Don’t trust me. Trust you. A guide to overcoming self-doubt.

UPDATE AUGUST 21, 2020: Quick heads up – my thinking on some of the topics in this article has changed. A lot. Please see points 1 and 2, here, for my latest thinking on the importance of expertise and education. Spoiler alert, I’ve done a 180. I think credentialed experts are of extreme importance. I’m also really glad that I finished my undergraduate degree. 


April 2009, 2:00am: It’s the stupidest decision in the world, but I’m moments away from making it.

Only two weeks until graduation, and I’m about to drop out. I see no point in completing my degree. I already know that I’m starting a business rather than getting a job. I feel like my professors are idiots. I’ve hated being in the classroom since I was in kindergarten. Why put myself through two more weeks of this?

I email a mentor explaining the situation. He tells me that I need to stick it out and that I’ll be glad I did. He talks me off the ledge; I thank him.

Since then, seven years have passed, almost to the day.

I can tell you from the bottom of my heart that the singular biggest mistake I’ve made in those seven years was failing to trust my instincts.

I should have ignored my (former) mentor and dropped out of school, even though I only had two weeks left.

More on that in a moment….


Have you ever known what you wanted to do and how you were going to do it, but for some reason, you couldn’t pull the trigger?

You told yourself that you lack resources, the timing’s off, or it’s just a pipe dream. In some cases, that may be true.

But what about those dreams that have endured for months or years? There were windows of time when you could have pulled them off, when you could have saved the money, when you could have gotten your ducks in a row.

But you didn’t.


You tell yourself that you weren’t ready, that you lacked confidence, or that you needed to do more research.

Those are lazy excuses.

The simple truth is that you don’t trust yourself with big life decisions. You’re afraid that you won’t be able to succeed, endure, or beat the odds. I get that. I spent more of my life than I care to admit feeling an intense desire but lacking the audacity to act on it. At various points, my lack of trust in my own ability left me living in a city I hated, running a business that was destroying me, being stuck in relationships I knew weren’t going anywhere, and forcing myself to sit in classrooms.

At it’s heart, learning to trust yourself is about acting on your truth, even when everyone else thinks you’re making a mistake.

What happens when you finally start trusting yourself?

Learning to trust yourself changes things. It makes taking action easier and more playful. Creating success and living in integrity happens passively. And though I don’t know how or why, the world can’t help but fall in love with you when you trust yourself.

As you start to trust yourself, your confidence and power will intensify. Significantly. Trusting yourself creates a strong feedback loop signalling that you are worthy and capable. The more you activate that feedback loop, the stronger and more capable you become.

At a deeper level, you’ll notice that when you trust yourself, the synchronicities in your life increase dramatically. The people around you will say that you that you live a charmed life. Behind your back they’ll talk about the inexplicable luck that seems to follow you around as though you shit four leaf clovers and rabbits feet.

I know that sounds bold, maybe even crazy. Don’t take my word for it. Instead, take the chance of being who you truly are. Trust yourself. and see what happens…

Why we don’t trust ourselves, part 1: we’re trained not to

Right around the time you become self aware, you’re taught – out of necessity – that you can’t trust yourself. Your parents explained that even though you really want to help that weird, mustachioed man in the windowless van find his puppy, you can’t.

As a teenager you were mocked (or worse) when your opinions and preferences differed from the other kids in school.

When you were in college, you were required to cite other people’s arguments and opinions if you wanted your own to have a chance of being considered valid.

As an employee you were rewarded for “in-the-box” thinking, being a team player (that is to say, agreeable and hard working), and doing as your boss told you.1

To further complicate the matter, even in circles where conversations about things like confidence and vulnerability are common, discussions about learning to trust yourself are rare. Unless your parents or a skilled mentor intentionally taught you to trust yourself, it’s unlikely you ever learned.

Why we don’t trust ourselves, part 2: the fear of failure

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game winning shot, and missed. I’ve failed over and over and over again in my life. And that is why I succeed. – Michael Jordan

One of the strongest counter-forces to trusting yourself is the fear of failure. When you risk trusting yourself, you also risk failing and being wrong. More specifically, when you trust yourself, you’re forced to own the results of your actions; you can no longer outsource responsibility for your mistakes to external sources.  

But is failing really a bad thing? I don’t think so. I think it’s something to seek out. Everyone you admire has made more mistakes than you have. They’ve “failed” more than you too.  

Failure has this eerie quality that makes it seem like it’s a permanent state. It isn’t. When you get results that you don’t like, it’s your job to try something new. New actions will produce new results. Old actions will produce old results.

Failures and mistakes are signs that you’re on the right path; as long as you’re using experience as a teacher, you’re that much closer to succeeding.

Going a bit deeper, failure tends to exist more in your head than in reality. Reflect back on your life. You’ll notice that when you took a chance, everything worked out just fine. During the rare instances when it didn’t, you were able to bounce back. One of the most enduring (but apparently, hidden) lessons life teaches is that things have a way of working out.

It feels like trusting yourself is risky. In reality, the risk rests in not trusting yourself.

Why we don’t trust ourselves part 3: we trust “experts” far too much (and experts are often dead wrong).

In 2015, Science, a reputable, peer-reviewed journal, published a meta-study about the reproducibility of psychological studies. In theory, if an experiment is done well, you can repeat the experiment and get the same results nearly every time.

The results of the meta-study were alarming. When a team of researchers attempted to reproduce 100 published psychological studies, they found that only about 39% were reproducible.2

The implication of this study is that as many as 61% of published psychological experiments reported false findings. In other words, the majority of what psychologists believe to be true, may be in fact be false.

This alone should make you realize that so-called experts aren’t as trustworthy as we’ve been led to believe, but the rabbit hole gets deeper.

In 2016, Science, the same journal, published another article; this one claimed that the initial 2015 meta-study was poorly done and should not be trusted. The article goes on to claim that most psychological studies are easily reproducible and report sound findings.3

To be clear, the same reputable journal published two articles from “experts” claiming exactly contradictory findings.

What. The. Fuck.

Before you write that off as a quirk of psychology, realize that this sort of extreme confusion occurs in many fields.4

Of course, if we’re having this issue with esteemed journals and credentialed experts, imagine how much bad information exists on blogs, podcasts, TED and TEDx talks, online forums, etc.

So should you be suspicious of everyone? Not exactly. I suggest letting select advisors, mentors, and thought leaders earn your trust. Get in the habit of experimenting with ideas that intrigue you. As you experiment with them, trust your direct experience.

The nice part about all of the confusion among experts is that it gives you permission to trust yourself. Since the experts aren’t as trustworthy as we’ve been led to believe, you’re free to act on your own truth, logic, and intuition, and then see what happens.

Why we don’t trust ourselves part 4: the biggest demon of them all.

The biggest demon of them all is a quiet one. As already discussed, societal conditioning tricks us into believing that we can’t trust ourselves. The fear of failure makes us reluctant to take risks. We outsource our opinions and behaviours to “experts” who haven’t earned our trust and are often more confused than they let on.

All of those factors blend together and trick you into believing that you aren’t trustworthy, scaring you off from testing that (flawed) assumption. This creates the illusion of being smaller, less powerful, less intelligent, and less capable than you truly are.

Trust that you can achieve whatever you throw your heart and mind into (and I promise, you can).You’ll see: you are far more capable than you’ve been led to believe.

Ok, so how do I actually start trusting myself?

In 2014 I attended a small conference filled with famous thought leaders. I was in awe.

Many of the thought leaders were drinking coffee blended with globs of butter and coconut oil. It seemed like the most repulsive thing in the world.

But since they were doing it, I tried it too. Sure enough, it was repulsive. Not only did it taste gross, it made me feel nauseous and jittery. I went on to drink that stupid coffee concoction three more times over the next few weeks. In fact, there’s a chance I’d still be drinking it if an ex-girlfriend didn’t point out how absurd my behavior was.

If I trusted myself, I would have been secure in my direct experience and never tried the coffee again, but I didn’t trust my direct experience. I assumed that since all of these fancy people enjoyed butter coffee, I must have been missing something. I wasn’t. I was just another one of the audience members pretending that I could see the emperor’s new clothing; I’d bet that many of the other attendees were faking it too.5

Trusting yourself is about believing your direct experience is valid. To make this simple, your direct experience is valid. Feel an authentic desire? Act on it. Friends raving about something that seems ridiculous? No sweat, they’ll still love you (and you’ll notice that several confide that they think it’s ridiculous too). Drink a butter coffee and think it’s the worst thing since Comcast? Stop drinking butter coffee.

Trusting your direct experience does not mean that you’ll always get it right. A skilled magician can make you feel as though you’re having a direct experience with the impossible. A skilled marketer can create fake desires that feel like real desires.

Trusting yourself means being cool with getting it right most of the time, and learning that it’s no big deal when you don’t.

There is no singular behavior that will allow you to suddenly trust yourself. However, a collection of small actions compounded over time will alchemize and inspire an unshakable sense of trust.

Read through the actions below. Experiment with the ones that you’re drawn to. The more you play with them, the more trust you will build in yourself.

Default to your first thought. If your mind is like mine, you often have multiple thoughts in response to…everything. There’s the initial thought, but then you question it, look at it from different angles, weigh previous experience, etc. To help you see how capable you are, just go with your first thought. Do this with responses to questions, orders at restaurants, jokes you’re thinking of making, courses of action, etc. Often, out of habit, I think of three or four responses before remembering that trusting myself is more important than being clever. Then, I return to my initial thought.

You’ll discover that your first instinct often works well. More powerfully, you’ll realize that even when it’s not effective, you can bounce back with minimal – if any – consequence.

Spend time in silence. It’s hard to know who you truly are when you live in a noisy world. There have been many times in my life when I was sure obtaining something would make me happy. As soon as I got it, I felt disappointed. This happened because I was out of touch with myself and acting on fake desires.  

If you’re acting on fake desires, trusting yourself is irrelevant. To separate your true desires from the false ones, spend time in silence. This can be done at the daily level by literally creating silence in your life (meditation, journalling, chilling without your phone and computer, long walks with no distractions, etc), or at a broader level by secluding yourself for a day or two. You’ll notice that your core desires and truth burn much brighter than the fake desires.

When considering other people’s advice and opinions, ask yourself, “Do I want to be like this person?” If the answer is yes, give their perspective more weight than if the answer is no. If the answer is no and you still take their advice seriously, you are signaling to yourself to trust people you don’t admire more than you trust yourself.

Stop reading so much personal development and self-help. Instead just do it. Seriously. You’ll be surprised how easily results come when you trust yourself. This is because you are more capable and talented than you’ve been led to believe. When you don’t get the results you were looking for, you’ll learn. By the way, taking action, seeing what happens, and tweaking variables is exactly what people who achieve absurd levels of success do.

When you’re curious about something, try it. See what happens. To experiment in life is to realize that you got this shit. To spend your time in your head and in the books and to default to untrustworthy “experts”  is to fear your own power.

Stop pretending like you need a plan. One of the biggest inhibitors to success is the belief that you need to have a complete plan before you start. You don’t. Extensive planning and research is symptom of not trusting yourself.

All you need is a strong desire and the audacity to take the first step. The first step will lead you to the second. The second step will lead you to the third, and so on.

Think of it as driving by headlight on a foggy night. The headlights illuminate 15 feet ahead of you. That’s enough for you to move forward, and as you do, the next 15 appear. This keeps happening until you get to where you’re going. The same concept applies to trusting yourself.

Be as honest as possible. Being honest not only requires not lying, but also speaking your truth and acting in integrity, even when it’s uncomfortable. If you make a strong commitment to honesty, trusting yourself and taking action happens automatically. Do not underestimate the raw power of choosing to be honest in both word and action.

Why I wish I dropped out of college…

I wish I dropped out of college. Looking back, it wouldn’t have affected my work one way or the other. People have always hired me because of my track record for getting results, not because of my dime-a-dozen credentials.6

Dropping out would have enabled me to lead by example when I encourage others to leave the beaten path. Today, my college education makes it harder to do that, and while it may not seem like much to you, it’s something that plagues me. I feel like I’m not quite the man I could have been. Had I trusted myself to leap, I would have signalled to myself that I was worthy and capable of acting on my truth.

When you act on your truth, you create deep, unshakable integrity. Staying in college for those two final weeks delayed the development of my personal integrity and stunted my ability to trust myself by several years.

I’m not saying that the secret to trusting yourself is dropping out of school. The secret is acting on your truth.

You don’t need a net

Learning to trust yourself is leveling up in life. As you learn to trust yourself, confidence and self-love are also developed in tandem.  

In the beginning, trusting yourself feels like leaping without a net.

After you’ve done it a few times you realize that you never needed a net to begin with.

As trusting yourself becomes habit, it feels more like a super power than anything else.

As you trust yourself more and more, you’ll notice that you’re far more capable than anyone expected. Additionally, you’ll notice that you’re far more capable than you expected. You’ll find that happiness, success, and confidence are byproducts of living in integrity. Don’t take my word for it. In fact, taking my word for it would be counter-productive. Instead, screw your courage to it’s sticking point and see what happens when you trust yourself and start living your truth.

How to handle the emotional chaos of change

August 2015: I’m in the viewing car, watching the sunrise and clutching a black coffee as the world speeds by my window.

All at once, everything I’ve been avoiding hits me. The distance from my friends and family back East, the reality that my ex and I aren’t getting back together, the lack of clarity about my work, and the ongoing struggle to find my path. Hell, I don’t even know where I want to live. More than anything, it feels like an emotional free fall.

When the tears finally come, I don’t bother trying to choke them back.


Over the past few months, many of the people I love have endured major changes that will affect huge parts of their lives.

Some chose to make changes, like R* who is to leaving his job in order to spend four months traveling before going back to school.

Others have had change forced upon them. For instance, K* who was broken up with and then lost his grandfather, or L* who  was fired from his job with only one month’s savings to his name.

A few fell somewhere between choice and circumstance. M* who is separated from his wife and trying to make it work, or J* who is graduating soon and unsure of what to do next.

As I write, I am finishing an eleven-month span of dramatic change in my life. It started in May when a long-term girlfriend and I broke up. Two months later, I sold my possessions in Washington, DC, and left to find a new home. Along the way, I decided to suspend my work as a professional speaker, start, and experiment with a wide variety of new projects.

At times, the constant change had me choking back tears; I was unready to give up my old life. At others, it rendered me so wildly alive that I experienced more in a week than many people experience in a year.

These are my personal notes on how to handle life when just keeping your head above water is a full time job. I’m sharing them here for my friends, family, readers, and clients alike, since all of us get caught up in the tides of change.

It’s normal to feel scared, lost, and stressed

As a strategy for streamlining our lives, we unconsciously assume that tomorrow will be similar to today. We assume that when we wake up the people we love will be alive, we will have the same job, and we will hold onto the same dreams.

Ninety-nine percent of the time these assumptions are accurate, which allows us to organize, predict, and control our day. These assumptions bring a certain calm and freedom that enables us to place our attention on other parts of life.

During times of transition, some these assumptions no longer mirror reality. Our lives stop behaving like they used to. The sheer act of existing takes more time, energy, and effort than before. Stress levels and emotions spike.

The painful part of the process is scary. You are trading a known present for an unknown future. I call the process of slowly adapting to your new reality, “Recalibration.”

It’s also normal to feel alive, exhilarated, and confident

Counterbalancing the fear, you will also feel huge rushes of excitement and vivacity. You are ushering in a new era of life and with it, the opportunity to become a better version of yourself.

My wish is that you leverage the changes in your life to become more you.

Yes, there will be times when the process feels crippling. Endure. Those rushes of energy and exhilaration hold more truth and more promise than the moments of fear and despair. The trick is learning to weather the storm…

Weathering the storm: 8 reminders for dealing with change

Remember: you can handle this. Things will work out. Most of us have been tricked into believing that we are less capable than we truly are.1

The truth: you are an overwhelmingly capable person filled with more talent and potential than you’ve been led to believe.

When you find yourself freaking out because everything feels unstable and unpredictable, repeat to yourself, “I can handle this, I can handle this, I can handle this.”

Though it may not feel like you can handle it in the moment, I promise you can.

Lean on your support system. A lot. I bet that you would leap at the opportunity to help someone you love. Despite the willingness to provide help, many people find it difficult to ask for help (and yes, that happens to me too). It’s time to get over that.

Here’s the rule of thumb: if you need help, ask for it. Be honest, vulnerable, and open. Email a friend, call your family, or meet with your mentor. The more you lean on your support system, the easier it will be for you to keep your head above water.

If you’re reluctant to ask for help, remember this: you’ve experienced the joy helping someone you love numerous times. By failing to ask for help when you need it, you’re not only depriving yourself, you’re also depriving the other person of the happiness that comes from helping a friend.

Say “No” more often. You can’t handle as much during transition as you can when you’re stable. Remember that whole recalibrating process we talked about earlier? Yeah. It’s taking up a lot of space in your life.

Get used to saying, “No” to the stuff that you don’t want to – or can’t – do. Saying “No” can be challenging. My uncle taught me an elegant approach. He suggests, “I’m so honored that you’ve asked me to do this. It really means a lot to me, but unfortunately, I can’t.”

While you’re at it, get in the habit of dropping balls from time to time. Skip the wedding you said you’d attend. Tell your boss that the report is going to be late. Step down from the volunteer organization. The less you care about something, the quicker you should let go of it, especially during times of transition and reinvention.

Allow yourself to feel the pain of transition. At the beginning of this article, I mentioned breaking down on a train. That was the first time I allowed myself to feel the fear, pain, and confusion that I had been suppressing. It felt good to break.

If you’re not allowing yourself to feel the chaos of transition, you’re doing it wrong. Transitions suck. They’re hard. The fastest way to get back to yourself is to feel the pain in real-time.

Be easy on yourself. One of the tricks to making transitions work is lowering your standards a bit. If you’ve been going to the gym four days a week for the past year, but your grandfather’s recent death has made you too depressed or too busy to hit the gym, don’t beat yourself up for being less than perfect.

Here’s a trick: most people are more compassionate to their best friend than they are to themselves. When you’re starting to be hard on yourself imagine that your best friend is in the exact same situation you’re in. What advice would you give her? How would you want her to treat herself? Now transfer that compassion and advice to you.

And while you’re at it, start celebrating the small victories you experience each day like making a healthy breakfast or answering your emails. Don’t hold yourself hostage from feeling good until something big happens; instead, find the joy, success, and happiness in little things. You’ll be back to taking over the world soon enough.

Practice “Do nothing days.” From time to time, hide away from the world and spend the day decompressing. Spend your time watching movies and reading books. Ignore the outside world and your normal responsibilities. Rent a hotel room if you need to. Allowing yourself to stay in a neutral, stress free state for a day or two is revitalizing. You’ll be shocked by how refreshed you feel after a day of doing nothing.

Take it one step at a time. It’s tempting to think of changing your life as one giant project.

The problem: giant projects are overwhelming and have no clear starting points. They are easy to think about, but almost impossible to do. Instead of taking the transition as a whole, break it into smaller tasks and tackle them one at a time.

I’m new to Denver, and I’m working to build a life here that I love. Without breaking it down, the task is so big and vague that I wouldn’t know where to begin (and because of that, I wouldn’t begin). For me, a great life in Denver includes:

  • A gym that I love
  • A coworking space filled with people who inspire me
  • A group of friends I see often
  • A volunteer position helping neglected kids
  • …Etc.

By breaking it down, the transition from “New to Denver” to “A great life in Denver” becomes manageable. More importantly, it doesn’t seem as daunting and stressful.

Even transitions as common as starting a new job are best taken step by step.

  • Get the appropriate clothing
  • Figure out how you’re going to commute
  • Go through orientation
  • Befriend a few coworkers
  • …Etc.

By breaking the transition into individual tasks, it becomes easier to handle. You’ll be able to see the progress you’re making and won’t be deceived by the illusion of spinning your wheels.

And if you’re wondering where to start, begin with the task that is going to be the highest leverage for you. In my example above, finding a great coworking space will make it easier for me to create a group of friends that I see often.

Hold on to the still points in your life. As everything starts to change, it’s important to keep a few things steady. They don’t have to be big to offer a sense of stability and predictability. Personally, I’ve been listening to the Sara Bareilles album “Brave Enough” almost every day for the past 8 months and watching “The League” when I need to decompress. I also maintain a morning routine (meditation and gratitude) that follows me everywhere I go.

The important part is to pick things that are meaningful to you – music, TV shows, movies, foods, exercise routines, etc. – and infuse them into your daily life during transitions. Then, even in the most unfamiliar circumstances you’ll be able to find something that feels normal.

You’re more capable than you’ve been lead to believe…

During times of change and transition, you are surrendering an old version of your life to allow space for something new.  Doing so is scary and destabilizing.

I want to leave you with one thought, and it applies to anyone in a state of transition: you’re more capable than you’ve been led to believe and you are stronger than you know. Weathering the storm will prove it to you.

Looking for happiness? First, let the crippling pain of existence destroy you.

“In the midst of winter, I found there was, within me, an invincible summer.

– Albert Camus


There is a reliable path to happiness, but I warn you: it’s a path for warriors. It requires casting away the fog that prevents you from dwelling in reality, and feeling the pain you’ve been avoiding.

What follows are instructions for your heart, not your head.


Walk down the street at rush hour and look into the eyes of the people you pass. You’ll notice that where there should be fire and light, there is vacancy.  These people are living with muted feelings and clouded minds. They are dazed by a quiet sense of being disconnected from themselves.

I know this feeling of being disconnected; I’ve been there many times before. It’s a side effect of living in a society that expects people to behave more like cogs in a machine, than the vital forces of nature they truly are.


Being human means dealing with suffering. Even if your life is better than average, you will still experience an abundance of loss, heartbreak, anxiety, and despair. To cope, most people rely on numbing agents to dull the pain. The most common numbing agents:

  • Getting caught up in stress and busyness
  • Regularly using alcohol, weed, and other drugs
  • Surrounding yourself with drama, fear, and anxiety
  • Filling your day with the white noise of background music, podcasts, and perpetual small talk
  • Staying in bad relationships – romantic or otherwise – in order to avoid being alone
  • Pretending that you’re less capable than you truly are
  • Depriving yourself of sleep, nutrition, exercise, connection, play, and nature
  • Staring at televisions, computers, smartphones, tablets, and other tools that induce trances
  • Lying, either overtly or subtly

These forces keep you away from yourself by dulling your emotions. In moderation, they are harmless. In excess – which is more common – they are deadening.


One thing I can promise you is that bouts of slap-me-in-the-face-this-is-too-fucking-good levels of happiness are available to you. Even as you read this, they are resting within you, waiting to come out.

To access them you must begin by clearing out all of the pain you’ve been holding on to.


Temporarily remove whatever you rely on to avoid feeling the full force of life. For a few days, keep your electronics off, get plenty of sleep, eat healthy foods, don’t touch intoxicants, and be alone with yourself, undistracted. Spend time journaling and reflecting in nature.


You may notice that you are bored.


Do not fall into the trap of distracting yourself. In this context, boredom is your mind’s last line of defense. Lean into the boredom. Ask yourself: what is my mind trying to prevent me from seeing or feeling right now?

This is the beginning of dwelling in reality. You’ll be surprised by what you uncover.


You’ll start to notice the pain you’ve been avoiding. The failures you’ve tried to forget. The wounds that never quite healed. The friends who betrayed you. The embarrassments from your past.

Your job is to feel it all.

It may feel like you’re breaking. That’s good. Lean into that feeling. Instead of choking back the tears, surrender to them. Allow yourself to break.

Do what you must. Scream, smash plates, punch the wall, destroy the pillows. Do it all while blasting heavy metal and cursing at the top of your lungs if you would like.

Release the pain that has been building in you. It’s been holding you back from becoming the force of nature you truly are.


You’ll notice that behind the wall of pain rests a stable sense of happiness and power.

That happiness is always there for you. You may return to it as you wish.


Once you have found your core of happiness, here is how to maintain it:

  • Let go of the need to be happy all the time. You are a force of nature, not a Disney character.
  • Align your life with your true desires. If you want to be a writer but you’ve been working as an accountant, start writing more. You don’t have to quit your job, but denying what you truly want is a step in the wrong direction.
  • Fill your life with the people and activities you love. Strip away those you hate.
  • Reduce the numbing agents in your life and allow yourself to feel the full pain of existence more often. This makes accessing the happiness within easier.
  • Remember: beauty is found by embracing the rough edges, not in the frightened attempts to be perfect.

When you allow yourself to feel the full force of existence, you will be able to dissolve the pain that has been holding you back from truth, power, and, ultimately, happiness.


On giving up alcohol for a year


I was 17 the first time I got drunk. K*’s parents were out of town and we threw a huge party at his house. It was awesome. Since then, I’ve spent at least one month each year sober to ensure that the habit is in check (alcoholism runs in my family).

In 2015 decided to take on a new personal challenge: go the entire year without having a single drink. I would still go to bars, parties, bachelor weekends, etc. I just wouldn’t drink.

There are plenty of things you can expect to happen when you quit drinking (your sleep and health improve, you don’t see your drinking buddies so often, etc.). Those are well covered in other articles around the internet. Here, I’m going to share what surprised me about the year of sobriety – both the good and the bad.

5 things about sobriety that surprised me…

1) I wasn’t perfect. This helped me become more forgiving of myself and others. I approached this challenge in the same way I approach pretty much everything in life: I expect to be perfect (which of course, is delusional).

There were six times in 2015 when I chose to have a drink. So technically, I failed the challenge. Being forced to own my imperfections created an opportunity for growth.

My first reaction to not living up to expectations is to beat myself up. With the help of a mentor, I used this as an opportunity to practice self-forgiveness, instead of self-punishment. It helped me accept the reality that making mistakes and being imperfect is no big deal. In fact, it’s completely human.

I’ve found that by being more forgiving of myself, it’s much easier to be forgiving of others.

2) Three people went out of their way to make me feel bad about the year of sobriety. I’m used to making decisions that most people don’t understand, but none have been as controversial as giving up alcohol for a year. In fact, several friends went out of their way to make me feel bad about it.

  • One guy called from France to tell me he felt sorry for me. He felt that I was making a real mistake in depriving myself of the “Joys of alcohol” and that I should seriously reconsider.
  • Another friend of 15 years emailed me saying it was a stupid experiment and that I was setting a bad example for my readers and audiences. He also cc’ed our mutual friends on the email. No one responded.
  • A woman I was dating during part of the experiment yelled at me because she felt I was neglecting her desire to go out and have fun with the people she loved. When I reassured her I’d still go to bars and parties, she said it wasn’t the same and stormed off. To be fair, she’s not actually wrong, and I’ll share more on that later.

While those were the only three instances where people went out of their way to be discouraging, few people in my life put any real effort into understanding why I’d bother giving up booze for a year.

The default attitude towards drinking is that everyone drinks. If you don’t drink, it’s either because of your religion or you’re in recovery.

This challenge put me in the blue unicorn category. I had no reason not to drink, beyond curiosity, growth, and a hunch that my life would be significantly better without booze.

Because of my unusual choice few people understood what I was doing.  

3) During the year of sobriety, a long term girlfriend and I broke up. Sobriety magnified the pain and then sped up the healing. Normally after a breakup, I would mourn the loss by going to the bar for a few (or rather, a few too many) drinks.

In 2015, this wasn’t an option. By staying completely sober through the breakup, I was forced to confront my pain head on. This created moments of intense, intense pain. It also sped up the healing process.

The loss of love is one of the most painful things people endure. To avoid the pain, we use a wide variety of tools to distract ourselves (alcohol, casual sex, staying busy, pretending like we’re not hurt, etc.). While avoidance seems like a good idea in the moment, it’s ultimately an exercise in futility. In time, you will be forced to confront the inner struggles you’ve been suppressing.

Alcohol numbs. Take it away and suddenly, the highs are higher, and the lows are lower. The lows don’t last as long, because you’re forced to come up with new, more effective ways of mitigating the pain.

My advice to anyone going through a breakup (or any difficult spell) is to feel the full pain of your loss, instead of numbing yourself. Experiencing your pain will help you bounce back faster.

A note about dealing with intense pain: one of my commitments to you is to be realistic. So often, writers babble on about how everyone should be perfect. Fuck that. We’re humans, not robots. My advice is to stay sober and clear during intense pain. However, if anyone – my future self included – uses alcohol or any other fairly safe form of escape to weather a storm or two, I will not fault you.

4) Sobriety made dating easier. When was the last time you had a first kiss without alcohol?

Before the year of sobriety, I was probably 17. Maybe younger.

Alcohol is a nearly permanent fixture of the dating scene. At first, the year of sobriety made dating – especially first kisses – intimidating.

After a few sober first dates though, something weird happened: dating became easier than it had ever been.

It’s easier to get to know someone when you’re sober than when you’re buzzed. It’s also easier to sense chemistry (as opposed to lust or the need to alleviate loneliness) when you’re sober.

A common question I get from friends is, “How do women react to your decision not to drink?” Most respond neutrally. Generally they have a few questions. That’s it. I’m sure that there are women who wouldn’t date me because I don’t drink; I’m probably not interested in them either, so nothing is lost.

5) I was reminded that the strongest form of leadership is leading by example. Before the year of sobriety began, I wrote a Facebook post about what I was attempting and why I was doing it. I invited people to join me.

Several friends decided to give up alcohol for the year, and dozens of people committed to spending at least one month sober.

Ultimately, this reminded me that persuasion is a waste of time compared to the efficiency of living out loud.

The unexpected benefits

I saved thousands of dollars. Alcohol adds up. I was accustomed to paying $30 for a round, $15 for a bottle of wine, and $5 for a beer.

Individually, none of those purchases are particularly expensive. Collectively, they emptied out my wallet.

If you’re in the habit of spending $50/week on alcohol (and I suspect that a lot of people are, even though they don’t realize it), you pay $2,600 annually for booze. That’s a good chunk of change that could easily be put towards something else (debt, travel, starting a business all, etc.).

I stopped running in existential circles.  Most of our actions are the result of habits. Some are obvious: wake up, make coffee, brush your teeth, check your email. Others are subtle: you’re bored or uncomfortable, so you take out your phone and check Facebook, reddit, and twitter.

For me, drinking was a habit. I’d have a drink after a speech to wind down. When I went out for dinner, I’d order a beer. Most Fridays, I went to happy hour with friends.

When I stopped drinking, my habits changed automatically. I started going for long walks after speeches. I ordered water or juice at restaurants. I convinced my friends to play Frisbee after work on Fridays.

The habit of drinking becomes a hole that many people fall into on a routine basis. For most, it takes up valuable space in your life subtly reinforcing the bad habits. When you stop drinking, you eliminate one of the holes on your path, and encourage growth.

I started stringing multiple good days together. For most of my life, I would have two or three good days in a row, followed by a crappy one. I spent a lot of time trying to figure out how to have more good days without the bad ones, but I could never find a solution. When I quit drinking, it happened automatically.

It became easy to string more good days together because of the space sobriety created in in my life. I had more money, more time, and more energy at my disposal.

Are all of the days in my life great now? Of course not, but I’m having far more  good ones than in the past.

The downsides

Even the most positive changes have some negative side effects. To ignore the negative is to dismiss reality.

I felt left out. There were a few times when my friends were doing wine tastings or having craft cocktails where I just felt left out and lonely.

While I’m glad I consistently said, “No” in 2015, moving forward I’ll say, “Yes” a bit more often now that the challenge is over (more on that in a moment).

Not drinking makes some people who drink uncomfortable. I mentioned earlier that an ex-girlfriend and I had a fight over my choice to give up drinking. She said going out wouldn’t be the same if I was drinking seltzer and she was drinking whiskey. She was right. We were no longer sharing the experience as closely as when we were both drinking or both sober. This made her uncomfortable. Honestly, she wasn’t the only one.

I know this may be discouraging but if you choose not to drink, it will make some people uncomfortable. Inspiring discomfort in some people takes a bit of getting used to, but eventually you realize that their discomfort is their problem, not yours.

My recommendation to you…

If you’re interested in experimenting with sobriety, here is what I suggest.

First and foremost: have all the drunken nights you think you want to have. Seriously. If you feel pulled towards going out and getting drunk, do it. Lord knows I’ve had plenty of drunken nights in my life, and if I’m being completely honest, I can think of a few nights that were wayyyy better because I was drunk. I’m glad I got it out of my system.

It would be sad to die feeling as though you missed out on something fun. If drinking feels important to you, go for it. Alcohol itself is amoral. Your actions while drinking is where right or wrong comes into play. As long as you’re responsible to yourself and others, there’s no need to deprive yourself.

Over time, reflect on your experience. You’ll notice that after a certain number of nights out, you’ve already had every alcohol experience that there is (or at least all of the ones you want to). They are:

  • The night you hooked up with someone
  • The night you did something crazy
  • The night you had tons of fun
  • The night you were more vulnerable and open than usual
  • The night you spent wayyyy too much money
  • The night you were alone and lonely
  • The night you drank to numb the pain
  • The night nothing much happened
  • The night you did something you regret
  • The night something bad happened
  • The morning after where you swear, “I’m never drinking again.”

That’s about it. Once you’ve done all of the above, you’ve had 90% of all drinking experiences. Maybe more. Of course, most people will go on to repeat the same nights again and again and again (I did), but eventually, you’ll realize that you have to get off the hamster wheel if you want to move forward.

If you’re a regular drinker, consider taking one month off every now and then. Why? To make sure you are in control of your intake and to see how it’s affecting you.

Alcohol is an addictive drug that influences who you are, even if you’re not an alcoholic. Because drinking is so common, most people lose sight of how it affects them.

Some months are much easier to spend sober than others. January is probably the easiest.

If you’re saying to yourself, “I can do a month, but I won’t,” then check yourself. Become curious about why you’re so dead set on drinking that you can’t go 30 days without a drop. Are you running from yourself? Have you made a hobby out of something toxic? Is it because alcohol plays such a large role in your life that you fear its absence? Do you depend on it for socializing or relaxing? Are you worried about what other people will think?

If you’re saying to yourself, “I can’t take a month off,” then that’s great information. I admire your honesty. Most people don’t have the courage to admit that. Please get the help you need. You’re an amazing person deserving of an amazing life.  

Want to take more than one month off or reduce your consumption in general? Here are a few approaches to tapering your consumption. Experiment with the ones that seem right for you:

  •      Limit your consumption to a specific number of drinks per week (or night)
  •      Stop doing shots
  •      Stop drinking liquor
  •      Only drink on the weekends
  •      Only drink on special occasions
  •      Only drink on extremely special occasions (that’s where I’m at)
  •      Stop drinking altogether

So, will I start drinking socially again?

My friends keep asking, “So now that the year of sobriety is over are you going to start drinking again?”

My answer: not really.

On very special occasions, I can see having a drink from time to time. I wouldn’t say, “No,” to a Guinness in Ireland or a Tequila shot in Mexico. I’d raise a flute of champagne at a wedding. I’d definitely have a few scotches at my brother’s bachelor party.

But in the grand scheme of things, no, I’ll never go back to drinking socially like I used to. The benefits of being 99.97% sober are so significant for me that I’m happy to pass.

My wish for you is that you take the time to find the relationship to alcohol that helps you be the best version of yourself.

Loving yourself is really f***ing hard: here’s how to do it

UPDATE AUGUST 21, 2020: Quick heads up – my thinking on some of the topics in this article has changed. Though I broadly stand by this article, there is a little fine tuning that needs to take place. Specifically, I no longer believe it is appropriate to consult a coach, mentor, or “guide” when developing self-love. If you choose to include a professional, I think it is important that you work with a licensed therapist. I also believe that learning to love other people, and letting them love you, is a critical component of self-love.  Please see points 4 and 5, here for more.  The original and unedited article can be found below.


July 2012: I’m awake and hung over. Against my will, reality has come crashing back down. I can’t stop my mind or my heart from reciting the facts of my recent past.

  • Three weeks ago my best friend moved away.
  • Two weeks ago E* and I broke up after several years of being together. We used to talk about getting married.
  • A few days ago R* passed away. He was 28 years old.

I’m terrified of the future, afraid that it will only hold more pain, more loss, more suffering.

I don’t know how many days it’s been since I collapsed and I don’t really care either.

I drag myself out of bed and look in the mirror. I look exactly how I feel.

Suddenly, almost like it does in the movies, it hits me: if I ever want to get back on my feet, I need to learn to love myself…

That moment was the first time I realized that I had a relationship to myself. It inspired three years of study during which I read countless books and articles, experimented with dozens of ideas, worked with professionals, and eventually repaired the broken relationship I had to myself.

Here is what I learned about how to love yourself. I hope it is of service to you…

The negativity bias, attentional filters, and other things that make loving yourself difficult

Imagine that two articles about you have just been published. The first raves about you and your work. It claims that you are God’s gift to humanity, showers you in praise, and encourages everyone to follow your lead.

The second proclaims that you are a complete idiot and a blight upon this world. It insults you and dismisses your work as a waste of time. It encourages people to completely ignore you.

Which of those two articles would get more of your energy and attention?

If you’re anything like me the negative article would be far more impactful than the positive one. As it turns out this is normal. It’s the result of what psychologists call the “Negativity Bias.”

The negativity bias is the phenomenon that if there are two equally charged stimuli, the negative one will attract more of your mind’s attention.

The funny thing about the negativity bias is that from an evolutionary perspective, it was a huge competitive advantage. Say that you are a hunter-gatherer out looking for food. Suddenly, a poisonous snake starts slithering up to you and a wild boar that could feed your family for weeks runs across your path. Your subconscious has milliseconds to decide which animal to pay attention to.

Choose to hunt the boar and you’ll be vulnerable to the snake and likely to get bitten. Choose to defend yourself against the snake, and you will avoid getting bitten, but the boar will get away.

All of our ancestors who naturally paid attention to the positive stimuli in their environment (the boar) died out because they failed to identify the threats around them (the snake).

In the past, the negativity bias was a useful adaptive response. Today it just makes you pay too much attention to what’s wrong with you and the world.

Attentional filters: in any given moment you are bombarded with more stimulation than your mind can actively process. In order to function in an environment that is supersaturated with data, your mind filters out almost all of the information around you. This is called attentional filtering.

A side effect of attentional filtering is that the world ends up looking like whatever it is you’re focused on.

For example, as you read this sentence, you are not not actively paying attention to how your toes feel in your socks; however now that your attention has been called to your toes, you notice them. That’s the attentional filter in action.

The combined effect and the media: minds are not very good at processing reality. First, your mind is much more likely to pay attention to what’s wrong, than what’s right (the negativity bias). Second, your mind is forced to filter out almost all of the stimulation in any given situation (attentional filters).

Because of this, your mind has a tendency to view you as being far less intelligent, capable, good looking, charming, and ultimately, worthy of love than you actually are.

This is further exacerbated by a media culture that preys on fear, and an advertising culture that strives to make you feel small unless you’re up to date with all of the latest trends.

Simply put, if you are having trouble loving yourself, there is nothing wrong with you. It’s a side effect of modernity.

Fortunately, loving yourself is a skill that can be learned and mastered. The first step is realizing the truth about your importance…

You are the singular most important person in your world.

Everything in your life flows from your relationship to yourself. Learn to treat yourself like someone worthy of love, respect, and compassion, and your life will flow more effortlessly, abundantly, and joyfully than you can imagine.

Treat yourself like someone worthy of contempt, disdain, and indifference, and each day will be a struggle to keep your head above water.

The unfortunate part is that most people never put much energy into their relationship with themselves. They drift through life acting as their own worst critic, working to inhibit their potential, and keeping their hearts and minds guarded.

I know that sounds dramatic, but pause for a moment. If you spoke to your friends the way you speak to yourself in your head, would you have any friends left? Before I started working on my relationship to myself, I wouldn’t.

Or at a deeper level: have you ever felt fully loved by yourself or someone else?

You’d be surprised by how many people’s honest answer is, “No.” I’ll come back to that in a bit.

I spent years of my life quietly but cleverly telling myself I’m not worthy. I obsessed over mistakes from my past. I endlessly replayed embarrassing moments (while somehow neglecting the beautiful ones). I failed to forgive myself for being a human, (a very real part of me wants to be a demi-God).

If you can relate to any of that, don’t worry; it just means you’re human too.

Long time readers will know that I tackled the topic of self-love several years ago. At the time, I shared everything I knew. But here’s the truth: I still had a few boulders preventing me from fully seeing and loving myself when I wrote that article (though I wasn’t aware of them at the time).

My journey isn’t complete and never will be (self-love is a process, not a destination), but I have come a long way in my practice, and hope to help you with yours; because the truth of all this is that loving yourself is really fucking hard. It shouldn’t be, but it is.

The easy path is to distract yourself with drugs, alcohol, stress, white lies, busyness, bad relationships, external validation, and pretend happiness. But doing this makes you more of a cold, unfeeling robot, than a vivacious, hot blooded human. One of my deepest wishes is that you wake up to how amazing and powerful you truly are. That journey requires finding the courage (and it does take courage) to live and love while you’re still alive.

The four levels of self-love: an overview

Think of your relationship to yourself in four levels:

Level 1: the day-to-day. Do you treat yourself like an important person who deserves love and respect, or are you subtly placing unreasonable expectations on yourself? What do your behaviors say about your relationship to yourself?

If you do not treat yourself as you would treat someone you love, you’ll never feel the love that flows from your core.

Level 2: embrace your dark side. Do you accept and acknowledge your dark side when it surfaces? Do you embrace the part of you that is pessimistic, lazy, depressed, violent, crude and offensive? Or do you pretend that everything is rainbows, gumdrops, and unicorn shits. Do you pretend that every day is a good day?

To be human is to be stormy and tempestuous one day (or moment), and then calm and sunny the next. To pretend otherwise is to deny who you truly are, and denying your truth is an act of self-loathing.

Level 3: the deep work. Have you truly seen yourself for who you are? Can you grasp that your imperfections are what make you perfect? Have you owned the reality that life was inflicted upon you without asking and with it came trauma, abuse, disappointment and eventually death? Do you acknowledge that these struggles will forever shape your life until you confront them and begin the healing process?

One of the most beautiful truths about the human experience is that it’s never too late to become the man or woman you truly are. You can begin healing, growing, and flourishing now. Doing so requires the courage and clarity to see yourself, so that you may begin the process of tearing down the walls that protect your heart.

As you do this you will open to the flow of love and life around you.

Level 4: the highest form of love. Every single person was born with unique gifts. The gifts can be anything from athletic performance, to empathy, to humor, to spirituality, to business acumen, and everything in between.

The real work of learning to love yourself is learning to see who you truly are and accepting it all. Along the path, you’ll discover deep gifts that you were born with.

The highest expression of love for yourself and the world is sharing those gifts freely and abundantly.

Your path is yours and yours alone…

What follows are guidelines for learning to love yourself. They are the things that consistently get results, laid out in a sequence that is congruent with how the heart and the mind tend to work.

But there is no singular path forward. Your job is to find your path. I’ll do my best to help, but you’re the one who must walk it.

My advice to you: when you find a step or a suggestion that excites you, experiment with it. See if it opens you and makes you happier. If so, keep working with it. If not, let it go.

When you find a step or suggestion that inspires fear, reluctance, or disgust, approach it with curiosity. Ask yourself why you’re having such a strong reaction. Instead of allowing intense emotion to be a brick wall, use curiosity and patience to feel through it.

Let your strong emotions be your guides.

Level 1 – do you treat yourself like someone you love?

The complicated relationship between feelings and actions. One of the secrets of human behavior is that how we feel and how we behave act reciprocally upon one another. In other words, if you treat yourself like shit, you’ll feel like shit. If you treat yourself like an amazing person, you’ll feel like an amazing person.

Pause and take inventory of the actions that you perform throughout the day. Are they reflective of the actions you would take if you truly loved yourself?

For most, the answer is no. Most people don’t get enough sleep or exercise, have crappy diets, work in jobs they hate, and go to great lengths to avoid spending any real time in their own company.

You can take a huge step forward by treating yourself as though you are intrinsically worthy of love. By creating the behaviors and signals that you are in fact an amazing human you’ll notice that you begin to feel that way.

There is no prescriptive blend of behaviors that works for everyone. However the actions below are unusually effective and worth experimenting with. You’ll notice that none of them are obscure or complicated. In fact, they are common. Don’t dismiss these ideas simply because you’ve heard them before. Instead try one or two. Take the risk of treating yourself well and see what happens.

  • Prioritize sleep: aim to get enough sleep so you wake up feeling refreshed. The easiest way to do this is to get up at the same time each day, and go to bed when you’re tired.
  • Exercise: spend at least 30 minutes a day 3 days a week getting decent exercise. This can be jogging, lifting, frisbee, yoga, team sports, whatever.
  • Meditation or silent reflection: personally, I practice Vipassana (Pali for “Insight”) meditation. My suggestion to you is that you experiment with a few different forms until you find one that resonates.
  • Express gratitude: share your sincere appreciation for the people around you. Or write down a few things that you’re grateful for each day. I use the Five Minute Journal for this and love it.
  • Hold space for your religion or spirituality: attend services, study groups, prayer sessions, or read from the texts.
  • Eat a healthy, nutrient-dense diet: if you need guidance on understanding health and nutrition, I suggest starting with Michael Pollan’s excellent (and quick) book, “Food Rules.”
  • Set boundaries: are you allowing toxic people, activities, or habits into your life? If so, slowly start removing them.
  • Play: are you having fun, and enjoying your day-to-day? If not, play more! Shoot your coworker with a Nerf gun, play mini-golf with your friends, or take an improv class.
  • Give yourself small treats throughout the day. Treat yourself to a soy latte. Watch a few cat videos guilt free. Go for a walk. Call in “sick.” Wear your favorite shirt. Giving yourself small gifts throughout the day signals to yourself that you’re an awesome person worthy of a nice life.

The more you act like someone who loves yourself, the more you’ll feel like someone who loves yourself.

Level 2 – embrace your dark side

When I was living in Montreal, I had a roommate who pretended that every day was amazing. She said she loved God, loved life, and felt grateful just to be on Earth.

She also drank a lot, kept a terrible diet, complained that she didn’t have a boyfriend (while also sleeping with countless men), struggled at work, and lacked a social life.

There was a huge disconnect between the stories she told everyone (including herself) and her reality. She wanted every day to be bright, sunny, and joyful.

Just one little problem: it’s not possible to make every day a good day. In fact, I’m not even sure it’s desirable.

Look to nature. Even the most beautiful, ancient forests are sometimes struck by lightning and burnt to the ground. At first glance, this seems like tragic, wasteful destruction. But it’s not. It’s all a part of the natural cycle of life. The fire destroys the forest; the ashes feed the soil; the soil provides a stronger, more nurturing environment; the forest grows back more radiant than before.

Beneath the pain, darkness and destruction rests a quiet core of growth, love, and beauty. This is true of a forest, and this is also true of a human.

To step fully into the human experience you must embrace the darkness. At it’s highest level, this means internalizing that you will die one day (as will everyone you’ve ever loved and everyone who ever loved you). At a more mundane level, it means realizing that suffering is part of the human experience. To deny your suffering is to deny your humanity.

To pretend that you are ok when you’re broken, that you are unafraid when you’re terrified, or that you’re calm when you are rageful is to deny your true nature.

You are a human. Sometimes you’re stormy. Sometimes you’re placid. Sometimes you’re in between. You can’t be any other way. And that’s perfect.

The second level of learning to love yourself is embracing who you really are. Cast away the societal bullshit of trying to be happy and content every second of your life and step into the greater reality of being honest about who you are and how you experience life. By doing so, you will create space to give and receive love.

Doing this requires being honest about who you are, and that means embracing that you have a shadow side.

Three tips for embracing your shadow

  • Forgive yourself for the mistakes you’ve made. You’re not a computer. Your perfections are found through your imperfections. If you didn’t fuck up from time to time, you wouldn’t be a human. If you’ve been beating yourself up for things that happened in your past, release yourself. Accept that you’re human and flawed, and that it’s ok. Stop expecting yourself to be perfect. Instead, revel in the imperfections that make you beautiful.If you’re having trouble forgiving yourself, begin by being more forgiving of others.
  • Realize that it’s human to be disgusting, lazy, jealous, and aggressive from time to time. It’s normal to have dark thoughts and feelings. You can even act on these feelings as long as you find a safe outlet to do so without harming yourself or others. I like to release rage from my system by throwing temper tantrums alone in my apartment. Bottling strong feelings is never a productive idea. An even worse idea is pretending that you don’t have strong feelings or rough edges. Instead, see the truth of who you are. Accept it. When you do, you’ll notice that you can more fully surrender into love.You’d never fault a cat for being a cat. Don’t’ fault yourself for being a human.
  • Spend time alone in silence. Most people fill their lives with white noise. They use podcasts and music and TV and gossip and busyness and the internet and a million other things to avoid being completely alone in their own company. If you ask someone why they fill their lives with so much noise, they’ll say it’s because they hate boredom. In reality, they are afraid of what they may find if they spent time alone and undistracted.In order to fully see yourself, you need to spend time in silence. Turn your phone and computer off and be by yourself. Alone, in silence, undistracted. Don’t be afraid of what comes up. If it’s darkness, trust me, it will pass.

    You might be surprised to find a neglected sense of enchantment, joy, and compassion resting deep inside, waiting for you to create the space for it to come out.

Level 3 – the deep work of removing the walls that protect your heart

Let’s return to one of the questions we started with: have you ever felt fully loved?

I know that’s a heavy question, and I’m not going to ask you to share the answer with anyone besides yourself, but pause for a moment and contemplate deeply into your life. Have you ever felt fully loved?

Far more people than you’d guess have never truly felt love in their lives. I know this because I’ve dealt with this myself, and I have worked with thousands of people who needed help allowing love in.

Realize this: it’s not your fault. I promise; it’s not your fault. We live in a world that values a head far more than it values a heart. The only way a heart could survive is to protect itself with thick walls.

The third and most difficult step involves finding, accepting, and removing the walls that protect your heart.

I’m going to share what I can, but I want to be upfront about something: most people will need a guide to help them fully surrender into their true nature. Personally, I’ve worked with coaches and mentors to do the deep work. I had a huge blind spot around being a child entertainer, that I simply could not have seen without a talented professional.

Be sure to pick your guide carefully because many people who claim to be able to do deep, open hearted work, simply can’t. Look for someone who has already done the hard work of opening herself, is deeply empathetic, unintimidated by other people’s realities, and who you feel very comfortable with. You’ll know you’ve found her when you meet her. You’ll recognize the rare resonance of someone who can truly help you.

If you’d like to start moving down the path on your own, here is what I suggest…

Begin by digging into your life story. The easiest way to do this is to create a space where you can express yourself freely. I suggest either writing in a journal or engaging in a verbal monologue, out loud, to yourself. Your task is to tell your life story from start to finish.

Keep a photo of yourself as a child nearby while you go through these exercises. It’s often easier to love the innocent child you were than the experienced adult you are. The picture helps cement that though you’re older and bigger, you’re still you and totally worthy of the love and light you’ve been yearning for.

As you express yourself, go out of your way to be honest, vulnerable, and forthright. Lean into your rough edges, your humanity, and your rawness.

Within your story, look for a few things:

  • Times when you were being cruel to yourself in a way you wouldn’t be cruel to a loved one.
  • Times when you misperceived reality.
  • Abuse – both subtle and profound – from caretakers. Many people are victims of emotional abuse though they don’t realize it. In fact many people confuse emotional abuse with love. A useful exercise here is to judge your parents.
  • Any traumas, blatant or hidden.
  • Recurring themes, feelings, and situations. Ask yourself, “What feels familiar here?” during particularly emotional episodes of your life.

It’s important to understand that everyone has experienced all of the above. We all beat ourselves up; we all get confused; we’ve all been victims of our loved ones’ bad decisions.

A word about traumas and abuse

One of my friends is a survivor of repeated childhood sexual abuse. Worse still, her parents were aware of the abuse and did nothing to stop it.

One of the many beautiful things about her is how deeply she’s worked on herself and learned to love through it all.

A few months ago, I was sharing something with her about how terrible it was being a child entertainer. In the middle of opening up, I got self-conscious and said, “I’m so sorry. I realize that I’m bitching about something trivial, especially compared to the shit you’ve been through.”

She simply looked at me and said, “Jason, pain is pain. There’s no judgment here.1

“Pain is pain” was one of the most beautiful, liberating phrases of my life. Until that moment, I had been a victim of myself. I pretended that my trauma wasn’t valid, simply because it wasn’t obvious. For years, I had been telling myself that doing 300 magic shows before my 18th birthday, at the expense of my childhood, had no negative effects on me.

The truth is, I was wrong. My past was affecting me. Deeply. And there is an extremely good chance that if you’re reading this, you have endured experiences in your life that were deeply traumatic too.

It’s time to stop lying to yourself. It was a big deal. It’s not your fault. And now, it’s time to heal.

Trauma and pain can be caused by obvious things like being raised by abusive parents, subtle things like a cruel word, and everything in between. Your pain is yours, and it’s real. Where it comes from is not a reflection of your worthiness, strength, or ability as a human.  As you embrace this, you will start to feel an opening.

The deep work of learning to love is done by shining a bright light on yourself and accepting the truth about things that happened in your past.

Level 4 – the highest form of love: accepting yourself and sharing your gift


I am tempted to picture a fully formed, loving human as someone who lives in total bliss. She’s always happy, and her radiance and commitment to love is so strong that her mere presence alleviates suffering. Fawns eat from her hand and humming birds land on her shoulder to share their secrets.

Only one problem with this image: it’s complete and utter bullshit. If a creature like that existed, it wouldn’t be a human.

To be human is to be both stormy and sunny. It is to always be moving through the levels of self-love and self-compassion.

There will be times in your life when it makes sense to do the deep work. Take those opportunities when you can.

There will be times when you’ll accept your shadow and your daily habits will be on point.

There will be times when you’ll step fully into your power.

There will be times when you can feel – and even influence – the flow of the world around you.

And life ebbs and flows.

There will be times when stress catches up to you and even your favorite person pisses you off.

There will be times when you lose someone you love and you’ll be wrecked for months.

There will be times when you wish you didn’t have to deal with being human.

And it’s all ok.

The practice of love involves working with yourself wherever you’re at. Having a shitty day? Accept that. It’s ok. In one of those stretches where everything you touch turns to gold? Beautiful. Use it for good.

Your ultimate work in self-love is simply this: step fully and boldly into your life. When times are tough, be gentle on yourself. When times are good, relish them.

As you grow closer to yourself (and you’ll notice that in doing so, you become more powerful) your final task is simple: use everything you have in service of yourself and in service of others. Share your gift.

When you do this, everything in the world will burn brighter because of you.

Calling my shot…

I’ve been told that it’s a stupid idea to start a single author blog these days.

I’ve been told that it’s all about social media, split testing, and sales funnels, rather than content.

I’ve been told that I shouldn’t leave speaking, that I’ve got it made.

I’ve been told that succeeding online is more about luck than anything else.

I’ve been told that I need to post all the time if I want to get attention as a writer.

But you know what? Fuck that. I’m not going to bother playing other people’s games (I’ve also been told I shouldn’t curse so much…).

Here is the singular bet that I’m making with this project: if I go all in on helping leaders, entrepreneurs, artists, and trailblazers step fully into their lives, then my life will flourish because of it.

My commitment to you is to show up authentically and use what I’ve learned in service of others.

I’m going to work hard to put out articles that are a reflection of my truth, defaulting to honesty and vulnerability, instead of trying to manipulate your perception of me.

I’m going to create content designed to help other people live better lives and improve their communities. Sometimes this will be high-level stuff like learning to love yourself, developing authentic confidence, and knowing when to leave the beaten path. Other times it will be more strategic like how to say, “No,” whether or not entrepreneurship is right for you, and how to bounce back from failure.

I’m going to play the long game, valuing individual readers who truly resonate with my work over chasing traffic.                               

I’m going to ignore the latest trends in business and focus on fostering alignment between what I create and who I am (honestly, I don’t even know what a sales funnel is…).

Here’s why: every time I try to play someone else’s game, I feel like I’m betraying myself (even when I win).

I don’t know if life is long or short. Sometimes I want everything to slow down so I can savor it all. At other times, I want it to speed up so I don’t have to be a human for 60 more years.

But I do know this: life is too short to deny what your heart desires. For as long as I’ve been aware of blogs, I’ve wanted to build a great one. Until just now, I haven’t had the courage to actually chase that dream and follow my heart.

Welcome to This might not work.