The three pillars of selling

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

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

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

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

Connection – form an authentic connection with the other person.

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

Ask – Invite powerfully towards the outcome that you want.

Authentic Connection

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

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

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

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

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

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

Tell Them Stories

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

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

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

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

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

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

The Ask

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

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

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

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

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

Until next week,

The Line Between Habit & Addiction

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

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

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

What Is Addiction?

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

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

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

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

A Little Escapism

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

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

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

Altered States of Consciousness

We all enjoy altered states of consciousness.

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

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

How I Differentiate Between Habits & Addictions

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

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

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

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

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

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

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

Until next time,

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

Habits for Combatting Resistance

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

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

Ask yourself “why”

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

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

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

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

Make it tiny

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

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

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

Make the tiny habit inevitable

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

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

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

Stack your habits

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

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

Decide what you are going to give up

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

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

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

See you next week,

Habits for Sleep

I’ve always had a contentious relationship with sleep. As a child, I’d get up after the house was quiet to enjoy a few hours of time alone and as a result I’d chronically wake up tired.

In college the common refrain was “you can sleep when you’re dead.”

It wasn’t until I recognized the profound impact a good night of sleep had on my physical performance (in ballet, specifically) that I decided to prioritize sleep. And even so, it has taken me another decade to cultivate robust sleep habits.

Here are a few of the habits I’ve found helpful:

Catch dawn and dusk

Prompted by Andrew Huberman, I dug into the research around sunlight. Getting a bit of sunlight at sunrise and sunset resets your circadian clock, and makes falling and staying asleep easier.

Cold plunging in the morning

My current habit is to spend 6 minutes in my 39 degree cold plunge in the morning. This doubles as my sunlight exposure and an abrupt way to wake up in the morning. The release of cortisol and adrenaline, and afterwards, dopamine, are the best way I’ve found to start the day.

(While I love cold plunging in the morning, or anytime before sunset, doing so after dark interferes with my sleep.)

When I’m the most tired is when I’m least good at going to sleep

I’m world class at procrastinating going to bed and turning a 20 minute bedtime routine into multiple hours. I’ve learned to set up the hours leading towards bedtime into as efficient a process as possible. There’s no problem that isn’t better to tackle first thing tomorrow, instead of late tonight. 

“Just go to bed earlier. You’ll feel better in the morning.”
This is a phrase from my childhood, meant to sooth a discontented child (i.e. me). And it still holds true today. There’s no problem that isn’t better to tackle first thing tomorrow, instead of late tonight.

Don’t watch television at bedtime

Television doesn’t get in the way of my falling asleep, but after a show or a movie my sleep is much more restless. Interestingly, it doesn’t matter what kind of television.

Tracking helps

I’m not big on tracking everything about myself, but spending several weeks tracking what time I fall asleep was really helpful in moving my bedtime earlier. The Oura Ring is the best tool I’ve discovered for tracking what time I fall asleep and how much of each type of sleep I get. (REM, Deep Sleep, etc.). I’ve gotten competitive with the Oura Ring’s report of what time I should go to bed, and now always try to go to bed before it says I should.

Sleep Supplements

Here are some supplements I’ve been enjoying.

Hot bath or cold shower

I’ve taken hot baths at bedtime since I was young. This doubles as my favorite time to read physical books. Lately, though, I’ve been also enjoying cold showers just before bed. Hot baths prompt the body to cool off quickly. Cold showers get the body to warm up. Maybe it is something about the temperature change, but either a hot bath (with enough time to cool down before bed) or a cold shower (so long as I get in bed quickly) puts me right to sleep.

Sex Helps

I notice that I sleep better at night if I’ve had enough sex in the preceding days. Everyone is different, but I fall asleep faster, and stay asleep longer.

Exercise the dogs – and the people, too

The dogs will sometimes bark in the middle of the night, particularly at the raccoon that lives in the oak over my house. Getting the dogs enough physical activity before bedtime solves this issue entirely. And when I get a good cardio workout I sleep better, too.

What are tools or habits you’ve discovered for sleep? I’d love to hear!

Until next time,

Habits for Fasting & What I’ve Learned from Not Eating for 5 Days

I haven’t had anything to eat or drink except for water for five days. That would have sounded bonkers to me just six months ago, but this is my fifth multi-day fast this year. ( Here’s a video about my first 5-day fast.)

Tomorrow, I’ll eat my first meal in 130 hours. I’m really excited! But, honestly – I’m feeling great, have a ton of energy, and haven’t been hungry in two days!

Several years ago, intense stomach pain forced me to consider my digestion. But, it wasn’t until four close friends were all diagnosed with cancer last year that I began to study the benefits of fasting – both to improve my gut health and prevent cancer. And I went down the rabbit hole!

I had a lot of reasons to fast: To improve my digestion and gut health. To explore the performance-enhancing aspects of fasting. To be able to support my friends with cancer. Because I like new experiences! The more reasons we have to try a new habit, and the clearer those reasons are, the easier it is to begin.

Even without realizing it, I started small. I’ve been doing intermittent (partial-day) fasting for years without knowing it for years. When I danced ballet, I didn’t have time to eat for 6+ hours at a stretch. In the last few years, I haven’t made time for breakfast between work meetings. All of these were small steps towards fasting, even though I didn’t realize it at the time. The only way to attempt something big is by starting small.

Here’s what else I’ve learned:

We are capable of so much more than we think

I had no real notion that the body is capable of going multiple days without food. Having done something new that I used to believe was impossible, I’m inclined to consider what else might be possible that currently feels out of reach.

The benefits of delayed gratification

The marshmallow test, or our ability to delay gratification, is predictive of positive life outcomes. Unfortunately, I’ve always believed that I was bad at delaying gratification. Through this experience, I’ve come to realize that this is not true, and actually been enjoying this experience.

As an aside: fasting is the most difficult form of delayed gratification I’ve ever tried.

We are designed to go without food

Humans are made to go without food. Prior to this year, I didn’t realize that there’s a switch that flips, and our bodies transition from using glucose for fuel to burning fat. Far from my body shutting down, I’m more alert, more present, and more capable during long fasts even than during my normal life.

This is an altered state

I’m an adrenaline junkie and enjoy the altered states from things like cold plunging or exercise. Long-term fasting is certainly an altered state. I wake up with a lot of adrenaline, need less sleep, and have a very different kind of focus than usual. I couldn’t live like this all the time, but it is certainly an interesting experience.

Hunger pangs go away

I’ve always been afraid of what happens when hunger pangs get bad. It turns out that on the other side of hunger is… nothing. During the first 2 days of this fast, I was mildly hungry, on and off. Since then, I’m simply not hungry anymore.

I still get mildly hungry for a few minutes a few times a day, andI certainly have fantasized about food over the past five days! But, by and large, I feel great.


If you’re interested in trying fasting, I thought I’d share my top three habits for fasting:

Drink more water

Most of us would benefit from drinking more water. I still haven’t successfully created the habit of drinking enough water when I’m not fasting, but even during an intermittent (partial-day) fast, I carry a full water bottle with me everywhere. A key to my longer fasts is drinking a lot of water, especially when I feel hungry.

To start: Have water nearby as a cue to ask yourself the question, “Do I want a drink of water?”

Go without breakfast

Skipping breakfast has become a popular form of intermittent fasting, or eating all of your meals within a prescribed 8- or 10-hour window. The main goal of this habit, though, is to learn that hunger pangs go away, and that we aren’t fundamentally tied to eating every day or a specific schedule.

To start: Delay eating for a few minutes, when you get hungry. If you eat breakfast at 8am, try eating at 9am. If you’re comfortable swapping breakfast for brunch, try delaying brunch by an hour.

Pay attention

Most of us don’t pay attention when we eat. Amidst the demands of work and life, I often don’t. I’ve also used intermittent fasting as a crutch, when I don’t have time to eat. But skipping a meal is useless if you aren’t still paying attention along the way.

My number one habit for someone starting out fasting is to pay more attention. It turns out that the intense stomach pain that got me started on this journey was the result of years of stress, drinking coffee on an empty stomach, and a lack of attention. I wasn’t aware of how much the stress and astringent coffee were combining.

To start: Notice the sensation of eating a bite of food or a drink of water. When you feel the first glimmer of hunger pains, sit with them for a moment instead of immediately reaching for food.

Let me know if you like today’s focus on fasting! If you want to learn more and try fasting yourself, just reply to this email and I’m happy to share more thoughts with you, directly.

As ever, thanks for reading!

Until next time,

P.S. Nothing here is, or should be construed as medical advice. Please consult with your physician before trying fasting, or anything that might impact your health.

Habits for Mental Health & Addiction

A video I made recently, about talking someone down off of a bridge, has gone viral. The video, and the story behind it, has me thinking a lot about mental health.

There’s a lot of addiction in my family. My uncle died of pills, and my grandfather died of alcohol. I have always been leery of my own addictive tendencies, and tried to steer clear of the worst of those patterns. Fortunately, my addictions – to things like exercise and cold plunging – have a lot of tangible health benefits, and are harder to abuse than, for instance, alcohol.

I started drinking regularly while running Robin’s Cafe and at my peak would have a drink every evening of the pandemic. Then, in September 2021, I gave up alcohol entirely. (This continues to be a bit of a challenge, since my girlfriend makes exceptionally good cocktails.)

In reading Wonder Boy, I see facets of myself in Tony’s story. He saw the world differently, and that allowed him to accomplish great things, but led him to struggle to exist in our shared reality. I’ve done things that people told me were impossible, and, as a result, found myself in situations that felt nearly impossible to handle.

I haven’t carried the level of responsibility Tony did. And, perhaps I also wasn’t born with Tony’s heightened gifts/challenges. But I do understand facets of what Tony faced. Even as I am, today, in the best physical and emotional health of my life, I worry that things might change. Life is extraordinarily fragile. In a moment, and without warning, things can shift, again, and we find ourselves in completely different – and worse – situations, and have to build back from there.

I don’t see a concrete way around this, beyond celebrating when things are going well, and reaching for gratitude even when they aren’t. All any of us can do is focus on the daily habits that build in the direction we want to go. I like who I am when I exercise a lot, so I take small steps towards building a life where I train movement for several hours each day. Building healthy habits and routines while things are good have given me a stable foundation to fall back on during tough times.

For you, that might be starting with 10 minutes a day – or some other habit entirely. Don’t compare yourself to me, or anyone other than who you were yesterday and who you want to be tomorrow. I often think of a quote from James Clear: “Every action you take is a vote in the direction of the type of person you wish to become.”

Who do you want to become this afternoon? Tomorrow? Let next year and other people worry about themselves. Just take one step in that direction of who you want to become.

Until next time,