Why does success feel so empty?

Last week: Z*, who founded a 30 person company, is staying with me for the night.

When I show him my apartment, I awkwardly say, “I know people in our circle are supposed to have huge, flashy apartments, but I just have this small little studio.”

He says, “What are you talking about, man? Have you seen my place? It’s almost exactly this size.”

For the millionth time, I’ve fallen for a huge trap: instead of being content with my life, I feel inferior because I’m not world-stoppingly-successful.


So many of the people I know are preoccupied with success. They want more money, status, and influence. They’re chasing a better body, a better relationship, and a wilder social life. They need to change the world, start a business, and leave a legacy. In fact, they get so distracted by their ambition that they fail to notice how great life is in the moment. This happens to me too. I spend more time thinking about how to improve my life, than feeling content.

The results of all this striving are unfortunate…

Amazing people feel inferior when they should feel like rock stars

A* runs a blog that her readers love. In fact, they send her poems and videos expressing their gratitude. But when you ask her if she’s happy with her work, she sighs and says, “No. I feel like I should be rich, but I’m not. If I were truly successful, I’d be making more money.”

S*, a brilliant economic analyst, has made millions trading currencies. He’s emerged as one of the most influential people in his space. When I tell him, “Wow, what you’ve done is truly amazing,” he dismisses the comment. Instead, he tells me that he’s lonely and wishes he had a better social life.

M* is one of the most charismatic people you’ll ever meet. He can make a stranger feel like his best friend in just a few minutes. Yet, if you ask him what it’s like to be so wildly likable, he tells you that he wishes he spent less time partying and more time focused on his career.

J* is going back to school to become a nurse. Soon, he will heal people for a living. He loves his job, but in vulnerable moments, he admits that he’s self-conscious about not being a doctor.

T*, a former entrepreneur, just took her dream job as a marketing executive. Her work is a 15-minute walk from her house, the company has an amazing culture, and it gives her the predictable income that makes raising her family easier. Yet, the decision to close her business and get a “real job” made her feel like a failure.

Why are so many objectively amazing people feeling inferior?

The cognitive illusions that sabotage self-worth

There are three cognitive illusions that make feeling successful, worthy, and valuable more difficult than it should be.

The negativity bias – though I’ve written about this before, it’s worth reiterating. Our minds are wired to give more attention to negative stimuli than positive stimuli. This is called the negativity bias. The negativity bias is the reason we are more affected by criticism than compliments.

A billion years ago, it was an evolutionary advantage that enabled us to quickly identify the threats in our environment. Today, it just tricks us into feeling like an asshole when we shouldn’t. It creates an inner world that is disproportionately negative and blind to the stunning success and beauty that defines you.

One of the best ways to overcome the negativity bias (and experience a more pure form of reality) is to actively notice what’s going well in your life and in our world.

The black hole problem (and its cousin, the auto-crave problem) – virtually any metric of “success” renders you victim to the black hole problem: if you’re trying to obtain something tangible, you can always obtain more of it. Because of that, you’re unlikely to ever be satisfied.

When I was speaking, I often fell into the black hole. I used to happily take Greyhounds to my gigs. Eventually I started telling myself, “If a client ever pays for me to fly, then I’ll really feel successful.”

One day my clients started paying for flights. As soon as I got used to that, I told myself, “If a client ever pays to fly me first class, then I’ll feel successful.” Had I stayed on that hamster wheel, I would have wanted to fly in private jets, then on my own plane, and then my own highest quality private jet, and so on and so forth.

To further complicate the matter, our minds seem to be set to auto-crave. That means that as soon as we are content with something, we start craving something else, completely forgetting about the contentment that defined us moments before.

This happens all the time with food. After a big dinner, you’re sure that you’re full. That is, until someone brings out dessert. Suddenly, you realize that you have exactly enough room left for a brownie sundae!

The comparison trap – Since we were kids, we’ve all been told that comparing ourselves to others is a losing game. Still, we’re all human, and there are two subtle elements of comparison that make us feel particularly inferior.

1) Beginners tend to compare themselves to advanced practitioners.

It’s tempting for me to compare myself to the writers I admire. I’ve been working on the craft for a year or two, when they’ve been working for decades. To compare myself to them is insane, but I still do it all the time.

In the beginning stages of a business, we ask ourselves, “What would Zuckerberg do here?” When we’re trying to exercise more, we use images of fitness models to motivate us.  

By doing this, you’re effectively comparing a beginner’s rough draft to an expert’s finished product.

2) We assume that the people we admire have perfect lives and since our lives are imperfect, we assume we aren’t yet successful.

Spoiler alert: no one has a perfect life.

No amount of success allows you to escape being human. Even the best of the best struggle with doubt, insecurity, dirty dishes, and the occasional case of explosive diarrhea. They fight with their spouses over stupid shit, half-ass the projects they dislike, and watch too much Netflix. When you effectively take them off the pedestal, you realize that you’re much further along the path than you thought.

When we compare ourselves to people we perceive as perfect, we feel much more flawed for being human.  

How to feel the success you’ve already earned

First, learn to fall in love with process. No matter what you’re working on, the process is likely to demand more of your attention, energy, and time than the results will.

It’s important to create a day-to-day that you really enjoy. Take good care of your health, spend time with a community you love, and do meaningful work. Doing so will create more stability and happiness than success ever could.

Second, adjust your understanding of success. Many people – and I was one of them – think that “success” will eliminate all of their problems. I told myself that if I could just accumulate enough money and status, everything would be perfect: L* and I would never miscommunicate, I’d enjoy eating salads, and I’d become the strongest guy at my gym.

Bull shit, bull shit, bull shit.

At best, success can give you options. L* and I could set aside long periods of time to iron out sticky issues, I could hire a chef to make salads for me, and I could workout with a trainer at the gym.

But success doesn’t solve any of the existential problems that come along with being a human. Success won’t make you feel happy, worthy, or content; those are entirely different skill sets.

PS: Would success even change all that much? Possibly not.

A few weeks ago on a late Saturday afternoon: L* and I are having a tea on her patio. We’re talking about a project that I’ve been working on for the past few years. If it succeeds, it will make a dramatic difference in my finances.

L* goes inside to take a phone call, and I start daydreaming about what life will be like if the project succeeds and makes me rich and famous. My external life would become flashier. I’d pick up the tab more often, donate more to charity, get a fancy new apartment, and possibly buy a Jeep Wrangler.

But my inner life? I was shocked to realize that it probably wouldn’t change at all.

I suddenly understood that if I’m not content with what I have, getting more of it will only exacerbate my problems. If I can’t find happiness in this moment, more money won’t change that. If I don’t feel connected to or loved by the people I surround myself with, no amount of external validation will change my feelings.

It was a jarring thing to realize.

How to affect change in your country (even when things suck)

For many progressives – and conservatives – the past few weeks have been disturbing.

First, the President of the United States escalated a cold war with North Korea. Then, he failed to calm the country after a surge of white supremacy. In fact, many feel that he (perhaps unintentionally) stoked the flames.

In moments like this, it’s tempting to get angry and claim that the other side (regardless of who the “other” side is) is evil and needs to be stopped. Within that, there’s unspoken permission to hate your opponents.

And while I understand – and even sympathize – with those feelings, I fear they are unproductive and misguided.

To continue to define yourself in opposition – especially emotionally charged opposition – to others is to forget that we belong to one another.

To fight hatred with hatred only magnifies the exact things we are trying to extinguish.

Instead, we need a far more grounded, loving, and inclusive approach to social change.   

Like countless others I’ve been asking myself, “What can I do to make a difference? How can I help? How can anyone help?” I spent a lot of time thinking about it. More importantly, I called my friends who work in the government, nonprofit, and community organizing, and asked them.

What follows are the best answers we could come up with regarding how individual citizens can make a difference. If you have additional suggestions, please leave them in the comment section.

Step 1: Begin by taking good care of yourself

We’ve all heard, “Put your oxygen mask on first. After that, help others with theirs.”

If you’re feeling beaten down by the world, you won’t be able to serve anyone. Heck, you won’t even be interested in living. Begin improving your community by making sure that you’re taking good care of yourself.

Even if you already excel in self-care, times of trauma and chaos can obscure things that are otherwise apparent. So, as a quick refresher:

  • Get plenty of sleep and exercise
  • If you drink or do drugs, do them in moderation
  • Keep a (basically) healthy diet
  • Ask for help when you need it (including calling a friend to vent or turning to a professional)
  • Give yourself small treats throughout the day
  • Embrace your imperfections
  • Take a break from following the news if you need to.1

Step 2: Check in on your people (especially the minorities)

I can’t emphasize this enough: reach out to the people you love, especially if they are a minority. Ask how they’re holding up. Tell them that you’ve been disturbed by what’s happening in our country. Tell them that you love them.

Most people will feel affected by the past few weeks’ events, and by being open, you can provide a lot of support to those you love.

Step 3: Get informed

Once you’ve touched base with the people you care about, it’s time to figure out what’s actually happening. Having accurate information is incredibly important. If you debate with someone of an opposing perspective with incorrect information, they will dismiss you (and rightly so).

The most recent election has made it clear that internet and TV resources are not always reliable. Do your research before believing everything you read. A few outlets that I personally trust include:


  • The Economist – in my opinion the singular best source of unbiased and accurate news available today, (leans conservative)
  • The New York Times – accurate, well researched, and up to date, (leans liberal)
  • Wall Street Journal – focus on business, economics, politics, and the instruments that influence them, (leans conservative)
  • NPR – accurate and reliable (and at times funny), but notably liberal and occasionally unfriendly to conservatives

The best bet is to comb through multiple news sources to figure out what’s happening. Ask one of your history nerd friends to give you a quick overview of how we got here in the first place.  

And, as annoying as it may be, read a few articles from popular news sources that you consider unreliable, racist, or idiotic. Try to read them with an open mind. Even if you disagree with everything they’ve written, it will help you understand the other side.

Talk to people whose views differ from your own. When you do, lead the conversation from a place of curiosity, not judgment. Ask questions. Seek to understand their conclusions.

Finally, if you want to understand a huge – and often ignored – population of Americans whose voice and influence is growing, consider reading JD Vance’s book, “Hillbilly Elegy.” It’s about America’s rural poor in the Appalachian Mountains.

Step 4: Practice random acts of kindness

Get in the habit of performing random acts of kindness.

The tension in this country is insanely high right now. Your goal should be simple: get a few random people to smile each day. It will make you happy and will make other people happy too. Besides, we can all use a bit more kindness these days.

A few ideas:

  • Pay for the coffee, toll, or lunch of the person behind you
  • Write something uplifting or funny on the sidewalk with chalk
  • Give compliments to strangers
  • Carry around a bunch of $1 bills and give them to whoever asks for money
  • Play the “Make a stranger smile” game with your friends. The game is simple: whoever makes the most strangers smile (by whatever means) wins.
  • Volunteer for an organization you believe in
  • Put a few books in those free libraries that keep popping up

Step 5: Get directly involved in a way that makes sense for you

Finally, get involved. If all you’re doing is worrying and complaining to your friends, then you’re not doing enough.

There are plenty of ways to get involved, and if you have additional ideas, please leave them in the comments.

Host an event and invite people with differing worldviews. One of the most consistent ways that people overcome prejudice is by forming personal relationships with people that they are prejudice against.

If you have a particularly diverse friend group, host a dinner party and introduce everyone. Don’t be afraid to lay some ground rules and set boundaries. Personally, I tend to (gently) enforce a “No talking politics” rule when I host groups that are likely to clash.

I’ve noticed that by eliminating the elephant in the room, people are more likely to form personal relationships, which are far more impactful than political debates. To see a great example of this playing out, check out Heineken’s unexpectedly enlightened commercial, “Worlds apart.”

Donate to the front lines. The ACLU, Black Lives Matter, and Planned Parenthood are all critical organizations right now. If you’re a talented promoter or event coordinator, consider organizing a fundraiser. If you have a bit of extra income, consider donating to a cause you believe in.

Contact your elected officials and let them know how you want them to vote. Some politicians still care about what their constituents think and are influenced by public thought. We can leverage this by contacting them. If you’re looking for their contact information, you can find it here.

Get involved with local politics. Go to rallies. Volunteer. Organize a fundraiser. Donate to the campaigns and candidates you believe in. Sign a petition. Better yet, start a petition.

Run for office. This is a really bold solution, but if you’re good with people, have a high-risk tolerance, and think you can do a better job than the powers that be, you should consider running for office. As I’m sure you’ve noticed, the system has changed and is increasingly accessible to people who are not career politicians.

Use your voice (even when you think it will fall on deaf ears).  When you see something wrong, speak out against it. This might be calling out racism when you notice it, writing a Facebook post denouncing hate, or attending a protest. Regardless of the approach you take, staying silent is dangerous. This is especially important if you are a conservative.  It’s your job to show your peers that the Republicans are not a part of hatred and discrimination.

Finally, when you talk with people of opposite views, stay open. Better yet, kill them with kindness and curiosity. Listen more than you speak. If you sense that someone is open to change, resist the urge to say, “Told ya so!” Instead, express admiration for their openness and intelligence.

Postscript 1: does one person’s actions really make a difference?

Whether or not you believe an individual’s actions makes a difference, depends on how you view the world.

If you look at the world as just a collection of 7.5 billion humans and assume that change is only meaningful when you can touch everyone, then nope, your actions won’t make a difference. Even if you scale down to just the US, a country of 323 million, it’s still not realistic to hope to change everyone.

However, when you realize that the world is made up of individuals – each one of us having a vivid human experience of struggle, pain, love, joy, fear, laziness, and everything else – things change. You realize that you can change our world and you do so by influencing the individuals within it. If you’ve helped to alleviate suffering or increase the joy of an individual or a small community, then you’ve made a tangible difference. When you scale this by doing consistent and thoughtful work, you inevitably build a better world.

Postscript 2: a note to thought leaders and people who shape public opinion

Many of my readers are far more influential than I am. If you fall in that category, listen up…

Way too many leaders, podcasters, bloggers, entertainers, entrepreneurs, and executives kept their mouths shut during the 2016 election. Yeah, I get it: you don’t want to alienate your audience/clients/friends/family/investors.

All I have to say about the issue is this: fighting for civil rights is way more important than being a people pleaser. If you’ve taken the time to accumulate influence, then it’s your obligation to speak up.

When I ran an article about how I thought voting for anyone besides Clinton was unethical, my team was placing bets on how much damage it would do to my businesses.2 But still, we ran it. More importantly, it worked. Readers wrote in telling me that it changed their voting behavior.

And I’m small fries when it comes to the Internet. If I was able to help change people’s minds, you can too. To assume that your audience can’t handle you taking a stance or that rational argument doesn’t change people’s opinions is to deeply insult your audience. In fact, if you’re not willing to speak out about the issues you believe in, then you don’t deserve a platform. Easy as that. 

Living in a world where your body is obscene

“If war is holy and sex is obscene,
we’ve got it twisted in this lucid dream” -Alicia Keys on “Holy War”

– 1 –

It’s easy to be compassionate when a loved one is going through a tough time. Without thinking, you offer warmth, empathy, patience, and playfulness. You encourage her to take a bit of time off, relax, breathe, and go easy on herself.

If you’re like most people though, when you’re the one struggling, your actions are different.

You beat yourself up. You accuse yourself of being lazy, stupid, disorganized and incompetent. You’re angry and disappointed in yourself. You compare yourself to everyone else in the world, and you can’t help but notice how poorly you’re doing.

Instead of extending the grace and compassion that you effortlessly give to others, you’re merciless with yourself.

Of course, you’re not unique. We all do this.

The question is, why are we so much harder on ourselves than we’d ever be on a friend?


– 2 –

In the modern world, we are constantly cut open by messages saying we aren’t attractive, successful, efficient, healthy, or happy enough. We’re told that if we buy some widget, attend a training, go to a meditation retreat, do a cleanse, lose some weight, or whatever, then maybe – just maybe – we’ll be worthy and ok.

When that doesn’t work, we turn to personal development, which – instead of teaching us to accept ourselves for who we are – nudges us towards other people’s definitions of success, happiness, and contentment.  

Most of us have been convinced that unless we are multi-millionaires with the body of a Greek God or Goddess, the sex life of a porn star, the meditation practice of a monk, and a rom-com worthy relationship, there’s something wrong with us. I fall for this shit all the time.

But of course, those are just the obvious insecurities. There are more subtle ways in which we’ve been made to feel flawed without even realizing it.


– 3 –

It may seem like I’m going out on a limb here, but bear with me for a moment.

Imagine what would happen if you stripped off your clothing and walked down a crowded street.

Even if you’re wildly attractive with great hygiene, you’d quickly get arrested for “indecent exposure.”

I know, you’re thinking, “Yeah, duh, that’s the law,” but that’s not the point I’m trying to make.

We have literally created a world where your naked body is considered “indecent.”

You – the real you, the one who is vulnerable, raw, undisguised, and unabashed – is considered unfit in the eyes of the law.1

That’s really, really fucked up.


– 4 –

Of course, it’s not just our bodies that are considered obscene.

Our minds are too. We’ve all secretly:

  • Wished suffering upon our enemies
  • Been attracted to people besides our monogamous partner
  • Contemplated whether or not we could get away with lying, cheating, or stealing
  • Felt envious of someone else’s (ostensible) success and happiness
  •  …And a million other “horrible” things

In reality, most of us experience far darker thoughts and fantasies than anything I’ve written here.

Yet if anyone explicitly expressed these thoughts – even with the disclaimer that you’d never act on them – you would be reprimanded, shunned, or deemed unstable.  

So we try to pretend that our minds don’t have dark corners. On the rare occasions that someone admits that her inner life is sometimes grim, we tend to get uncomfortable and change the subject instead of opening up and quietly saying, “Yeah. Me too.”


– 5 –

Do you see what happened here? We’ve created a society that implicitly and explicitly discourages us from being who we truly are. Neither our bodies nor our minds are allowed to be naked without serious repercussions.

So we learn to suppress huge parts of ourselves. We water down our opinions, hide our darkness, and fight against our urges – even when they wouldn’t harm anyone. We become strategic in what we communicate and how we behave.

The more we hold ourselves back (a necessity if we are ever to fit in) the more we dull ourselves. You can’t close yourself to being hated without also closing yourself to being loved. You can’t ignore the parts of you that are dark, without also drowning out the parts of you that are light.


– 6 –

Because of all of this, most people end up living muted lives. We trade most of our time for money, and even then, the money doesn’t go as far as we’d hoped. We avoid having hard conversations and pretend that problems don’t exist.

Slowly but surely, we suffocate ourselves by adhering to the norms forced upon us.

We toy with the idea of leaving the beaten path, but are forced to admit that it’s risky. If you start a business, you must first accept that you could lose everything you have. If you travel for six months instead of climbing the corporate ladder, people will tell you you’re playing Russian roulette with your career. If you fight for the causes you believe in, people will tell you you’re wasting your time

And of course, each of us is dealing with more pain, suffering, and anxiety than we admit. For many, the suffering is so intense that they use television, drugs, alcohol, the internet, or other distractions to put themselves into a low-level trance just to get by.


– 7 –

Consequently, extending compassion to yourself is far harder than it should be. The world constantly makes you feel flawed and inadequate, and sometimes, you can’t help but believe that you are.

Fortunately, there is a path forward, but it’s tricky. It takes courage and a clear head. You must believe that you are sane and that the world you live in is insane.

– 8 –

To start this process, do your best to laugh at all of the insanity around you.

I mean, think about it.

We’re all just running around like chickens with our heads cut off, discussing sports scores and stock market trends, draping ourselves in status symbols, babbling about work, entrepreneurship and grad school, trying to accumulate more and more, and gluing ourselves to screens and shitty jobs, while holding in our farts until no one’s around.

If you’d just pause and catch your breath for a moment, you’d notice something incredible: you’re pretty alright just as you are. In your own way, you’re beautiful. You’ve been able to handle everything life has thrown at you so far, and you’ll continue to be able to do so in the future. Besides, even if this moment is shitty, there’s always hope the for the next. In fact, if you work a bit to improve this moment (and that includes taking a nap!), the next one will follow along nicely.


– 9 –

Once you’re able to see the absurdity of the world we live in, it becomes easier to let go and be gentle with yourself.

Work to accept yourself for who you are, instead of beating yourself up for who you wish you were. In most cases, the person you wish you were has been superimposed on you by the outside world anyways.

Remember that being a human can be pretty fucking hard sometimes. There’s nothing wrong with you.

If you’re having trouble extending compassion to yourself, try this: think about how you would treat a friend who was in your exact position. If you notice that you’d be more compassionate to your friend than you are to yourself, do your best to transfer some of that compassion over to you. You deserve it.


– 10 –

From there, start accepting others as they are instead of trying to shape them into the people you wish they were. Love them when they’re being messy, chaotic, and annoying.

The more you accept the humanity in others, the more you’ll accept the humanity in yourself.

How to quit (and why it leads to happiness)

May, 2004: I’ve just stepped off stage from my last magic show ever. It feels… anticlimactic.

I imagined that I’d be emotional, but I’m not.

It’s as though today’s show held little significance. I didn’t even tell the audience that it was my last show.

Though I admit I feel a little guilty. Over the past 12 years, my manager, parents, and brother have poured tons of time and energy into my success. In some ways, my decision to quit feels like a betrayal.

But instead of worrying too much about that, I pack up the show, load up the car, and exhale. It’s nice to be done with this shitty job.


Have you ever had the experience of getting exactly what you wanted – a certain amount of savings, a job, a relationship, a cool apartment, a status symbol, whatever – only to be disappointed shortly thereafter?

Most of the time we tell ourselves, “Oh, well I guess I just need more!”

While the tendency is understandable, it’s also misguided. Once you’ve created a life you enjoy, adding more tends to have diminishing returns. However, you can create huge wins by removing the stuff that doesn’t work or is causing friction.

In this article, I’m going to make a simple argument: the path to happiness is lined with eliminating all of the shit that doesn’t serve you. I’ll also give you practical tips on how to quit, explain why doing so is often terrifying, and advise on how to deal with haters.

Why quitting leads to happiness

Imagine for a moment that every day you get out of bed and stub your toe on the nightstand. In a situation like this, you have two options:

1) Accept that the nightstand will always be in your way and hope that you learn to avoid it or grow numb to the pain.

2) Move the nightstand.

Obviously, you’re best off just moving it.

Of course, quitting your job, ending your marriage, or giving up cigarettes is a hell of a lot more emotionally demanding than moving a piece of furniture. However, thinking about the simple things that cause you pain can be instructive. Many people choose to adapt to situations when they would be better off changing them.

The problem is that changing your life can be tricky. It almost always requires courage and a decent amount of work. Because of that, many of us never make the changes we want (or need) to.

Adapting to a situation that doesn’t serve you is a bad idea (unless the situation can’t be changed, in which case learning to adapt is wise). It wears you down and holds you back from fully stepping into your life. When you finally quit something that has been draining you, two things happen.

1) All of the frustration that came from whatever used to bother you? It vanishes. This alone is a huge win.  

2) You create blank space in your life. That space can be scary, of course, because it means that you’re dealing with the unknown. However, the space makes it possible for you to replace whatever wasn’t working with something that will help you flourish. It’s difficult for new things to appears in your life, if you don’t have the space for them.

How to overcome the fear of quitting

We are often told, “Better the devil you know, than the devil you don’t.” The idea is that it’s better to deal with familiar circumstances – even if they suck – than to take the risk of dealing with something new because that might suck even more.   

Honestly? That’s horrible advice. A better approach is to continue taking calculated risks and engaging with the world until you create a life you love.

The problem is that change can be scary. Most of us prefer the familiar to the unknown. Fortunately, there are ways to overcome this.

Realize that the devil you know is way scarier than the devil you don’t. Think about the thing(s) you are considering quitting. Ask yourself, “What happens if I don’t quit?” The answer is that life is likely to get worse.

You’ll either get worn down or the frustration you feel will continue to grow and expand. When you reflect, you realize that the bigger risk isn’t the unknown, it’s choosing to stay on a path that you know doesn’t serve you.  

Use the worst-case scenario as a thought experiment. When we consider quitting something, we often feel a quiet sense of dread. That dread prevents us from further examining whether or not we should quit. It closes us.

However, when you pause to examine your fears, you’ll notice that many of them are nothing more than phantoms of the mind. You’ll realize that things that felt prohibitively frightening when they were unexamined become manageable in the light of day.

Spend time figuring out how you could bounce back from the worst-case scenario if it ever occurs. Let’s say that you want to quit your job, but you’re afraid that you’ll run out of money before you get a new one.

There are countless ways of fixing this problem. Maybe you learn to be more frugal before you leave your job, so your savings will last longer. Maybe you start renting out a room in your apartment or driving for Uber to supplement your income. Maybe you decide that you 100% will quit your current job, but not until you’ve landed a new one. Maybe you ask friends or family if they’d be willing to let you crash with them. Maybe you take out a loan.

The important part is to realize that you are capable of handling almost anything that life throws at you (often with more grace and ease than you anticipated).

Figure out how you’re going to do it. One of the reasons quitting is so intimidating is because people rarely take the time to figure out how they’re going to do it. Though going cold turkey is entirely possible, baby steps are often more effective.

There was a decent gap between when I decided to quit professional speaking and when I actually quit. During that time, I saved money, figured out what I was going to do instead of speaking, and explained my decision to my friends, family, and clients.

Recruit help. If you’re struggling to quit something, recruit help! This can be a friend, an accountability buddy, a coach, a therapist, a 12-step program, whatever. As always, there’s no need to go it alone.

Finally, realize that few things in life are permanent. When we make big life decisions, we often feel as though they are destined to become permanent. In reality, almost nothing is permanent.

If you realize that your life was better before, you can always return to that lifestyle. Sure, there will be some differences – you may not work for the same company or live in the same apartment – but you’ll be able to create something close enough. Once you realize that you can fix almost any “mistake” you make, taking a chance in life becomes much easier.

18 Things to consider quitting

I’ll leave you with a list of things to consider quitting.

As always, the time to start is now. Even if you’ve invested tons of blood, sweat, and tears – like I did with magic – if something no longer serves you, it’s probably time to let it go.

  • Being an entrepreneur or freelancer (a lot of people who were seduced into being entrepreneurs would be much happier being an employee, regardless of how successful their business may become)
  • Spending time with the people you only pretend to like
  • Watching tons of TV
  • Going to college (virtually everyone should complete high school, but in my opinion, higher education isn’t for everyone – a very real part of me wishes I didn’t waste my time)
  • Drinking, doing drugs, or smoking cigarettes
  • Living in a city you don’t like (moving from DC to Denver was one of the best decisions I’ve ever made)
  • Pretending that you care about politics, sports, or fidget spinners
  • Staying at a job you hate
  • Obsessing over personal development (there’s nothing wrong with you, I promise)
  • Playing small
  • Staying in a relationship that just doesn’t work – even if you love the person (but move slowly and carefully here to make sure you’ve exhausted every option; keep in mind that all relationships go through rough patches)
  • Eating junk food or having an unhealthy relationship to food
  • Neglecting your mental health
  • Treating yourself poorly (you really should treat yourself like a rock star)
  • Spending time with people who tear you down
  • Lying
  • Feeling guilty for prioritizing your needs (I’ve had to deal with this numerous times, including when I quit magic)
  • Pretending that you aren’t happy, capable, beautiful, confident, bold, or awesome (soooo many people live under this delusion)

Post script: how to deal with the haters

When you really grab life by the reins, haters start to crawl out of the woodwork. The shitty part? Many of them will be people close to you.

Nine times out of ten, their reactions have nothing to do with you and everything to do with unaddressed issues in their lives. There’s a good chance that observing your proactivity makes them uncomfortable; it reminds them that they are responsible for themselves and that they aren’t doing a very good job with that responsibility.

It’s tempting to try convince them that they’re wrong. Don’t waste your time.

Instead, listen politely and say something along the lines of, “I appreciate your perspective.” Don’t bother trying to get them to understand you. Instead, revel in being misunderstood.

How to find a good therapist (and my experience with an abusive one)

2016:  C*, my first therapist, and I are on the phone when she says, “I’ll send over a draft of the article I’ve been working on. Your job is to edit it, put it in your voice, and then post it on your site. You’re getting a lot of traffic and interesting clients these days, so be sure to include the links back to my site too, ok? This piece needs to work for both of us.”

I have trusted C* to help me heal. I have trusted her with some of my deepest insecurities.

Her request that I post an article about her skill as a therapist with a link back to her site confused me. It seems like she’s using me.

Yet, we are in the middle of the therapeutic process. I have been talking to her for 2-3 hours a week for several weeks. Following her instructions has improved my life. Suddenly removing my trust would be incongruent. In a way, I worry that if I don’t follow through with the article, I would hinder my progress or upset her.

I told a few of my friends about C*’s request to post an article promoting her business, and they were enraged. They helped me see just how unethical she was. One even offered to call and threaten legal action.1


I never spoke to her again.


In retrospect, C*’s actions were obviously unethical. Still, C*’s behavior was fairly mild compared to other forms of therapeutic abuse. One of my close friend told me that her therapist made sexual advances on her during sessions.

Finding a good therapist is harder than it should be. Because of the mental health stigma and the difficulty in finding a good therapist, many people give up hope about healing their mental wounds or turn to unqualified life coaches with fancy marketing.

This is the second article in a two-part series on mental health. The first article discussed the taboo around mental health, especially amongst men. This one will outline how to find an effective and ethical therapist who will be able to help you.  It will also cover the advantages and disadvantages of other approaches to healing.

Why I wanted a therapist instead of a life coach or plant medicine

Many people struggling with mental health turn to self-help or coaching rather than therapy. A much smaller (but growing) population turn to psychedelics, or “plant medicine.”

Before seeking counseling, I invested a lot of time and money into self-help and coaching. The results were shitty. At best, a good book or a charismatic coach offered something akin to a sugar high. At worst, they messed me up.

Since I’ve already detailed my views on why I think life coaches do more harm than good here, I’ll stick to the topic of finding a good therapist in this article.

Plant medicine presents an interesting issue. These days we all know someone who has taken MDMA, mushrooms, LSD, ayahuasca, or some other form of psychedelic, only to report that they have been “cured” or maybe even enlightened.

In fact, there is a growing body of research suggesting that plant medicine can heal certain psychological wounds. I’m optimistic, but going down that path presents a whole new set of problems.

First, you have to find a reputable provider. While they certainly exist, finding them can be difficult because the doctors working in plant medicine are either underground or practicing in a different country. Working with a bad provider or attempting to self-medicate creates a huge amount of risk.

Second, you have to ensure that the drugs you’re doing are pure. Even with established “Plant Medicine Centers” in Central and South America, treatments are often laced with additional substances. The only available alternative is buying drugs on the street, which is always dumb.2

Finally, many of the people who claim to be cured by psychedelics seem to still be ruled by the same demons that have always possessed them. More than that, they appear mildly addicted as they discuss their fairly regular “maintenance doses.” It seems that plant medicine offers a blend of gentle addiction complimented by the illusion of health while failing to achieve the goal of healing the individual.3

For all of these reasons, I realized that I needed to talk to a therapist. I suspect I’m not unique. Virtually all self-help, coaching, personal development, and plant medicine junkies would likely be better served by a therapist, but most are unwilling to admit that they need help.

The singular best way to find a good therapist (and a close second)

After my experience with C*, I knew that I needed to be careful in my approach to finding a therapist. After a lot of research and experimentation I learned that the best way to find a great provider is to ask a trusted mental health professional for a recommendation.

In my case, I have a close friend, B*, who is a talented mental health professional. I told her a bit about the problems I was facing and asked, “Do you know of any therapists who would be a good match for me?”

B* gave me a list of therapists and helped me get in touch with them. This led me to P*, a wildly talented practitioner who helped me heal wounds that I didn’t even know existed.

Of course, this creates a chicken and the egg problem for many people. Luckily, there’s another approach that works well.

Tell a few close friends that you want to improve your mental health. Ask if they know of any good therapists or contacts that may be able to make a recommendation. You’ll be surprised to find that many people you know – including those close to you – have quietly seen a therapist at various points in their lives.

If neither of those techniques work for you…

If neither of those techniques works, don’t worry; there are other approaches:

  • Call or email 5-10 therapists in your area to ask who they recommend you speak to. Doing so will generate a list of admired and likely effective therapists in your community.
  • Ask your primary care physician for a recommendation.
  • If you work with a chiropractor, nutritionist, physical therapist, or other individual in the health and wellness space, she’s likely able to make a recommendation.
  • If your company has a Human Resources representative, ask her.
  • If you’re a member of any sort of support group like a 12-step program, a men’s or women’s group, a business mastermind, or anything else where people are encouraged to be open and honest with one another, check there.
  • If you are a member of a spiritual or religious community, the head of that community should be able to make a good recommendation.

If you can, avoid searching online for a therapist. That’s how I came across C*. However, I understand that for many people searching online is the best option. If that’s the case, be sure to pay extra attention to the guidelines below.

6 Things to consider when evaluating a therapist

Approach finding a great therapist in the same way you would approach looking for a great surgeon. When you find the right provider, you’ll know it. Though you may struggle a bit to open up and be vulnerable at first, you won’t question whether or not this person is trustworthy and capable. Determining whether a therapist is right for you may take two or three sessions before you have clarity.

Keep searching until you find someone that you trust, respect, and have a strong sense of rapport with. If something feels off, leave. Don’t worry about hurting the therapist’s feelings. Seriously. If you’re unsure about a situation explain it to a few friends or family members and trust their opinions.

In addition to trust, respect, and rapport – which are non-negotiable – the following guidelines were important to me when I was shopping for a therapist. Consider whether or not they matter to you.

1) What does your gut tell you? Honestly, my gut told me to run the hell away from C*, but I didn’t trust myself. If your gut tells you that this is a bad provider, then keep shopping.

2) Is she making promises she can’t keep? I asked the therapists I interviewed, “Will I be able to get better?” While this was a vulnerable question, it offered great insight into the therapist’s integrity. If she said, “Yes, I can 100% heal you,” then I knew she wasn’t the right one. Someone who promises results is either lying or ignorant. A provider cannot promise that she’s capable of healing you. There are too many variables outside of the practitioner’s control.

A much more grounded response is something along the lines of, “What I can promise is this: I’ll do my absolute best to help you. My patients tend to get better, so I’m optimistic about your future. Still, no one can promise results.”

3) Do her clients work with her for a while and then leave? If so, that’s a good sign. Staying with the therapist indicates that her patients trust her. Leaving after some time suggests that her patients tend to heal. If her clients stay with her forever (indicating a sense of dependency) or for just a short period of time (indicating a lack of faith), there’ a good chance that they are incompetent.

4) Does the therapist provide an off ramp for her patients? Many therapists work with their patients for years at a time without any clearly established guidelines for figuring out when / if the patient should end treatment. Personally, I wanted something more defined. I wanted to put concentrated effort into healing, and then taper off therapy as I began to feel healthy. My therapist encouraged this approach, which is one of the many things that helped me realize she was right for me.

5) What modalities do they incorporate? There are a wide variety of therapeutic modalities ranging from those that are firmly grounded in science to others that have no scientific basis.

When considering a therapist, consider which modalities she incorporates. Does her approach make sense to you? If so, that’s a good thing. My experience combined talk therapy and Eye Movement Desensitization and Reprocessing (EMDR).  There’s no right or wrong approach here, but it is important that you respond well to methods your therapist uses.

In general, if you trust your therapist, it’s reasonable to trust the modalities she suggests. I was skeptical of EMDR when we began. However, it turned out to be incredibly healing, useful, and efficient.

6) What type of provider do you need? There is a wide variety of psychotherapists, ranging from those with an education but no licensure, through those who are licensed Medical Doctors.

Depending on the mental health issues you need to address, you’ll want to consider what level of training and licensure is required.

Though classifications of different therapists are too nuanced to get into here, in most cases starting with a Licensed Professional Counselor (LPC) with a good reputation is a safe bet. LPCs are educated, licensed, and often covered by insurance.

If you need a different provider or some sort of prescription, your LPC will be able to refer you to a specialist.

It takes a village…

As I mentioned in the first article, discussing mental health and getting good information about it is tricky. There’s a big ass stigma around it, and there are a ton of shitty providers.

If you have additional guidelines or tips for finding an effective therapist, please leave them in the comment section below. I’ve set it up so that you can use a pseudonym if you’re not comfortable using your real name.  

Post script: What you should do if your therapist is abusive

If you’re a victim of therapeutic abuse, I feel for you. As I mentioned, my first therapist tried to take advantage of me.

If you suspect that your therapist has engaged in abusive, exploitive, inappropriate or unethical behavior, I urge you to report her to her licensing board. The easiest way to do this is by searching for “[your state/country] licensing board for therapists/psychologists/psychiatrists.”

From there, contact the board and issue a complaint. If it’s not obvious who you should speak to, go to the contact page on their site and ask.

Your courage in reporting bad therapists will prevent future cases of therapeutic abuse, and that is a gift to the world.


The hidden agony of men and their mental health

When I turned 30, I decided to focus on my mental health, which included spending six months in therapy. For a while I didn’t tell anyone, not even my inner circle. When I did start telling people I noticed that the men in my life had two types of reactions.

While many were supportive, a few were not. Four conversations stand out:

  • Over lunch, a childhood friend tells me, “It’s good that you’re taking care of yourself, but keep in mind that therapy is mostly entertainment. It doesn’t really do much.”
  • At a party, a college friend, now a lawyer, responds, “You can talk to a psychologist if you want to, but it’s not really necessary. Just give me a call when you need to talk. I can help you.”
  • Walking home from the gym, two of my friends have opposite reactions. One is encouraging. The other responds, “I don’t think you should talk to a psychologist.”
    “Why?” I ask.
    “Because it’s weak. Men should deal with their problems on their own. You’re smart and successful. You don’t need help.”
  • I call a friend while I’m on a speaking tour and on the verge of breaking down. He tells me, “You don’t need a therapist. I mean, if you go they’ll find something wrong with you and try to fix you, but that’s because it’s their job. Dude, look at you… you just got a standing ovation from a crowd of 800 people. You’re the last person who needs a therapist.”

On every count, these men were wrong:

  • I did need professional help rather than a friend’s advice.
  • Though I was “successful” when I entered therapy, my professional success didn’t have much to do with my mental health.1 
  • Leaning into the therapeutic process required more courage and strength than I could have anticipated; it certainly didn’t feel weak.

We could easily dismiss these men as insensitive or emotionally handicapped, but they aren’t. They’re thoughtful, loving people who are consistently there for me and remain close friends to this day.

They were reacting to the stigma around men’s mental health and were trapped by outdated models of masculinity.

This is the first of two articles in a series on mental health. In this article, I’ll discuss why it’s so taboo for men to deal with their mental health issues and what we can do about it.

In the second article, I’ll discuss how to find a great therapist and my experience working with a horrible one. I’ll also cover alternative modalities for healing, including life coaching, self-help, and psychedelics.

The chasm between the inner and outer world

To a casual observer, I didn’t appear to need therapy.

My business was booming, hundreds – sometimes thousands – of people attended my speeches, my social life was a bit too much fun, and I was at the center of a robust professional network.

Externally, my life was perfect.

Internally… not so much.

I feared that I might never be able to form a healthy relationship with a woman I admired, I struggled to enjoy my success (I was sure it was going to slip away), and my self-worth was shot to shit. 2

Though my inner and outer worlds seemed to describe two entirely different people, they don’t, they describe me in my late twenties.

People tend to believe that unless you exhibit the outward signs of mental illness (talking to imaginary people, intense anxiety, crippling depression, addiction, etc.) there’s no reason for you to seek therapy.

In reality, that’s simply not the case.

Many people who flourish externally are plagued by cruel demons internally. Many people believe that their demons are component parts of themselves. They’re trapped feeling that their pain can’t be cured, controlled, or cast away. In my experience, that’s just not true. As far as I can tell:

  • You are neither bound nor defined by your pain. Healing is always possible. A good therapist can speed up the process.
  • Virtually all of us can benefit from the care of a good therapist. If you’ve been toying with the idea of scheduling an appointment, stop putting it off. Your future self will thank you.
  • If you’ve been dealing with persistent psychological problems, seek the help of a professional, even if you think it will be fruitless. It’s unlikely that enduring problems will go away on their own or respond to self-help.

Outdated concepts of masculinity

Most men learn that being in touch with one’s emotions is akin to weakness.

When F*, a close friend, was six years old, his Dad told him, “You know, one of the great parts about being a guy is that we don’t need to deal with our emotions like women do. We don’t have them.”

Another friend, M*, turned to his father for relationship advice. His father said, “It’s a lot easier for men to have healthy relationships because men don’t have strong emotions and don’t need to talk about their emotions.”3  

These stories aren’t rare. The vast majority of men have been told that it’s better to ignore, suppress, or deny negative emotions rather than confront them head on.

Across society, men are faulted for being emotional. They’re told to get a grip on themselves and encouraged to “Be a man.”

Men are praised for their “emotional mastery” when they act unaffected by touching or difficult events. This is why we see stoicism – an emotionally stunted philosophy that died out thousands of years ago – regaining popularity in modernity.

We are never taught that raw vulnerability leads to enduring strength.

The end result is a profound sense of shame around difficult emotions, leading men to disconnect from themselves.

Many would rather live with an extreme amount of pain instead of doing the hard work of healing because they are afraid of seeming weak. Far too often, men forget that the more we heal, the more strength we develop.  

The stigma around men’s mental health

There is a huge stigma around mental health for both men and women.

If I broke my arm, everyone I know – literally everyone – would urge me to go to the hospital so that I could heal under the supervision of a trained professional.

However, if I were suffering from mental pain, especially pain that is difficult to understand or explain, few would encourage me to seek help. In fact, some would actively discourage me.

It’s tempting to blame everyone else in the world for the stigma around mental health, but it’s not quite that simple. We tend to be open about sharing our physical pain but not our mental pain. When we do, we often water it down.

In fact, most of us feel like expressing our mental anguish is risky. We feel like letting other people know that we sometimes struggle with mental health exposes us to social and professional liabilities. Many can’t even admit their struggle to themselves.

Unfortunately, we are all exactly wrong. Improving your mental health improves every other area of your life. My business runs more efficiently and more profitably than before. My relationships are richer, deeper, more stable, and more fun. And overall, life feels more vivid, exciting, and engaged.

The trick is to be honest with yourself about your mental health and to seek help as needed. The alternative is to live in denial, subtly sabotaging yourself moment by moment, living with more pain than is necessary and perpetuating the mental health stigma.

If – and this is a big if – you ever get to the point where you’re comfortable sharing your experience with others, do so. This will help normalize your inner life while chipping away at the stigma. However, you should be selective about what you share and who you share it with. There’s no need to leave your comfort zone before you’re ready.

Advice for supporting the men in your life

We’ve created a culture that largely fails to nurture people’s emotional needs. Many people are struggling just to keep their heads above water while simultaneously telling the world that everything is just great!!!

If you want to live in a world filled with emotionally fluent humans, we need to heal the wounds that are holding us back from connection, empathy, and courage.

This starts with taking good care of yourself and valuing yourself enough seek the help you need. Why deal with more pain or suffering than is absolutely necessary?

From there, gently encourage others to do the same. As more individuals heal, the world we co-create will begin to heal too.

What no one tells you about leaving the beaten path

A note to the reader: this is an updated version of an article I wrote in 2014. It’s an ode to the artists, entrepreneurs, activists, athletes, entertainers, and rebels who fight against the status quo. More so now than ever, we need you. Godspeed.


“Dude, you can’t expect your life to look like other people’s if you’re living differently than they are. You’re fine.”  -K*, a close friend.

December, 2005: My college roommate W* and I have a weird tradition. On the last night of each semester, we push our beds together and admit to all the stuff we’ve hidden from one another (I told you it was weird…).

For the most part, our confessions are mundane. It’s stuff like “I used your deodorant for a week,” or “I ordered a pizza on your account, and then told you that I bought it for us.” But this time, I have a real confession.

I’m afraid.

W* knows that I plan to drop out of college and start traveling soon. He doesn’t know that I fear I’m veering too far off the beaten path. I already feel isolated and disconnected from the world around me, and worry that leaving the straight and narrow will create even more distance.

I tell W*, “I’m afraid that my life experience will be so different from the norm that I won’t be able to connect with people anymore. I’m afraid that chasing my dreams leads to isolation.”

W* thinks for a moment and says, “Yeah, that’s entirely possible. I think you should do it anyway.”

So I did.

I dropped out of college and spent three years traveling the world. It went on to shape my entire life.


W*’s reassurance helped me to live as authentically as I could and subjected me to difficulties I never imagined. I…

  • Suffered multiple breakdowns that left me directionless and depressed. Two stand out: the first was in Southern Spain in my early 20’s. The second was on an overnight train in the American Midwest in my late 20’s.
  • Felt deeply flawed as many of my close friends got married and had kids while I was struggling just to hold down a healthy relationship.
  • Watched the lives of my loved ones play out from afar, while longing to be by their side.
  • Was so broke that I couldn’t even afford a $2 slice of pizza with friends on the weekends. When they invited me out, I used to lie and say I was busy. This went on for several years.

But all of the lows? They were counterbalanced by highs that felt like lucid dreams. I…

  • Worked with members of President Obama’s White House, Fortune 100 Executives, professional athletes, and multi-platinum recording artists.
  • Toured the world as a speaker working with incredible audiences.
  • Was a groomsmen, officiant, or Best Man in many of my friends’ weddings.
  • Built profitable businesses that allowed me to control the vast majority of my time and attention.

We are often told that we should blaze our own trail, but no one ever tells us what it’s actually like. In my experience, it’s a blend of amazing, agonizing, and downright insane.

The amazing parts of leaving the beaten path

More than anything, finding the courage to leave the beaten path enables you to fully step into the arena. It releases you from the chains of conformity and expectation while allowing you to explore the bounds of culture and reality for yourself.

It creates space for you to access your true potential. The vast majority of people’s lives follow a predetermined path: get an education, get a job, find a partner, buy a house, spend one week a year on vacation, and try not to lose yourself in the margins.

Though this path is well worn, it doesn’t lead anywhere desirable. In fact, it leads to soul crushing mediocrity. In the United States of America, the average person:

  • Is overweight (in fact, 70.7% of Americans are overweight)1
  • Watches five hours and four minutes of TV per day. That’s over 76 days per year. That’s a lot of TV.2
  • Is likely to be dissatisfied with their job3 (which is a shame because most of us spend the majority of our waking hours working)

The straight and narrow smothers your potential. It snuffs out your vivacity and replaces it with deadening ennui and apathy.

When you find the courage to leave the beaten path, you open the door for something much greater than what you’ve inherited.

It allows you to influence the rules of the game. If you follow the beaten path, huge chunks of your life are spent reacting to circumstance. Without realizing it, you’re trapped in a game whose rules you never agreed to in the first place.

Behind schedule on a project? Better work overtime; you’ll be in trouble if you miss the deadline.

Dreaming of a trip to Thailand? Hopefully you can squeeze it in during your 12 vacation days a year.

Wish you had more time to read? Maybe you can get some audiobooks and listen to them in the background.

None of these solutions are horrible, but what if you were the one who got to define the rules? Maybe you’d just cancel the project, or call the client and tell her it’s going to be late instead of sacrificing your personal time. Maybe you’d hop on the jet now and spend six weeks traveling in Thailand. Maybe you’d structure your job so that you’re required to read for an hour a day.

It’s easy to dismiss these things as pipe dreams, but they aren’t.

Creating freedom in your life is entirely possible but it requires creativity, grit, and courage. Of course, luck helps too, but luck’s outside your control.

It reignites the fire and vivacity that so many of us have lost. Whenever I walk around the city during rush hour, I’m shocked by the expression on people’s faces. They seem to lack the fire and vivacity of one who is truly engaged by the world.

The moment you reclaim control over your life’s direction, your vivacity begins to return. It feels like everything clicks vividly into HD. You feel the amazing intensity of simply being alive. You notice the stunning magic in the mundane. You realize that even the shitty days have a certain beauty to them. You understand that this is what you were meant to be doing all along.

The agonizing parts of leaving the beaten path

Leaving the beaten path comes with its own set of unique challenges…

It’s way harder than it seems. Let me state this bluntly because no one ever seems to mention it: leaving the beaten path is fucking hard- both logistically and emotionally.

When you see people do it on TV, whether it’s building a business, traveling, or just embracing their true selves, it seems fun and quirky.

When you do it yourself, it seems confusing, scary, exciting, messy, joyful, easy, and impossible all at once. The idea of conforming to the norm becomes appealing again.

But something interesting happens if you stay true to yourself: you find your lane. When you do, life speeds up in the best possible way. So many good things happen that you stop keeping track.

It’s terrifying. On two separate trips (one to Asia and one to Africa), my brother, R*, asked, “Are you nervous?” as he drove me to the airport.

Before that moment, life was a blur of obtaining visas, planning, packing, saying goodbye, and all that stress. I hadn’t bothered to check in with myself.

In both cases, right after R* asked, I realized, holy shit, yes, I’m terrified.

As I connected to the fear I had been ignoring, I considered scrapping the trips even though I was en route to the airport.

But of course, I didn’t.

And I’m glad I didn’t. Many of the best things in my life began with staring fear straight in the eye. The well-worn path lures us in because we know where it takes us. Forging our own path is terrifying because we sacrifice stability and predictability.

It’s lonely and isolating. Leaving the beaten path tends to be lonely. You’ll notice that fewer and fewer people are able to relate to your experiences. You’ll feel the distance.

When I first dropped out of school to travel, I used to get emails from friends talking about the great parties, funny stories, and gossip I was missing. It was hard to read those emails. A very real part of me wished that my friends’ lives would hold still in my absence. Reading those emails made me long for a type of connection that can only come from being physically near the people you adore.

Worse still was when the emails started to trickle off over the years. I still struggle with this.

The insane parts of leaving the beaten path

Finally, when you leave the beaten path you experience all sorts of insanity (in a good way, mostly).

Your internal and external worlds start to behave like a rollercoaster. Leaving the beaten path requires an openness that few people have experience with. At times, you’ll feel overwhelmingly fragile. I have vivid memories of being driven to tears by random episodes of “How I Met Your Mother” during a particularly turbulent period of life.

Then, you’ll cross over an invisible line, and you’ll notice that everything you touch turns to gold. You’ll close more deals and attend more parties in a month than you did all of last year. You’ll feel electric.

You wake up the next day, and suddenly, everything is back to normal.

With time, you’ll become accustomed to the ebb and flow of reality. You’ll be able to lean into the good times while reminding yourself that the bad times will pass.

Your life becomes defined by synchronicities that make you feel like a demi-God. In Paulo Coelho’s book, The Alchemist (one of my all-time favorites), he mentions that when you start to live your personal legend, you get little winks and nods from the universe along the way.

You’ll land a huge client just before you run out of money. You’ll bump into an old friend you haven’t spoken to in years while exploring Kabul. When you least expect it, love, success, and joy invite themselves into your life.

Sometimes the synchronicities are simple “coincidences.” Other times, they feel like the world has bent over backwards to accommodate you. I have no idea how or why this happens (or if it’s just an illusion that comes with changing your perspective), but I’ve noticed that it does.

Your life looks different than everyone else’s, and it can be confusing. A few years ago, I wrote to a close friend from high school, K*.

Every guy in our group of friends is married now except for he and I. I asked him, “What’s up with that? Where did we go wrong?”

K* has also gone way off the beaten path. Though he’s a brilliant engineer, he’s spent most of his adult life working as a ski bum and house painter. He’s also lived in Hawaii, driven across the country several times, and started a small business.

When I asked K* what was wrong with us, he laughed and said, “Dude, you can’t expect your life to look like other people’s if you’re living differently than they are. You’re fine.”

Well said my friend.

People find you polarizing. When I started telling people that I was going to drop out of college almost everyone had one of two opposite reactions:

1) They would tell me that’s the stupidest thing they’ve ever heard and that I was fucking up my life.

2) They would be wildly encouraging, enthusiastic, and happy for me.

The same exact thing happened when I quit magic, speaking, and coaching. Even when I left Washington, DC, without a plan, some people were excited and encouraging while others freaked the fuck out.

Despite the discouragement, in all cases, departing from the norm was the right decision.

I have a theory as to why this happens. We all have the ability to be true to ourselves and chase our deepest desires, but few of us do. When you start living on your terms, you end up holding a mirror to everyone else in your life. Many people aren’t thrilled by what they see.

They start to notice (perhaps unconsciously) that they’re failing to live their dreams. Instead of learning to conquer what’s holding them back, they freak out and try to drag you down. For them, it’s easier to discourage you than it is to fully step into their own lives.

On the flip side, the people who are encouraging get it. Something very alive in them is responding to something very alive in you. In a little way, they share your experience.

So, should you leave the beaten path?


Just simply yes.

Go blaze your own trail. Find one that feels true and follow it for a while. See where it leads you. If you decide it’s not for you, you can always find a new path, or just get back on track with everyone else.

My concern of being isolated and unable to relate to most people turned out to be very valid. To this day, I still have wild successes and crippling failures that leave me feeling weirdly disconnected from even my closest friends and confidantes.

But those are just the things on the fringes; it’s the sort of tax that we pay for having unusual levels of beauty, awesomeness, and serendipity in our lives. Because more than isolation, I’ve found deep levels of connection to myself, the people I love, and the world we all share. You will too.

Overcoming low self-worth

Autumn, 2014: It should be impossible to feel like shit right now, and yet, somehow, I do…

On paper, my life is beyond perfect. My speaking tour sold out a month ago, and I’m getting standing ovations at most talks. I’m dating a model who has an advanced degree from one of the best universities in the world. My social life is filled with incredible friends and wild parties.

I have more external validation than any human could dream of.

Still, I feel inadequate. I feel like I don’t deserve any of the accolades or relationships. I fear that once people notice who I really am, everything will slip through my fingers. I’ll become a cautionary tale.

It’s like some omnipresent dread is following me around, whispering, “Jason, just wait, it’s all going to leave you the second they see who you really are. You’re a fake man. You don’t deserve this.”


Though many people find it hard to believe, I struggled with self-worth for most of my 20’s.

Though I was “successful,” I didn’t feel successful. I felt like a fraud. I felt like I was growing apart from the people I cared about who would leave me once they noticed how different I was from them. I worried that one day I’d wake up and find myself completely alone.

While intellectually I understood these concerns were nothing more than phantoms, they still possessed me.

I spent two years experimenting with (almost) every conceivable approach to developing self-worth and self-esteem.

Today, I’m no longer possessed by the phantoms that used to stalk me. When I go looking for them or when they rear their heads, I notice only an echo of their former presence. They no longer have the soul crushing grip they used to.

In this article, I’m going to explain how to develop a healthy sense of self-worth. In doing so, I’ll clear up a few common misconceptions while helping you avoid the traps that I fell into.

Before we begin…

I am not a psychologist. If you’ve been struggling with self-worth for a while, seek the assistance of a trained mental health professional, not a blogger.

Understanding self-worth (and dispelling a common misconception)

We tend to give ourselves what we feel we deserve. If you’re struggling with self-worth there’s a good chance that something deep inside of you has been tricked into believing that your needs, desires, and aspirations are unimportant especially when compared to everyone else’s.

Self-worth is not about your external situation. It’s common for someone to spend a fortune pampering herself, while still feeling like shit. On the flip side, plenty of people live quiet, minimal lives and feel amazing about it. Most of us have experience with both sides of this coin.

Self-worth is marked by feeling that the real you deserves to be loved and seen.

It’s about accepting and pursuing your true desires and knowing that even if you fail, you will be ok. It’s about leaning into the hard conversations and opening up to the people that matter. It’s about knowing that your needs matter. It’s about understanding when to be gentle with yourself and the world and when to be ruthless.

Your past, present, and future

I know that this is a controversial belief, but it seems simple to me: everything that happened in your past created the person you are in this moment.

Who you are right now will create the person you become in the future.

So, if you want to heal, begin by digging into your past so that you can improve your present. By improving your present, you will be able to improve your future.

Ignore the self-help gurus: real change comes from the inside out

It’s trendy in self-help to approach internal problems with formulaic external solutions.

Feeling unlovable? Repeat, “I love myself” over and over, and you’ll soon trick yourself into believing it!

Struggling with focus, anxiety, or discipline? Make sure your morning routine includes cold showers, meditation, 30 grams of protein, a microdose of LSD, lifting heavy at the gym, and Whim Hoff breathing. Then you’ll be optimized!

And I get it. This approach almost makes sense. It seems like you should be able to manipulate your external behavior in order to fix your internal problems.

Unfortunately, it doesn’t work. In fact, it’s a crock of shit. Real change happens from the inside out.

To merely change your external behaviors rather than confronting your inner demons is, at best, treating the symptoms instead of the causes. At worst, you’re putting whipped cream on dog shit and calling it an ice cream sundae.

To heal, you have to dig into your life story and shine a bright light on yourself.

The breadcrumb trail of recurring pain, tension, fear, and anxiety

In order to heal, you must lick your wounds. For some, this is easier said than done. Many of us have learned to adapt to our greatest pain instead of confronting and healing it. The trick is to look for recurring negative patterns in your life. That’s where your path begins.

Look for the little moments, obsessive thoughts, or unusually strong opinions that routinely make you feel inferior, afraid, or angry. Money, love, sex, appearance, status, food, intelligence, religion, fitness, and fame (or lack thereof) are all common culprits.

During a silent meditation retreat, I first noticed two problems that had been plaguing me for over a decade.

The first was a struggle to form healthy romantic relationships. I either dated women who I didn’t care about, or failed to open up to the women I had feelings for.

The second was intense anxiety around money. Regardless of my financial situation, I lived with constant fear that I was going to run out of money in the near future.

I spent years attempting to solve these problems with behavioral change. I worked on being more vulnerable with my girlfriends, and I told myself, “Once I have X amount of money in my bank account then I can relax.”

It didn’t work. The vulnerability felt forced and hollow and even when I hit my savings goals, I remained insecure.

I realized that if I wanted to heal, I needed to dive deeper.

Leaning into the pain

Disclaimer: this process will be more effective if done with the help of a mental health professional. They have access to tools and techniques that laypeople – including life coaches – have never even heard of, let alone been trained in.

Once you’ve identified the parts of your life that need healing, follow their threads into your past.

Though cliche, digging into your childhood and adolescence will likely be fruitful. As I was healing, I had to wrestle with things that happened 25 years ago.

The best thing to do is to start with the wounds you’ve noticed and become curious about them. Ask yourself, “Why do I feel that way?” again, again and again.

Let’s say you notice that you often feel lonely during the weekends, even though you have a few people you regularly hang out with.

When you ask yourself why, you realize that you don’t actually enjoy spending time with these people very much. When you explore why you’re spending time with people you don’t like, you find that you’re afraid to ask people you do like to hang out. When you’re curious about that fear, you notice that you’re scared of being rejected by people you admire.

Eventually, you realize that whenever you asked your older siblings to play with you as a child, they repeatedly ignored your requests and made you feel left out.

Though you’re older now, there is an indelible link in your head between seeking the companionship of people you admire and rejection. Today, this link manifests as a reluctance to put yourself out there and leads to complicated feelings about relationships with your peers. A few (but by no means exhaustive) examples of potential root causes of low self-worth:

  • Abuse, trauma, rejection, and neglect that led you to believe your needs are unimportant
  • Emotional distance or ineptitude from people close to you, especially caretakers and confidantes from both your past and current relationships
  • Bullying by classmates, “friends,” or siblings
  • Living in a culture that doesn’t accept you, i.e. being gay in a very homophobic city or faith
  • Being exceptional 1 or otherwise overtly different than most people in your community
  • Childhood or teenage health problems, such as obesity and bad acne

I know that digging into your past can be unpleasant and potentially jarring; it’s also the best path forward. Stay strong. You’re a warrior. By examining your past, you’re raising your self-awareness. Once you’ve found the roots of whatever is sabotaging your self-esteem, you can begin to heal.


The healing process looks different for different people.

For some, simply raising your awareness or performing a ritual for yourself will be enough.

Others will require a significant amount of help and intervention along the way.

Most fall somewhere between the two extremes.

Regardless, once you’ve noticed your old patterns and understood their roots, it’s time to feel the pain you’ve been avoiding. Allow it to ripple through your body. If needed, let it break you. Accept yourself as you are, not as you wish you were. Take your time here, this stuff is intense.

After you’ve done this, heal your wounds with new feelings and behaviors. Set stronger boundaries that prioritize your needs. Build healthy relationships on your terms. Seek comfort when you’re disturbed. Let go of past grievances.

And again, move slowly. This stuff is new for you. Be gentle with yourself.

As your sense of self improves, you’ll start to engage with the world differently than when you were insecure.

You’ll stop hanging out with some of your toxic friends. You’ll uncover natural confidence and compassion within. You’ll experiment with vulnerability and intimacy in ways that you never have before. You’ll be more comfortable with uncertainty. You’ll begin tackling some of your bolder dreams. You’ll spend more time indulging yourself in guilty pleasures (but they won’t feel so guilty anymore).

You’ll realize something that’s been hidden in plain sight the entire time: you are entirely worthy of love, respect, connection, and joy.

Postscript: A note on false healing and false sickness

Before we go, I want to warn you about two traps that people tend to fall into on the path towards healing their sense of self.

The first is the false healers that litter the path towards health. There are many life coaches, psychologists, and drugs (or plant medicines) that can make you feel healed, without actually healing you.

The true litmus test: do the positive feelings last?

If, after intense work, your sense of self-worth is dependent upon the healer you worked with, there’s a good chance that this person (or drug) was a false healer.

Your best bet? Cut your losses and find new approach to healing.

The second is the denial of your own health. This is a trap I fell into. When I finally found a steady sense of self-worth, I was afraid that it would be ephemeral. I struggled to accept my own health because it felt unfamiliar and I worried it was all smoke and mirrors. It wasn’t.

Here’s the deal: if you’ve done hard, earnest work on yourself, and if you’ve recruited the help of qualified professionals as needed, you can feel comfortable trusting the results.

And if you need to heal, I hope you start as soon as you can. I hope you spend as much time feeling great, allowing yourself to be seen, and living as vividly and lovingly as possible. You deserve it.