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. 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.

How to understand, cultivate, and focus your energy

July 2nd, 2016, Washington, DC: I’ve just delivered the Best Man toast at W* and E*’s wedding. People are shaking my hand and giving me compliments on it. I do my best to look delighted and let the compliments land, but the truth is, I can’t feel their warmth right now. I’m too exhausted. It’s been a long couple of weeks.

I step outside to steal a few moments for myself.

A panhandler approaches. He goes into his pitch, preparing to ask for a buck or two. I interrupt him, hoping to speed this up, and ask, “How can I help you, sir?” I tried to ask the question gently, but it came out brusque and resentful.

For the first time, he really looks at me and sees beyond the 30-something guy dressed in a rented tux. He turns to me, and gently says, “I’m so sorry. I didn’t mean to bother you” and walks away.  

I didn’t mean to send him away. I would have given him a few dollars. But I had become so burnt out that I couldn’t even extend a bit of warmth to someone who needed it.

In that moment, I realized that I had nothing left to give.

Energy is your most important resource

Have you ever been in a situation where your life appears to be perfect – you have money, time, friends, family, and health – and yet, there’s still something missing? That’s happened to me many times. In most cases the problem is that you’ve misallocated your energy, making it difficult to connect with the moment.

Learning to cultivate, manage, and strategically invest your energy will dramatically improve your life. In fact, the success of almost any endeavor hinges on the amount of energy and attention you invest, not the time or money.

By energy, I’m referring to the cross-section of how energetic you feel (hyper, sleepy, etc.), and the predominant emotion you’re experiencing (playful, creative, etc.).

When you feel energetic, confident, and creative, it’s easy to engage with life. When you feel tired, depressed, and dark, doing anything is a struggle.

The aim is to make decisions that flood your system with positive energy, and then focus that energy on the people and projects that mean the most to you. Doing this begins with treating your energy as though it’s an extremely valuable currency.

Energy is a currency

Think of your energy as a currency –like time or money- that can be invested, saved, given away, stolen, or wasted. When making decisions, ask yourself, “Do I really want to invest my energy in this?” If the answer is unclear, unpack the question by asking, “What are the likely consequences of pouring my energy into this?”

You should invest as much energy as possible into the things you want more of, while withdrawing it from the things you don’t want.

An example from my professional life. A few years ago a partner and I were working on a project for a well-known entrepreneur. When we sent him the bill he refused to pay.1

Even though we could have sued him and won, we chose not to.2 A lawsuit would generate huge amounts of stress, resentment, uncertainty, and anger. It would dominate our thoughts and calendars. It would take us away from friends, family, clients, and ourselves. Simply put, it wasn’t worth it.

The world is dark and difficult enough on its own. By investing your energy into something that’s likely to produce more shit, you’re making life harder for yourself (and probably others, too) than is necessary.

As you start making decisions based on whether or not you want to invest your energy you’ll notice new – smarter – behaviors emerging. Instead of trying to win arguments you’ll start saying, “Maybe you’re right” and changing the topic. Instead of spending hours trying to find the best deal, you’ll buy things based on convenience. Instead of getting tangled in drama (like a lawsuit) you’ll let it go and move on.

Avoid energy thieves

One of the best ways to create an abundance of energy is to minimize your exposure to energy thieves. The most common culprits:

Toxic people: when identifying toxic people, there’s an important distinction to make between loved ones who needs support, and the truly toxic. A loved one going through a tough time is likely to command a lot of your time and attention. Even though this can be draining, I’d suggest giving it to them as generously as you can. Leaning on the people you love, and allowing them to lean on you, is one of the most meaningful, intimate experiences you’ll ever have. It’s also the literal foundation of a strong support system.

A truly toxic person is different. Truly toxic people consistently leave you feeling drained, anxious, and small. If you have people like this in your life, it’s best to spend less time with them. Don’t return all of their calls. Ignore their invitations. Say no when they ask you to do something you aren’t enthusiastic about. Avoid hanging out with them one on one. Yes, this is kind of cold, but it’s even colder to lie about wanting to spend time with someone while withholding your full presence.

Prioritizing the desires of those who bring you down signals to yourself that your needs are less important than the needs of people you dislike. Please don’t do that to yourself.

Lying: lying – especially white lies and lies of omission – is so normal that most people don’t even realize they’re doing it. It’s also extremely draining.

To successfully lie, you have to construct a fictional reality and then try to convince someone– often someone you care about – that it’s the truth. Then you have to keep track of the lies you’ve told, and who you’ve told them to, so you don’t get caught. Through it all, you have to shoulder the burden of knowing that you’re not showing up authentically in the world.

At a deeper level, many people lie to themselves by failing to pursue their burning desires and avoiding the conversations they need to have.

When you commit to living without lies (a surprisingly difficult task) you’ll notice that it frees up a huge amount of energy for you to invest in other areas of your life.

Mindlessly staring at screens: computers, phones, tablets, and televisions are unavoidable. The question you need to ask yourself is what’s happening while you’re looking at them. If you’re engaged by the work you’re doing, entertained by the Pokémon you’re chasing, or enjoying the conversation with your friend, that’s fine. But when you find yourself zoning out, entranced by whatever is in front of your face, then the screen is stealing your energy. Work to set boundaries around your interaction with electronics to prevent them from draining you.

Toxic jobs: most people spend a lot of their time at work. A bad job has the ability to infect every area of your life. If you find yourself consistently wishing you worked somewhere else, it’s time to develop an exit plan. Yes, I know, quitting is scary. It forces you to deal with the unknown. That’s ok. It’s far better to quit than to suspend yourself in a reality that drains you.

Being overcommitted: this is the mistake I made at the top of the article. Over the course of three weeks, I committed to being in three weddings in three states, spending a week leading an 80 person staff training in a fourth state, and catching up with friends and family along the way. I wasn’t allowing enough time for rest. I failed to prioritize myself and, as a result, burnt out.

If you’re wired to be a people pleaser (like I am) then it’s important that you learn to say, no. Alternatively, if you do say yes to many things all at once (like I did), then make sure that the price is worth the cost. Personally, I needed a solid week of rest before I was able to fully engage with life again.

Neglecting your health: many people willingly sacrifice their health by putting diet, exercise, and sleep on the back burner, perpetually telling themselves, “I’ll handle my health tomorrow.” Bad idea. Health is the foundation of energy. A few basic guidelines:

  • Diet: a simple approach is to have a smoothie for breakfast, a big-ass salad for lunch, and a sensible dinner. Experiment with eliminating alcohol and caffeine to see how they affect your energy. Personally, I am much more energetic when I consistently go without caffeine.
  • Sleep: the goal is to wake up feeling refreshed in the morning. The easiest way to do this is to wake up at the same time every day and go to bed when you’re tired. If this doesn’t work for you, try turning your electronics off an hour or two before bed. If that doesn’t work, experiment with eliminating caffeine and sleep aids. If you’re still struggling, I suggest reading, “The Insomnia Workbook.” This book made dramatic improvements in the quantity and quality of my sleep.
  • Exercise: find something you enjoy and aim to do it a few times a week. If you’re completely lost, I suggest starting with Couch to 5k, a tiered jogging program for people who aren’t runners.

As with any change, it’s easiest to begin with small, sustainable, actions that move you in the right direction.

Identify and protect your peak times

Most people get the majority of their work done in two or three predictable bursts throughout the day. If you start observing your own behavior you’ll notice that there are consistent times when it’s easier for you to be creative, focused, and in the zone. These are your peak times and they are extremely valuable.

You can find your peak time by keeping track of your energy throughout the day. Over the next two weeks, check in with yourself every hour while you’re awake. During these check-ins, rate the following on a scale of 1 – 10, your:

  • Energy
  • Focus
  • Happiness
  • Creativity
  • Stress

At the end of the two weeks, review the data that you’ve collected about yourself. You’ll start to notice natural ebbs and flows of energy. Keep in mind that things like caffeine, sleep deprivation, and changing time zones can skew your results. Control these elements to the best of your ability during the experiment.

Once you’ve found your peak times protect them on your calendar. These are the times when you’ll most easily be able to step into the flow and create whatever it is that you desire. I suggest using them for the most important projects in your life.

Personally, my peak times are from 9:30am – 11:30am and again from 9:00pm – 12:00 midnight. I dedicate the first one to writing and working with clients and the second one to whatever feels most important that day.

A lost secret

One of the lost secrets of life is that energy – not time or money – is the most valuable resource.

By focusing and channeling your energy you can create nearly anything you desire: love, connection, money, art, fun, joy, adventure, etc. The trick is to understand that creating a better future starts by focusing your energy in the present. From there you are limited primarily by your imagination and your belief in yourself.

On life, death, and the moment



Summer of 2010: I was on a camping trip with 11 guy friends in Quebec. We were all healthy, playful and happy. M* died on that camping trip. He drowned. He was 27.

Winter of 2011: I was in Washington, DC preparing for a speaking tour. One night, C* called me. He told me that our close friend M* (a different M*) was dead. M* took his own life. He was like a brother to C* and I. He was 24.

Summer 2013: I was in New England for the week. As I was leaving a friend’s house, I got an email from L*. She told me that R* was dead. His heart stopped while he was in China. He was 28.


If you want to evaluate your life, the most important question you could possibly ask is, “Am I loving to the best of my ability?”

We’d all like to believe that we love fully, but the truth is more complicated; living from the heart is difficult. It requires facing – and then transcending – your core fears.

There’s a key that makes facing your fears easier, but it requires insane courage. Its gravity is so significant that it’s nearly impossible to comprehend. That key?

Accepting your own mortality.


Let’s start with the simple truths: one day you will die. So will everyone you have ever loved and everyone who has ever loved you.

A more complicated truth: you have no idea when your day will come.


The denial of death is the denial of self. Death is woven into every fiber of your being. It cannot be separated from life.

And yet, most people avoid acknowledging the presence of death. They refuse to talk about it, let alone open their hearts to it. To do this is to deny the truth of being alive.

Most of us get swept away by the sheer inertia of life. We become entranced, repeating the same flawed routines again and again and again. We allow ourselves to be manipulated by toxic people, the media, politicians, our demons, and the culture we exist in.

Reminding yourself that all of this ends, can help snap you out of the trance, and give you the confidence to take control.


When you open your heart to the inevitable reality of death you’ll notice that it creates a renewed sense of urgency about living.

Realizing your own mortality connects you to the innate potential of this exact moment. Mortality strips away the lies, excuses, and illusions that have been holding you back. Beneath them, you’ll find abundant reserves of power, freedom, and agility.


A few practical approaches for opening yourself more fully to life even in the face of your own inevitable death:

  • Make love to your partner like it’s your last night together
  • Drop to your knees and offer yourself in pure devotion to whatever, God, Goddess, spirit, or science you believe in
  • Quit the job or close the business that’s been eating you alive
  • Allow yourself to finally break and feel the things you’ve been avoiding
  • Rent a fast sports car and drive it through the twisting mountain roads
  • Book the trip you’ve been dreaming of
  • Strip away the white lies you’ve been telling yourself and the world (even when it hurts)
  • Stop playing it safe

Risk living your dreams. It’s ok if you don’t have a plan. Your path will emerge as you walk it. Cast away the illusion of not being ready, or worthy, or capable, and begin. Now is the time. It always has been.


“But isn’t this risky?” you ask. “Can’t things go wrong when you speak your truth, chase your dreams, and confront the things you’ve been avoiding?”


And that’s the point.

Maybe you will run out of money. Maybe your heart will break. Maybe the plane will crash. Maybe the conversation will go poorly. Maybe you’ll have no idea where the path is leading you.

That’s ok.

Because you know what else is completely possible? Dwindling your life away at a job you hate, mindlessly clicking on link after link after link online, getting caught up in drama, and being controlled by fear and anxiety only to die shrouded in lies and regrets. In fact, it’s not just possible – it’s normal.


A tool for connecting to all of this: imagine that you’re on your deathbed, looking back at your life. Imagine two different versions.

The first version was ruled by fear. You wanted to quit your corporate job to work for a non-profit, but you were afraid of making less money, so you remained in a career you hated. You wanted to open up to the people you love, but you were afraid of vulnerability, so you remained closed off. You wanted to have a richer life experience, but you were afraid of getting the help you needed, so you treated yourself as though you were unimportant.

The second version was ruled by love. You wanted to quit your corporate job to work for a non-profit, and you did, despite the salary cut. You wanted to open up to the people you loved, so you took the risk of being vulnerable, even though it was massively difficult. You wanted to have a richer life experience, so you got the help you needed, even though admitting that you need help felt next to impossible.

Now pause and reflect on the two different paths. The life led by fear ends up bleak and incomplete. The life led by love ends up vivacious and dynamic. Both are realistic and available to you. Both are created by decisions made in this moment. The question is, do you have the courage to walk the path with heart? (The answer, I promise, is yes. You do have the courage.)


Should you start to lose faith in yourself, come back to this moment and stare death straight in the eye. Acknowledge that soon, you’ll no longer exist. Allow the life force to come back into your body. Return to yourself, and begin again


I’ll leave you with a quote from the Dalai Lama that I think of often. He was once asked what surprised him most about humanity. He answered,

“Man. Because he sacrifices his health in order to make money. Then he sacrifices money to recuperate his health. And then he is so anxious about the future that he does not enjoy the present, the result being that he does not live in the present or the future. He lives as if he is never going to die, then dies having never really lived.”

Don’t let that happen to you. Live and love while you still can, because one day, you’ll no longer be able to.

The art of giving back: an unconventional approach to negotiation

April 2015: “I’m torn. I want to work with this conference in Guadalajara, but they can’t afford my keynote fee. I could give them a discount, but I’ve noticed that the clients who pay reduced rates end up treating me poorly.”

C*: “So, basically, they’re asking you to donate a chunk of your time and energy, right?”

Me: “Yeah, that’s one way of looking at it.”

C*: “Respond by asking them to donate their time and energy. Get the conference to do a community service project or something similar in exchange for the discount. If they’re open to it, then it’s a win all around.”

Me: “You’re a genius.”

When I told the conference coordinator that I’d be happy to offer a discount in exchange for community service, she leapt at the opportunity. The end result was amazing. Together, we activated hundreds – maybe thousands – of hours of community service. It was magic.


One of the hidden-in-plain-sight secrets about the human experience is that we are all deeply connected. Another secret: we all belong to one another. Many people succeed at creating amazing lives for themselves while still feeling like something is missing. This sense of lack or hollowness is a result of forgetting to invest in other people’s success as well as your own. Ultimately, a failure to invest in others’ happiness and stability is a failure to invest in yourself.

Fortunately, there are simple and effective ways to use your existing job – whether you’re a business owner, executive, or employee – to improve the world around you.

The uncomfortable tension between making money and being generous

Many of the most talented people I’ve met used to dream of making the world a better place. Now, they hide behind lies of powerlessness by telling themselves, “I can’t change the world” or “I’ll focus on giving back when I’m rich.”

And I get it. What they’re really trying to do is resolve two truths that seem to contradict one another:

  1. Making money for the sake of making money is inescapable. You have to pay the bills. Unfortunately, the mere act of making money and being successful, while addictive, is not intrinsically fulfilling.
  2. Being generous for the sake of being generous is extremely fulfilling.1 Unfortunately, it’s also unsustainable on its own; the act of generosity does not usually generate enough income to live off of.

In an ideal world the solution is simple: dedicate half of your time to making a living and the other half to giving back.

But the reality is much more complicated. Volunteering can always be pushed to a later date, while paying the bills can’t. As a result, many people find that their goals change from giving back, to making enough, to making more. That’s exactly what happened to me. When I started working, I focused on reducing global poverty, but the demands of the real world interfered with my plans. Without noticing, I began spending more time thinking about my sales cycle and less time figuring out how to help others.

It was only when C* suggested requesting a volunteer project in exchange for a discount that I returned to using my business for social good. The trick is to harness what you’re already doing for the better good.

Using your job to give back part 1: entrepreneurs, executives, and people who can negotiate

If you’re a business owner or an executive, the approach I recommend is simple: if a client needs a discount, offer the discount in exchange for community service. This strategy can be effective with a wide variety of customers. I’ve used it with speaking, consulting, and coaching clients. C*, the friend who gave me this idea, works in film production, and he’s used it with his clients as well.

A few guidelines to make this feasible and effective:

  • Request a small amount of community service if your client needs a small discount. If they need a large discount, ask for a large amount of community service. On one side of the spectrum, I’ve asked for entire organizations to dedicate a full day to volunteering. On the other, I’ve requested that everyone involved bring a can of food for the local food pantry.

  • Focus on organizations that serve your client’s community. This makes it easier for your clients to say yes. It also extends the reach of your generosity, which is a deeply satisfying feeling.

  • Make sure that your client has partnered with a reputable organization that you respect. In other words, if you’re not an animal lover, and your client proposes working with the local animal shelter, politely decline and suggest a different organization. It’s important that you feel great about the social good you’re creating. Personally, I’m disturbed by poverty and homelessness. Because of this, I request that my clients partner with organizations addressing these issues.

  • Most importantly: take time to feel the impact that you’re creating. Your generosity and creativity benefits you, your client, and a group of benefactors. That’s true power. You deserve to feel amazing for becoming one of the people who actively makes our world a better place. If more people behaved like you, everyone would be better off.

Why this works: if you’ve ever given a discount to a client, there’s a good chance that you felt weird about it. I used to. In fact, many of the clients I formerly gave discounts to treated me worse than the clients who paid full price.2

There are two schools of thought as to why this happens. The first believes that people who are likely to negotiate tend to be high maintenance and difficult to work with. The other believes that when you negotiate, you signal that you are low-status and easily pushed around.

I don’t buy either of those theories. People treat us how we allow them to. If you give a discount without asking for something equivalent in return, you’ve indicated that you don’t fully believe in the value of what you’re selling.3 By asking for something valuable -like your client’s time and energy- in exchange for a discount, you signal that you’re confident in your ability to deliver.


Using your job to give back part 2: employees, bosses, and owners

As crazy as it sounds, employees can use their company’s resources to give back to the local community too. The trick is to help your boss understand how she and the company benefit by getting involved with community service.

Here’s how to do it:

1) Begin by finding an organization that is somehow related to your company. Though there doesn’t have to be a logical connection between your company and the organization, having one helps. A few examples:

  • An accounting firm partnering with a mathematics tutoring center
  • An ice-cream stand partnering with a homeless shelter
  • A summer camp partnering with an overseas HIV/AIDS program for children.4

If you can’t find a logical connection between your company and a philanthropic organization, aim to partner with an organization in your community. Local ties are very appealing to business owners.

2) Make volunteering beneficial for the company. The easiest way to do this is to contact the local media and let them know about your company’s efforts. Don’t overthink this. It’s the journalist’s job to cover local events. Most of them welcome tips about stories in their community. Of course, this is also a huge win for the company because it will generate free publicity and media coverage. 

3) Schedule a time to chat with your boss. I suggest sending your boss an email asking if she’d be available for 15 minutes to discuss a new project.


4) Start by asking for a small commitment. Make it as easy as possible for your boss to say yes. A few guidelines:

  • Ask if you and any interested employees could spend one Friday afternoon volunteering. Mention that Friday afternoon is the perfect time for volunteer work because employee engagement is already low.
  • Tell her that you’ll handle the logistics and organization. Let her know that all you really need is her permission.
  • Mention that this project can bring good publicity for the company, and to increase the likelihood of this happening, you will personally reach out to at least three journalists before and after the event. If you come prepared with a list of journalists and their contact information, it will be even easier for your boss to give you permission.
  • Remind your boss, if appropriate, that creating an opportunity to serve the less fortunate will boost company morale.
  • Tell her that you’d love it if she joined, too.

5) Pause to appreciate how exceptional you are, regardless of the outcome. If more people cared as much as you do we would have fewer problems and more joy. The world needs people like you. I hope you pause to feel good about that.


6) After the volunteer experience, have everyone sign a card for your boss and the owner of the company. You want to make your boss feel proud of the good work that “she” enabled. Yes, you’re really the one who did all of this, but it’s beneficial to give the credit away. Doing so will make your boss feel important and make her more likely to green-light volunteer projects in the future. Also, repeat step five.


7) Assuming everything went well, ask if you can do this once a quarter. There’s a very good chance that your boss will say yes.


I know that a lot of people are going to dismiss this idea, telling themselves it would never work at their company. If this is you, my hope is simple: challenge your assumption by talking to your boss and seeing what happens.5 To dismiss an idea that excites you, without even attempting it, is to fail before you’ve begun.

The myth of powerlessness

It’s unrealistic for most people to dedicate their lives to building a better world. Because of this, many of the most generous, kind, and capable people have fallen victim to the toxic myth that their need to make money negates their desire to make a real difference in our world.

While this is a common belief, it’s also divorced from reality. No matter where you are in your job or business, there is always a way to generate profit while contributing to the creation a better community. Anything less should be considered a failure to express your true power, creativity, and generosity.