There is no path: lessons from a monk and a billionaire

April, 2014 at a small conference in Toronto: I know that I’m on the wrong path in life, but I don’t know how I’m supposed to find the right one.

One of the speakers at this conference is a Hindu monk who dedicated years of his life to meditation. He seems to have deep insight into the human condition. You can almost feel his presence in the room.

Another speaker is a billionaire. He knows more about the world of business and commerce than anyone I’ve met.

It’s a very intimate conference and I have the opportunity to chat with them one-on-one.1

Separately, I told the monk and the billionaire, “I’m lost right now. I’m modestly successful, but it feels wrong. How do I find my path?”

I assumed that both men would offer very different answers. To my shock, they gave nearly identical suggestions. It felt like I discovered the secret to success. I was giddy.

Here’s the path they laid out:

1)   Spend time getting to know yourself and your authentic desires. Use open-ended questions to search deep within yourself. For example:

  • How would your life change if you suddenly inherited $100,000,000 dollars?
  • What would you do if you only had six months left to live?
  • What do you want your life to be like when you’re 90?

They both advocated taking this process slowly. They promised that with reflection comes clarity.

For several months, I spent Sunday mornings in a café with just a pen and paper to learn more about myself.

2) As you start to connect your vision, describe it in lucid detail. This can be done with words, magazine clippings (think vision boards), clays, paints, or whatever medium resonates with you.

Personally, I like writing, so I described the life I wanted in words. It involved growing my speaking business, vacationing in Costa Rica, giving back to the homeless, and building a thriving social circle.

3) Once you have a clear vision, reverse engineer it. In other words, figure out how to get from point A to point B.

If you want to become a rock star, perhaps you begin by researching different instruments. Then, you buy a guitar. Next, you learn how to play it. After that, you make a few musician friends….

The important part is to have each step lead to the next.

With time I figured out how to increase my stature as a speaker, book a trip to Costa Rica, work with the homeless, and host weekly dinners at my apartment.

4) Finally, take action. If you fail at any point, return to your vision for yourself. Let your vision flood you with energy, inspiring you to overcome your setbacks. Continue taking action.

Both the monk and the billionaire found success following this path.

The monk claimed (and seemed) to be content. He felt he was on the path to enlightenment. The billionaire claimed (and seemed) to be happy and felt like the world was his oyster.

So what happened when I tried this?

I followed this path for two years. In that time, I achieved almost everything I set out to.

But through the entire process, I felt weirdly hollow. More than that, I still felt lost.

It’s not that the path the monk and billionaire laid out didn’t work.

Though it made me successful, it wasn’t my path. The moment I tried to follow their paths, I unintentionally departed from my own. If your goal is to fully engage with life, you can’t follow someone else’s path; you have to blaze your own.

Think about it for a moment. Truly successful people tend to have two things in common:

  • They are passionate about their pursuits (which boils down to self-awareness and self-confidence)
  • They blaze their own trails, allowing their lives and their work to be expressions of their truth.

Barack Obama, Mother Teresa, and Steve Jobs all changed the world, but they did it in dramatically different ways. They did it their way.

When I realized that the monk’s and billionaire’s paths wouldn’t work for me, I tried something else. I paused and asked myself, “Do I know what the first step on my path is?”

I did.

In fact, I knew the first few steps. They were: end a relationship, leave a city, and quit a job.

If you look deep within yourself, you’re likely to find the first step on your path. If you can’t see the second step (and often, you can’t) trust that it will appear after you’ve taken the first. And if you can’t find the first step, take a step – any step. Sometimes you have to walk down the wrong path to recognize the right one when it appears.

Your job is to stumble around until you can tell which way is forward. From there, trust yourself…


Why I’ve lost faith in Tony Robbins (and most life coaches)

December, 2009: It was one of the most embarrassing moments of my life – and it happened while I was completely alone. I had just graduated and was trying to start a business. It wasn’t going well, and my confidence was shot to shit. In an attempt to improve myself, I picked up a copy of Tony Robbin’s book, “Unlimited Power.”

In it, he teaches a Neuro Linguistic Programming1 technique, which he claims will rewire my mind for peak performance.

The procedure was simple: lay down, focus on the thoughts that are sabotaging me, and then yell, “WOOSH” while throwing my arms above my head.

Though it seemed ridiculous, I tried it for a while. Something about how Tony writes and how successful he is made me think it might just work.

After 20 minutes of “wooshing” I felt like a complete jackass. I realized that I was chasing the emotional equivalent of a “get rich quick” scheme. My confidence was the worse for wear.


I know the personal development industry well. When I worked as a professional speaker, I often found myself coaching individuals, motivating large crowds, and speaking about the limitless potential resting within each human.

More than that, I was a junkie. I attended seminars, read every book, and tried a lot of eccentric stuff.

Today, my feelings about personal development are conflicted. When done well, it can transform a life. But most of the time it’s little more than glorified entertainment, sugar highs, and empty promises. Occasionally personal development can become deeply destructive.

In this article I’ll shed light on the emotional sleight of hand within the personal development industry, explain times when personal development tends to work, and show you how to find more effective avenues for growth.

Understanding the deception in personal development

The biggest problem in personal development is that most people who work in the space, really shouldn’t. Instead of giving life advice to the masses, they should be talking to a therapist in private.

However, since most people in the industry don’t truly understand themselves (and consequently, can’t understand others) personal development is filled with psychological and emotional deception. It happens on three levels.

Level 1: the blatant lies. A shocking number of coaches simply lie to their customers. This includes everything from fake testimonials (you can buy those on Fiverr), PDFs teaching you “this one weird trick,” and charlatans who promise the world but deliver a steaming pile of shit.

In most cases, these deceptions are transparent, so we won’t spend too much time here. As a rule, if something seems too good to be true, it is.

Level 2:  subtle lies mingled with profound truths. Most of the industry rests here. The majority of people drawn to personal development can make small changes that will produce dramatic results. A passable coach, speaker, or author can help you make these changes. They’ll explain the importance of the skill you’re developing, hold you accountable for a few weeks, and cheer you on. Your life will be better. These small changes include:

So far, all of that is legit. The deception comes after the client has begun to get results. The coach will then begin promising things that she can’t possibly deliver. Because she’s already produced great results, you’re likely to trust her. You want to trust her. We all want the easiest path to success possible. If all we have to do is continue paying a seemingly helpful professional, we’d be crazy not to.

This is where whimsical ideas about working four hours a week, manifestation, a seven-minute cure to stuttering, rock hard abs in minutes, and endless orgasms come in. We want these things to be possible, so we surrender to their glaring illusion.

Level 3: deep layers of manipulation masked by truth, hope, assertiveness, and charisma. Imagine for a moment that you’re attending a seminar led by a talented speaker. She says, almost offhandedly, “Write down the names of five people you love.”

Obediently, you write down the names of your parents, your brother, your lover, and your best friend.

The speaker proceeds to tell her dark secret. When she was younger, she battled with depression, alcoholism, poverty, and an eating disorder.

After years of searching for solutions, she decided her life wasn’t worth living.

Just as she put the gun to her head, she had an epiphany: she never learned to love herself. In fact, she realized that for most of her life, she hated herself. In that moment, she felt clarity and relief for the first time.

Since learning to love herself she’s become rich, happy, and successful.

Next, she returns your attention to the list of people you love the most. She asks if anyone in the room has written their own name. No one raises their hand. Suddenly, everyone starts to realize that they don’t love themselves as much as they should. The audience members feel as though they just uncovered the deep-rooted secret about what’s holding them back from the life they “deserve.”

The trainer goes on to teach a few good strategies for self-love and explains that she expands upon them in additional seminars, books, courses, and one-on-one work. The audience is hers.

But did you see what happened there?

First, she asked a trick question. Even folks with dangerously large egos would fail to answer, “Myself” when asked, “Who do you love the most?”

Next, she created huge amounts of vulnerability in the room by telling an intimate story.

Finally, she presented a solution. She explained that she’ll share what she can now, and if you want to learn more about the secrets to success, she has follow-up workshops, books, and courses you can buy.

In addition to hinging on a trick question (which creates a false reality in the audience’s mind), she also implies that the follow-up services will speed up success. In most cases, this just isn’t true. Once you’ve learned the basics, it’s up to you to do the hard work. There are no shortcuts.

But of course, there’s no need to take my word for any of this. You can see for yourself by watching the documentary: Tony Robbins: I am not your Guru.

Why I believe Tony Robbins abuses people for profit

Before we begin, we need to establish a few facts about Tony Robbins, the world famous “Peak performance” coach.

  • He has helped countless people, including world famous athletes, celebrities, and politicians.
  • He is not a psychologist, psychiatrist, doctor, or licensed mental health professional of any sort.
  • He is likely less intelligent than he seems. He spent years of his life eating fish several times a day, yet still seemed surprised when he got mercury poisoning (see Robbin’s interview on the Tim Ferriss show, episode 178).
  • He is likely less authentic or self-aware than he seems. In the documentary, he says that he never gets stage fright, yet we witness him going through an elaborate “Priming” ritual before his seminars.
  • His raw confidence, charisma, voice, and tall, handsome, broad shouldered appearance combine to make him nearly irresistible. People can’t help but get sucked into his aura and take what he says for fact. Heck, this happens to me.

But to truly see Tony, you need to observe his actions separate from his magnetic draw.

The documentary, Tony Robbins: I am not your guru allows us to do just that. It captures Robbin’s six day “Date with Destiny” event.

During the event he gets the audience pumped up and teaches them to focus on themselves and their authentic desires. He tells brilliant stories that help people understand our world and their role within it. He teaches people to connect with their confidence and to lean into some of the harder conversations in their lives. All of this is good. He’s providing real value.

He starts to blur the line between reality and fiction when he states that someone’s life can, “Change in a moment.” We all know that enduring change doesn’t happen in a moment; it takes time. Still, we’re so seduced by Robbins and the possibility of fixing our problems that we allow ourselves to be duped.

Throughout the documentary, Robbins goes from telling hopeful – perhaps even innocent – lies, to being a flat out douchebag. He:

  • Bullies a woman into calling her boyfriend and breaking up with him while 2,500 people watch. Spoiler alert: they get back together after the seminar.
  • Encourages a survivor of systemic childhood rape to tell the story of her abuse without preparation (or really, consent) in front the entire audience. He then encourages her to form artificially deep and vulnerable relationships with three random ass dudes from the audience who are supposed to check in on her. She is to refer to these men as her “uncles.” What. The. Fuck.
    If Robbins were a licensed trauma counselor that would be one thing, but he isn’t. He’s a glorified entertainer, and the entire audience watches on as he exploits a young woman for emotional effect.
  • Asks people dealing with suicidal ideation to identify themselves to the entire group. Robbins doesn’t seem to understand the full scope of the mental illness and forgets that suicide can sometimes result from people opening up before they are ready. Robbins then singles out a young man, stands in this man’s personal space, talks to him about his desire to kill himself, mocks his shoes, and then claims that the guy is cured.

Bull shit bull shit bull shit.

Of course, all of this can be quite difficult to see. Robbin’s charisma is blinding. More than that, the deceit, manipulation, and flat out exploitation is infused with genuinely good advice, humor, and overwhelming confidence. It makes it dangerously easy for the line between reality and fantasy to blur.

But what about everyone else in the personal development industry?

I actually think Robbins is well intentioned and gifted in many regards. I also think he’s completely failed to understand the limits of his gifts. If he did, he’d stick to being an entertainer who helps people develop confidence, focus their lives, and master business.

Most people in personal development start off well intentioned. They help a lot of people. They get tons of positive feedback, which – ironically – is often the root of the problem.

Along the way, many coaches get high on their own supply. When this happens clients become victims of the coach’s blind spots.

I’ve seen this happen up close. Over the past few years I’ve watched multiple gifted coaches unintentionally (or perhaps intentionally) harm their clients.

A short list of examples includes: encouraging their clients to go into debt to continue working with the coach, needlessly rushing sensitive conversations, mishandling abuse recovery (and often leaving the client worse for it), forcing extreme vulnerability, and taking control of large chunks of the client’s personal and professional life.

How to avoid the con artists

Despite everything I’ve written, I still believe in personal development. Almost every area of my life has been improved by it. The secret to successful personal development lies in identifying the coaches who are gifted and ethical. Here are a few guidelines to help you find them:

  • If you are the survivor of trauma (and a lot of us are…) then work with a therapist, not a coach. Yes, a lot of coaches claim to be able to help you. Don’t trust them. These coaches are failing to understand the limits of their abilities. Coaches have minimal – if any – training in this area. Psychologists, especially specialized ones, have tons of training.
  • Is the person guaranteeing that you’ll get results? Do her claims sound too good to be true? Is she offering a quick fix? If so, she’s a con artist. There are no quick fixes or secrets, and no coach can ever guarantee results.
  • Coaching is filled with people who fail to practice what they preach. Many “health” coaches have unhealthy relationships to food, exercise, and their body image. Many “life” coaches lead vapid, unengaged lives and are quietly self-loathing. Many “relationship” coaches are lonely and afraid of intimacy. Most (and yes, I do mean most) speaking coaches are mediocre speakers who failed to make it as a pros.
  • When you hire a coach, it’s important that she demonstrates that she is a true master of her craft. Don’t trust the testimonials on their site. Don’t allow yourself to be mesmerized by a sales call. Do your research. If possible, get a referral, and in general trust your gut when hiring a coach.
  • Does the coach focus on one specific skill or issue? If so, consider that a good sign. Coaches who are focused on specific areas of development tend to be more aware of their own limitations. In fact, coaching can be an amazing medium for learning discrete skills like: overcoming anxiety, negotiation, public speaking, self-love, sales, confidence, charisma, etc.
  • Certifications mean absolutely nothing in coaching. Seriously. You’re just as likely to find an amazing coach with no certifications as a scum of the earth coach with a dozen letters after her name. Certifications are not like degrees; literally nothing governs a certification board.
  • With both coaches and therapists, you want to look for ones who have high attrition rates. In other words, are their clients staying with them for a few months and then leaving? If yes, that’s a good thing. It indicates that they tend to be effective.

Post script 1: you cannot divorce yourself from human nature

One of the main reasons people turn to personal development is because they feel broken.

I’ll make this easy for you: you’re not broken. You’ve just been misled about the truth of the human experience.

We’ve been sold an idea that it’s possible for us to simultaneously make a million dollars, be madly in love with our partner, have explosive sex, wake up looking like a model, and tackle every single day brimming with happiness and excitement. Worse still, the personal development industry has tricked us into believing that if we aren’t experiencing those things, there’s something wrong with us.

In reality, that’s not how humans are. Humans are messy, dynamic, imperfect creatures with glaring rough edges. There are going to be days when you’re depressed. Your relationships will be riddled with friction. Apathy, lethargy, and ennui will stack up and make you feel worthless. You’ll yo-yo on and off your diet. You’ll get excited to overhaul your life and then completely fail to stick with the program. You’ll be ripped apart by your insecurities. If you have the potential to be truly exceptional at something, you’ll have to sacrifice a lot in order to pursue it.

What is often missed is that this pure chaos makes us beautiful, happy, and effective. We need the insanity that comes along with being humans. If we try to run from it or pretend it’s inessential, we betray our true nature.

Postscript 2: on therapy and psychologists…

A very simple truth that makes many people uncomfortable: if you’ve been into personal development for a while, you probably need a psychologist.

There is no secret hidden in the next book, seminar, or course that will finally “fix” you. There is only doing the hard, vulnerable, raw work of baring your soul to a trained professional. The good news is that therapists tend to be more effective than coaches and less expensive.

If you’ve been dealing with persistent issues in your personal, social, or professional life and a few months of coaching or personal development hasn’t gotten the results you’re looking for, get a therapist. There is no need to deal with more suffering than is absolutely necessary. Your future self will thank you.


2017: the year of hell yeah or guilt free no

At the beginning of every year, I choose a new trait to develop in myself. Past traits have included:

In 2017, I’m going to focus on saying, “Yes” to the opportunities, projects, and invitations that I’m genuinely excited for and saying, “No” – without feeling guilty about it – to everything else.  

I’m calling it the year of “Hell yeah or guilt free no.”

“Hell yeah or no” is not my idea. I first read about it in Mark Manson’s article “Fuck Yeah or No,” but Mark was inspired by Derek Sivers’ article, “No ‘yeah.’ Either ‘HELL YEAH’ or ‘no.’”  

Why “Hell yeah or guilt free no?” Because people pleasing sucks…

I have a pesky habit of being a people pleaser. While there are some upsides to this, it primarily leads me to friction, wasted time, and subtle self-loathing.

On the surface, people pleasing results in:

But there’s a far bigger problem than that. People pleasing contains a very real psychological and existential liability.

People pleasing prioritizes others’ needs, desires, and happiness above my own, which is almost always a bad idea. It reinforces the non-conscious belief that I’m not worth much, and sabotages chunks of my life.

Pausing to ask myself, “Am I feeling ‘hell yeah’ about this?” before I commit should solve many of these problems.

I expect that adopting this stance in life will have predictable benefits for myself and anyone else who tries it, including:

  • Strengthening my sense of self and reinforcing the idea that my needs come first.
  • Reducing friction in my life. Imagine how vivid one’s experience will become if she only engages with the activities and people she loves.
  • Reducing the number of commitments in my life. I’ve noticed that having blank space on my calendar increases creativity, intuition, serendipity, and rest.
  • Making it easier to show up fully and authentically in all areas of life.

In truth, I’ve already been doing this for a few weeks and love it. I’ve said no to professional introductions that didn’t interest me, chosen to ignore a few texts and emails I didn’t want to deal with, and took an entire day off from work simply because I wanted to.


The aim is simple: when making a decision, ask yourself, “Am I so excited about this that it makes me say, ‘Hell yeah!’?” If so, move forward. If not, don’t do it. Try to release yourself from any guilt that comes with saying, “No.”

There are predictable problems that come with “Hell yeah or guilt free no,” so I’ve created a few guidelines:

You have to keep your life running well. I pretty much never say “Hell yeah” to paying my credit card bill or choosing salad over pizza but those things keep my life running well. They matter. “Hell yeah or guilt free no” cannot be used as an excuse to shirk responsibility or be unnecessarily difficult.

This project is not an excuse to do stupid shit. You cannot use it to cheat on your partner, do endless lines of coke, or gamble away your retirement savings. Calculated risks – even calculated hedonism – are cool. Being needlessly destructive isn’t.

You are not obligated to explain yourself. It feels pretty badass to just say, “No, that doesn’t interest me,” without explaining why. You don’t need to justify your decisions to anyone besides yourself. Of course when an honest explanation of your decision may help the other person, it’s nice to offer one.

Gracefully accept other people’s decisions when they say, “No.” No fighting, no arguing, no whining, just acceptance and respect.

Saying “No” can no longer be a source of guilt. I often feel guilty when I say no. Since the guilt does nothing for me, I’m going to do my best to let go of it. This is easier said than done but it should be well worth the effort.

This project does not make sense for everyone. If you are just getting started in life, moving into a new field, or working to get yourself out of a rut, you should get in the habit of saying “Yes” to nearly everything. This will create a more engaged, vibrant and dynamic life. Once there are more demands on your time and energy than you can field, then you should shift to saying “No” more often.

Wanna join me?

If the idea of approaching life from the perspective of “Hell yeah or guilt free no” excites you, I’d love for you to join me. You can tell me about your vision for yourself and any related, cool stories in the comment section below. You can also reach me directly by subscribing to this blog.

If “Hell yeah or guilt free no” doesn’t resonate with you, I encourage you to come up with your own theme for the year. Aim for something that will help you live a life you love. When you come up with your theme, let me know – I’m always looking for great ideas.

Here’s to making 2017 the best year yet!

2016 personal review: the victories, losses, and lessons

2016 was – by far – the best year of my life. It was also one of the most demanding. This is not a coincidence. To live a truly vivid life, you have to find the courage to step into the arena. Doing so will tax nearly everything you have, but when you do, you’ll be handsomely rewarded. You’ll also discover that you are far more capable than you suspected.

In this article, I’m going to share my biggest successes and most scarring failures of 2016 as well as the lessons I learned along the way. But first, I want to share two quick things that don’t easily fall into any of the categories:

  • For the first time since 2009 my income declined. In fact, it declined by about 30%. This happened because I quit professional speaking to pursue writing and consulting. Now that I know the literal cost of chasing my dreams, I can’t help but ask, “Would I do that again?” The answer: hell yes!
  • From June 19th – July 3rd I officiated two weddings and was the best man in a third. Though this sequence was intensely demanding, it was also one of the highlights of my life. During this time, I rented a sports car to treat myself, making me feel like a total rock star. I also got a speeding ticket in said sports car. I’ve included one of my favorite photos from each wedding below.

With W* (I was his best man) moments before the reception, Washington, DC.

Officiating J* and A*s wedding, Colorado

Officiating a close friend’s wedding, Massachusetts

What went well this year…

1) I quit professional speaking! My first paid speech was in 2006, but I didn’t start speaking full time until 2009.

In three years, I had clients flying me around the world on elaborate speaking tours. Halfway through my 2012 tour, I knew I wanted to leave speaking, but I was too afraid to actually do it… until this year.

I’ll never forget getting back from my final tour in late February of 2016. As I waited at the airport for my friends to pick me up, I listened to “Home” by LCD Soundsystem on repeat. I was so excited to move on to the next chapter of my work and life, that I was flooded with waves of goose bumps.

2) I finally took the leap to focus on writing, and it’s made all the difference. Though I’ve wanted to be a writer since high school, I was always afraid to pursue it. First, I had no clue how writers made enough money to support themselves1 Second, I was afraid to actually begin living my dream. I worried that, if I failed, my life would feel tarnished and disappointing.

I’m glad that I (eventually) learned to ignore those fears, because my work as a writer has been one of the best experiences of my life. A short list of what’s happened since this blog’s launch in March:

  • grew from a few hundred readers per month when it launched to nearly 10,000. In truth, this is a shared success. I am supported by: two advisors, a mentor, and my right-hand woman, A*. Without their help, this project would have never worked. Of course we could not possibly do this without you, my readers and clients. You make all of this work possible. You have all done more for me than you could ever imagine. From the bottom of my heart, thank you.
  • One reader told me that the article on self-love helped bring her back from the precipice of suicide. I have no words to express how good this makes me feel and how grateful I am for that note.
  • The article on quitting professional speaking went viral. In a weird twist, a famous speaker got my number and called me multiple times demanding that I change the article. I think she resented how I portrayed the life of a professional speaker. Maybe I was ignorant, but I didn’t know that people actually did stuff like that…

3) I felt more happy, playful, and centered, than ever before. Don’t get me wrong, there were shitty days, but overall, I felt great. I woke up excited and energized more often than not, and I think this is the result of a few things:

  • I cut wayyyy back on personal development. I know that sounds counter intuitive, but here’s the thing: the personal development industry has a weird knack for tricking you into feeling like you’re broken. In fact, the market kind of depends on it. Truthfully, there’s nothing wrong with you. You’re not broken; I promise.
  • I let go of my life as a pro speaker and instead used my time to write.
  • I got older. I know this isn’t a sexy reason for being happy, but as far as I can tell, happiness broadly trends with age. If you find yourself getting unhappier as you get older, consider talking to a professional. There’s no need to deal with more suffering than is necessary.

Where I messed up…

1) I failed to set effective boundaries and created unnecessary volatility in my life. A lot changed for me this year. In many cases, I failed to respect the learning curve that the change required. This resulted in three instances where I was so burnt out that recovering required multiple days in bed. I ignored my limits, and I suffered the consequences.

Looking back, I realize that I failed to give myself the same gentleness, respect, and understanding that I would readily offer anyone else in the world. Now, when I notice myself approaching limits or dealing with something difficult, I try to pause and ask myself, “If one of my close friends were in this exact situation, what would I say to him?” I then attempt to transfer that advice to myself.

2) I caused serious pain for (at least) two people I love. Some of the things I have written hurt them. Honestly, I get it. When I put myself in their shoes, I understand. I have no real excuse for my behavior, and if I’m being honest, part of me sensed the risk. I clicked publish anyways.

In one case, the person texted me after he read the article. I called him, and we had a long chat. We’re fine now. In fact, the hard conversation brought us closer.

In the other case, the person emailed me several months after she read the article. We exchanged 13 long (in some cases 1,000+ word) emails and a few dozen texts.

We don’t really talk anymore.

I think about her all the time. I fear we’ll never rebuild the friendship we had. I fear I did too much damage. Looking back, I wish I handled the article that hurt her differently.

I’ve become much more thoughtful in how I portray the people in my life when I write about them.

3) I kept too many of my relationships in the grey. In fact, there were three different ways that I failed to fully show up in my relationships:

  • In two instances, I was slow to breakup with a woman I was dating. I knew I was out of integrity and was being unfair, but lacked the courage required to end things.
  • There were numerous occasions when someone I dislike invited me to hang out, and I said yes, instead of rejecting the invitation. I allowed people pleasing to get the best of me. No one benefitted from this. Correcting this problem will be one of my main focuses in 2017 (more details in my next article).
  • In more instances than I care to count, I chose passive aggression over gentle confrontation. In two cases, I was passive aggressive for several months. Though I ended up apologizing for my behavior and leaning into all of the hard conversations, I wish I did it sooner. I wish I were less of a dick. I wish I were more direct, honest, and loving.

The most important lessons I learned

Note: I’m planning to write in-depth articles about each of these topics in 2017. If you’d like the articles delivered to your inbox, you can subscribe here.

1) There is extreme value in speaking and living your truth (and the corollary: lying and deception offer no enduring benefits). My aim for 2016 was to be as honest as possible, in both word and action. This created closer personal relationships, a higher quality of work for my clients, and an overall increase in happiness and contentment.

But it wasn’t easy. I had to learn to prioritize being honest over being a people pleaser. I needed to disillusion people who thought I was more successful, influential, confident, or experienced than I am. It forced me to give crisp definition to my reality, even when I didn’t want to. In a few instances, it required admitting that I had been misleading. Perhaps most valuable of all, it made me confront a few of the lies I was telling myself.

None of this was easy, but the benefits of being raw, vulnerable, honest and open are so wildly significant that they make choosing honesty over deception a no-brainer.

2) I learned to access the part of me that is unassailable. For most of my life I felt like I had little control over my emotions. Halfway through the year, on the precipice of a nervous breakdown, that changed. I learned to access what Albert Camus calls the, “Invincible summer” inside of myself.

When readership on the blog spiked, I became a nervous wreck. I worried that if I wrote an article that was less than amazing, my readers would abandon me.

When I sat down to work, I’d type half of a paragraph, call myself an idiot and a fraud, and then hold down the delete key. This would go on for hours. On several occasions it brought me to the edge of a panic attack.

I mentioned this to one of my advisors who then suggested I shift my attention away from worrying about what people would think (which I can’t control anyways) and just focus on writing from my heart.

He then suggested that when I feel fear or anxiety, I sit with the feeling, instead of fleeing it.

I’ve discovered that when I return to my internal motivation and acknowledge any difficult emotions that come up, I can consistently step into the arena. It allows me to stay centered within myself even when it feels like my world may collapse. I no longer lose myself in the darkness.

So, how do you access your own inner citadel?

  • First, you need to gain awareness of your inner experience. Meditation and journaling will speed this up.
  • When you notice a difficult emotion, stay with it. Most people’s natural tendency is to flee from it through distraction, denial, or delusion. Don’t do that. Instead, stare the emotion straight in the fucking eye. Feel it trying to kill you. This will be uncomfortable.
  • You’ll notice that the emotion burns off, and resting beneath the negative feeling you will find the part of you that cannot be defeated. This will reconnect you to yourself and your power.

3) Every few years you have to surrender who you were in order to become who you are. This is exactly where I’m right now. I realize that many of the behaviors that shaped me into the man I am today no longer serve me. I know that I have to let go of everything that no longer feels true or serves me, even if I used to cherish it.

I used to be a guy who cherished vegetarianism, sobriety, and personal development. Now, none of those feel as important as they once did. Of course those external changes are indicative of much deeper internal changes.

It’s hard to let go of how I used to define myself. It’s disorienting. It throws me off. It makes me a bit afraid that the people who liked the old Jason, may not like the current Jason.

But I’ve realized something simple: if I want to stay true to myself, I must first let go of the man I used to be, to create space for the man I am, even if it scares me.

A guide to meditation: how to do it, how it changed me, its risks, and more…

February 2013, Washington, DC: My college friends C* and B* are visiting W* and me.

We’ve just gotten back from the bar and are sitting in a circle in our underwear (it’s not what you think, but don’t ask).

C* declares that it’s time to meditate. He picks up my metal water bottle and hits it with a stick while yelling, “GONGGGGG!” at the top of his lungs.

Once I stop laughing, I close my eyes and attempt to focus on my breath for 15 minutes. Halfway through, I notice that I feel really close to C* and B* (W* isn’t a meditator and excused himself at the beginning of the session).

At the end of the 15 minutes, W* sneaks up and shoots at us with a Nerf gun.  

We all start laughing.

Later that night I shyly mention to C* and B* that I felt really close to them while we were meditating. I expected them to tease me, but instead, they said that they unexpectedly experienced the same closeness.


Over the past seven years I’ve spent about 30 minutes in meditation (nearly) every day. Some of the sessions lasted for several hours while others were literally one minute. I’ve studied with a wide variety of teachers from multiple lineages and spent, cumulatively, about two months in silent retreat.

My aim in this article is to help you understand meditation. We’ll cover how to do it, why it might be worth your time, why it may be a waste of your time, and how it’s changed my life. I’ll also share a list of resources for those looking to dive deeper into their practice.

Five ways meditation has improved my life

People often fail to distinguish their direct experience from the universal truth; they believe that since something is true to them, it must be true to everyone. In reality, direct experience and universal truth are two different animals. Everything in this section is true as it pertains to my experience with meditation. However, I make no claims about universal truths. I’m not sure that I – or any human – actually has the ability to access universal truth (if it even exists).

And I want to be clear about something else: meditation has affected me profoundly. It’s drawn me into the moment, made it easier for me to access my innate confidence, and fostered a deep sense of connection between the universe and myself. Still, I don’t always feel like that. I flick in and out of the moment, my confidence falters, and I feel isolated from time to time. What I have noticed though is that with each passing year, the benefits of meditation become more stable in my life.

With that in mind, here are the ways mediation has changed me personally. Your results may vary:

1: I’ve increased mastery over my thoughts and feelings. In Nov of 2014, I was scheduled to speak at a conference in Paraguay. I flew from Boston to Detroit and was supposed to fly from Detroit to Paraguay. When the gate agent in Detroit asked for my passport, I realized something dreadful: my passport was gone. I couldn’t board the flight to Paraguay.

The short version of the aftermath: I flew back to my nearest birth certificate in Boston, used my birth certificate to get an emergency replacement passport, and then explored every feasible option to get to Paraguay ASAP. In the end, my lost passport delayed the conference of over 500 people by an entire day.

Through the chaos, I was able to remain centered and focused. In fact, the people around me were shocked by my composure. While I didn’t like the situation, I also understood that getting upset would be counterproductive. This enabled me to channel all my energy into solving the problem at hand, rather than being eaten alive by it.

When you practice meditation (and I’ll explain how in a moment) you start to realize you are not your thoughts. The chaos inside your head? It’s not you. Don’t get me wrong – thoughts are deeply captivating. They can be empowering. They can change the world. They can wreck shit. But they aren’t you.

As your practice deepens, you’ll begin to notice something else: you aren’t your feelings either. In fact, thoughts and feelings work together to distract you from your true nature.

When you cut through the trance, you’ll notice that there is a source of consciousness and life deep within you. Though there are a wide variety of names (and often explanations) for this source, it’s usually referred to as one of the following: the soul, God, the Universe, genetics, epiphenomena, the true self, or the Source.

Realizing I am neither my thoughts nor my feelings allows me to intentionally shape my life. It allows me to control my actions (and on a good day, my reactions), while accepting the circumstances I’m dealt.  This makes it easier for me to revel in the good times, keep my head above water during the bad times, and remain playful throughout.

2: I’ve found a deep sense of unity and connection between others, the world, and myself. At first glance, the human experience is characterized by isolation, separation, and disconnection. As far as I can tell, the sense of being separate from the world and its people is an illusion.

When you allow yourself to cut through the trance of thoughts and feelings, you’ll notice that the sense of separation from the world vanishes. In its place, you’ll find a deep sense of connection. I think it was this mutual connection that made C*, B*, and I feel close to one another when we were meditating together.

Once they know what to look for, most meditators will be able to feel some sort of connection to the Source. I’ve noticed that the more I stay true to myself, the more easily I can feel my connection to everything. Many meditators will feel the connection so deeply (if also fleetingly) that they end up believing the separation between life forms is nothing more than an illusion.

3: On a good day, I understand that the past and future are mental constructs and that I have everything I need in this exact moment. Anyone who has ever smoked a joint or taken a high school physics class has had some variation of the following conversation, “Dude. Time isn’t real. We just like, made it up, you know?”

And while it’s easy to say that nothing exists outside of this moment, truly embracing it is difficult.

The concept of time is built into how modern humans experience life. Divorcing your experience of this moment from the concept of time is challenging. It feels like dismantling the scaffolding you’re standing on. However, once you understand it, you gain an extreme measure of power over yourself, your experience, and your reality.

I’ll do my best to explain how to do this, but fair warning: words aren’t an ideal medium for understanding the dissolution of time.

First, notice that the past only exists as memories and concepts in your head. Yes, all your memories from the past really did happen (or most of them, at least), but they aren’t happening now.

If you’re experiencing emotion or fascination about something that happened in the past, you’re manufacturing that emotion in your head. There’s nothing wrong with manufacturing thoughts or feelings, but realize that when you do this, you’re living – quiet literally – in a fantasy.  

Next, notice that the future is purely hypothetical. You can worry, plan for, and get excited about the future if you’d like, but don’t trick yourself into believing that the future you imagine holds any bearing in reality. Your future (like your past) exists purely in your head. It’s nothing more than a concept.

Finally, as you realize that the past and future are little more than mental constructs, you’ll realize something else: the present isn’t a mental construct. You realize that the present moment is filled with inexplicable potential.

You start to understand that the present moment is also the only permanent thing in your life. When you experienced things in the “past”, you didn’t say to yourself, “Wow, I’m in the past now” while you were experiencing them. You experienced them as the present. Similarly, when the “future” arrives, you won’t say to yourself, “Holy shit, I’m living in the future,” instead you’ll say to yourself, “This is what’s happening now.”

And that’s really cool, because when you realize that this moment is all you’ve ever had and all that you’ll ever have, you can begin to create anything you want and make up the rules along the way.

You may not be able to draw $1,000,000, the love of your life, and a tropical vacation into this exact moment, but you do have everything required to begin the process of finding and creating those things. When you start, you’ll notice that you can create your dreams more fluidly than you’ve been led to believe.

You’ll realize that by improving the quality of this moment, you will improve the quality of “future” moments. Your job is to avoid the trap of manufacturing artificial realities from the past or future and stay grounded in the only thing with true potential: this moment. When you do this you will access more potential than most people realize is possible. A stable meditation practice helps.

4: I’ve gained easy and fluid access to my own innate resilience, confidence, calm, and courage. After you understand that you can only ever experience life from the lens of the moment, you realize that you can handle anything thrown your way.

I don’t mean that life suddenly becomes unicorn shits and gumdrops. In fact, in some ways, quite the opposite is true. What happens is you become familiar enough with the world’s darkness to understand that it will pass. You become familiar enough with the world’s joy to fully revel in it when it appears. You become familiar enough with your own resilience and tenacity to realize you’re a warrior. You notice that even when you’re extremely anxious, afraid, or hopeless, you can handle it. You realize that when you improve this moment, even just a bit, the next one will be better.

A tangible example: a few weeks ago I wrote about a painful sequence of events in my life. I went through a breakup, I feared for the state of my country, and someone close to me was diagnosed with brain cancer. There were multiple times during that phase when I was driven to tears, yet I never lost myself; I knew that no matter how bad it got, the darkness would pass.

When you realize that you can handle anything life throws at you (and I promise, you can) it feels like you’ve been handed the ability to ever so slightly bend the world to your will.

5: The benefits virtually everyone experiences: increased happiness, increased resilience, decreased anxiety, and a renewed ability to focus. All of these benefits seem to be nearly universal – and often pronounced – among mediators. In fact, most of them are so immediate that I don’t want you to take my word for it. Instead, spend two minutes meditating every day for the next 10 days. See how it affects you. You may be surprised…

How to meditate



The first thing to understand about meditation is that it’s more difficult than it seems (kind of like running a marathon). If you find yourself struggling a bit, don’t worry. That struggle is – in essence – the point.

At its core, meditation is the practice of trying to fix your mind on a single point of focus.

I’ll walk you through a simple approach and explain which variations are worth exploring and how to make meditation a habit.

1) Sit in a chair with your feet flat on the ground and your spine straight. Place your hands in your lap, on your thighs, or on your knees. Your palms may be either face up or face down, depending on which is more comfortable for you. The goal is to position yourself so that you are both relaxed and alert.

2) Close your eyes.

3) Focus on your breath (to the best of your ability). You can do this by focusing on any of the following: your stomach or chest rising and falling, the feeling of your breath right below your nose, the breath moving in and out of your nose, or the sound of your breathing. Again, do whatever is easiest for you.

Do not force yourself to breathe, just notice what’s happening in your body.

I like to begin by counting my first ten breaths, because it helps me focus and relax. If you do this and lose track of what number you’re on, simply start again at one. Once you’ve reached ten, stop counting and focus purely on your breath.

4) You will notice that your mind drifts. While you’re trying to focus on your breath, you’ll start thinking about the day ahead, an embarrassing memory from sixth grade, your outfit for the Christmas party, food, money, gossip, sex, and a million other things.

When you notice your mind drifting, simply bring your attention back to your breath.

The process of attempting to focus your mind, noticing that your attention has drifted, and bringing it back, is the entire practice of meditation.

Many people believe that the goal of meditation is to empty your mind. That’s not possible. The goal is to concentrate on a single point of attention. Sometimes this will be easy. Sometimes it will be impossible. Both are fine. Your aim is to increase your comfort and presence in this moment. This is done by noticing when your attention has drifted and then bringing it back.

Modifications to your practice:

There are countless ways to modify your meditation practice. Experiment with the options below to see what works for you. Also, consider taking classes in different styles to find which is best for you.

Focal point: if focusing on your breath doesn’t work for you, consider focusing on a mantra, the flame of a candle, a flower, a chant, the ground in front of you, the sounds around you, or the weight/feeling of your body.

Posture: the most common form of meditation is seated, either on a chair or a cushion. If you’re sitting on a cushion, you may sit cross-legged, in half-lotus, or lotus. However, you don’t need to be sitting. You can meditate standing up, lying down, or while walking. If you’re meditating while walking your focal point should be a specific part of your stride. I focus on my heel and toes striking the ground.

Eyes: I keep my eyes closed, but it’s fine to keep your eyes open during meditation. If you do, just be sure to use a soft, gentle focus.

Fidgeting vs sitting still: most schools of thought suggest that you should sit perfectly still while you meditate (or at least attempt to). I can’t do this. If you need to fidget, stretch your legs, crack your knuckles, or even stand up, simply shift your attention from your normal focal point to the movement that you’re creating in your body.

How to make meditation a habit:

There are two approaches to creating a daily meditation practice.

The first is to dive in with a multi-day retreat led by a teacher. The idea is that you will have a powerful and direct experience with meditation and that you’ll see the benefits so quickly and so clearly that it becomes a permanent fixture in your life.

This strikes me as unrealistic. Few people are able – let alone willing – to invest multiple days into a skill they have minimal experience with. I wouldn’t.

The second approach, which I believe is superior, is to slowly develop the habit. As with any new behavior, it’s easiest to start small.

Begin by spending two minutes a day in seated meditation. Try to meditate at the same time each day. Once you’re comfortable with two minutes (and this could take weeks), try three. Then do four, and so on and so forth. Only add time to your practice when you really, really want to. Building your practice this way will integrate meditation into the flow of your life. If you miss a day or two, don’t worry about it.

The quiet risks of meditation

Like anything else, meditation is not without its risks. Unlike most things, people almost never talk about the downsides of meditation. These are the common pitfalls to look out for and a few guidelines to help you avoid them:

Using meditation as a tool to avoid reality. Many people who need to diet, talk to a psychologist, lean into hard conversations, or pull their lives together use meditation as an excuse not to do so. They tell themselves, “I just need to meditate more, and then everything will be ok.” Bull. Shit. This is nothing more than a thinly veiled form of fear and procrastination.

Meditation is a great tool for studying your mind and the moment, but it is not a panacea. If you find yourself using meditation to “prepare” for something in the future, you need to stop meditating and go fix the problem you’ve been avoiding.

A very simple rule of thumb: if you’re experiencing a problem in your life, assume that meditation cannot solve it. Address the problem directly.

For some people meditation is a massive waste of time: meditation is not for everyone. I have several friends who have tried meditation and gained nothing from it. I’ve met people who have dedicated huge chunks of their lives to meditation with little to show for it.

Many people fall into meditation in the same way that others fall into religion. They never ask themselves, “Do I enjoy this?”, “Do I believe in this” or “Does this provide benefits for me or the world?” Instead, they just go through the motions hoping for a miracle.

Here’s the rule: if it seems like it’s benefitting you, stick with it. If you’ve experimented with it for a bit and it feels like a waste of time, let it go.  

The time you spend in “meditation” is actually time spent lost in thought: the vast majority of people who claim to be meditating, aren’t. What they’re really doing is thinking. They’ve become so captivated by their thoughts that they don’t even notice they’re thinking.

For almost everyone, the rule is simple: if you never noticed your thoughts during a meditation session, you weren’t meditating. You were literally lost in thought. This is the opposite of meditation. Meditation is the act of noticing your thoughts, letting them go, and returning to a single point of attention.

Expecting meditation to do something for you in the future. Meditation is entirely about the moment. If you’re meditating so that you may be different in some distant future, then don’t waste your time. Instead of trying to manipulate an imaginary future, improve this moment right here. Doing so will improve the next moment.

Claims about meditation that may or may not be BS

The more you study meditation, the more outlandish the claims of its power become. You’ll hear of yogis who can hold their breath underwater for days at a time, immortal beings walking among us, monks who can float, and genuine alchemists who can turn any metal into gold. To me, all of those claims seem like obvious bullshit.

However, there are a few claims that seem absurd at first glance, but may hold water. Two that I think may be possible, but I am yet to have direct experience with (and thus remain gently skeptical of): meditation will help you uncover latent psychic abilities and meditation will give you access to hidden dimensions of reality.

I’m open to these ideas because some of my teachers, mentors, and friends claim to have had direct experiences with psychic abilities and deeper dimensions of reality being uncovered through meditation. These people are not the new age weirdos you think they are. Several of them built multi-million dollar businesses and accumulated true influence in government and entertainment. Because of their grounding in reality, I can’t help but approach their claims with curiosity.

My recommendation to you is quite simple: stay open and judge for yourself.  Trust your direct experience over the claims that others make.


If you’d like to deepen your practice or continue exploring meditation, here are a few resources:

Peace is Every Step” by Thich Nhat Hanh -This is my favorite book on meditation. It’s short, readable, and clear. I particularly like the “Tangerine Meditation” and used to use it at my advanced leadership trainings.

What’s magic about Thich Nhat Hanh (often referred to as “Thay”) is that you can feel his calm presence in the words he writes. Others have found Thay’s book “The Miracle of Mindfulness” to be a great introduction to meditation. While I enjoyed Miracle, I thought Peace was stronger and more readable.

Mindfulness in Plain English” by Bhante Gunaratana – If you’re looking for a clear, accessible approach to understanding mediation, this book is a great introduction. It’s fast, easy, and precise. I think Gunaratana is a bit stricter than necessary, and I find some of his claims dubious, but still, this is an excellent text.

“Waking Up” by Sam Harris – Unlike many authors who attempt to explain how meditation affects the brain, Harris is actually a neuroscientist. While I don’t agree with everything Harris writes, if you’re even passively interested in the intersection of meditation and neuroscience, this is the book for you.

Insight Meditation Timer – I’ve used this app daily for five years. It includes tracking which is a great feature for people starting out. What I particularly love is that it works in airplane mode so you can effectively disable your phone’s ability to distract you while you’re meditating. Many of my friends use Calm or Headspace. I have no direct experience with these apps, but have heard good things.

Meditation groups and classes – most cities and many towns have meditation classes. I like the Insight Meditation Community and have attended their classes in Washington, DC and Denver, CO.  Transcendental Meditation, commonly referred to TM, is also extremely popular, but the price point makes it prohibitive for many people (which makes me question their motives). Many yoga studios also offer meditation classes. Shop around until you find the one that’s right for you. Just keep in mind that many meditation teachers don’t actually understand what they’re attempting to teach, so if you get a weird vibe, keep searching.

How to draw the good out of people (and yourself)

Scene 1: My Lyft driver has a 5-star rating. I assume he’s new.

When I get into his car I ask, “How long have you been driving?” He says, “Oh, about six months.”

This blew my mind. To have perfect rating for anything after six months is almost unheard of.

I say, “You must meet a lot of interesting people.”

He replies, “Oh yeah! Everyone I’ve met has been amazing. Either they sit quietly and we enjoy the music together, or they tell me the most interesting stories. There was only one person in six months who I didn’t really like.”

Scene 2: L*, a friend of a friend, is telling me, “Yeah, so I met this girl last weekend. She’s into me, but she’s the type of girl that’s totally disrespectful to everyone. The kind that needs to be put in her place, you know? I texted her, but she ignored my texts. Bitch.”

I stare at him blankly. I always feel uncomfortable when I talk to this guy.

Unbeknownst to L*, I know the exact woman he’s talking about. She’s lovely. She’s bright, playful, and disarmingly funny. It was weird he thought she was a bitch.

A hidden quirk of social behavior

In any given moment, I have the potential to experience a wide array of feelings. I don’t mean this in a spiritual sense; I mean this pretty much literally.

If one of my charismatic and extroverted friends calls, he could convince me that we need to go to the party tonight. In his presence, I would be social, talkative, and playful.

If one of my centered and spiritual friends calls, she could persuade me that attending meditation class tonight is a must. In her presence, I would be calm, focused, and present.

As I’ve mentioned before, the world tends to feel like whatever you focus on. Focus on the potential dangers around you and your anxiety levels spike. Focus on the beauty around you, you’ll fall in love with life.

The same phenomenon applies to human interaction, but the dynamic is more fluid and subtle.

In its most simple form, you tend to draw out the characteristics of people that you expect to see in them. Likewise, people’s expectations of you can (and often do) influence your behavior and attitude.

In other words, if you expect people to be shitty, you’ll notice their shitty parts. If you expect people to be amazing, you’ll notice their amazing parts.

What makes this interesting is that you can elicit different sides of an individual based purely on your expectations of them and how you express those expectations.

And it’s not a coincidence that the Lyft driver feels that his passengers are great people. He expects people to be great. When he interacts with them, he interacts from a place of, “I can’t wait to spend time with this awesome person.” This draws the greatness out of them. Consequently, people like being in his presence. Together, they create a sense of mutual appreciation, respect, and fun.

It’s not bad luck that L* had a negative interaction with the woman he met. He expects people to be terrible. When he interacts with them, he does so from a place of, “Great, here comes another shallow, flakey, idiotic person.” This draws the worst out of people. Consequently, people feel uncomfortable in his presence and do their best to get away from him.

All interactions are co-created

Of course, this brings up a really interesting question: if the Lyft driver were to spend time with L*, how would the interaction play out?  Would the driver succumb to L*’s negativity, or would L* feel uplifted?

It depends. In virtually all interactions, the person with the stronger sense of self will succeed in controlling the frame and vibe of the conversation. In other words, if you’re more committed to making me smile than I am to being pissed off, eventually you will make me smile.

Putting it into practice (or how to manipulate people)

So, how do you actually draw the good out of people and begin shaping their behavior and feelings? Good question.

The first step has nothing to do with the other person. As mentioned, whoever has the stronger sense of self in any given moment is most likely going to control the vibe. This means that the more deeply you fall in love with yourself, the more easily you’ll be able to help others fall in love with themselves.

From there, assume that the people you interact with are great people. Assume that they’re funny, open, insightful, and playful. Assume that spending time with them will improve your day. Assume that their pain and complaints are valid and should be met with warmth and compassion.

You’ll notice that simply assuming the best of people begins to draw the best out of them.

If you want to take it up a notch, try the following:

  • Find something you like about the other person (their bracelet, their smile, their mind, whatever), and tell them that you like it.
  • Ask playful questions and listen carefully to the answers. A few of my favorite questions right now: “Pretend we’re best friends – tell me about what’s actually going on in your life”, “What was the highlight of the past month for you?”, and “What’s the most embarrassing story you’re willing to share? I’ll tell you mine…”
  • Be the first to open up and make yourself vulnerable. You don’t have to share everything or even very much, but by opening up you’ll signal to the other person that she’s worthy of trust and respect.
  • Ask for advice. You don’t actually have to take the advice, but giving someone the chance to help you is a deceptively powerful way of drawing their best selves out.

You’ll notice that the more you create an opportunity for people to be amazing, the more amazing they’ll become. At a deeper level, you’ll notice that the more you improve people’s lives, the more you’ll feel like your life is filled with purpose, charm, and meaning.

Post Script: the cost (and appeal) of leveraging this phenomenon to create misery

Of course, everything that we’ve discussed can also be used in reverse to make people feel like shit.

Quietly assume that the people you’re with are terrible, and you’ll ruin more days than you’d expect. Ask questions or make statements that draw out the worst in people, and they’ll feel crappy in your presence.

Plenty of people intentionally spread negativity. Heck, I’d be lying if I told you that I’ve never gone for the jugular when I was having a bad day.

It comes at a cost. By creating more darkness in the world, you deepen the darkness within yourself. Treating others with disdain, ultimately, is an act of self-loathing.

On finding the strength to get back up

“He not busy being born, is busy dying” – Bob Dylan on “It’s Alright, Ma (I’m Only Bleeding)”

– 1 –

November 9, 2016 it’s midnight or 2am or something: My apartment is lit by flickering candles. Dylan’s album “Bringing It All Back Home” is playing. Though I rarely drink, I’m pouring myself a stiff scotch.

The past 10 days have tested the limits of my resilience. I’m as lonely and afraid as I ever get.

Last Friday, I broke up with a woman I had been with for a few months. It felt like it took everything I had to look her in the eye and tell her that my feelings have changed.

Then someone I love was diagnosed with brain cancer. My hand shook as I picked up the phone to ask, “Did she survive the operation?”

And just now, my country has elected a President who may want to watch the world burn. Getting out of bed the next morning seemed nearly impossible.

– 2 –

All of this? It reminds me of something that we never talk about. It’s simple and universal, but also difficult and frightening. At times, being a human feels hopeless and defeating.

Still, there’s a magic in talking about it. Talking about it connects us. It reminds us that even in our darkest moments, there is something that is worthy of love and light in us. It makes it clear that we’re all in this together, and if we keep fighting, we can create better lives and a better planet.

It reminds us that we are worthy.

– 3 –

Every day, people are tricked into believing that they are unworthy. They bring their dreams to the pyre and light the match themselves. This frees them from some of the pain of existence, but it blunts their vivacity and vision.

These same people used to talk with a feverish energy about social justice, travel, life, death, sex, music, dreams of making a million dollars, art, and love.

Now they talk about TPS reports, Nordstrom Rack, their mortgage, celebrity gossip, and whether or not they can digest gluten.

It’s tempting to write these people off as foolish, naïve, weak, and inauthentic, but that would be cowardly. A very real part of me yearns to be one of these people and feels betrayed by my need for excitement and calculated risk.

A very real part of me worries that all this love will be in vain.

Sometimes I want to lay down my weapons and stop fighting.

– 4 –

And I toy with the idea of giving up.

Maybe I’ll marry the next girl with kind eyes, a nice smile, and a passable reason to love me. Even if we’re not perfect, I’m sure we could figure it out. I think that’s how most people do it anyways.

Maybe I’ll trade my downtown apartment for a sensible home outside the city. Instead of sprinting from CrossFit, to dinner, to wherever my friends are meeting up, I’ll spend my weekends running errands and working on little projects around the house. I’ll be in bed by 11.

Maybe I’ll get a real job. The offers come across my desk often enough. I bet it’s nice to have a 401k match, a boss who makes the hard decisions, and a predictable income.

Maybe I’ll pretend that the world isn’t filled with needless suffering. It wouldn’t take much. All I need to do is get in the habit of averting my eyes and guarding my heart.

Part of me wants to numb myself against the raw exposure of being alive and to throw in the towel.

– 5 –

I can’t bring myself to do it.

A much bigger part of me knows something simple: complacency is the enemy. I am – and always will be – a work in progress.

So are you.

So is our world.

It’s tempting to cling to something that has already passed or to long for something resting in the future. However, in doing so, we subtly deny our ability (and responsibility) to work within this moment.

All we can do is allow ourselves to evolve with as much compassion and authenticity as we can muster.

We must resign to keep fighting the fights we believe in, even when we have nothing left to gain.

– 6 –

It’s hard to admit that I’m not the man I used to be and that we don’t live in the world I thought we did.

– 7 –

When I think about it all, I come to the conclusion that every now and then, the world will break you. It’s not about shielding yourself from the pain; it’s about finding the spark that enables you to pick yourself back up.

It’s about living as vivaciously as you can, even when you feel like there’s no point.

It’s about allowing space for the inevitable evolution of a life and a community.

It’s about being gentle, catching your breath, and surrendering to joy when you can.

It’s about remembering that no matter how bad it seems, love runs much deeper than hate.

Because at the end of the day, the real goal is simply this: live so passionately that when death finally comes, she hesitates for a moment before striking you down.

How to make hard conversations easier (and why I had five in one day)

Aug 28th, 2016: My hand shakes as I start dialing S*’s number. I can’t help but notice the irony. I used to give speeches for thousands of people, and my hand never shook then. Now, calling someone I’ve known for years is making me anxious.

Today is going to be one of the most emotionally demanding days of the year. There are five hard conversations that I’ve been putting off. Today, I’m going to have all of them.

On my agenda:

  • Explain to S* – an extremely close friend – why I’ve been so distant (and in some cases, downright cold) over the past year. I also need to apologize to him for being passive aggressive instead of confronting the issue.
  • Apologize to a family member for being a jerk.
  • Apologize to D* for teasing him wayyyyyy too much at his wedding last year. We haven’t spoken since. I’m ashamed of this one.
  • Tell my coach that even though I committed to a yearlong intensive with him, I’ve changed my mind.  

  • Call P* to tell him that I love him, that I’ve noticed he appears to be considering suicide, and to let him know that I’m here for him.

As I go into this first call with S*, I am unbelievably nervous. I know that the next few hours are going to tear me apart. However, beneath the anxiety, there’s a sense of calm. I know that continuing to put these conversations off is cruel to everyone involved – myself included. Tackling them is an act of love.


It’s easy to put hard conversations off. Heck, I’d been telling myself that I’d call D* for over a year. I thought about it all the time.

Still, I continuously put it off.

Almost everyone I know has pending hard conversations. You need to talk to your lover about the distance growing between you. You want to set clear boundaries with your sister. You have to tell your friend that it hurts when he doesn’t return your texts. You want to ask your boss for a raise.

By putting off hard conversations, you’re betraying yourself and the person you need to speak to. In doing so, you’re blunting the overall quality of both lives.

My aim in this article is to make having hard conversations easier. We’ll cover why you should stop putting them off, how to prepare for them, how to choose a medium, how to approach them in different ways, and how to be kind to yourself throughout the process. We’ll also discuss what to do when you just can’t bring yourself to start the conversation.

Why you should tackle the hard convos sooner rather than later

1) When I finished the conversations, I felt lighter and happier than I had in a long time. In the following days, I noticed that I was consistently more focused, playful, and creative.

If you lean into the conversations you’ve been avoiding, you can expect similar results.

2) Avoiding these conversations is putting you in pain. In most cases, you’re also hurting the other person. Usually the other person can feel a quiet thread of resentment coming from you, even if they can’t pinpoint its cause.

Even if they’re living under the illusion that everything is fine between you, you’re shielding them from reality and preventing both of you from living to the fullest.

You’re also signaling to yourself that your needs are unimportant and that you’re best off pretending to be someone you aren’t. The more you tell yourself that you’re unworthy, the more unworthy you’ll feel.

3) There will never be a perfect moment in the future (but now is good enough). We tell ourselves that we can’t have the hard conversation now because the kids are home from school, we have a trip coming up, he’s in a bad mood, etc. Those are all excuses designed to mask a simple truth: you’re afraid.

It’s reasonable to fear having a hard conversation, but it’s unreasonable to let that fear rule you. Realize that there will never be a perfect moment for a hard conversation. Instead of perpetually making excuses, accept the reality that the sooner you have it, the better off everyone will be.

Picking a medium

In general, it’s best to speak in person. However, in person communication comes with serious barriers.

First, if the person doesn’t live near you, you’re going to have to wait until you see one another.

Second, in-person communication requires huge amounts of courage. If you can summon the courage, terrific. If you can’t, don’t worry. There are other avenues available to you, and it’s always better to say what you need to say, than continually put it off. A few alternative avenues:

Write a letter and then read it to the person – one approach to making in-person conversations easier is by writing a letter to the person you need to speak to and then reading it aloud to them. Since this technique allows you to get the wording right while also fostering face-to-face communication, it is an extremely effective approach.

Phone call/skype – as the second best option, it offers a lot of the same advantages of an in person conversation without the need to actually be in the same room.

A recorded message – using your phone, webcam, or an app like Soundcloud, record a personal message and send it to the person you need to talk to. Recordings capture a lot of the non-verbals that are difficult to express in writing. However, recordings make it difficult to have a two-way conversation. If you begin the conversation with a recording understand that at some point you may need to switch to a more interactive medium.

Email – with an email, you can take the time to get your wording exactly right. It’s also easier to send an email than make a call. However, emails tend to feel impersonal, and unless you’re a talented writer, you may end up coming off as cold when you don’t intend to. I wouldn’t recommend having a hard conversation over email, but if this is the only option that feels doable, go for it. Consider sending the email during the evening or weekend, so that the recipient doesn’t have to deal with personal issues during work.

Text message – I’ve literally never seen this go well and strongly discourage you from using texts. In addition to being extremely impersonal, it’s also such a noisy medium that focusing on an important conversation is borderline impossible. It also favors short form communication, which is likely to be counterproductive.


In my case, none of the people I needed to speak to live near me, and I wasn’t willing to put the conversations off any longer. Since face-to-face wasn’t an option, I ended up recording two messages and calling everyone else.

Looking back, it would have been better to personally place calls to everyone, but I didn’t have enough courage. Instead of pushing myself beyond my limits or failing to communicate, I decided to live in the cross section of being compassionate to myself while also getting the job done.


The biggest mistake people make about hard conversations is failing to have them. The second biggest mistake is failing to prepare for them.

Before you begin, give yourself space to figure out exactly what you want to say and how you want to say it. Here are a few guidelines:

Begin by journaling about your situation. Write down all of your thoughts and feelings. Be as candid and honest with yourself as possible. Don’t worry, you won’t have to read any of this stuff to anyone. The point is for you to understand yourself and the situation.

I had a big blind spot when it came to my relationship with S*. At first, I felt that he was just a jerk and that I no longer wanted to be his friend. When I took the time to ask myself, “Well, why do I feel like he’s a jerk?” I realized something I had been missing: S* is a really good guy and a very loving friend. However, there were a few times when I needed him to be there for me, and he wasn’t. I also never told him that his failure to show up for me hurt. I was letting a few isolated incidents ruin our relationship.

By taking the time to reflect on the situation, I was able to figure out what the real problem was and how to talk about it.

Use I-statements instead of accusations. An I-statement is an honest declaration of feelings. An accusation is a statement about the other person (often implying intent on their part). I-statements are much more effective.

An easy formula: “I feel like X when you do Y.” If you’d like to make it softer, you can add, “And I imagine that’s not your intent.”

Let’s say that you feel like your parents belittle you by telling you how to do your job.

If you’re using an I-statement to express your pain, you would say, “I feel like you don’t respect me when you tell me how to do my job.”

If you’re accusing them, you would say, “You don’t respect me or my work.”

The difference is both subtle and important. I-statements create space for both people to express themselves. Accusations make the person feel attacked, leaving little room for meaningful conversation.

In my conversation with S*, I said, “I want to do two things. First, I want to apologize. I’ve been distant and aloof in our relationship, and that’s really unfair to you. I’m sorry. Second, I want to explain why I was behaving that way. There have been a few times when I asked for your support, and it felt like you weren’t there for me. That hurt, though I doubt that was your intent. Moving forward, I’ll do my best to make it clear when I really need your attention, and I’d love it if you were willing to give it to me quickly.”

One thing to keep in mind about I-statements is that getting them right requires work. It’s much easier to make accusations than it is to speak your truth.

Practice the conversation before you have it. This may sound absurd, but I literally rehearsed the conversations ahead of time. Some of them I even practiced more than once. I also mentally and emotionally prepared myself to stay open to responses and questions.

While it may sound silly to practice a conversation, think about it: you’re going into a situation where you’re going to feel vulnerable. Might as well take a few moments to practice before you begin. This will make the conversation go more smoothly.

Doing it

The moments leading up to the conversation are often much more difficult than the conversations themselves. My hand was literally shaking as I made my first phone call. Despite my nerves, four of the five conversations went exceptionally well.

S* and I are now closer than ever. My coach was disappointed that I won’t be attending his program, but we’re still cool. In fact, he invited me over for dinner. My family member accepted my apology. My friend who was struggling with his mental health sincerely appreciated the love and concern.

However D*, the guy I teased at his wedding, didn’t respond to my message. I saw that he listened to the recording I made for him a few times, but he never called or emailed me. I’ve likely lost him as a friend. Had I offered an apology more quickly maybe we’d still be friends today.

Do I regret sending the message to D* even though nothing came of it? No. Not at all. I’m glad he knows how I feel. I’m also glad to have that burden off my shoulders.

As you gear up for difficult conversations, think of them as a roller coaster: climbing up the track is much more terrifying than going down the hill. Going up, you’re filled with dread. Going down, you’re purely in the moment – there’s no room for dread or fear.

If you’re like me and need to have multiple hard conversations, it’s up to you whether you spread them out or do them all at once. Personally, I’m the type of guy who prefers to rip the bandage off instead of slowly removing it, so I did mine all at once.

Regardless, realize that these conversations almost always go better than expected and that everyone benefits by having them sooner rather than later.

Finally, be gentle with yourself

It’s easy to beat yourself up thinking, “Why was I such a jerk in the first place?” or “I suck for not having addressed this years ago.”

To the best of your ability release yourself from the guilt. You’re human. You’re allowed to make mistakes. It’s no big deal.

In fact, there’s a good chance that both parties have made mistakes. Everyone will be better for working through the tension and laying bad blood to rest.

Though the conversations are difficult, they are true acts of love. You deserve to feel good about them.

Post script: what to do when you just can’t bring yourself to say it…

Sometimes the conversations we need to have are so frightening that we just can’t bring ourselves to spit the words out. That’s ok. Again, be gentle with yourself. There’s another approach; this technique is slower, but far better than nothing.

Begin by admitting that in avoiding hard conversations, you’re lying (through omission and inaction) to the people you need to talk to.

Once you understand that you’ve been failing to show up authentically, your job is to slowly increase how genuine you are with others. In other words, when you have an opportunity to be honest about your experience, take it.

Let’s say you’ve been in a three-year relationship and you’re starting to drift. You no longer feel as close as you used to, but you aren’t able to talk about it just yet.

You realize that part of the reason you feel distance is because you haven’t been as forthright as you could be. In cases like this, you can use small events as springboards to improve your communication.

Let’s say that you’ve wanted to do standup comedy, but you’ve never mentioned it to your partner. One day, you spontaneously sign up for an open mic, and your boyfriend responds by saying, “I feel like I don’t even know you. I had no idea you wanted to do standup.”

If communication is already strained, your natural reaction will be to shrug the comment off, saying, “Yeah, I guess I never mentioned it before. I’m excited.” And in fact, in the moment, you’ll probably do this. No big deal.

After you notice that you failed to fully share yourself, revisit the conversation (even if it’s a day or two later).

Follow up by saying, “Hey, I wanted to share a bit more about the standup with you. First, I’m sorry I that never mentioned the desire to get into standup to you. I kind of failed to fully share myself there. Sorry. Let me fix that now… I’ve actually wanted to be a comedian for a long time, but I’ve always been afraid of actually chasing that dream.

Something about standing on stage and making people laugh really excites me. But it also scares me. I’ve never mentioned it because I was afraid. I was afraid… I don’t know… that you’d push me to chase the dream before I’m ready or that you’d dismiss it as silly. Chances are you’d do neither of those things, and I really wasn’t being fair to you. Sorry about that. I’ll do my best to be more forthright in the future.”

If you do this once, the results will be fairly trivial. However, if you get in the habit of being increasingly honest with the people you need to talk to, you’ll notice that some of the hard conversations occur spontaneously. Those that don’t will be easier to engage in because you’ve built more rapport and skill. You’ll be surprised by how smoothly many of them go.