Why I won’t vote for a third party this year

Tuesday Nov 2nd, 2004, Florida: The United States government and its leaders disgust me. Over the past four years we’ve spilled the blood of countless innocents, allowed the rich to exploit the poor, and let the media shape public conversation around whatever will sell the most advertisements.

I’m sick of this shit.

In an act of protest, rebellion, and hope, I cast my vote for a third party candidate.

More on that in a moment…


The 2016 election has alienated millions of Americans, myself included.

It’s obvious that our country has work to do. We’re plagued by racial tension. There is an alarming gap between the rich and the poor. And mass shootings – including those at schools – have become borderline common.

In a normal election year, at least one of the Presidential candidates would offer the hope (if not promise) of dramatic improvement to the country and its people.

However, in 2016, there is little hope to be found. One candidate is the definition of a Washington insider, while the other appears to be genuinely evil.

I’ve noticed that many of my friends have reacted by disengaging from the political process. In protest, they’re planning to waive their right to vote, write in a friend’s name, or vote for a third party that stands no chance of accumulating influence.

While I understand the decision, I believe it’s gravely misguided. Here’s why….

A decisive victory sends a clear message about nuclear disarmament, Islamophobia, xenophobia, bullying, discrimination, the democratic process, and rape culture.

Trump’s campaign will be studied and emulated for decades to come. Before this campaign, Trump had no political experience. He should have struggled to gain influence and power, yet his tactics were so undeniably effective that he gained a presidential nomination with a large chunk of the country intending to vote for him.

Over the course of the election, Trump has encouraged the spread of nuclear weapons, Islamophobia, xenophobia, bullying, racism, and rape culture. He’s also threatened to disregard one of the cornerstones of democracy: the peaceful transfer of power between leaders.

The closer he comes to winning, the more likely we are to produce politicians who peddle in fear, discrimination, and hatred like he does.

As I write, it seems likely that Clinton will win the election. The real questions are, “By how much will she win?” and “What does her margin of victory suggest about the US electorate?” The answers are deceptively important as they will influence countless politicians present and future.

Consider the possible outcomes and implications:

Outcome 1: Clinton wins the election by a landslide. If this happens, the US electorate demonstrates that it does not tolerate the type of fear, hatred, and divisiveness that Trump advocates. Trump-like candidates, campaigns, politicians, and policies will begin to disappear.

Outcome 2: Clinton loses, wins the election by a narrow margin, or fails to get the popular vote. If this happens, it will send a clear message that a candidate who trades in fear and hatred can win a large chunk of the US electorate. This will create an influx of Trump-like politicians in the near future.

If you are a liberal who chooses to abstain, write-in, or vote for a third party candidate, you will narrow the margin of Clinton’s victory. In doing so, you unintentionally signal that Trump’s demeanor and approach to politics is effective in the United States.

Voting alone will not create a viable third party

One of the reasons I voted for a third party candidate in 2004 is because I thought that in doing so, I would be contributing to a more diverse political climate.

Unfortunately, I was wrong. Recent history has repeatedly demonstrated that the power of a presidential vote doesn’t extend beyond the selection of a Democrat or a Republican.1

I’ve learned that if we want a viable third party, a more progressive presidential candidate, tighter gun control, or accountability for Wall Street, we need to do more than vote. We need to speak up about the causes we believe in, while strategically donating our time, money, and energy to their success.

Change doesn’t come from throwing votes at a third party candidate and then disengaging. It comes from the ground up. You have to organize frustrated voters like yourself, along with activists, and community leaders around a focused issue. Change happens by creating or supporting grassroots campaigns and patiently nurturing them as they gain momentum.

For me, this is a growth area. In the past, I’ve voted for stricter gun control and better welfare systems. Still, little has changed, and I remain dismayed. It has become clear to me that voting alone is not enough to affect real change.

 As you decide for yourself whether or not a singular vote for a third party has any real power, remember that the more narrow Clinton’s victory becomes, the more likely we are to see a spike in candidates (and eventually lawmakers) like Trump.

Postscript: fighting hate with hate is a losing game.

One of the most disturbing elements of this election is the faction of “progressives” who hate both Trump and his supporters. To strongly dislike Trump for what he represents is one thing. To dislike or disregard his supporters is entirely different.

Yes, some of Trump’s supporters do belong in a “basket of deplorables,” but they’re few and far between. Most are decent people who are either misinformed, controlled by fear, or party line Republicans who dislike Clinton even more than they dislike Trump.

To fight hate with hate is to throw fuel on the fire; in doing so, you become the exact thing you are railing against. When we shame, mock, ridicule, or insult Trump supporters, we reaffirm the divide between liberals and conservatives. Doing so leaves no room for anyone to gracefully change their mind without losing face. It creates a chasm that becomes increasingly difficult to bridge.

Instead of hating Trump’s supporters, find ways to love and respect the people you disagree with. Learn to love the person, even if you disagree with their beliefs. When you allow love to run deeper than hate, you embody the attitude that so many of us have found frighteningly absent in this election.

3 days of silence

The past year has been whirlwind. A lot in my life has changed.

I quit my job as a speaker to focus on writing and starting a new business. I moved to Colorado. I made new friends. I got a speeding ticket in a rented sports car. I officiated two weddings and was the best man in a third. I got my first piece of hate mail. I watched one of my mentees go on to become substantially more successful than I am (that was interesting…). I held a few of my friend’s new babies. I went on dates. I advised a reformed mob boss, a multi-platinum recording artist, one of the United State’s leading surgeons, several investors, and countless entrepreneurs. I spent a day babysitting a 10 month old and a 3-year-old. I hosted close friends and family when they came to visit. I had hard conversations that I had been putting off (most of them went really well – I wish I hadn’t put them off). And I quit drinking caffeine… several times.

But what I hadn’t done – until two weeks ago – was give myself time to come down from it all, to process everything that happened, and to reconnect to myself and the flow of the world.

And truthfully, it was starting to show. I had become frayed at the ends. The energy and excitement that inspired me to chase one adventure after another was waning. The stable sense of purpose and enchantment I rely on felt blurry and difficult to access.

So I spent three days in silence at an ashram hidden away in the Rocky Mountains. My aim was to reconnect to the passion and energy that inspires me to live as vivaciously as possible.

In this article, we’ll cover what happens when you decide to step away from the stress and noise of modernity, and focus exclusively on yourself for a few days. More than that, you’ll learn how to consistently find stability within a shockingly destabilizing world.

You’ll learn how to use a personal retreat to reconnect to your sense of purpose, flow, power, and enchantment. In fact, many people will find that going on a retreat will provide the same benefits that they would normally expect from a skilled psychologist or coach. And don’t worry, intense silence and isolation isn’t always necessary for reconnecting to yourself.

I’ll also share what I learned from spending three days in silence, disconnected from the world.

Step 1: Prioritize yourself by calling in healthy

The world we live in is chronically destabilizing. We’ve become convinced that if we aren’t stressed, we aren’t working hard enough. The personal development industry has tricked us into believing that we aren’t ok. The news wants you to believe that we live in a dangerous world. Texts, emails, and social media are constantly fracturing our attention.

This leaves you feeling as though you’ve fallen behind. You feel that if you’d just push a bit harder, you can catch up – maybe even pull ahead. The sensation of always being behind makes you feel small and robotic. You become reluctant to invest time in doing nothing; you fear that if you do, you’ll fall back even further.

And there’s the rub: if you’re reluctant to take a few days for yourself, you clearly have indicated that the demands of the world are more important than your needs and happiness. They aren’t.

Begin the process of reconnecting with yourself by literally scheduling time in your calendar for you. At the very least, hold one full day for yourself. If you’re able to schedule more, even better.

Step 2: Alone or with a companion?

When I recharge, I like to be alone. However, many people find they are happier and more lucid when they bring someone they love.

If you decide to bring someone with you, ensure that they share your desire to recenter and that you are comfortable opening up and being vulnerable around them. When done correctly, personal retreats create deep insight into your heart and mind.

Step 3: Find your haven

I like to spend time at the ocean, in the mountains, or in the forest. For me, the sheer act of being in nature is healing.

Of course, you don’t actually need to go anywhere. You can recenter from your own home. You can also rent a hotel room, crash at a friend’s place while she’s out of town, or go camping.

The important part is that you find a place that allows you to disconnect from the demands of the outside world. This will allow you to focus on yourself.

Step 4: Disconnect

In order to reconnect to yourself, you have to temporarily disconnect from the outside world. I recommend keeping your phone and computer off for at least a day, and ideally the entire retreat. You may be surprised to find that after the initial discomfort, you feel relieved to be untethered from the digital world.

Be sure to put up an out of office auto-responder and tell the people that you’ll be unavailable for a few days.

If you feel the need to stay in touch with a few people, schedule the calls before you leave so that you remain as disconnected as possible. If you do this, make sure you’ve turned off your phone’s notifications so that you aren’t tempted to check in with your digital life.

I know that many people are reluctant to consider spending even a few hours without their phone. If you’re one of these people, ask yourself why you’re so reluctant to disconnect. Many people will find that they’re afraid of boredom. If you can relate to this, it’s a sign that you need to lean into your boredom. Just beyond it, you’ll discover quiet but profound truths about yourself

Step 5: Be intentional about your mental and emotional inputs

Several weeks prior to my retreat, I binge watched the cartoon Rick and Morty. (Note: if you haven’t watched Rick and Morty, you’re missing out). During the retreat, I found myself thinking about Rick and Morty quite a bit. This was a sharp reminder that our minds and hearts are sensitive instruments; they respond to whatever we allow in. I spent time watching cartoons, and two weeks later, I was still thinking about cartoons.

Once you’ve disconnected from the digital world, it’s tempting to fill the space with music, audiobooks, podcasts, novels, magazines, activities, and if you’re like me, cartoons.

Resist the urge.

Spend at least a few hours with minimal inputs. Allow yourself to become bored so that your mind starts to wander. You’ll notice that as it does, you gain clarity and insight into yourself. Your thoughts and feelings will start guiding you toward new levels of insight. You’ll notice emotional or behavioral patterns that you had previously been unaware of.

The deeper your awareness becomes, the more power you’ll wield over yourself and the world around you.

Here are the inputs that will speed up the process of finding clarity during your retreat:

  • Gentle exercise like hiking, walking, yoga, or calisthenics
  • Good books
  • Healthy foods
  • Music you love
  • Reflective, open conversation
  • Massages
  • Time in nature

Step 6: Relax, reflect, and recharge

This is the most important part of the retreat. First, you need to rest. You can’t reconnect to yourself if you’re exhausted. Most people -especially if they’re living in a city- are running on less sleep, less relaxation, and less rest than they need.

If you have to spend a day or two lying in bed, reading, and listening to music, more power to you. You’ll notice that after a bit your energy levels and excitement about life begin to spike. Many people will feel more energetic than they have in a long time. I did.

As your energy returns to you it’s time to begin the deep work of reconnecting to yourself. The goal is to gain insight into the psychological and spiritual knots that have been hindering you. Different approaches work for different people. Pick the approach that feels right. The most common ones are:

  • Meditating
  • Journaling
  • Praying
  • Walking in nature
  • Holding space for pure silence
  • Speaking openly and candidly to a trusted companion
  • Interviewing yourself

There’s no need to force insight. With time, space, and reflection, you’ll automatically deepen your understanding of yourself. Resist the urge to be critical. Instead, approach yourself with warmth and compassion, since this will heal you much more quickly than judgment.

Step 7: Notice what’s going well in your life…

Our minds are wired to spend more time attending to the bad aspects of our lives than the good ones.1

Because of this, we judge the world and ourselves far more harshly than is warranted.

End your retreat by noticing what’s going well in your life and the world around you. I like to make a list.

By focusing on positives, you will return to your normal life with a refreshed and empowered perspective. This perspective can be used to create happiness, vivacity, abundance, and joy.

So, how did my 3 days of silence go?

When I started my silent retreat, I was genuinely nervous. I was anxious about disconnecting and spending time in solitude. I didn’t enter the retreat with a strict plan. Instead, I let my body and intuition guide my decisions.

I spent most of the first day resting. As I rested, I noticed a growing sense of energy and excitement returning to my body.

I spent the second and third days meditating, journaling, hiking, and doing nothing. I could feel the stress melting away and my mind slowing down. This created space for suppressed emotions to surface.

I noticed that the excitement of the past year obscured a few truly painful experiences that needed my attention. I held space to feel the pain that I had been avoiding. I allowed myself to feel sympathy before releasing the pain. I noticed knots around love and money that have been preventing me from stepping fully into my life.

As I processed my thoughts and feelings, I felt them dissolve. In their place, I regained a sense of purpose, clarity, drive, excitement, peace, and connection.

It’s been over two weeks since I returned from my retreat. I still feel a strong sense of flow, enchantment, calm, clarity, and excitement. With an open mind, and a few days for yourself, you can expect similar results.

Letting go of a dream: why I left professional speaking

From August of 2013 through March of 2016, on paper, I was leading a dream life. It was the peak of my speaking career. I made more in a night than most of my friends made in a month. I had a global waiting list of clients. When I travelled for work, it was on someone else’s dime, often in luxury. And in its own little way, I felt like my work was helping people.

I trained Fortune 500 executives, university presidents, professional athletes, psychologists, best-selling authors, and senior members of multiple governments. In a particularly surreal moment, I even advised a member of President Obama’s Cabinet.

This was a dream come true for me. I remember watching a professional speaker in high school and thinking to myself, “Wow. That’s so cool that he makes a living giving speeches. I wish I could do that!”

Yet, in March of 2016, at the top of my game, I left professional speaking.

I’ve never shared the full story about why I chose to leave speaking, not even with my closest friends or family. When people asked me why I quit, I mumbled something about being burnt out from the perpetual travel and the demands of being on stage, but that wasn’t the whole truth.

I didn’t quit speaking for the reasons you expect. There was no hidden drug addiction, financial mismanagement, debilitating anxiety, or psychological collapse.

Instead, this is a story about how something I used to love took over my life as I became increasingly successful. Though it took me a while to understand what happened, something that started as dream come true turned into something that prevented me from living the life I wanted to live.

My aim in sharing this story is to help speakers cut through the inherent isolation of the job. I also hope to help emerging speakers avoid the mistakes I made. Along the way, I’ll share tips about how to build a thriving speaking business. I’ll conclude by discussing what I learned about success when I had to start a 40 date speaking tour days after one of my friends died.

Live performances are more isolating than anyone realizes

To be a successful speaker you have to understand something simple but often unnoticed about modernity: nearly all of the information in the world exists online for free.

That means that when someone goes to hear a speaker speak, she isn’t really interested in the information that the speaker is going to share (even though she may think she is). What she’s really interested in is how the speaker will make her feel.

In other words, the speaker’s job is to inspire intense feelings for the people in her audience. The more precisely she can create the feelings that her audience has been yearning to feel, the more successful she’ll become.

To do this, I spent months writing and testing material. I shared deeply personal stories that required earnest vulnerability. I obsessed over the talk’s structure and flow so that I could create a strong emotional connection with my audiences.

When I was on stage performing the speech I wrote, it felt like I was opening a vein. I wasn’t just sharing the bleeding edge of my life’s work; I was sharing every ounce of who I am. Though it can be difficult for people who haven’t spent much time on stage to understand, when you approach speaking like this, you end up falling in love with your audiences and yearning for them to love you too.

If I had the chance to truly get to know the individuals in my audiences, this would have been an amazing, deeply intimate shared experience. But of course, it’s impossible for a speaker to get to know each person. There’s one of me and hundreds of them.

After opening myself to audiences for years on end, it felt like I created thousands upon thousands of one-way relationships with people around the world. Though some speakers don’t seem to struggle with this, I did. I used to go back to my hotel room after a speech feeling hollow and lonely. In fact I used to tell my friends that working as a speaker made me feel like a high-end prostitute for people’s emotions. Though they laughed, I wasn’t joking.

If this only happened once or twice a year, it would be a non-event, but this was my job for nearly a decade. It happened every week.

The lifestyle creates a penetrating type of loneliness

The first time I saw the George Clooney film, “Up in the air,” I started crying because it hit so close to home. At my peak, I spent over 200 days a year on the road. I missed countless amazing events with friends and family. I spent so much time away that some of my friends just stopped calling. When I was home, I was often so exhausted that I didn’t have the energy to spend quality time with people I love.

I experimented with different ways of solving this problem. I invited my friends and girlfriend to come with me when I travelled. I offered discounts for speeches in cities where my friends and family lived.

Unfortunately, it didn’t work. When someone came with me to an event, I felt torn between two worlds. On one hand, the event was literally paying for my presence and attention. On the other hand, by paying full attention to the event, I was neglecting the person I brought with me. When I spoke in cities that friends lived in, I rarely got to spend good time with them; most of my time was spent recovering or prepping for the next event.

However, I did find one solution that worked well: incentivizing clients to hire my speaker friends to speak with me. Pulling this off required a small miracle (the client needed a budget, and the friend needed to be available and a good fit), but when it worked, it was amazing. Though this only happened a few times, it consistently created some of the most positive experiences I’ve ever had. In fact I remain enthusiastic about speaking at conferences that my friends are speaking at.

Touring makes mental and physical health borderline impossible

Several things that are bad for your health: having extreme levels of stress and neglecting diet, sleep, and exercise. Unfortunately, professional speaking requires all of them.

Even if you’re fairly confident on stage, there are so many moving pieces that public speaking can’t help but become an extremely stressful experience.

A very abbreviated list of details that working speakers need to keep track of while traveling for work:

  • Getting to the airport on time
  • Having a backup plan for missed, delayed, or cancelled flights
  • Ensuring that there is a driver or rental car waiting for you at the airport
  • Remembering personal details about your client and her life (when someone spends a lot of money on you and trusts you to speak at their event, they get offended if you don’t make them feel cared about)
  • Verifying that there are no mistakes in your slides and that it is customized to your audience
  • Making sure that the batteries in your mic and clicker are fresh
  • Understanding the logistics well enough so that you can get to the venue in time for your first event (often a dinner with the sponsors for which you’re expected to be “on”) and that you can return to the airport in time for your next flight
  • Remaining pleasant and playful towards all of the people you meet throughout the event (again, if you can’t show up generously and enthusiastically for the people you’re working with, you’re doing it wrong)

And then of course, there’s that 60-minute talk that you have to know cold and be confident performing in front of hundreds or sometimes thousands of people.

While all of these things are going on, you’ll also have to deal with the annoying reality that you can’t maintain your diet, exercise, or sleep on the road as well as you can at home.

In moderation, the demands of giving a speech can be pretty exciting and the departure from your normal wellness habits is trivial. But when you do this every single week, it becomes deadening.

Speaking for small crowds in big rooms is common. It’s also mortifying.

Any business owner deals with an insane amount of rejection in the form of unreturned calls and emails, unsolicited criticism, and straight up, “No’s.”

For speakers -and anyone else selling themselves-  this rejection runs the risk of feeling extremely personal. If you don’t learn to untangle your professional identity from who you truly are, you run the risk of being eaten alive by the world.

After a year or two, I learned to detach myself from most forms of rejection. Still, there was a subtle form of rejection that I could never get over, and it mortified me every time it happened: speaking for small crowds in big rooms.

There is a huge difference between speaking for 100 people in a room designed to hold 75 and speaking for 100 people in a room designed to hold 500. Even though the number of people attending remains the same, the feel is completely different.

Speaking for 100 people in a small room will make you –and the audience- feel amazing. The energy and excitement will be almost tangible. Speaking for 100 people in a huge room will make you feel like an embarrassment. It’s impossible to ignore all of the people who were expected to show up, but didn’t.

On any given night, I ran the risk of dealing with something that felt terribly embarrassing, and often I did end up playing for small crowds in big rooms. In fact, there were three speeches where the event coordinator was planning for at least 200 people to show up, but fewer than ten showed up. Yeah, that sucked.

While there are ways to pivot around this problem (like turning an unexpectedly small event into an intimate conversation), it’s still horribly embarrassing. Unfortunately, this is a problem that all non-celebrity speakers have to cope with.

Ultimately, my heart was no longer in it

I don’t know exactly when it happened, but all of the above problems blurred together and left me feeling depressed about my job. Though I loved the hour or two I spent on stage and the time spent with my clients and audience members, I dreaded everything surrounding it. I especially hated the way it took me away from my personal life.

I also lost faith in the idea that giving a one-hour speech is a good way to change the world. Can it be done? Yes, of course, but it only seems to happen once every few decades.

Will I give speeches again in the future? Absolutely. There’s a lot of things I love about speaking, but it is unlikely to ever be my primary professional focus again. For me, the price isn’t worth the cost.

It’s been eight months since I gave my last professional speech, and truthfully, I don’t remember the last time I was this happy.

Advice to emerging professional speakers

I know that many people want to pursue a career in professional speaking, and I get it. Though I’m glad I left, I’m very grateful that I pursued it for as long as I did. For those interested in building a speaking business, here are my best tips:

Be honest with yourself about your motives: though few are willing to admit this, most people who are drawn to speaking are driven by the desire for validation. They believe that approval from audiences or clients who fly you around will make them feel worthy and successful. I’ll save you a lot of time and heartache: if you’re primarily motivated by the validation or money, don’t waste your time. The only speakers who succeed long term are the ones who want to give back to the world through speaking. If you’re just looking for money and accolades, there are far easier ways to get them.

Focus on a centralized market. I spoke on very niche topics: leadership for millennials and self-compassion for high performing individuals. Though there is an active market for both of these topics, it’s decentralized. This means that I had to travel for most of my gigs.

It’s entirely possible to make a healthy living as a speaker without ever getting on a plane. The best way to do this is to speak about a topic that has a broad appeal (sales, leadership, business, or personal development), and focus all of your sales and marketing efforts on local or regional markets.

Develop a complementary source of income. One of the main reasons I spoke as much as I did is because it was my only source of income. You can increase your earnings by having a book, course, product, coaching sessions, or consulting services to offer your audience. In fact, the only speakers I know personally who make more than $250,000/year are those who sell additional products or services.

Try to take both praise and criticism impersonally. Love and validation are not things that you need to earn; they are things you must search for within yourself. You are not your business. It’s ok if some people don’t love you. Conversely, even if you get standing ovations every night, this does not excuse you for being a jerk to your brother.

In the beginning focus on two things: sales and your speech.  Social media, branding, networking events, your logo, a fancy website, and all of that other stuff is a waste of time when you’re starting. Focus all of your attention on developing the best speech that you can and selling yourself. Many speakers go to great lengths to avoid selling themselves. Let me make this easy: selling yourself is unavoidable, so you might as well start now.  No amount of twitter followers or Facebook likes will change that.

Continually invest in your ability as a speaker. To be blunt: most people who think they are good speakers, aren’t. Holding an audience’s attention for an hour and leaving a client feeling like that hour was worth thousands of dollars is exceptionally difficult. Even if you are an amazing speaker, you should always work to refine your craft and provide a better experience to your audience. Study improv comedy, standup comedy, storytelling, acting, and screenwriting. If you can find a good speaking coach (unfortunately, they’re rare) work with her.

Post Script: what you learn when your life collapses right before a national speaking tour

In July of 2013, my personal life collapsed. My girlfriend of several years and I broke up, my best friend moved away, and a close friend died. All this happened in one month’s time. I was a wreck. For days on end I drank myself to sleep and struggled to get out of bed.

One month later, in August of 2013, my professional life flourished. I began a 40 date speaking tour that would take me across the United States and back. I was more successful than most speakers could ever dream of.

These side-by-side experiences allowed a very rare glimpse into the reality and power (or lack thereof) of success.

I learned something that I still cherish today: my personal life is far more valuable than my professional life. The success that I had worked so hard for did nothing –literally nothing– to alleviate the pain I was experiencing.

I learned that I would rather build my life around my relationships and figure out how to fit my work in afterwards. I learned, cliché as it is, that status is no replacement for physical and mental health.

I learned that, at its best, success will magnify how you already feel about yourself. At its worst, it will chew you up, spit you out, and walk away with no regard whatsoever for your well-being. So pursue the projects that you care about; in fact, pursue them with as much of your heart as you possibly can. Just don’t fall into the modern trap of believing you can enjoy life without time for the people you love.

The emotional imprisonment of the modern male

Nov 2013, Washington, DC: I fell in love with R* way too quickly. I was on the heels of a serious breakup and trying to convince myself I was ok. She was getting over the pain of a failed engagement. It seemed like we fit together perfectly (if also, toxically) and dated for a few weeks. It felt big and real and exciting.

Then, without warning, she vanished.

I was wrecked.

I was depending on this relationship to make me complete. Without it I could feel my already fickle happiness and confidence slipping through my fingers.

When I realized R* was gone, I went on a seemingly endless walk along the National Mall.

I thought to myself, “That’s how life is. People will make you happy for a little while, but then they’ll hurt you mercilessly. You’ll have to pull yourself up, find another person to make you happy for a bit, and try to delay the inevitable pain. Enjoy the next 60 years asshole…”

I don’t remember the exact moment or what triggered it, but being abandoned by R* made me realize something important: I am directly responsible for my life experience.

My happiness, health, emotional well-being, success, and everything else that I care about? They’re my responsibility. I can’t outsource them to anyone else, not even a girlfriend. Somehow, I had missed that for the first 27 years of my life.

The subtle crisis of masculinity

When I look at the boys and men of my generation, I notice that we seem to be experiencing a crisis of masculinity.

Many of the men I meet struggle to understand their emotions, fail to form deep connections with the people around them, lack a sense of vision, and fail to source drive and validation from within. This leaves them feeling isolated and alone and deprives the world of their potential contributions.


What follows are the six biggest problems I notice men dealing with today. In each section, you’ll find an explanation of the problem, as well as practices, ideas, and guidelines on how to solve it.

Along the way, we’re going to cover everything from erectile dysfunction and the fear of being unlovable to flawed masculine archetypes. I’ll conclude with a call for men to embrace their raw masculinity.

This article clocks in at nearly 4,000 words. If you’d like to jump around, you can find an overview of the article below. Clicking the link will bring you straight to that section.

Problem 1: A lack of deep purpose

Problem 2: An unexpressed fear of being unlovable

Problem 3: Sexual shame, confusion, and posturing

Problem 4: Difficulty embracing, expressing, and processing complex emotions

Problem 5: Flawed male archetypes

Problem 6: The delusional desire to be self-sufficient

Practices for the modern man

A return to raw masculinity 

1: A lack of deep purpose

Many of the men I meet drift through life. They find a job that pays the bills, marry someone they almost love, have 2.4 children, and then fill the remaining space with beer, TV, video games, and other sources of white noise. This isn’t a terrible existence, but it lacks a deep sense of purpose.

I’ve noticed that many men -myself included- live more vibrantly and powerfully when they are rooted in a sense of personal purpose.

One man may find purpose in striving to become the best athlete at his gym. Another may feel driven to write poetry. A third may want to end poverty. The specific purpose varies from man to man and is likely to evolve over time. What matters is that a man pursues his purpose purely for himself.

The best way to find purpose is to spend time alone. Create silence within your life. Do not distract yourself with books, friends, or TV. Go for long, undistracted walks. Meditate. Journal. Remain open to the thoughts, ideas, feelings, and realizations that come to you. It’s difficult to predict when clarity will come. Don’t be surprised if it comes quickly. Don’t worry if it takes time.

If spending significant time alone and in reflection doesn’t feel right to you, consider discussing your search for purpose with a few people you trust. Listen carefully to their feedback, but don’t feel bound to it. Trust yourself.

When you feel a sense of purpose starting to animate you, ask yourself, “Does this feel like the best way for me to engage with the world?” If the answer floods you with energy and excitement, you’ve found the seeds of your purpose. Now begin living that purpose. Your purpose may change, expand, contract, or morph over time so be sure to periodically check in with yourself.

2: An unexpressed fear of being unlovable

When men fail to process and express complicated emotions, they build walls around their hearts. These walls make receiving love very difficult. Many of the men I know readily give love and compassion to other people, while being exceptionally hard and cruel to themselves.

If you have never learned to love yourself, consider approaching the problem from two angles. First, ask yourself the question, “If I deeply loved myself, what would I do differently?” Chances are you’d prioritize your health, fill your day with treats for yourself, and set stronger boundaries in your personal and professional life. When you start doing these things, you’ll begin to chip away at the walls guarding your heart. Start now.

Secondly, you should work to heal old wounds. This includes digging into your life story, feeling the pain and sadness that you’ve been avoiding, and accepting yourself as you are, warts and all.

This work is best done with a coach or psychologist who specializes in this style of heart opening work. However, if you’re going to attempt it on your own, here is what I suggest: write out your entire life story in a stream of consciousness narrative. Do not judge anything that comes up. Instead, pay attention to the times when you were being cruel to yourself and the times when others were cruel to you. When you notice these instances, connect to the emotion and sit with it.

3: Sexual shame, confusion, and posturing

The messaging men get about sex is as straightforward as it is destructive: the more women you sleep with, the more of a man you are.1 If you choose not to have many partners – or if people don’t find you sexually desirable – you’re not much of a man. Men are also told that sex is primarily a physical (as opposed to emotional) experience.

Obviously, this is bullshit, but it’s bullshit that runs deep in men’s psyches.

On one end of the spectrum is the man who becomes consumed by sex. He studies pick up artists, builds his social life around trying to meet women, and measures his worth by the number of partners he’s had. Without necessarily meaning to, he ends up thinking of women as objects and failing to understand them as humans. Many of these men end up feeling as though women are adversaries and that love and sex is a power struggle.

The other extreme is the man who feels shame around his sexual identity and attempts to suppress it. Instead of pursuing love and sex, he quietly resolves to stay in and masturbate. When he does have sex, he feels guilty, as though his partner is doing so at her own expense. When these men fall in love, they find themselves perpetually being friend-zoned. This becomes discouraging, and they end up feeling plagued by fears of being unlovable or undesirable. They feel tragically flawed.

What men need to do is develop a healthy attitude towards love and sex. They need embrace their sexual identity, without becoming defined or consumed by it.

Doing so starts understanding a few simple truths that most men fail to realize about sex:

  • Sex is one of the most vulnerable, intimate things that two people can do together.
  • It’s normal to be uncomfortable about sex. Unfortunately, the discomfort leads to men avoiding real conversations about it.
  • Though many men deny this, sex – even casual sex – is a highly emotional experience. If it weren’t, men would stop pursuing women and just stay at home masturbating. Obviously, that’s not what happens; the physical presence of another human matters. A lot. If you can connect with the other person emotionally, the experience is better.
  • Sex with strangers tends to be isolating.
  • Erectile dysfunction is deceptively common. To put it bluntly, about half of my guy friends have called me at one point because they were experiencing erectile dysfunction.
  • Premature ejaculation is also deceptively common.
  • If you suffer from either erectile dysfunction or premature ejaculation, the first step is to talk to your partner about what you’re going through. Yes, doing so is hard. However, virtually all men are delighted to discover that their partners are accepting and nurturing. In many cases, honest conversation helps solve the problem. If it doesn’t, consider talking to your doctor.

Overcoming sexual shame requires being honest with yourself about your experience with sex and love. From there, the approach to getting what you want from your love life varies from man to man. Here are my best suggestions if you’re struggling:

If you are afraid to make a move, or if you are plagued by isolation, stop watching pornography and spend less time masturbating. Try to eliminate pornography entirely and only masturbate once or twice a week. This will build up the sexual energy in your body and force you to dwell in reality. Many men find this extremely difficult so if you slip up be sure to be easy on yourself.

If you’ve been putting a lot of pressure on yourself to date, get laid, get married, or if your life is dominated by the search for love or sex, remove the pressure. Intentionally take a month or two off from dating. Doing so will force you to find happiness and validation from other sources. Earlier this year I took four months off of dating to focus on myself. My goal was to build a life I loved on my own, and then find a partner. When I decided to start dating again, it took almost no time at all to find a great partner.

If you’ve been going on dates from time to time, but struggling to connect, change your goal.  Your goal should be getting to know the person you’re dating, nothing more. Ask questions. Listen. Instead of being quick to judge, seek to understand. If they ask questions about you, be as honest and vulnerable with your answers as you can.

If you’re ashamed of sex, dig into your past. What did your caretakers, religion, or culture tell you about sex that made you ashamed? Did you have a traumatic experience like rape, molestation, or sexual embarrassment that you’ve been avoiding? The more you understand the root of your problem, the easier it will be for you to unravel it.

4: Difficulty embracing, expressing, and processing complex emotions

B* is a close friend of mine. When his wife was in her second trimester, they had a miscarriage. B* didn’t tell anyone. In fact, the only reason I know they miscarried is because his wife told me.

Of all the problems I see facing modern men, the most significant is the inability to connect to and process their emotions.

Boys learn not to express vulnerability. As children we are told that, “Real men don’t cry.” If we do cry, we’re likely to be mocked. Boys who express fear or sensitivity are called, “Pussies.” Through years of social conditioning, emotional suppression becomes habit for most guys.

If a man never works to rewire his relationship to his feelings, all of his negative emotions remain unexpressed and pent up. This blunts the positive emotions and leads to a deep, penetrating sense of isolation. It also results in temper problems and unpredictable flashes of anger.

Fortunately, all people can learn to connect to their emotions. Here’s how:

First, get clear about how you feel. The easiest way to do this is through honest reflection. For connecting to simple emotions, going on a walk or journaling works well. For untangling more complicated emotions, you’ll likely need a few days of reflection. Personally, I like to go into the mountains or to the sea. If you are not the type to spend several days on your own, another approach is to talk through the issue(s) with people you trust. It’s important that you feel comfortable being honest and vulnerable around them and that they won’t shame you for your vulnerability

By holding space for reflection, you’ll be able to connect to yourself. You may be surprised by what you discover. Do not judge what comes up – that will only create further closure. Instead, stay open. If you cry, you cry. If you laugh, you laugh.

Second, use curiosity to get to the root of your emotions. Upon reflection, you may notice, for example, that you’re frustrated because your girlfriend lectures you about appropriate social interaction. When you notice a feeling that you find difficult, ask yourself why you feel that way.

Perhaps you’ll discover, “I get frustrated because I don’t think I need any help with social interaction.” So you ask, “Why does it bother you when people think you need help with social interaction?” And so on and so forth until you get to the root of the feeling.

Third, once you’ve uncovered a difficult emotion and gotten as close to its root as you can, express it. Expressing your emotions can happen through a wide variety of methods, including, but not limited to:

  • Artistic creation (music, painting, wood work, etc.)
  • Controlled rage (like smashing plates, pounding pillows, hitting a punching bag, etc.)
  • Conversation
  • Sports
  • Writing

Finally, if you’ve noticed that you need something, give it to yourself. Perhaps you need time away from your spouse, you need to rest more, or you need your kids to respect your boundaries. Start giving yourself the things you need. By prioritizing yourself, you’ll be better equipped to take care of the people you love and influence the world around you.

The end goal is to be able to understand what you’re experiencing in any given moment. Many men will discover that the more adept they become at expressing and understanding their emotions, the more smoothly their entire lives go.

5: Flawed male archetypes

One of the biggest problems facing modern men is a lack of healthy male archetypes. The three most common have tragic flaws:

The 1950s man. These are the guys who get caught up in gender roles and feel the need to be the provider. They get insecure if their partner makes more than them. They deny the value – and at times, the existence – of their emotions. When they are struggling with something, they remain closed off to the world and the people around them. They’d rather suffer in silence than risk being vulnerable and asking for help.

The millennial man-child, more commonly known as the nice guy. These are the guys who lack a strong sense of self and are afraid to be assertive. They can’t handle emotional friction and avoid confrontation. They have a quiet sense of entitlement that prevents them from taking responsibility for their lives. When I was dating R*, I was one of those guys.

The third, and perhaps most common, is the reformed frat boy. He can hold down a job, but lacks genuine ambition. He makes an ok boyfriend, husband, and father, but fails to form deep connections with himself and the people he loves. He’s learned to use humor to disarm uncomfortable situations, instead of doing the hard work of leaning into them.

Missing from all of these archetypes is what I believe to be essential for the modern male: a drive to shape the world, emotional fluency, and a reverence for calculated risks. More on that later.

6: The delusional desire to be self-sufficient

Men seem to suffer from the delusion that in order for their success to be valid, they have to achieve it entirely on their own.

In reality, there is no such thing as a “Self made man.” There are only those who ask for help when they need it and those who fail.

Personally, I’ve relied heavily on help from friends, family, and professionals. They’ve helped me financially, emotionally, mentally, materially, and physically. Assistance from other people has grown my business, led me to happiness and purpose, healed me after breakups, and delivered Gatorade when I was hung over.

But asking for help doesn’t come naturally to me. It’s a skill I had to learn. It felt like swallowing my pride. If you’re a man that needs to learn to ask for help, I’d encourage you to go through the same process I went through:

First, reflect on the times when you’ve been asked to help other people. There’s a good chance that you felt happy someone asked for your assistance. It probably made you feel needed and important. Realize that other people will be happy to help you. You’ll contribute to their inner desire to be needed.

Second, start by asking for something small. Ask to borrow a few bucks from a buddy at work. Once that becomes more comfortable, ask for advice on a project. Keep moving the line until you’re able to ask for all the help that you need. You’ll notice that in doing so, everything you care about comes more easily to you.

Finally, when other people ask you for help, provide assistance with as much grace and humility as you can.

Additional practices for the modern man

Though I’ve included suggestions on how men can embrace their masculinity throughout the article, I’d like to make a few additional recommendations. As always, pay attention to the ideas that excite you and make you nervous.

Stop pretending to be strong and allow yourself to break already. Virtually all men pretend to be stronger than they are. This is a form of emotional immaturity, and it leads to self-loathing. Allowing yourself to break from time to time will improve your life by clearing negative emotion and offering perspective. Additionally, when you finally allow yourself to break and feel the pain you’ve been denying, it will burn off. In its place you’ll find a stable base of resilience and true strength.

Spend time in solitude. This can be a road trip, a camping trip, a silent retreat, whatever. The point is to spend time alone, focused exclusively on yourself. For a few days each year, minimize your engagement with the outside world. It’s easiest if you keep your phone and computer off.

Learn to master your vices. For most people, this is as easy as intentionally taking a month off from them. This allows you to regain control over yourself. If you smoke cigarettes and drink coffee every day, stop smoking and drinking coffee for a few weeks. If you go to the horse races after work, take time off. If you’ve been playing video games daily since college, take a month off. If you always watch porn when you masturbate, eliminate pornography for a while. You may return to your vices if you choose, but make sure that you’ve mastered them first. The goal is to be in possession of yourself.

Periodically host or attend a guy’s night. Personally I like poker nights, but going to a baseball game, hitting a cigar bar, or doing a whiskey tasting all have a near universal appeal.

Reach out to your guy friends more often. Call to say hi. Invite them to a game. Tell them a funny story. Whatever. I promise they are just as lonely as you are, and they will be delighted to hear from you. In fact, if they’re being honest, it will likely be the highlight of their day.

Learn to deepen your presence in this world. One of the greatest masculine gifts is presence. The more you deepen yours, the more powerful you will become. You can do this through meditating, reflecting, journaling, focusing on one task at a time, and spending time in solitude.

A return to raw masculinity…

I’ll leave you with a sketch of a man who has embraced his masculinity. This is the man I strive to be, and it’s the man that I so often see lacking in modernity.

He has the courage to face – and shape – his internal and external reality. He is engaged by building a life that is an authentic representation of his truth. He knows that there is a time to lead and a time to follow, and can distinguish between the two. He accepts that he is – and always will be – a work in progress.

He keeps his body and mind sharp. When he enters a room you can feel his presence. He approaches his shame, fear, anxiety, tension, and truth with openness and vulnerability. He embraces his sexual identity without letting it define him. He knows that he must periodically enter solitude to connect to himself. Doing so allows him to share his deep gifts with the world.

He periodically approaches the precipice of his comfort zone, and then peers over the edge. He invests in himself and the people around him. He understands the importance of making himself vulnerable, even when it’s scary. Especially when it’s scary.  

He measures his success in life based on two simple questions: is my life an authentic expression of my truth? Are the people and communities that I care about better because of my involvement? He trusts that if he can answer, “Yes” to these questions, money, sex, love, connection, happiness, meaning, and eventually contentment will follow.

Defeating your inner critic


“An old Cherokee told his grandson, ‘My son, there is a battle between two wolves inside us all. One is Evil. It is anger, jealousy, greed, resentment, inferiority, lies, and ego. The other is Good. It is joy, peace, love, hope, humility, kindness, empathy, and truth. The boy thought about it, and asked, ‘Grandfather, which wolf wins?’ The old man quietly replied, ‘The one you feed.’” –Cherokee parable.

March 10th, 2016: For two weeks, I’ve been trapped in existential limbo. I finished my last speaking tour 10 days ago. JasonConnell.co doesn’t launch for another five days.

The gap between the two projects is just enough time for me to begin seriously doubting myself.

Endless thoughts of “What if” fight for space in my mind. “What if I’m not a good enough writer to build a following? What if I burn through my savings and go broke? What if my previous success as an entrepreneur was a fluke? What if I fail? Shit. I might fail!”

I mention all of this to one of my close friends and advisors, T*. I tell him, “This is the first thing I’ve worked on in a long time where – if I’m being realistic – there’s a serious chance of failure.”

T* looks at me and says, “I don’t think you’re going to fail. In fact, I know you’re going to succeed. I also think you know you’re going to succeed too. I don’t know what sort of game you’re playing by pretending to doubt yourself, but you should stop. It doesn’t serve you.”

That comment from T* was one of the most important comments anyone has ever made to me. It made me realize that there is a quiet part of me that believes in myself, but it competes with a much louder inner monologue that makes me feel incapable.

In this article you’ll learn a simple – and consistently effective – method for defeating your inner critic and releasing yourself from your insecurities. This is a tool that I routinely use myself and one that I teach to all of my clients.

The Big Self and Little Self

For just a moment, imagine what it would be like if you stopped letting your demons run the show and stepped fully into your life. Maybe you’d quit your corporate job to become a house painter. Maybe you’d come out of the closet. Maybe you’d lean into the hard conversations you’ve been avoiding. Maybe you’d throw it all to the wind, sell your things, and move to Costa Rica.

When most people imagine taking control of their lives, they go through a predictable process:

First, you’re flooded with energy and excitement about living more boldly.

Next, a loud voice explains why your dream isn’t feasible. It reminds you that you’re busy, that you lack the requisite talent and courage, that you’re likely to fail, and that you’re not rich, energetic, or young enough. But most of all it reminds you that chasing your dreams is hard work. We’ll refer to that voice as the “Little Self” or the “Small Self.”

The Little Self encourages you to quietly accept that your dream isn’t realistic. You resume moving in whatever direction your life was already going.

This narrative is extremely common. It’s also incomplete. If you sit with your Small Self it loses power. Though you may think that the Little Self will gain power because you’re paying attention to it, like all phantoms, it’s power rests in the ability to hide in the dark.

What most people fail to realize is that hiding beneath the Little Self is a calm, confident, stable voice. This is the voice that knows you can create whatever you truly desire. We’ll refer to that voice as the “Big Self.”

Your Big Self knows that you can handle anything thrown your way. It knows that you’re more capable than anyone – yourself included – has ever imagined. Your Big Self knows that reality is more malleable than you’ve been led to believe and that you can work to shape it.

Distinguishing between the Big Self and the Small Self

We all have a Big Self and a Little Self. The Little Self is the one that allows your insecurities to hold you back from living. The Big Self is the one that allows you to come fully to life. The goal is to strengthen your Big Self, while weakening your Small Self. This begins with understanding the difference between the two.

The Small Self:

  • Comes up with excuses
  • Avoids negative feelings and fears surrendering to the positive ones
  • Plays small
  • Points blame
  • Is afraid of silence and honest reflection
  • Avoids tension and difficult conversations
  • Lies
  • Focuses on limitations

The Big Self:

  • Trusts that you can blaze your own path
  • Leans into negative feelings and revels in the positive ones
  • Embraces its own power and ability
  • Accepts circumstances and works to either improve or appreciate them
  • Allows space for reflection, rest, and serendipity
  • Addresses tension from a place of openness and vulnerability
  • Shows up honestly even when it hurts
  • Notices countless possibilities

Most people unconsciously lead their lives with their Small Selves. The Small Self bludgeons them into submission and tricks them into accepting mediocrity.  

Defeating the Little Self

Fortunately, it’s possible to defeat your Little Self. To do so, you must learn to identify and then sit with the tension that your Little Self causes. Here’s how:

Step 1: become aware of your Little Self. When you notice fear, anxiety, tension, scarcity, laziness, apathy, your inner bully, an urge for validation, or anything else holding you back, pause. Notice that the feeling is sabotaging you. This is your Little Self trying to run the show.

Allow the negative emotion to act as a meditation bell, letting you know that your Little Self is present. This type of self-awareness can be difficult. If you struggle to gain awareness of the emotion or thought that you’re experiencing, you need to deepen your self-awareness. You can generate awareness by spending a few minutes each day doing any or all of the following: silently reflecting, meditating, journaling, or engaging in deep vulnerable conversation.

Step 2: when you notice your Little Self trying to run the show, eliminate all distractions and sit with her. Allow your Little Self to express herself without interruption. She’ll say some nasty things. Realize that the more effort your Little Self invests in fucking you up, the bigger your reward will be for defeating her. The only time fear is deployed as a weapon is when there is a very real chance of losing the battle.

Your Small Self will be very compelling and convincing. She will generate difficult thoughts and feelings. Your natural reaction will be to distract yourself or give into the thoughts and feelings, mistaking them for the truth. Don’t. Instead, let them run their course. Don’t flee from the tension. Just stay with it. In a few moments, the Small Self will become weaker and weaker.

Step 3: as the Little Self weakens, turn your attention to the growing sense of confidence resting within you. As your Small Self exhausts herself, you’ll notice that there is still a part of you that wants to live boldly. This can be as simple as asking someone on a date or as profound as transforming your life. This is your Big Self. In the same way that you sat with your Small Self, sit with your Big Self.

Allow yourself to become excited by the possibility of getting exactly what you want in life. Open yourself to the possibility that the process may be fun, and that the results may come easily.

Don’t dismiss the ideas that come to you – only the Small Self writes things off as impossible. The more you sit with your Big Self, the easier the path forward will become.

If you can, smirk at your Little Self in the way that you’d smirk at an irritating child who tells you what to do.

Step 4: take the first step, and take it now. Once you’ve felt the power of your Big Self, start living it. You do this by taking action (even if it’s just a very small step). If you do not take action of some sort, the Little Self has very subtly – but decisively – won.

Step 5: accept that the battle is never over. Continue working through the process of sitting with your Little Self and embracing your Big Self as needed. The more you do this, the more powerful you will become.

Which Self is telling the truth?

As you become aware of the competing senses of self, you’ll wonder, “Am I the Big Self or am I the Little Self?”

The lazy answer: you’re both.

The deeper answer: you are the self you choose to focus on.

If you allow your focus to be controlled by your Little Self, then you’ll feel and act small. To do this is to perceive limitations within your life. Eventually you’ll surrender to the Little Self’s limitations and become your Littler Self.

If you allow your focus to rest primarily on your big self, you’ll feel and act as though you are capable of creating the life and world you desire. To do this is to perceive opportunities within your life. Eventually, you’ll embrace the Big Self’s opportunities and become the bigger self.

So at the end of the day, the answer is simple: both the Big Self and the Little Self have the potential to be the true you. The question you need to ask yourself, “Who do I want to be today?”

Escaping the prison of unworthiness

Years ago, one of my friends shared an allegory that changed how I think about myself and the world. The allegory:

You wake up and realize that you’re locked in a cell.

Time slips through your fingers. The days and weeks blur and crash into one another, each as empty as the last.

One day, without thinking about it, you reach into your pocket. Inside, you discover a key. You understand that this key will release you from your cell and that, strangely, you’ve possessed the key the entire time.

You gather the courage to free yourself. When you put the key in the lock, you notice that there was never a cell to begin with. It was all just an illusion. You were free the whole time.  


Though few of us realize it, we all live in imaginary cells that were built before we were even self-aware.

When you were born, you became a citizen of a country. In turn, you were bound by its laws. Then, your parents raised you in accordance with their beliefs about religion, education, diet, morality, and self-worth. As you grew older and more self-aware, the society you found yourself in encouraged you to observe its customs about fashion, relaxation, health, holidays, sexuality, ethics, and appropriate behavior. Along the way, expectations about almost every aspect of your life were forced upon you without your request or consent.

Sure, you may have gone through periods of rebellion, but the truth is simple: many of your biggest life decisions were made for you. Since none of us chose the circumstance we were born into, few people ever flourish to their fullest potential, similar to a plant’s growth being stunted by the size of its pot.

Soon, all the beliefs and expectations from the outside world alchemized to influence almost every aspect of your life. They created the illusion that you were unworthy. They hardwired demons, feelings of anxiety, and insecurities into your system.

I know that sounds far-fetched, but pause for a moment and reflect. How many times have you blurred the truth or failed to show up honestly and vulnerably? How often have you struggled to accept a compliment? Have you ever written your successes off as a matter of circumstance or coincidence? Are you able to see and feel the magic found in the mundane? Do you have a nasty habit of putting other people’s needs ahead of your own?

I’ve wrestled with all of the above.

These tendencies indicate that you’ve been tricked into believing that you aren’t worthy. They are evidence that you’re imprisoned in an imaginary cell. The power of the illusion rests in its ability to infect both your thoughts and feelings. By making you feel small, you’re much less inclined to believe in your own capability.

Feeling like you aren’t worthy has a nasty ripple effect. It makes you feel as though:

  • You’re not ready (so you perpetually tell yourself, “I’ll start tomorrow”)
  • You’re not lovable (so you pretend to be someone you’re not)
  • You have to work hard to get what you want (so you toil away day after day)
  • The future will be worse than the present (so you’re manipulated by your own anxiety and continually play it safe)

But thankfully, once you’ve learned to see the cell you live in, escaping from it is deceptively simple. Begin by asking yourself:

  • “If I felt like I deserved an amazing life, what would I be doing right now?”
  • “If I were ready to begin living my dreams, what would my first step be?”
  • If the real me were truly lovable, how would that change my actions? How would that change the conversations I’m having with myself and the people in my life?”
  • “If I assumed that success could come easily to me, what would I do to make that happen?”

Of course, the changes would be dramatic. You would become more fully yourself and feel more deeply powerful and connected. You would be fully alive.

The trick is to answer these questions with actions rather than thoughts or words. Respond with your life. Begin living as though you are worthy, ready, lovable, successful, and capable. Doing this will unlock your heart and mind. You will illuminate the truth about your own power, worthiness, and ability. You will notice that the cell you found yourself in was nothing more than a compelling illusion.

The truth about entrepreneurship

May 4th, 2016, on the phone with S*: “I’m going to close my business and get a real job. I’m done” she tells me. I’m shocked. S* is very successful in a competitive market.

She goes on to explain that she’s burnt out, and has been for a long time. She feels that the physical, emotional, and spiritual cost of running a business is no longer worth the freedom and income it generates.

As I listen to S* speak, I notice something unexpected: I’m jealous. A very real part of me wishes for a real job too.

A few days later, I mentioned all of this to a famous entrepreneur. After pausing for a while, he quietly said, “I wish I had a real job too.”


I started my first business as a professional magician when I was six. By the time I was 18, I was performing for Fortune 500s and professional sports teams. Since then, I’ve built three other businesses. Two succeeded, one failed. I’ve also consulted for hundreds of entrepreneurs and executives in every stage of the game.

It’s easy to get swept away by the romanticism of entrepreneurship. It seems like building a business is fun and exciting and that owning one creates a lofty life.

In reality, entrepreneurship is not nearly as glamorous, fun, or easy as most have been led to believe.

In this article I’m going to unpack the truth about entrepreneurship as I’ve experienced it, both as an owner and an advisor. We’ll cover the good, the bad, and the surprising. I’ll help you figure out if being a founder is likely to make you happy and explain how to increase the possibility of success while maintaining as much sanity as possible.

The good

You gain control of your time and focus. When you start your business, you will be its slave. It will demand far more from you than you expect. This will last anywhere from 6 months to several years.

If you’re able to push through, something amazing happens: you gain almost total control of your time and focus. This creates the potential for a deeply engaged, vivacious life. The ability to drop what you’re doing to see a friend, hop on a jet, or take a personal day with very few repercussions is amazing. For many, myself included, this alone makes the struggle worth it.

You get to choose how much money you make. In fact, doing so only requires developing three things: a product or service that people want, a way of letting people know that it exists, and an effective sales process. Sales and marketing are easier to learn than you expect. The hard part is developing something that people will enthusiastically purchase (more on that in a moment). Once you’ve done that, your income will directly correlate with the amount of energy you invest in your business.

Be aware that the ability to choose how much money you make is also a trap. Many people become enslaved by the desire to make as much money as possible. To do so is to waste your life.

The bad

You will sacrifice your mental health: Six months ago, W*, a very successful non-profit founder, asked, “Do you think it’s possible to build an organization without hating yourself at least some of the time?” My honest answer: no.

If you decide to start a business, your mental health will suffer. Rejection, disappointment, extreme stress, isolation, embarrassment, and intense self-doubt are woven into the fabric of entrepreneurship. I know this sounds like an exaggeration. It’s not.

Here’s one example (of many) from my old speaking business; every entrepreneur has a similar story.

McGill University was hosting a global leadership conference, and I was on the short list of keynote speakers they were vetting. To my delight, they decided to hire me.

I sent them the contract and told my friends and family about the deal.

Several days later, McGill called back. They found a famous speaker who was willing to work for free and decided not to hire me. For several days, I was miserable. I had no interest in seeing my friends, I couldn’t focus on work, and my belief in myself was shaken to the core.

If this only happened once or twice a year, it would be manageable. But this happened once or twice a month and went on for several years. Of course, it was intermingled with just enough success to keep me going, but it was a true struggle.

Unfortunately everything about that story is normal for entrepreneurs. Your self-worth gets tied up -almost entirely- in the performance of your business. As it fails you’ll feel crushed. It will take everything you have (and perhaps a bit more) to pick up the phone and take a shot at your next sale.

As you build your ability to generate leads and close deals, you learn to trust yourself without getting attached to outcomes. For most, this will take several years, but if you pay attention to the process, you’ll notice incremental gains, which will boost your confidence. Until then, it’s normal to feel bipolar as you revel in each new victory, while crumbling with each new defeat.

Isolation is a normal side effect of entrepreneurship: the sheer act of blazing your own path in life is always isolating. It means that fewer and fewer people will be able to relate to what you’re experiencing, and the more you succeed, the fewer peers you’ll have.

Aside from that, almost all new businesses require tightening the belt, which often leads to social isolation. When I was starting out, I’d tell my friends I was too busy to hang out. In reality, I felt like I couldn’t spare $3.00 for a beer. The sad part is that some of those friends stopped calling.

The unexpected

Despite appearances, most entrepreneurs are making a middle class income. Many business owners have become adept at appearing far more affluent than they are. I did this during my first four years as a speaker. I’d act casual as I picked up a tab for my client while secretly fearing that I wouldn’t be able to make rent. I did this because I felt like I needed to appear successful in order for clients and potential clients to trust me. I also wanted my friends and family to admire me.

This type of behavior is common among entrepreneurs. I recently had dinner with the owners of two well-regarded marketing firms. I asked how much they make per year, expecting them to be well into the six-figures. Nope. They were each making about $60,000. One of my friends runs an international software company that services Fortune 500s. He employs eight people. He made $47,000 last year. Another runs an elite cyber security company with 18 employees. He made $41,000 last year.

Are there business owners out there making millions? Of course. But they’re far less common than you’d imagine.

Luck and privilege are deceptively important factors for success: anyone who claims that luck isn’t a major factor in success – and especially quick success – is delusional.  Anyone who denies that being privileged makes success substantially easier (whether that’s through economics, education, family support, gender, race, or other means) is ignorant to how our world works.

Countless self-help and entrepreneurship “gurus” claim to have uncovered the secret to success (or productivity, or profitability, or whatever). That’s a great way to sell books and trainings, but it’s also BS. Luck and privilege make a huge difference and influence almost everything in your business.

Successful people tend to assign undue credit to themselves for both victory and defeat. It leads people to believe that they have more agency than they really do. Don’t get me wrong, you’re responsible for the effort that you put in, but in most cases, you won’t actually be able to control the results.

When you succeed, express gratitude to the fates. When you fail, express compassion to yourself.

Owning a business is not as glamorous as it seems: the bitch work will always outpace the glamor. In fact, it’s a willingness to consistently do the bitch work that makes people successful.

A huge amount of your time will be dedicated just to keeping your shit together: when you work for yourself, every single decision comes down to you. You will also be responsible for managing a near infinite number of details. Staying sane and organized is half the battle.

Success does not lead to contentment. Many people believe that once they achieve their goals, they will be content. Unfortunately, it doesn’t work like that. Contentment and success are two different skills that don’t have much to do with one another. Success is about achieving your goals. Contentment is about learning to desire that which you already possess.  

Should you start a business?

If you’re thinking about starting a business, my advice to you is simple: if you can be happy doing anything besides starting a business, don’t start a business. For most people the price isn’t worth the cost.

However, if something deep inside of you is yearning to build a business, or if you need the freedom that comes alongside owning your own business, honor that. It will be much more challenging, and much more rewarding than you could ever imagine.

Protips for those starting businesses

For most people, it’s best to work on your business at night and on the weekends. Once the business becomes viable, then you should quit your job.

Get a mentor: the singular best tip I can give you if you want to become an entrepreneur is to find a mentor. While there are people who offer this as a professional service, it tends to be more effective as an informal relationship. The best way to foster this relationship:

  • Find someone who you want to be like in 10-15 years.
  • Email her. Tell her that you admire her and ask if she would be willing to chat for 20 minutes. If possible, propose meeting in person. Make it easy for her by offering a variety of options, including meeting at her office.
  • When you meet, come prepared with broad, open-ended questions about how she became successful. Make sure that she’s doing most of the talking.
  • After the meeting, send a thank you card.
  • Follow her advice, even if it doesn’t make sense.
  • Several months later, update her with your progress. If she responds, ask if it would be possible to get together again.
  • Rinse and repeat.

The trick is to show her that you sincerely value her time and are following her advice.

In the beginning, focus exclusively on product and sales. When you’re starting out, social media, a cool logo, a flashy website, and networking groups are huge time wasters. All that matters is building a product or service that people want and learning how to sell it.

This raises the question, “How do I know if people want my product?” The answer: create a basic version of your offering, and try to sell it. Let’s say that you want to create a new type of chalk for rock climbers to put on their hands. First, make a batch of the chalk at home.  Show it to a few rock climbers and ask if they’d like to buy it from you. If people buy it, you’re on the right track. It’s important to pay attention to what they do, not what they say. If people aren’t buying, they aren’t interested. Pitch your product to at least 50 buyers before attempting to judge whether or not it’s viable.

Over time you’ll refine your ability as a salesperson. Reading books on sales will help speed up your success, but if all you’re doing is reading (and not actually selling), then you’re doing it wrong.

Create or join a mastermind. Running a business is isolating and difficult. One of the best ways to cut through the isolation while also speeding up your success is to join a mastermind.

A mastermind is a small group of people who meet on a regular basis to invest in one another’s success. The mastermind that I am a part of consists of four entrepreneurs. We meet on Monday mornings. Each week we check in with one another, offer solutions/perspective on the problems we are facing, and make a commitment for the following week. The three people in my group have become some of my closest friends and most trusted advisors. Their guidance has improved every area of my life.

You can create your own mastermind by finding a small group of entrepreneurs and meeting with them on a regular basis. During your meetings, everyone should be open, honest, vulnerable, and willing to help.

So, why haven’t I gotten a real job?

August 2nd, 2016, back on the phone with S*: “How’s the new job going?” I ask.

“I hate it. I think I’m going to quit. I like having a steady paycheck but I can’t stand my boss. I miss being able to pick the projects I work on.”

“So are you going to look for a new job?”

“No. I’m going to start a new business. I’ve got a few ideas…”

At the top of the article I mentioned that I sometimes find myself wishing for a real job. And yet, I choose to ignore that wish.

I’m one of those people who is happier working for himself despite the significant toll that it takes. Yes, I could figure how to be ok working for a boss, but it would feel like a betrayal.  I get restless and depressed when I’m forced to work on projects I don’t love.

In 2009, my mentor said to me, “Jason, your curse in life is that you are an entrepreneur. It’s your job to figure out how to make that a blessing.” Those words still ring very, very true.

Reminders to myself

When I fail to give my mind any sort of structure or organization, my world grows dark and crazy. I find myself fixating on embarrassments, disappointments, and mistakes from my past. I worry that the future will be worse than the present, and that I’m destined for failure and loneliness. I find myself discounting, or even ignoring, all of the beautiful things that have already happened, and all of the amazing things that are currently happening.  

However, I’ve found that when I give my mind guidance – usually in the form of gentle reminders – that I become much more focused, happy, and in touch with my ability to live my dreams.

I like to think of the reminders as training wheels for my mind. I scatter them around my apartment, on the desktop of my computer, and set alarms for them on my phone. After a few weeks, I no longer need the reminders; they’ve become a familiar part of how I think about myself and the world.

What follows are ten reminders that I need in my life right now. They’re the thoughts I want shaping my reality. They revolve around courage, integrity, trusting myself, and the moment.

I share these reminders to help solidify them for myself, and with the hope that a few of them will serve you too. If they do, integrate them into your life. The more familiar something becomes, the easier it is for your mind to accept it.

1) Your demons will attempt to tear you apart. Whether they succeed or fail is up to you. They will begin by encouraging you to check social media when you should be working. They will remind you that you can easily put everything off until tomorrow.

If that doesn’t work, they will tell you that you’re likely to fail and that you’re an imposter. They will remind you that no one gives a shit about what you’re up to anyway. Your demons will make you feel small. They will be very convincing.

Do not let them dictate your actions. Instead, observe them. Let them run their course. They will exhaust themselves. You’ll notice that beneath the demons rests a stable sense of confidence and creativity. Trust that. That’s the real you.

When you can, use curiosity to conquer your demons. Ask, “Why are you scared right now?” or, “Why are you feeling anxious?” or, “Why are you procrastinating?” Don’t settle for the first answer. Go deep. Keep asking why until you get to the root of the issue. This will drain your demons of their power.

2) Honesty – especially when it’s hard – is the key to integrity. Integrity makes life flow more easily and more vibrantly. On a simple level, this means you must tell the truth. On a deeper level, this means leaning into the hard conversations. It means that your actions should mirror your thoughts and desires. Anything else is a betrayal of self.

Some people will be disappointed by what they learn about you when you’re completely honest. That’s ok. It’s not your job to protect other people from your reality. It’s better to disappoint them than pretend to be someone you’re not.

3) It’s ok to be single. The majority of my friends are married. Most of those who aren’t married are in serious relationships. Me? I’m single.

When I compare myself to my friends, I fear that I’ve fallen behind. I fear that maybe there’s nobody out there for me. But these fears are phantoms. I’ve taken a very different path in life than most of my friends. I can’t expect my results to look like theirs.

More broadly, obsessing over the gap between where I am and where I want to be is dangerous. It misses the point. There is a lot I love about this stage of life. I love that I can stay up late, lying on my couch and listening to music without bothering anyone. I love being able to get to know my readers personally. I love being able to spontaneously drop what I’m doing to see a friend. And once this stage of life ends, I may never be able to return. I need to enjoy it before it slips through my fingers, because one day, I’ll miss all of this.

4) I am enough.

5) The only way to improve the future – either for myself or others – is to improve this moment. Doing this will improve the next moment.

6) Playing it safe is one of the most dangerous decisions I could ever make.


7) When in doubt, assume that getting exactly what you want in life will be easy. In fact, there seems to be a reliable process:

  • Get crystal clear on what you authentically desire. Focus on one thing at a time. Finding clarity may require journaling, experimentation, or prolonged periods of silence and reflection. This is the hard part.
  • Once you’ve found clarity about what you desire, write your vision in vivid detail. Use pen and paper. Keep working on your vision until it feels right.
  • Assume that you will succeed; begin taking action as though you already have.
  • Be open to the possibility that getting exactly what you want will be easy and that it may show up differently than you expect.
  • Now let it go. Release your attachment to outcomes. Literally burn the piece of paper that you wrote your vision on.
  • Finally, take the first step. Then the second. You don’t need to see the entire path as you walk it. Just trust that everything is unfolding exactly as it should.

8)  Go easy on yourself. It’s ok to be imperfect. Remember that more than anything it’s your rough edges and imperfections that make you human. It’s ok to sneak a scotch or a cigarette every now and then. Even though you’re a vegetarian who avoids caffeine, it’s no big deal if you eat a bit of meat or have a cup of coffee.

If you’re having trouble forgiving yourself, or treating yourself with compassion, imagine that a close friend is in the exact same situation that you’re in. How would you want him to treat himself? Of course, you’d tell him to be gentle and forgiving. Treat yourself the way that you would treat anyone else you would love; transfer the advice you would give to your friend over to you. Zenfully, by relaxing your standards and leaning into your imperfections, you’ll become happier and more effective.

Besides, you’re already on your path. You’ll get to where you’re going. The business will grow, your influence will expand, and you’ll meet a woman who helps you flourish. It’s a question of when, not if. As long as you stay true to yourself and keep moving forward, you’ll get there.

9) Abundance isn’t about having a certain amount of money in your bank account. It’s about realizing that you already have everything you need to begin living your dreams. It’s about realizing that if you ever run out of money you have friends and family who will let you stay with them while you get back on your feet. It’s about living fully so that you may die with as few regrets as possible.

It’s in money’s nature to ebb and flow. Hoarding it is the opposite of abundance. Hoarding inspires fear and a lack of faith in self. It prevents the natural flow of affluence.

In fact, the fluidity of money is built into the language that we use to talk about it. The word “affluence” comes from the Latin word, “affluentia” which means “flowing towards.” The word, “currency” comes from the Latin word, “currens” which means “to run” (as in a river’s running current).

The key to abundance is to give freely (especially to the less fortunate), make huge investments in yourself, and to notice the amazing things you already have.

10) Leap. You don’t need a net.


Those are the reminders that I need in my life right now. If everything goes according to plan, they’ll help shape me into the man I want to become. I hope at least one or two of them resonated with you. If you have reminders that are particularly meaningful to you during this stage of your life, I’d love to hear them. You can post them in the comment section below.