage. An unconference makes use of that collective knowledge by allowing the attendees to determine the agenda.

Best case scenario:

The best-case scenario for an unconference is that it channels the focus of an entire group, and everyone walks away reenergized and with several new ideas.

Considerations:

The problem with an unconference by definition is that speakers and facilitators aren’t the highlight. This makes selling tickets against name-brand speakers and brands nearly impossible. An unconference can be a great experience for attendees, but it is much harder to monetize.

Gatherings and events are a competitive advantage in business, especially in an age of AI. Our loneliness epidemic and the enduring popularity of books like The Art of Gathering both demonstrate that humans want to gather in new, interesting, and immersive ways.

Any kind of gathering is better than not, but panels and happy hours need not be the only way we do so, and these three alternative formats provide some welcome variation.

The future is unpredictable

In 2015, the authors of Responsive.org wrote that “the future is becoming increasingly difficult to predict.” Today, with global instability, political partisanship, and a more rapid rate of change than ever before in human history, those words feel prescient.

The tension between organizations optimized for predictability and the unpredictable world we live in has reached a breaking point. Only organizations that adapt to this ever-changing world will survive.

We structure organizations the same way we did in decades and centuries past – built for a time when predictability mattered more than speed of execution.

I’ve had anything but a conventional career path. Across more than two dozen different industries – from circus acrobat to self-taught restaurateur – I’ve witnessed the same bureaucratic practices; the same good people stuck in outdated systems.

And nowhere is that unpredictability more obvious than in live events.

A few small fires

​Responsive Conference 2025 is next week. There have been a few small fires: a team member is in the hospital, a keynote speaker asking to change their call time, and nametags scheduled to arrive a week late.

A friend asked me recently if I was going to propose to my girlfriend on stage at the conference. My answer was – quite obviously – no. And not just because she wouldn’t want that kind of public attention.

Events are an act of service. Great events exist for their attendees, speakers – and only then for the organizing team. To take the spotlight with an engagement proposal defeats the purpose of producing an event. It takes the focus off of them and their experience. When the organizer takes up too much space, they undermine the service the event provides to the community.

The utility of community

On September 16th, the day before Responsive, my friend Jenny is producing the Conference for Conferences, a 1-day event about how to run more immersive and experiential events.

Then, Responsive Conference, which I often describe as a three-ring circus that we always design as an experiment in the very principles we gather to discuss.

Within the curation of Responsive Conference, too, there are sessions that address the intersection of community, change, and AI.

Suzy Welch, PhD is the creator of Becoming You, a popular NYU Stern course and book that helps individuals reinvent their careers. I’ll be interviewing her, alongside startup operator-turned-consultant Shelby Wolpa, about career reinvention.

Jesse Freese is the founder of a 2000-person community called StartupExperts which brings together HR, Operations, and Finance startup leaders. He will be sitting down with Marcus Sawyerr, who runs EQ, a network of executives, to discuss the role of community and how successful leaders leverage collective intelligence to keep pace with change.

Events are a competitive advantage

Running events is a logistical nightmare. From a team member in the hospital to last-minute schedule changes, there is always another fire! The work of producing events – selling tickets, organizing people, managing ambiguity – is largely thankless work. As with any good performance, you only notice when things go poorly.

But the community, trust, and a shared understanding that events create are priceless. In 2016, my producer and a speaker met and got married. I’ve been told “That moment at Responsive Conference changed my life…” dozens of times. Events aren’t just about gathering people — they’re about creating containers where community, trust, and possibility emerge. They create reference points people carry forward.

And running events creates leverage for the organizer. You become the community builder – the person people look to. They build trust much more quickly than singular conversations can.

The thankless work isn’t, in fact, thankless after all. In an age where AI makes everything faster, it’s messy, unpredictable human experiences that give us an edge.

With Responsive Conference only 25 days away, I’ve been thinking back to February 2016, when I ran my very first unconference. That experiment paved the way for the first annual Responsive Conference later that year, and the format has been woven into every Responsive event since.

An unconference flips the traditional model of a conference on its head: instead of a pre-set agenda, the participants themselves decide what gets discussed. It is deceptively simple, but it’s also one of the most powerful ways I know to spark connection and create unexpected breakthroughs.

I’ll be teaching a workshop on “How to Run an Unconference” at the ​Conference for Conferences​ the day before Responsive, and of course, we’ll be running unconferences throughout both days of Responsive Conference 2025.

Don’t have a ticket yet?
​There’s still time!​

What is an unconference

An unconference is any event where the agenda is set by those who attend. The rules of an unconference are simple:

1. Whoever shows up are the right people
2. Whatever happens is fine
3. Whenever it starts is the right time
4. It is over when it’s over

In less flowery language this just means ditch expectation and don’t try to control the experience.

Flow of the Day

After attendees arrive, an empty conference agenda is posted on the wall with time slots and a variety of meeting spaces. Leaders share a theme or question they would like to discuss and post it in a time slot. If you post a topic, it is your responsibility to turn up to that session and introduce your topic or question. If you are not hosting a session, you are free to attend whichever of the sessions you are interested in.

Attendees are encouraged to adopt any of a number of roles:

Leader — who is facilitating each breakout
​Scribe — is someone responsible for taking notes for each group
​Nomads — give attendees permission to move between break-outs

The Law of Two Feet

Everyone at an unconference is encouraged to practice the law of two feet. The law of two feet says that if you become uninterested at any point, you are encouraged to leave and join another session. In an unconference you are also invited to take breaks at any time, with the idea that it is sometimes in the breaks that the ‘A-ha’ moments arrive.

Roles & Responsibilities

There are three main components necessary to a successful event — recruiting, production, and a strong facilitator.

A Word on Recruiting

In my experience, it is helpful to have an extended network to help with recruiting, not just a single person. All other logistics can be handled by a single person.

Production

Among the organizers, someone has to be in charge of logistics, including:

• Venue sourcing and ongoing communication
• Setting the date
• Attendee arrival emails
• Day-of logistics
• Recruiting

Facilitation

A strong facilitator can make or break any event, but especially one with as fluid an agenda as an unconference. On the day of the event, the facilitator plays a crucial role. It is essential to have one strong facilitator overseeing each unconference, to welcome attendees and provide context for the event.

How to Facilitate an Unconference

Here are some tips, most learned the hard way over hundreds of hours of practice in the last two years.

Stay Centered

Despite having spent a fair amount of time on stage, I found myself getting nervous and feeling rushed in the hours leading up to a day-long unconference. My single biggest piece of advice for a facilitator is to arrive with plenty of time to spare so you won’t feel rushed. You are responsible for the framework within which the attendee experience takes place. As such, staying grounded and centered is the single most important thing you can provide, even though in the moment it may feel like it is more important to make sure the space is set up or the coffee is ready.

Don’t Participate

This one might seem odd. It can seem like the entire point of organizing an event is to participate. In my experience, doing so decreases the ease with which I was able to coordinate new sessions, lead an end-of-day wrap-up, and refocus attendees when necessary.

In my view, the facilitator of the unconference is there in service to the attendees. I have found it gets in the way of the attendee experience to actively participate in sessions and workshops that occur throughout the day.

Practice

The facilitator should practice before the beginning of the unconference. Review these guidelines for a successful unconference and be able to describe unconference rules from memory. Practice your welcome speech.

Incorporate movement

I have always found it very useful to incorporate movement into events. When we have short periods of movement interspersed with other kinds of learning, we shortcut the passive sit-and-absorb tendencies we all learned through the education system, and which have carried over into most events. Read this article on the importance of movement within events.

Conclusion

Events are a lot of work, and something I’ve learned to produce of necessity. However, in this hyperactive digital age, I’m convinced of the value of what Tony Hsieh calls “spontaneous collisions” — the value of people spontaneously crossing paths. If you’re considering putting on an event of your own, I encourage you to do so. When we create a container — an event or gathering — we create the opportunity for emergent possibilities to fill the open space.

I’ve been delinquent in writing Snafu this last week, because…

• I bought a house and moved in
• ​Responsive Conference is coming up in 32 days
• There have been some minor family emergencies
• I’ve had several Zander Media film shoots
• The state of the world? ‍♂️

Anyway, I thought I’d take this excuse to look back at some of my favorite essays of the last few years…

​How to run an unconference – I wrote this a decade ago, but still send people to it when they ask how to get started running events. In fact, I’m going to be leading a workshop on this topic at my friend Jenny Sauer-Klein’s the Conference for Conference on September 16th, which is the preamble to Responsive Conference 2025!

​The free pass system – I’ll be sharing this essay with new friends for the next decade. It’s such a simple reframing of boundaries and expectations in friendship, and has already improved mine.

​Some reflections on turning 39 – I got more positive feedback on this article than most. I think the mix of practical reminders and authentic reflection worked.

​Tilting at windmills – Choosing your battles is an essential skill, as is not arguing with reality. But the idea of going to battle against unrealistic odds when you choose to? It’s a little bit crazy, and I kind of love it.

​AI inflection point – One of the unexpected benefits of my foray into housing was this AI inflection point. This technology is transformational, and anyone who isn’t addressing it in their daily lives is going to be left behind.

​How to buy a used car – My girlfriend is buying a used car and I referenced this article to remind myself of what we should look out for. (I think that’s a goal for all great writing: write what you want to read and will reference in the future.)

​How to run a self-experiment – I’ve been running self-experiments since discovering the term from my old professor Allen Neuringer. The idea is to test hypotheses in small ways and on yourself, but to do so as rigorously as possible.

​How to fast – Another reference article and on the habit in my life that is the hardest thing I do. And also, likely, one of the healthiest.

​Discipline isn’t hard – In a world that is convenient and comfortable, we need manageable discomfort in our lives. But it doesn’t have to come through force. Instead, I want a re-definition of “discipline” back to the original meaning of the word.

​Habits for hiring – Hiring and managing people is hard work. And when you find great people, it makes a world of difference. These are some lessons about hiring and management I wish I’d learned a decade sooner.

​How to change someone – This article got me started. It is about my father, published with his grudging permission, and I think about it regularly. You can’t change people, and anyway it is none of your business.

I’ve never thought of myself as a great salesman. But a few months ago, two friends asked me for help with their sales and self-promotion.​

That resulted in teaching a cohort of ten people about sales. And when the 10-week cohort wrapped recently – just two months out from Responsive Conference – I didn’t have the time to run the cohort again.

Instead, I recruited some of my students and a handful of other volunteers to practice sales by selling tickets to Responsive.

I started the workshop by telling my own Responsive story, which goes something like this:

The future of work

In 2015, I was introduced to Responsive.org, a movement started by 6 organizational design nerds to describe the tensions facing organizations in the twenty-first century. As someone who’s worked in dozens of different industries – and seen a lot of the same dysfunctions across silos – I related to the challenges described. Moreover, the manifesto isn’t prescriptive. It doesn’t propose to solve everyone’s challenges.

I asked the authors of Responsive.org what I could do to help, and someone suggested I run an un-conference. I expected 30 people to show up, and instead we had 300 travel from across California for our free 1-day event. Attendees ranged from global CHROs to baristas from an employee-owned, self-managed community kitchen.

I realized there was an appetite for these topics and – never having been to an HR or organizational design conference, but as a longtime circus performer – decided to try my hand at building an event of my own.

7 months later, the first Responsive Conference was a resounding success. Chris Fussell came and gave a talk about “team of teams.” Joel Gascoigne argued that teams should be either fully distributed or entirely in one location, but nothing in between. Tony Hsieh (RIP) sat in the back with his entourage and took copious notes. I got lucky and the ideas espoused in the Responsive.org manifesto had struck a chord.

And those arguments – including “the rate of change continues to accelerate” and “the future is increasingly hard to predict” – have borne out a decade later. Once fringe, those ideas are now commonly accepted. And Responsive Conference continues to serve as an intimate, immersive gathering for founders, executives, and people leaders from around the world to build more resilient work.

What a story does

Having both lived that experience, and told that story a thousand times, I can reiterate with ease. But then comes the essential step of helping other people tell their own stories. Which means, first, we have to reverse engineer my story.

My story does several things:

• It’s entertaining – it shows how a circus performer can end up curating a business conference.
• It’s self-revealing – It helps people know a bit about me with some self-deprecating humor and humility.
• It’s intriguing – it invites the audience to consider learning more about the event or inspires someone to take a risk and start something of their own.

My story isn’t a hard sell. (I despise hard selling.) I don’t conclude with a “please buy a ticket to the conference!”

The goal is to connect, entertain, and leave the audience wanting more.

After sharing my story, I asked the members of our newly christened Sales Squad to draft their own stories about Responsive Conference for review.

If they’ve attended Responsive Conference previously, what impact did it have? If they haven’t, what’s their connection with the future of work that inspires them to participate?

Homework

Everyone has a story. Write a short version of your founding story – whether for a project, business, or personal mission – in less than 300 words.

What led you to start?
What problem were you trying to solve?

In a low-stakes conversation, tell this story to someone new. What questions do they ask? What do they laugh at? What lands?

A few weeks ago, a salesman from an AI lead generation company cold-called me.

I told him I was busy, but invited him to follow up with a short Loom video showing how his product could help Responsive Conference. I promised to watch the Loom and respond if I was interested.

He followed up – without the Loom, and with a generic pitch.
He lost the sale.

I posted about my experience on LinkedIn, with the takeaway that there are two types of selling:

❌ Coercive selling: fast-talking, pushy, ignoring requests to “follow up later.”
✅ Authentic selling: clear, respectful, tailored, and actually helpful.

Coercive selling might get short-term results, but it destroys trust. Authentic persuasion builds relationships. As BJ Fogg, PhD, says, it’s “helping people do things they already want to do.”

What’s surprising about this story is what happened next. My LinkedIn post blew up. A lot of people commiserated with the experience of being pitched but not listened to.

And other people – these are strangers on the Internet! – started lecturing me on the difference between a lead and a qualified customer, and told me that I owed it to the salesman to listen to his pitch.

I don’t think I was sharing a controversial take. I believe that coercive selling ruins trust. If a salesperson doesn’t listen to a simple request during the initial sale, they’re very unlikely to take care of the customer after the sale is closed. Great sales is about taking care of people.

These beliefs aren’t universally held. Apparently, there are angry salesmen on the Internet who are willing to fight about these ideas.

For the first time in my life, my response is: bring it on! I’m delighted to fight with these strangers; to tilt at these windmills.

Because the world needs more people who actually give a damn.

Homework

Find a moment (online or off) where you genuinely disagree with something. Don’t stay silent. Speak up. State your case clearly and calmly. The goal isn’t to win, but to practice not avoiding conflict when you really care.

A few years ago, a friend and I kept trying to make plans. I canceled several times – once due to a car crash – and after the third or fourth reschedule, she told me it wasn’t working for her and that she was going to deprioritize our friendship. I apologized, we talked it through, and agreed I’d take responsibility for reaching out.

I followed up for six months with no response. Eventually, she let me know she was no longer interested in being friends.

I was hurt. We’d had a clear agreement, and she’d gone back on it. That experience stuck with me – and led me to adopt my best friend’s “Free Pass System.”

When you notice someone does something that doesn’t work for you, you are responsible for telling them so. The key is to tell the other person before the issue has become insurmountable.

Tell the person that their behavior won’t work for you going forward, and why. Detail the specifics of what you want to change going forward.

They get a Free Pass up until this point – assuming you still want a relationship with this person. Grant them grace up until this point. That’s only reasonable because you haven’t told them that their behavior doesn’t work for you!

But you have to set clear consequences. Setting consequences is hard because most of us don’t have practice. First, articulate the boundaries for yourself. Then, describe them to the other person.

Consequences aren’t punishment – they’re about clarity. They tell the other person what you will do if the behavior continues, so that you’re not reacting or building resentment, but fostering the relationship that you want.

Here are a few examples:

• If someone is flaky after you’ve communicated that it doesn’t work for you, don’t schedule with them again.
• If someone shares a secret that you shared in confidence, don’t share private information with them in the future.
• If a client doesn’t pay on time, add delinquency fees to the bill.
• Boundaries can be small and nuanced – like the fact I don’t talk to my parents if they sound crabby at the start of a phone call because that’s when our conversations are most likely to go poorly.

To summarize the Free Pass System:

• When someone crosses a boundary, identify the boundary to yourself, and then to the other person.
• If you don’t want them in your life anymore, cut them out of your life.
• Otherwise, give them grace – a Free Pass – up until now.
• Describe to them the clear consequences if they do the unwanted behavior again.
• Then, if they exhibit the behavior again, enact the consequences you’ve communicated.

I don’t bemoan the loss of friendship with that person who wrote me off. As a result, I learned how to set better boundaries.

Whether in friendships, family, or business, the Free Pass System helps you set and hold boundaries. It won’t fix every relationship, but it will improve the ones worth keeping.

Homework

Sit down somewhere quietly for 10 minutes and write out for yourself one behavior that someone in your life does that bothers you. What is it, specifically, that you don’t like?

Then describe the boundary you will set – anything from a timeout to removing them from your life – if that behavior happens again.

Finally, share your Free Pass and its consequences with the person involved.

I just wrapped up ten-week series exploring a different approach to selling. During our last session, each attendee taught one of the topics we’ve spent the last few months discussing. These are a few of the takeaways…

• Sales as service – Sales is best conducted as a service. When we set out to provide an incredible experience for our prospective customer – creating “unreasonable hospitality” to quote Will Guidara – sales feels easy and the right customers feel silly saying no.
  ​
• Believe in what you are selling and who you’re selling it to – If you don’t believe in what you are selling, stop. If you don’t believe the person you’re selling to, stop. Authentic selling comes from trusting the person you are talking to.
  ​
• Attitude – Being present with your customer is a superpower. If you maintain an attitude of loving-kindness, you’re likely to be well-remembered.
  ​
• Emotional connection – Everything in authentic sales is predicated on establishing a connection between you and your prospect. People buy from people.
  ​
• Enthusiasm is a competitive advantage – As Kevin Kelly says, “Optimism is worth 25 IQ points.” When you’re showing up enthusiastic, you’re more believable, more likely to close the sale, and you’ll have more fun.
  ​
• Integrity – It’s useful to define “integrity” for yourself and what you mean when you think of integrity in sales. For me, that means selling and persuading without using force and while keeping my commitments.
  ​
• Two beliefs that are helpful:
  • There is abundance – You don’t need – or want – a sale that isn’t a good fit.
    ​
  • They know best – Your prospective customer always knows what’s best for themselves.
• What’s your founder/origin story – One of the essential ingredients in connecting with a customer is telling your founder’s story. Why are you talking about this topic, and why should someone else care?
  ​
• The four elements of story – There are a million ways to tell a compelling story. But one of the simplest is a four-part structure: setup, change, turning, and resolution.
  ​
• Help them, no matter what – One of the best ways to cultivate a long-term relationship is to help the person achieve their goal, even if that means recommending something outside your offering. Be like Santa in Miracle on 34th Street.
  ​
• Flexible goals – If you’re using pressure, you’re not maintaining flexible goals. If your goal is to help somebody, even over closing a sale, you’re not going to be disappointed if they say no.
  ​
• Asking questions – Ask enough questions to learn about your customer’s pain points. They’ll tell you what you need.
  ​
• How fast you can get to “no.” – Get to know your prospect and their needs as quickly as possible. There are 8 billion people in the world. If the person you are talking to is not a good fit, somebody else will be!
  ​
• The ask – Asking for what you want is usually the hardest part of a sale. But it doesn’t have to be hard with clear boundaries. The pressure most of us feel when we prepare to ask comes from a fear of rejection and being told no.
  ​
• Boundaries – Boundaries can be as simple as time-boxing meetings, arriving on time, or discussing what you say you are going to discuss. They can also be as nuanced – doing what you say you’ll do, not negotiating past your comfort, or saying “no” to a sale that isn’t a good fit.
  ​
• Be respectful of their time – At the start of a sales conversation, be clear about the purpose of the meeting. Clarifying your intentions at the beginning of a conversation makes a huge difference in the other person’s experience and your own comfort.
  ​
• Start on time – Always start a sales meeting on time. Arrive early and be ready to begin when scheduled.
  ​
• Check in at the beginning – At the start of the conversation, make sure now is still a good time. If it’s not, offer to reschedule.
  ​
• Keep your commitments – If you told your prospective buyer that the meeting would last 15 minutes, keep it under 15 minutes. Ideally, end 2 minutes early to demonstrate respect for their time.

The following is an expert from my 2017 book Responsive: What It Takes To Create a Thriving Organization​

Doug Kirkpatrick was one of the earliest employees at The Morning Star Company. Founded in 1990, Morning Star would go on to trailblaze self- management in business. But as might be expected of any start-up, let alone one committed to innovative management, the company’s early days were intense times.

Morning Star is a tomato-ingredients manufacturer based out of Sacramento, California. The agribusiness and food-processing industries are notoriously old-school, known for strict command and control structures and rigid bureaucracies. The small group of employees who initiated the Morning Star project had a six-month window to start up the first factory and had committed to beginning operations on a specified day and even at a specific hour. They were a high-performance group, and Doug describes those initial weeks as a high state of flow, with each person striving cooperatively to bring the new company into existence. The company consisted of seasoned employees, and Doug, at thirty-four, was considered quite young.

Several months before the factory opened, the owner of The Morning Star Company, Chris Rufer, called a leadership meeting. The Morning Star founder and twenty-four members of the team met on the job site. They pulled steel folding chairs into a circle, and Chris passed around a page titled “Morning Star Colleague Principles.”

The sheet included just two points:

• Don’t use force.
• Keep your commitments.

The group spent several hours discussing what these principles meant. Questions cropped up. What happens if you have to fire somebody? What if someone quits? In the end, no one found a reason to reject these ideas, and every person there had reasons to embrace them.

Together, the group concluded that these two points were necessary and sufficient, and they would make up the core of all human interactions at the company. Adopting these principles wouldn’t change the day-to-day operations of the nascent company, but they’d have clear guideposts by which they’d proceed.

What they perhaps didn’t fully process at that moment (and what Doug has spent his career implementing, first at Morning Star and now with companies all over the world) was the far-reaching ramifications of adopting those simple principles. Consider, for example, that “Don’t Use Force” effectively implies:

• No one can require anyone to do anything.
• No one can unilaterally make anyone do anything.
• No one can fire anyone unilaterally.
• Each person has a voice within the company and each voice is protected; no democracy or majority rules.
• Checks and balances will be inherent.

At the time, it didn’t register how profoundly that meeting, and its eventual outcomes, would impact the team, and its members individually. As Doug said, “What we did would end up being very radical—but we were so busy we didn’t necessarily see it since it didn’t seem immediately to impact our day-to-day lives.” More than two decades later, those principles—don’t use force and keep your commitments—continue to serve as the bedrock of a successful, self-managed company.

Shortly before opening, Doug and his colleagues celebrated his thirty-fourth birthday outside the same farmhouse where Chris Rufer had called that fateful leadership meeting. The company has gone on to become a model of self-management and the world’s largest tomato processor, handling between 25% and 30% of U.S. tomato crops.

I don’t run a self-managed business, but those two principles have stuck with me ever since first meeting Doug in 2016. Whether in management, sales, or personal relationships, these two simple statements are deceptively profound.

Management – It is possible to run incredibly efficient and effective companies without force. When you set clear boundaries, and stick to them, business works better for everyone involved.

Sales – One of the biggest reasons most of us avoid selling is a lack of clear boundaries. When you don’t use force in sales and are clear from the beginning that any answer is okay, selling becomes easy.

Personal relationships – The only difference between this and any other kind of selling is that the stakes are higher and it’s even more important to not alienate your “customer.” The best personal relationships are also predicated on these two principles.

Inspired by Ryan Holiday, I’ve made a practice of listing a few things I’ve learned over last year on my birthday. Here’s 37 and 38. And here are a few things I’ve learned in the last year.

Chaos

We’re living amidst more turmoil than any time in several generations. And, despite being relentlessly optimistic, I think things are going to get worse before they get better. I wish that weren’t true – I’d love to build my business and raise my family in peace. But the next decade, and likely the rest of our lives, are going to be chaotic. Assuming that, the question becomes: how do we stay resilient?

AI is here

To paraphrase William Gibson, “It’s just not evenly distributed yet.” I’ve known AI is important for years now. At Responsive Conference, we’ve curated about AI since 2019! But I hit an inflection point this spring and now I’ll talk about the coming AI storm to anyone who will listen. Among my peers, it is trite to say that AI won’t replace people but instead people using AI will replace people. That phrase is true – as far as it goes. But it doesn’t do justice to the amount of change and disruption that I believe is coming.

Adaptability

Fellow entrepreneurs have been asking me how I feel that my business of the last six years, Zander Media, may be replaced by AI. As someone who’s reinvented himself and his career more than a dozen times in the last fifteen years, I’m more prepared than most to adapt to change. That’s what it means to be an entrepreneur – and also a prepper.

Adaptability is among the most important skills in this century.

Optimism is a competitive advantage

If these first two items sound bleak – they are. I don’t think we’re headed into a gentle time in human history. Thus, optimism is even more important than ever. As Kevin Kelly wrote in Excellent Advice for Living: optimism is worth 25 IQ points. When we show up with optimism and enthusiasm, people are more likely to listen, to follow our advice, and to change. (Optimism is actually a secret to selling.)

Durable skills

During my first few months in San Francisco in 2008, a woman asked me what my “hard skills” were – and then had to define the term for me to mean technical skills like software engineering or graphic design. I responded that all of my marketable skills were soft skills – persuasion, storytelling, talking to people, and selling.

Recently, someone introduced me to the term “durable skills” and I like that one better. All my skills are still soft – or durable skills – and I’m good with that.

Sales

There’s a story my dad tells about driving with my grandfather through the Central Valley of California long after my grandfather had retired. My grandpa asked that they stop through a small town and stop by a specific depot. The adult children of the proprietor came out crying, “It’s the candy man! It’s the candy man!” Apparently my grandfather used to bring those kids candy in their youth, as a part of his route as a door-to-door salesman selling tractor hitches..

The ability to sell – not to manipulate, but to persuade – is a superpower. As BJ Fogg says: “Help people do things they already want to do.” Sales and persuasion are going to be important in the years ahead.

The Trades

A friend of mine recently left his senior position at a name-brand technology company, borrowed money, and bought an established plumbing company. An old colleague makes more as an appliance repair man than he ever did as a personal trainer. The Trades, and being able to work, quite practically with your hands, is going to become more important – and more lucrative – in the coming years.

Get into real estate

This one is personal. I don’t think most people should treat real estate as business, even if they want to own property. But I went down a real estate rabbit hole this spring. I’m going to dabble in buying and selling real property for the rest of my life.

Daily habits

I haven’t had my cold plunge available for most of 2025. (The horror!) For a few months, I exercised 45 minutes a day, instead of my more typical two hours. I’ve fallen out of keeping a journal. But my daily habits are so strong, historically, that I’ve been able to build them back with ease. When things are going a bit off the rails, I can easily get back to the basics because they’re well known habits.

Discipline doesn’t have to be punitive

Growing up, I was criticized for not being disciplined. As an adult, people tell me how disciplined I am. No surprise, then, that I’ve always struggled with the idea of discipline.

The word “discipline” originates from the Latin word disciplina, which means “instruction, teaching, knowledge, and learning.” It is derived from the Latin root discere, which means “to learn”. Over time, discipline has come to mean punishment and correction, but the core meaning remains rooted in learning and self-control.

Exercise every day

This isn’t new to me. I’ve been exercising every day since I was 19 years old. I was reminded again this spring – amidst a couple of very challenging weeks – that when I get enough exercise every day, life is better. In particular, I like finding a specific routine (currently: a 5 mile loop through the Oakland hills) and doing that on autopilot. My girlfriend was surprised to hear that I “work” during those runs – mentally processing a lot of loose ends.

Do hard things

I really like doing difficult things. When I’m feeling stuck at work, running a really hard hill makes everything better. When I have a difficult day ahead of me, a few minutes in my cold plunge makes the day easier.

Maybe it’s a study in contrast, but doing hard things really does seem like a secret to success.

Limit social media

I deleted TikTok a few years ago. I haven’t been posting on Instagram almost at all in 2025. For sure, this is to my professional detriment. But my mental health is so much better! Social media is a mixed bag – there are good and bad things about it, for sure – but I’m healthier without it.

Limit screens, generally

I’ve watched two movies so far this year and no television shows. I have a time limit on all of my most-used apps on my phone. When I’m not working or researching real estate, I’m doing my best to avoid screens. And life is better!

Community is strength

When I brought back Responsive Conference after a pandemic-hiatus in 2024, the deciding factor was because I appreciated the value of people gathering in person. For the same reason, I’ve been hosting a monthly potluck to gather people together socially. Humans are meant to operate within a community. Community is strength.

Get a dog (they’ll teach you about presence)

My dog Riley is eight years old. I’m traveling this week, and thinking about her. She’s my best teacher on one important topic: presence.

I’ve done a lot of meditation, and dabbled in a variety of “presence” practices. But nothing has been more useful for practicing presence than having a dog as my daily companion.

I was listening to this Conversation with Tyler with Anthropic co-founder Jack Clark. Tyler asked Jack when we’ll be able to communicate with dogs, and what they’ll have to say. Jack said we probably already know what dogs will say: “Walk!” “Food!” and “I love you!”

Find your rabbit holes

I’ve always been someone who dives deep down rabbit holes. This spring, I spent about a thousand hours on real estate.

As my friend Marie is fond of explaining, the word amateur comes from the Latin “amare” meaning to love. It used to refer to someone who does something purely for the love of it. I think it is really healthy for humans to specialize and to practice out of love.

History > News

Twice over the last year, I’ve developed the bad habit of listening to several political podcasts as I’m waking up in the morning. I’d wake up and immediately start listening to The Daily, followed by other political podcasts. Predictably, I felt depressed for the rest of the day.

I’m learning to limit my consumption. No podcasts or news before 10am or after 6pm. Instead, when I want to think about what’s going on in the world, I turn to history. There’s some comfort in recognizing how much chaos and violence the human race has been through.

Write to think

Writing is hard. Even after writing more than 200,000 words over the last two years, it doesn’t seem to be much easier. But I am a better writer. And my thinking is quite a bit more clear.

Writing isn’t the only way to train critical thinking (BrainHQ is also great), but it is one of the best ways I know.

You know more than you think you do

I’ve been writing Snafu for two years and am always surprised that I have more ideas to write about. Over the last six weeks, I’ve been leading a weekly workshop about a more authentic approach to selling. As I prepare for the workshop each week, I’m consistently surprised by how much I have to say – way more than I can teach in an hour a week! We all know more than we think!

Avoid “Grass is greener on the other side”

I’ve noticed a habit among entrepreneurs to chase a new idea, project, or business when the better course of action is to double down on the current business. I’ve done this a lot across a dozen industries in the last decade!

It is important to avoid sunk cost fallacy! Don’t keep going if you’re just digging the hole deeper. But also don’t jump to something new just because it looks more appealing than the hard work in front of you.

Keep going

Luck accumulates to the persistent. Just keep showing up.

Over the last few weeks, I’ve been teaching a workshop about sales. We get together on Zoom for an hour every week to discuss – and practice – a more authentic approach to selling.

I made my first sales at five years old at Robin’s Pumpkin Patch. Selling is a part of my work today. But I’ve always meant to study sales and persuasion more deliberately, so this workshop format provided me the excuse.

Last week, in a discussion of empathy and connection, I asked the workshop participants a question: “What characteristics make a good therapist?” Or, if you prefer, what makes someone feel like a safe and trusted presence in your life?

It’s not usually their credentials or how convincing they are. It’s how they show up. It’s the way they listen, make space for you to think, and are okay that you don’t have everything figured out. A good therapist isn’t trying to steer you toward a particular outcome, but instead helping you discover what’s true for you.

That same kind of presence is at the heart of my approach to sales.

The most effective salespeople aren’t pushing hard for a yes. They’re not over explaining, and they’re definitely not trying to be impressive. They’re doing something much harder – and much more generous. They’re holding space, asking real questions, and listening closely enough to help someone gain a clearer understanding of what they need.

In that way, sales and therapy aren’t that far apart. Both rely on deep listening, curiosity, and a quiet confidence. They’re about helping people see something they couldn’t quite see on their own – not because someone told them, but because they finally had space to recognize it themselves.

When sales are done this way, it stops being about persuasion. It becomes about partnership. It becomes a conversation that respects the other person’s agency. And when that’s the foundation, a sale – if it happens at all – feels more like a mutual decision than a transaction.

Homework

This week’s homework is to compliment a stranger on the street. Pick out someone in the grocery store or on the sidewalk and compliment them on something trivial – their hairstyle, an article of clothing, the brightness of their eyes.

When I started this habit a few years ago, I was scared. Before I spoke, my heart would beat fast and my palms got sweaty. Today, I compliment strangers with ease. More significantly, I feel more comfortable speaking up in public and I’ve never had someone respond poorly.

Next time you are in public, find something about somebody nearby to compliment and let me know what happens.

I was on a call with a client recently and found myself saying that the human desire to listen to Homer recite The Odyssey is timeless. Even when AI voices become as good as today’s best voice actors, listening to the best in the world tell stories is always going to be worthwhile. Or as Pixar animator Bobby Podesta said to me recently: “Storytelling is a method of value exchange.”

Today’s essay is about taste, an increasingly important skill in our noisy world.

I’ve raved before about Ezra Klein’s new book, Abundance. But I haven’t heard Ezra talk about his craft of writing before listening to a recent interview on the How I Write Podcast. The conversation covered the state of media and the role of AI, but the most interesting topic was the role of an editor. According to Ezra, a good editor is not somebody who makes sure that spelling and sentence structure are correct, but somebody who has taste. Taste, he says, is one of the most valuable skills – in writing and beyond.

I was reminded of a short blog post I read by up-and-coming author Billy Oppenheimer. Before he was a writer, Billy was a ski bum who supported his lifestyle by working part-time as a barista. And he argues that taste – understanding what customers want to drink, how they prefer their lattes, and providing exceptional service – is something that AI can’t replace, even if it does replace his writing career.

I developed taste growing up around my mother’s artwork. From the age of four, she would show me her work, ask for my opinion, and listen carefully to my feedback. I’ve never met a professional artist more open to feedback.

The aesthetic sense I developed as a kid has been a driving force behind my work at Zander Media. I’ve never struggled with a brand direction or critiquing our videos.

In an AI-enabled world, discernment is increasingly important. Creating work that moves people is a valuable skill. Taste is never going away.

My AI avatar logs into Zoom to chat with your AI avatar. Sounds great – fewer meetings! But then what? What happens when AI takes over both our mundane and creative tasks?

This question has been haunting me lately.

If you’ve been following along with the Snafu newsletter, you know that I had an AI inflection point a few months ago amidst attempting to buy my first home.

Even as I was confronted by the painful bureaucracy of trying to buy a house in California, my learning accelerated far beyond anything I’d ever been able to accomplish before. It was a very Responsive.org dichotomy; a tension between traditional bureaucracy and rapid innovation.

Over the course of a few weeks, I realized that AI wasn’t just another important topic, like blockchain, social media, or the Internet. It is much bigger.

Most nights after dinner, my girlfriend and I sit in the sauna. Invariably our conversation turns to AI.

My girlfriend is a data scientist, and has taken the rise of AI for granted for many years. She believes that in the next 18 months we’ll see widespread use of Zoom AI avatars. This led into a conversation about what humans would do instead when our AI avatars take our meetings. And, as someone who talks to people for a living, I’m really not sure.

My only solace is that humans are slow to adapt.

QR codes were developed in 1994, but it wasn’t until the Covid-19 pandemic that we got comfortable ordering food from a QR code taped to a table. And given the option, most of us still prefer a server. Even when we can chat with an AI doctor online, we’ll likely still want to be able to meet with a human doctor, in person.

As the rate of change continues to accelerate, some things are going to be slowed down by humans’ own inertia.

This brings me to a personal decision. I’m doubling down on those things that AI is going to have the most difficulty replacing.

• In-person meetings – even over the convenience of Zoom.
• Educating and selling in-person – instead of through email exchanges.
• In-person gathering – like those that happen at Responsive Conference.

Each of us is going to need to reinvent ourselves over the next decade. The most important skill is going to be adaptability and reinvention.

Today, I’m still taking a majority of my meetings on Zoom. But I’m beginning to default to in-person meetings because they’re harder to replace.

To adapt, we need to lean into work AI can’t easily replicate. But what that work is, I’m not sure.

Last week, I taught the first workshop in a series about selling – because knowing how to influence and persuade are essential skills for navigating chaotic times. I brought together a handful of friends and taught one of the most overlooked elements of selling: being of service.

When we think “sales”, we think of a car salesman trying to persuade you that his junker is just what your family needs. We’ve all received a call from a telemarketer who won’t take no for an answer. That kind of selling gives sales a bad name.

But there’s a growing group of salespeople who are goodhearted, aligned with their audience, and want to create wins for everyone involved. These people know that great selling is about service, not manipulation.

A groundswell

There’s a quiet groundswell of people reclaiming selling.

A son supporting his mother through a cancer diagnosis. A single parent who is struggling, valiantly, to get her daughter to bed on time. A first-time entrepreneur trying to get the world to hear about his new offering.

People taking risks, stepping out on their own, and advocating for what they believe in. This is the approach to selling that we need. And one of the best illustrations of sales as service comes from an unlikely source, a classic movie about Santa Claus.

A Christmas miracle

The example I often give to describe sales as service is the Santa from the 1947 movie “Miracle on 34th Street.” In the movie, an alcoholic Santa Claus is hired to give out candy canes and sell goods for a local Macy’s department store.

The Santa – apparently not caring very much about the job description of “sell things to customers” – answers customers’ questions honestly when they ask him where to buy products that his store doesn’t have in stock. He sends them across the street to the competition!

When the department store manager finds out, he’s furious. How dare this washed out Santa Claus send customers elsewhere, instead of just redirecting them to a different product that they already sell? Until customers begin to return en masse, praising Santa’s good advice and expressing their undying gratitude and loyalty to his store, for guiding them so well.

The department store manager does an about-face, celebrating Santa’s ingenuity.

Enlightened hospitality

Even though we’ve never met, one of my early mentors was restaurateur Danny Meyer, whose thoughtful approach to service has reshaped the hospitality industry.

Danny is the founder of the New York institution Union Square Cafe, and went on to build a variety of other famous restaurants, including Eleven Maddison Park and the global Shake Shack chain.

His approach, often referred to as “Enlightened Hospitality,” emphasizes the importance of caring for employees first, then guests, and then the broader community. If we support our employees, they’ll serve our customers, and the rest will follow.

Inspired by Danny, I designed Robin’s Café to prioritize employees, creating an employee and service-focused environment.

In service to our employees

When I opened Robin’s Café, it was with the clear intention to open a coffee shop in service to our employees who, in turn, would provide great service for our customers.

One night, about six months into running my old restaurant, I came in at closing to pick up some paperwork. The employee who was closing the cafe for the night, turned to me and said, “Robin this is the single best job I have ever had. Thank you for this opportunity.”

This employee worked irregular hours in a small café, serving hundreds of customers every day with no guaranteed minimum of hours. To hear this from him reminded me – and reminds me still – of the reason Danny’s “Enlightened Hospitality” matters. It creates environments in which people will do their best work.

Serving multiple stakeholders

The most skin-crawling sales people sell exclusively for their own betterment. They only serve themselves. A successful salesperson has to at least serve two stakeholders – the salesperson and the customer.

But a sales person who serves a multitude of stakeholders is more likely to succeed. There are more parties invested in their success!

Robin’s Cafe served 5 different stakeholders:

• Employees: in creating a fulfilling, supportive workplace
• Investors: return on investment and pride in supporting a meaningful venture
• Landlord: a vibrant, community-oriented tenant
• Customers: a welcoming, enjoyable “third place,” in addition to good food
• Me: a meaningful, rewarding endeavor, both financially and emotionally

Once you have identified the different parties that benefit from your efforts, it is helpful to delineate how each one benefits from your selling.

Service is selling

When we think of restaurants, we don’t usually think first of a sales environment. But they are.

When the server asks if you’d like dessert after a meal or the sommelier asks if you’d like another bottle of wine with dinner, they are upselling – encouraging you to purchase a more expensive menu item than the one you’d intended to buy.

But what restaurants do differently is sell through the act of serving their customers. By being of service and providing an exceptional experience, they’re creating an environment that we, as patrons, are pleased to pay for.

Whether you’re selling a product, an idea, or simply persuading a friend, selling is about genuine service. When you serve, you don’t just sell. You also create lasting value for everyone.