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.

What to do when the world grows dark


April 6th, 2016: Just yesterday S* asked me how I was doing, and I honestly answered, “You know, it feels like everything I touch is turning to gold right now. It’s amazing.”

But today, the world feels dark. Really dark. I want to get out of bed and at least try to make something of myself, but I can’t. Whatever it is that normally draws me into the world is nowhere to found. Not even a glimmer.

Life feels monotonous, bland, uninspired, and pointless. If I’m being honest, I kind of hate myself, and I think I’m a jackass who’ll never amount to anything much.

Though I had plans to write, take meetings, and go out in the evening, I am spending the day in bed, eating cherry pop-tarts, watching Netflix, and feeling like shit.

When I wake up the next morning, I feel a bit better. Not great, but better. By the end of the following day, I’m glad to be alive again. I even feel playful.


Every now and then, the world caves in on me. Temporarily, I feel miserable. More than that, I feel like I’ll never be able to get back to the place where I love myself and my life again.  

When this happens, I’m always tempted to think that I’m broken, flawed, or messed up. But almost everyone I know goes through periods of intense darkness or depression. As far as I can tell, my friends and clients who have the courage to live boldly, vivaciously, and creatively are more susceptible to darkness than those who stayed on the beaten path.  

So let’s start there: if you periodically feel depressed, there is nothing wrong with you. You’re not broken; you don’t need to be fixed. In fact, I would argue that it’s a sign of truly being alive. The only people I know who don’t deal with depressed periods are those who have avoided pain so much that they end up behaving more like robots than humans. They’ve chosen (perhaps unconsciously) to numb themselves. By avoiding pain, they’re also avoiding the full human experience and failing to dwell in reality. To numb yourself is to move through life with muted feelings.

Short intense bursts of depression are normal parts of the human experience and can offer deep insights. They may not seem normal, because most people suffer in silence, which leaves everyone feeling like they are alone.

It also doesn’t help that many mental health “experts” imply that perpetual happiness is possible. It’s not.  

The good news is that when the world grows dark, there are reliable ways to step back into the light. More than that, there are tools you can use to help you transform the darkness into something meaningful.

First, let the darkness in

Many people feel guilty for feeling bad. They think, “I’ve got food, a job, and friends. I shouldn’t feel like this. This isn’t ok. I should feel grateful for what I have.”1

This mindset signals to yourself that your naked feelings aren’t valid. The truth is much more simple: your feelings are valid, even if they don’t make sense or seem unwarranted. Telling yourself otherwise creates distance between yourself and your reality, which is counterproductive.  

Another common reaction to feeling bad is trying to reframe your feelings into something positive. An example from a conversation I had a few weeks ago:

Me: “It hurts that S* only returns my calls when there’s something in it for him. We used to be such close friends. It took me years to notice that the relationship has become toxic, and now that I see it for what it is, I’m wrecked and embarrassed.”

C*: “Dude, don’t feel bad about that. S* treats everyone that way, and I’m sure he’d be there for you if you really needed it. Besides, you’re a well loved guy. People adore you; focus on that.”

While C*’s approach to dealing with difficult feelings is common, it’s also misguided. Attempting to reframe your feelings about a situation is the same as saying to yourself, “How I feel is somehow wrong.” Once again, that’s a bad idea and a form of self-denial.

Feeling guilty for feeling bad and reframing your feelings builds walls around your heart.  While those walls are comforting in the moment, they come at the cost of divorcing you from your truth.

Instead of these mindsets, try something far bolder and more courageous: let the darkness in.

Feel the full force of your emotions and reality pressing down on you.

Succumbing to the darkness provides several counterintuitive benefits:

  • It proves to yourself that you can handle the adversity. It forces you to confront the reality that you are stronger than the darkness within. When that reality clicks, you gain deep insight into yourself and your power.
  • If you are meant to learn something from this bout of depression2, it will create space for you to gain clarity.
  • It will begin the process of cleansing your system of the negative feelings.

Instead of fighting your feelings (which only exacerbates them), surrender.

Next, create space for the light

After letting the darkness in, the next step is to release the demons that are causing emotional chaos. During this process, you usually begin to feel relief.

The following five approaches are the ones that I find most effective. More importantly, they’ve generated positive results for the friends and clients I’ve shared them with. You don’t need to use all five; just experiment until you find the strategy that works best for you.

1) The “fuck you” game (warning: lots and lots of f-bombs coming up, even for me). This is my favorite technique and one that I use even when I’m feeling great. Start by going someplace private. Then say, “Fuck you” out loud to everything that you want to say “Fuck you” to.  This can be to a person, a situation, an object, whatever.

The exercise looks something like this:

  • “Fuck Walter for making me feel like an asshole”
  • “Fuck money for being so captivating, so hard to come by, and so unfulfilling all at once”
  • “Fuck being single when all of my friends are married”
  • “Fuck my friends.”
  • “Fuck trying to lose weight”
  • “Fuck donuts”
  • “Fuck CrossFit”
  • “Fuck Kanye”
  • …etc.

It doesn’t matter if you fully believe everything you say. It doesn’t matter if you’re hypocritical or inappropriate (if you need to tell puppies to go fuck themselves, do it). What matters is that you suspend judgment long enough to release the pent up tension. This may take three minutes, or three hours. You’ll notice that after this exercise you feel much, much lighter and more playful.

2) Stop pretending to be strong, and be weak already. Most of us – especially men – move through the world pretending to be stronger than we are. This is another form of self-denial. Instead of pretending to be strong, allow yourself to finally be weak. Collapse. Break. Cry. Sob. Allowing yourself to be weak will help clear out whatever you’ve been holding onto that’s bringing you down.

3) Talk to yourself. Depression shrouds you in dark illusions about yourself and the world. It creates a fog that distorts your truth. One way to cut through the fog is to ground yourself in reality. You can do this by talking to yourself out loud.

Yes, talking to yourself is kind of insane. That’s ok. It will help you conquer the darkness. While it’s tempting to just think about this stuff, it’s important that you put your feelings into words. Taking the time to name and identify ongoing issues crystallizes the situation and removes the fog.

Start by asking yourself, “What’s wrong?” and then answer yourself, stream of consciousness style. Resist the urge to judge your monologue. Instead, be curious. Try to understand yourself. Be gentle if what you’re saying makes no sense or seems petty.

Your dialogue might begin by being mundane or walled off. That’s fine. Use curiosity and persistence to press through. An abbreviated example:

You: “I feel crappy today. Really crappy.”
You: “Yeah, I noticed. Why do you feel that way?”
You: “I have no idea. I think I’m just messed up.”
You: “Yeah, but take a guess about what’s going on. It’s fine if you’re wrong.”
You: “Well, I mean, I’m not thrilled that I still have this shitty job; I wish I could find the courage to quit.”
You: “You’re not thrilled? That’s a pretty big understatement…”
You: “Ok. I’m wrecked. I hate that every single day I wake up and know that 9 hours of my time are going to be dominated by some stupid boss at a stupid company that I neither like nor respect. Worse still, I’m too cowardly to quit.”
You: “Is there anything you can do about that?
You: “No.”
You: “Well, ok, but give me an idea, even if it’s a crappy one…”

And so on.

If it becomes clear that a certain person (or people) are causing dark feelings in you, talk through that too. For example:

You: “And I hate that Jessica is so aloof about our relationship.”
You: “What would you tell her?”
You: “I’d start by saying that I’m insanely – almost unfairly – attracted to her, but the way she ignores even my most basic emotional needs makes me feel really small…”

Many people suggest talking to loved ones when you’re depressed. This is excellent advice, and you should take it. Feeling the warmth of people you love will help you get back to your reality, but you should still talk to yourself. Even the most open people wear masks. To conquer bouts of depression, you need to take the mask off for a bit, and it’s generally easier to do this when you’re alone.

4) Rage! If you’re in touch with your body, then this strategy will be fun. Use physicality to clear your system of bad energy by throwing an adult version of a temper tantrum. Down a Redbull, blast some metal, and bounce off the walls. Beat the shit out of your pillows. Scream. Jump with all your force. Break plates on the ground. Throw mugs at the wall. Get one of those foam bats and whale on your couch.

5) Temporarily hold yourself to really, really low standards. We’ve already discussed how counterproductive it is to fight against your feelings. A much more effective strategy is to surrender to them. Spend the day in bed eating Pop-Tarts and watching Netflix. Let the clouds pass.

This is especially effective when combined with one or more of the strategies above. The combination of rest and release is often exactly what you need.

If you live with other people, let them know that you’re feeling down. You can also let them know that you’d like to be left alone.

As to which technique you should use – there’s no right or wrong here. Go with the ones that you’re drawn to. Different situations and feelings call for different techniques.

Take time to spot-check the basics

When working to improve mental health, it’s tempting to search for complicated and flashy solutions. You look for repressed childhood memories, subtle ways you’re sabotaging yourself, emotional vampires flying under the radar, and obscure micronutrient deficiencies.  All of those things are important, but they’re not starting spots.

Instead, use this period of darkness as a reminder to spot-check the basics. Are you exercising? Are you hanging out with people you love? Are you sleeping enough? How’s your diet? If you’re neglecting any of these areas, then start paying attention to them. They are disproportionately important for your mental health. You don’t need to make huge sweeping changes to your life. Just go for a brisk walk, write an email to a friend, take a nap, eat a salad, whatever.

Remember: this too shall pass

The hardest part about short bursts of depression is that it feels like they will last forever, but I promise that the dark spells pass.  You’ve experienced this before, and you’ve come out on the other side every single time.

One of your truths (though you may have forgotten it) is that you’ve been able to handle everything – literally everything – that life has thrown at you. This period of depression and darkness is no exception. The clouds will burn off.

Postscript 1: but what if the darkness doesn’t pass?

One of the most fucked up things we’ve done as a society is creating a stigma around mental health.

If your friend fell and broke her arm, you wouldn’t waste a second before telling her to go see a doctor.

Yet telling her that she should talk to someone to help her deal with her depression is a much more delicate conversation and one that generally doesn’t happen.

Admitting to yourself that you need help can be even harder.

So let me make this simple: everyone can benefit from a great psychologist. I mean literally everyone. You are not the exception to this rule (and of course, neither am I).

But even more to the point: if you’ve been feeling depressed for more than a few days or if your bouts of intense depression occur more than two or three times a year, please talk to someone. Being a human is difficult enough as is. There is no need to deal with additional suffering.

Yes, admitting that you need help is uncomfortable. Yes, you may not feel like you can afford it. Yeah, I know; you’re busy and don’t have the time. Yes, a lot of psychologists are idiots who aren’t smart enough to treat you.

I don’t care about any of that stuff. What I care about is you treating yourself well and getting the help you deserve. I promise you’ll be glad you did. By taking good care of yourself, you’ll create a better life for you. You’ll also be contributing to the creation of a world where mental health problems don’t come with the stigma.

Postscript 2: suicide

7:02pm, February 10th, 2011: I’ve just finished the final rehearsal for an upcoming speaking tour. The phone rings. It’s C*.

Me: “Hey, man! How’s it going?”
C*: “I’ve got some bad news… Remember M*?”
Me: “Yeah…”
C*: “He’s dead…. He killed himself…. I confirmed it with his mother. They found him in his apartment. The note said he had been depressed for a long time, and it was no one’s fault. I’m so sorry…”


I knew M* well. He, C*, and I hung out every day during senior year of high school.

Though some may consider suicide selfish, I don’t buy it.  I suspect that M* felt like he was being selfless when he killed himself.  I imagine that in M*’s darkest moments, he felt that asking for help was too much of a burden to place on someone he loved. I imagine he felt so deeply broken that professional help would just be an exercise in futility. Though he would have been wrong on both counts, the illusion of being hopeless was overpowering.

Looking back, I wish I called him more. Just to say, “Hi,” to ask how he’s doing, to laugh about the time he and C* went “Ultimate Hiking.”

And I wish he called me. It wouldn’t have been a burden at all. I would have been honored by his trust and vulnerability. I know C* feels the same way.

Life gets painful. Happiness, meaning, connection, and love can be elusive. There are days when the world grows impossibly dark; the idea of waking up and dealing with 60 more years feels unbearable. These are the times when suicide seems like a viable option.

If you start to feel this way, here is what I want you to do: search for the slightest flicker of light amidst the pure darkness. Something imperceptibly small – even trivial – will do. Perhaps it’s the memory of a pet, a nice thing someone once said to you, or the dream of living with less pain in the future.

Now use that glimmer of light and hope to pick up the phone and call a suicide hotline. If you’re in the United States, call: 1-800-784-2433. If you’re outside the US, google “Suicide hotline [your country],” and call the number. Someone will be able help you. You’ll be glad you called and so will be the people who love you.

From there, work with a professional to conquer the depression. Yes, the world and its people can suck. Yes, there are times when it feels like being alive isn’t worth it. Yes, the path forward may be a turbulent one. Despite all this, it can get better, and you’re not alone. I promise.


You’re not broken: the hidden dangers of personal development

January 2013: D* and I are eating breakfast and talking about the year ahead. Since my speaking business is doing well (finally), I’ve spent a lot of time thinking about who I want to become as a man.

I tell D*, “I want to be one part Richard Branson, one part Thich Nhat Hanh,1 and one part Greg Gillis.2 That would be awesome.”

D* looks at me, pauses, and says, “What’s wrong with being Jason Connell?”

I was speechless…

Looking back, I realize why I couldn’t answer D*’s question. My obsession with trying to improve myself left me feeling like Jason Connell wasn’t good enough.


Personal development is a funny thing. When done well, it’s beautiful. “The Inner Game of Tennis” taught me how to control my mind. “Love Yourself Like Your Life Depends on It” made me realize that I need to pay attention to my relationship to myself. BraveSoul, a retreat I attended, helped me connect to my intuition.

But the industry is victim to a catch-22.  If a coach, seminar, or book can create lasting results quickly, it’s bad for business because the customer will have no further need for personal development products. In other words, a customer who believes he or she is flawed, unworthy, or unready spends more money than those who believe they are fine.  Unfortunately, it is in the business’s best interest to nudge people into believing that they are missing something, even when they aren’t.

That’s exactly what happened to me. I got so involved in personal development, that I lost track of two simple and very empowering truths:

  1. Happiness only exists in the moment. It does not (and cannot) exist in the future.3
  2. I already have everything I need to achieve whatever I authentically desire. So do you.

All that remains is learning how to access your innate happiness and ability to create. The first step is to become aware of the hidden dangers of self-improvement. This will allow you to avoid the traps I fell into, while also speeding up your results.

Danger #1: the gross exaggeration of your flaws

Have you ever noticed that the world looks like whatever you focus on? For example, if you focus on crime, automobile accidents, and the negative aspects of society, the world is going to seem like a dark place.

However, if you focus on compassion, the natural abundance all around you, and good times with friends, the world will look like an amazing place.

The same thing happens with what you notice about yourself. If you notice what’s great about you, you’ll feel great. If you notice what sucks about you, you’ll feel crappy.

Marketing, advertising, and pop-culture all trick you into believing you are far more flawed than you truly are.4 Unfortunately, personal development does too. When combined, these aspects dramatically exaggerate your perception of your flaws.

The fix: reconnect to your truth

I have a secret for you: there is nothing wrong with you. You are not messed up, you don’t need to be fixed, and your haters really are assholes.

I have another secret for you: you already have everything you need to begin turning your dreams into reality. You can prove this to yourself by simply taking the first step and seeing what happens. Along the way, you’ll notice something surreal: the barriers to success that seemed so daunting were nothing more than figments of your imagination.

There are many forces trying to persuade you that you’re flawed, unready, or unworthy. Some are so compelling that they may have even convinced you. They’re wrong. The truth is, you are ready.

Danger #2: an obsession with the future

Personal development encourages you to sacrifice the present in exchange for a better future.

A few examples:

  • Entrepreneurs sacrifice sleep, sanity, and health in order to build their businesses.
  • Students pull caffeine-fueled all-nighters to get better grades.
  • People of all ages obsess over their diet and exercise in order to create good looking physiques.

This shouldn’t be an attractive offer, but  if you’re already focused on your flaws, then you’re not enjoying the moment anyways, which makes the offer much more appealing.

To further complicate the problem, the end goals obscure the reason you’re trying to improve your life in the first place. It’s not really the thriving business, GPA, or hot body you’re chasing. It’s the feeling that you expect the business, GPA, or body to create. In most cases, the feeling you’re chasing is happiness or one of its cousins (love, connection, stability,  respect, etc).

This presents a paradox. Personal development tells you that the reward for your effort, happiness, rests in the future.  However, happiness can only be found in the moment. These two ideas create a strong tension that bars many from accessing their innate happiness and ability to succeed.

Fortunately, there’s a way to resolve the tension…

The solution: coffee, chocolate croissants, and Netflix

When you ignore the present moment for long enough, you adapt by putting yourself into a low-grade trance. This trance leads to apathy and listlessness.5

If you’ve been involved with personal development for a while, there’s a good chance you’ve become entranced by the future. It’s time to come back to the present.

Start by spending a day delighting in the simple pleasures of life.

For me, this includes black coffee (and then regretting it later because I’m sensitive to caffeine), chocolate croissants, and Jessica Jones on Netflix. It also includes sailing, checking out used bookstores, and listening to music in the dark.

Many people have become so future-oriented that they’ve forgotten how to create joy for themselves. A few easy sources are:

  • Warm chocolate chip cookies
  • Puppies (if you don’t have your own, visit an animal shelter)
  • Massages
  • Concerts
  • Comedy shows
  • Pizza
  • Fiction (I’ve been loving “Snow Crash”)
  • Nerf guns

Don’t overthink it. As long as you enjoy the activity, you’re doing it right. A few tips to make this easier and more fun:

  • Call in sick from work. Yes, you could save the fun for the weekend, but it’s even better when you should be working. Additionally, calling in sick is a simple reminder that you are more important than your job.
  • Loosen the reigns and indulge. For example, if you’re dairy free but you absolutely love cheese pizza, order a cheese pizza.
  • Spend time away from  phones, computers, and tablets since they tend to interfere with enjoying the moment.
  • Avoid feeling guilty. If spending an entire day enjoying life makes you feel like you’re doing something wrong, say to yourself, “It’s my job is to enjoy the day. I can go back to worrying about the future tomorrow.”
  • Realize that things have a way of working out. One of the main reasons people obsess over the future is that they’re afraid of what it may hold. The truth is, you’ll be fine. You’ve been able to handle everything that life’s thrown at you thus far, and that’s not about to change.
  • If you’re on the fence about spending an entire day having fun, let me make this easy for you: you totally deserve it. Beyond that, orienting yourself in the moment will improve your effectiveness across all areas of your life.

Pausing to enjoy life reminds you that you have the ability to be happy in this exact moment.

After you’ve spent a full day reconnecting to the present, begin adding little moments of joy into your daily life.

The hard work…

As far as personal development goes, my suggestion is simple: let your emotions guide you. If you’re enjoying the process and it seems like it’s speeding up your success, that’s perfect. Otherwise, you’re probably on the wrong track. You don’t need any additional feedback or information beyond your direct experience.

When you feel as though you’re living for the future, slow down and do something you enjoy to draw yourself back into the present. When you’re feeling as though you’re too flawed for your dreams, challenge that assumption by taking action. Things will work out just fine.

The hard work rests in surrendering to the moment and accepting that you are ready to begin. As you do, you’ll be surprised by how naturally success and happiness flows to you. And if you happen to stumble or fall, dust yourself off, grab a chocolate croissant, and begin again.

How I transformed my life: a guide to personal reinvention

Spring 2015: For nearly a year, I’ve had this nagging feeling that something important is missing from my life. I run through the mental checklist:

  • Business? Running well.
  • Friends? I see them often enough. Those far away I talk to and email.
  • Love life? I have an amazing girlfriend.
  • Physical health? Check.
  • Mental health? There is something nagging at me…
  • City I live in? Eh, I don’t care for it it.

For the life of me, I can’t figure out what’s wrong. I just know that something is…


Looking back, it’s funny how much I was deluding myself. A more accurate version of the checklist above:

  • Business? My heart’s not in it.
  • Friends? I don’t see them nearly often enough.
  • Love life? The woman I was dating at the time was amazing, but we weren’t right for each other.
  • Physical health? Check.
  • Mental health? I should have been paying wayyyy more attention to that quiet nagging feeling (and you should too…).
  • City I live in? I hate this town.

What strikes me is just how out of alignment I was with myself.

From May 5th 2015 – May 5th, 2016, I went on a mission to realign myself with my truth. Doing this was not easy. Personally, it required ending a serious relationship, selling my stuff and leaving Washington, DC. Professionally, it required walking away from a thriving speaking business that I spent the better part of a decade building.

Before I began this process, I felt like I was just going through the motions. In fact, feeling subdued had become normal for me.

As I started reinventing myself, I began to feel alive again. The process was hard. A lot of the time it felt like a free fall. In any given week, I would feel on top of the world one day and dejected the next.

Today, I feel more like myself than I have in ages. Friends comment that I sound happier and more at ease. Things that I had to work for in the past come easily now.

Is my life perfect? Of course not. But it’s  better than it’s ever been (by far), and this is the direct result of finding the courage to reinvent myself.

What follows is my personal account of reinvention, as well guidelines for those who want to reinvent or recalibrate themselves as well.


Create an inflection point

Reinvention - inflection point

May 5th, 2015, Washington, DC. on the roof of N*’s car, watching the planes land. N* looks at me and asks, “So where are you at with our relationship?”

I’m not ready for this. I know we need to break up, but I want just one more month with her. Or at least another week. She’s amazing. I’m not sure I’ll ever find another woman like her.

I’m almost shaking as I open my mouth. I don’t want this to be real…

I take a deep breath. I tell her I don’t see this working out long term. She tells me she hasn’t been happy either, and suddenly, that’s it…


Let me guess: you’ve been wanting to change your life for a little while now.  You’ve read a few self-help books and told your friends about your bold plans. Maybe you’ve even taken a bit of action.

For some reason though, you’re still spinning your wheels.

Been there.

If you really want to change your life (as opposed to just talking about it), you need an inflection point.

An inflection point is a bright line that makes change inevitable. All you have to do is jump over it.

There are two types of inflection points: the ones you create, and the ones inflicted upon you. Each requires a different approach in order to be effective.

If you’re creating an inflection point, burn your ships:1  There was a lot in my life that needed to be recalibrated: my relationship, my city, and my work.

Changing all of those things at once was so intimidating that it felt impossible. In fact, on May 6th (one day after the breakup), I wrote to my friends, “Most of me feels as though I’ll have to live off the financial and emotional goodwill of my parents or friends or something… I hate that changing my business, my city, and my relationship are all things that I’ll have to do more or less at once. I wish I could do them one at a time, but that’s not really the hand I’ve been dealt.”

After N* and I broke up, I knew I needed to take life by the reigns. I was also afraid to make so many significant changes at once.  To ensure that I actually took action, I informed my landlord that in six weeks, I would be breaking my lease. Without an apartment, I would have to leave Washington, DC, which was something I’d been yearning to do (and putting off) for over a year.

If you need to create an inflection point in your life, here are a few ways to do it (just make sure that you’re leaving something that doesn’t work for you):

  • Ending a long-term relationship
  • Quitting your job
  • Starting a business
  • Embarking on extended travel, especially with a one way ticket
  • Getting professional help for persistent mental or physical health problems
  • Moving from somewhere you don’t like
  • Investing a large sum of money into yourself to help you become the person you want to be (going back to school, doing a personal development retreat, hiring a personal trainer, etc.)

If you’re struggling to create an inflection point, then you’re probably avoiding a lot of pain that you really should be feeling. Feel the pain you’ve been hiding from and let it inspire you to take control of your life.

If you’ve had an inflection point inflicted on you, use the inertia to change your life: Some events are so dramatic, that they will automatically create an inflection point. A few examples:

  • Being broken up with by an intimate partner
  • Getting fired from your job
  • Losing someone you love dearly
  • Surviving a serious injury or a near death experience
  • Coming into a lot of money
  • Losing a lot of money

If you’ve just experienced one of these things and you feel like you need to make sweeping changes to your life, now is the time to do it. Use the energy from the inflection point to fire you forward. Consider asking a friend to hold you accountable and to check in with you for the first month or two as you begin to make changes to your life.


Trim the fat

June 30th, 2015, my last day in Washington, DC: It’s surreal. Everything I own fits easily into a rented Jeep.

I grab a coffee and walk around the neighborhood to say goodbye. Then, I hop in the Jeep. As I drive away, my entire system floods with energy and emotion.

It’s taken more courage than I thought I had, but I’m starting to feel like myself again. It’s been… lets just say it’s been a long time.


One of the most common ways that people lose touch with themselves is by filling their lives to the brim.  

As you reinvent yourself, you need as much space in your life as possible. This means getting rid of the junk that’s not serving you. Be ruthless as you eliminate things from your life. A few areas to look at:

  • Relationships: do you get psyched to spend time with the people in your life? If not, spend much, much less time with them. It’s better to be lonely, than to roll with people who make you feel small or mediocre.
  • Professional organizations: are they actively improving your professional life? If not, leave.
  • Volunteer organizations: are you still enthusiastic about the cause and the organization? If not, resign.
  • Possessions: the things you own, own you. If your house, apartment, or office is cluttered, your life is cluttered. Get rid of the things you haven’t used in the past year (better yet, the past six months).
  • Extracurriculars: rec sports teams, clubs, classes, professional commitments beyond the scope of your contract, etc.  If it’s not making your life better, kill it.
  • Habits: if you have habits that work against your happiness, it’s time to ditch them. Common examples include mindless Internet surfing, watching more than 60 minutes of TV/day, shopping for the sake of shopping, eating unhealthy food.
  • Work: if you hate your job, it’s time to quit. Go on a financial fast and save enough so that you can get by for three months, then quit. Do this even if you don’t have another job lined up. If you’ve been spinning your wheels, there’s a good chance you need to quit before you get a better job. You can always pickup part time work at a coffee shop or drive for a ride share service.

It’s common to wait for perfect circumstances before you start changing your life. Here’s the thing: it doesn’t work that way. You cannot reinvent yourself by waiting around for some fictional deus ex machina to set everything up for you. You must begin by clearing out the shit. When you do this, you’ll create time, energy, and space to for the new you.

Here’s what I had to clear from my life:

  • Washington, DC, where I had lived for six years
  • Most of my possessions
  • Commitments to non-profits I was no longer aligned with
  • Speaking engagements
  • People who brought me down
  • Reddit
  • Conferences and organizations (including a few elite ones I was lucky to get into) that were not worth my time or effort


Start by addressing the real issues

July 2015, Ireland: I can’t stop crying. For the longest time, I’ve been telling myself (and everyone else) that I had a dream childhood.  I claimed that I felt blessed to have been a successful child entertainer. I thought that it laid the foundation of my current success.

Now, for the first time ever, I’ve admitted the truth: I hated being a child entertainer. Not only that, but it fucked me up.

Though I’m sobbing, I’ve never felt so free.


Let me be blunt: if you’re in a situation where you feel the need to make dramatic changes to your life, there is an underlying issue that needs to be addressed. The problem isn’t that you need to change your life; it’s that you have accepted a mediocre life for so long.

Something happened in your past that has tricked you into believing that you aren’t worthy of an amazing life. That same thing is making it hard for you to create the life you deserve. Use this period of recalibration to work with a professional and heal the wounds that are holding you back.

As much as I love self-help, there is nothing that compares to working with a professional. By professional, I mean any of the following, a:

  • Coach
  • Psychologist
  • Psychiatrist
  • Mentor

Personally, I went on a week-long retreat in Ireland led by a coach I trust and admire. Looking back, a good psychologist would have done the trick too.

Emotional wounds do not heal themselves; they grow old and sabotage you along the way.  These wounds need to be healed, and now is the perfect time to deal with them.

You can skip this step, but I hope you don’t. You deserve amazing mental health. By giving yourself the love and attention that you need now, you’ll be setting your future self up for even higher levels of happiness and success.

One thing I can promise: future you will be thrilled that present you gave yourself the care you need. If you don’t, future you will be pissed (and stunted).


You know those things you’ve been dreaming of doing for a few years? Do them.

For years, I dreamt of spending a solid week with my close friends from high school. I wanted to get to know them as the adults they’d become.

Sure, I saw them at Christmas and Thanksgiving, but it never felt like enough. I wanted an entire week. Spending real time with them was something I had wanted to do for years, but never actually got around to.

A huge part of reinventing myself was checking big items I had been dreaming of off the bucket list. For me, that included:

  • Spending time with my high school friends
  • Visiting the summer camp I grew up at while camp was in session
  • Kissing an ex from way back when who I was still attracted to (I don’t actually recommend this, though I’m glad I did it.)
  • Returning to Montreal, where I spent my early 20’s

Most of these things were insanely fun.

They were also deeply healing. Reconnecting with the people and places that shaped me reinforced my sense of self; revisiting my past helped me understand where I came from. Kissing my ex allowed me to let go.

If you’ve been dreaming of doing something for a long time, it’s important that you actually do it, and now is the time.

Practically speaking, it’s good to work it out of your system; it will allow you to tie up loose ends and create a fuller, more complete life.

Psychologically speaking, there’s a reason these things have been lingering on your mind, and it’s time to find out why. In doing so, you’ll learn more about your true self. You may also create emotional openings that will bring you closer to becoming the person you’re meant to be.

To be clear, I’m not saying that you need to revisit your past like I did. What you need to do is take action on all of those things that you’ve wanted to do for a while, but haven’t.


Resist the urge to plan everything out

August 2015, chatting with my family during a visit: “I’m going to spend a few months traveling and looking for a new home.  Though, honestly, I’m pretty sure I’m moving to Durham, NC. A bunch of friends live there, the cost of living is low, and it’s a quick flight to many of the people I love. I’ve also been there a few times and really enjoyed it. Durham is the perfect place for me!”

Only one problem: when I got to Durham, it was clear that it wasn’t the perfect place for me.


As you reinvent yourself, it will be extremely tempting to plan everything out and make decisions as quickly as possible.

Don’t. Doing so will close you during a time in your life when staying open is critical.

Besides, if planning was all you needed to do to solve your problems, you wouldn’t have any. You could just sit reflecting for a few hours in a coffee shop, and you’d be all set. In fact, I bet you’ve already tried that.

Stay open. Wait to make big decisions until you have clarity.

If you’re having trouble getting clarity, start by making small decisions to test the waters. As I was looking for a new place to live, I visited nearly 20 different cities trying to find the one that was right for me. When I found a city I liked, I stayed for a week or two feeling it out.

If you’re having trouble staying open during this period of reinvention, it’s probably because the constant change is wearing you down. I get that. Spend a day or two recharging. I like to hole up and binge watch Parks and Rec. (More on how to handle the emotional chaos of change, here).


Experiment. A lot.

October, 2015, Mexico: I’m clutching my coffee. For the life of me, I can’t remember why C*, S*, and myself decided to host this seminar at 8:00am. I don’t even like being awake before 8:30….

Regardless, the room is filling up, and I’m getting excited. As the seminar unfolds, I notice something amazing happening: every single person we’re working with has had a real breakthrough. In fact, they’re all crying right now because each one of them has gotten in touch with something they’ve been needing to feel or realize.

I feel completely in my element.


The only way to create a better life for yourself is to take action and see what happens. While you’re going through the reinvention process, say “Yes” to as many opportunities that intrigue you possible (just make sure they don’t become long-term commitments).

As you have new experiences, you’ll gain clarity about who you are and how you want to live. Once you find something that clicks, own it.

During my transformation, I knew that I wanted to leave my job as a speaker, but I didn’t know what I wanted to do instead. I dedicated all of October to finding out by seeking new opportunities and accepting invitations that seemed cool.

I learned that I loved giving keynotes with friends (as opposed to solo), that I had a surprising gift for one-on-one work, and that I thoroughly enjoyed running retreats for small groups. Today, these discoveries actively shape my business’ future.


As you complete your reinvention, reflect back on where you came from.

11:00pm, May 6th, 2016 at a coffee shop in Denver, CO: one year ago, I wrote a long email to my close friends. I was heartbroken and afraid of the changes I needed to make. I wanted to feel their love and support.

Today, it is exactly one year later, and I’m sitting down to give them an update

As I do, I go through that mental checklist to examine my current life:

  • Business? I love spending my time writing and doing one-on-one work with people. Not only that, but I’m on track to make more this year than I ever did as a speaker.
  • Friends? Though I’ve only lived in Denver for six months, I have a better, more active social life here than I did in Washington, DC.
  • Love life? I’m single. While it would be nice to be in a great relationship, I don’t feel the need to rush it.
  • Physical health? I’m in the best shape of my life.
  • Mental health? One of my friends mentioned that I’ve become effortlessly happy, confident, and relaxed. While I wouldn’t personally say it’s “effortless,” I am happier than I’ve ever been before.
  • City I live in? Oh hell yes!


Changing your life is turbulent, and the timeline for success is unpredictable. For me, it took about a year to make all the necessary  changes.

When you commit to changing your life so that you may live as authentically as possible, you are bound to succeed.

When success sneaks up on you, pause to take inventory of your new life. You’ll be delighted (and hopefully proud) when you realize just how far you’ve come. You’ll notice that in many instances, you exceeded your own expectations. You’ll notice that you’ve become the best version of yourself yet. That’s an amazing feeling.

Your final task is to celebrate yourself. Share the details of your transformation with your close friends (they’ll be glad you did), and buy yourself a gift. Make it something that you will use or see regularly. Let it act as a reminder of how powerful, capable, and downright awesome you are. Watches, necklaces, tattoos, jackets, or bracelets all work well for this. Personally, I bought a cool hoodie.


Final tips for reinvention

I want to leave you with two pro-tips on how to handle reinventing yourself.

First, prioritize your physical and mental health. For me, this meant a steady regimen of meditation, journaling, and exercise. Find what helps you stay grounded and healthy, and stick with it.

Second, be cool with being emotionally volatile. Normally, I’m pretty even tempered. During reinvention, my highs were higher, and my lows were lower. I may have even cried once while I was watching Parks and Rec (what?).  If you notice yourself swinging between the extremes, don’t worry; it’s a normal part of the process. My hope is that you reach out to someone who loves you when you’re feeling low.  


Still on the fence?

If you made it this far and you’re still on the fence despite being excited about reinventing yourself, I have one last piece of advice for you: go create an inflection point. Start now.



Getting to know yourself: eleven questions for deepening self-awareness

2008, my first (and last) date with K*: I didn’t know that it was possible to shock someone into self-awareness, but that’s exactly what K* just did. She asked a simple question, “What are your three biggest passions in life?”

I knew that I was passionate about building my speaking company, Ignited Leadership, but then I drew a hard blank. For the life of me, I couldn’t recall what my two other passions were.

In that moment, I had become so intensely disconnected from myself, that I couldn’t even name the three things in life I loved the most. That’s an intense level of disconnection…


Everything you experience in life flows from how well you know yourself.

Your self-awareness directly informs your day-to-day life. It also dictates whether or not you choose to chase your dreams, if you’re open to love and connection, and how you respond to everything from tragedy to joy.

In fact, when people struggle with being happy, being confident, or knowing what they want to do with their lives, the struggle is often the result of not knowing themselves well enough.

But knowing yourself is deceptively difficult…

The struggle for self-awareness

Most people have built busy lives defined by alarm clocks, stress, work, other people, bold aspirations, and busyness.

Downtime tends to be used for entertainment. The fleeting moments you do get to yourself are often punctuated by the background noise of text messages, social media, podcasts, Netflix, and music.

On it’s own, none of this is bad. In fact, a lot of it is fun. But it all blurs together to hold you back from dedicating time to focus on yourself. Without time to focus on you, you can’t know yourself, at least not at a deep level.

I know that sounds like a bold assertion, but pause for a moment: what are your three biggest passions in life?

If you’re like most people, the answer to that question is not immediately obvious. In fact, passions are one of those things that everyone talks about, but few have truly considered.

Or even more simply: are you happy?

Chances are you just had a conversation with yourself that went something along the lines of, “Hmm, am I happy? Yeah, I guess I’m happy. I mean, a lot of people have it way worse than me. I’m seeing my friends this weekend. I’ve got enough food. So yeah, I’m happy!”

If it took you a few beats to connect to your base level emotion, you have room to grow in your self-awareness. But don’t worry, almost all of us do.

In search of a better solution

Many people get hung up on a quest to “find themselves,” “get to know themselves,” or “figure out what they want to do with their lives.” The search often goes on for years on end, leaving many in a state of perpetual confusion. Most end up settling for mediocre answers about who they truly are.

I get it. I’ve been there.

To further complicate things, the common ideas about how to find yourself are clunky. They require considerable amounts of time and often require such significant effort that they become prohibitive. These include:

  • Traveling for months on end
  • Reading literature in hopes of finding yourself reflected in the characters
  • Reading tons of self-help/philosophy so that you can finally figure out what’s wrong with you and how to fix it (hint: there’s nothing wrong with you and you don’t need fixing)
  • Giving away your possessions so that nothing distracts you from yourself
  • Meditating or praying for hours a day
  • Engaging in years of Freudian style talk therapy

I’ve dabbled in most of the ideas above. Some, like travelling, can work well, but all of them are disruptive. What if there was a way to get to know yourself at a deep, penetrating level that didn’t require such an intense commitment?

Good news: there is…

How to get to know yourself

If you wanted to get to know someone else, you would spend time with them. You’d observe their habits. You’d ask them questions and listen to their answers.

You get to know your true self the same way you get to know someone else. You ask yourself bold, open-ended questions, and answer them as honestly as possible.

More on that in a moment…

On vulnerability and white lies

“Live by the foma* that make you brave and kind and healthy and happy. *Harmless untruths” – Kurt Vonnegut

Being vulnerable sucks.

It’s also the only way to grow.

When you’re vulnerable with yourself, you’ll form a stronger connection to you. The stronger the connection, the better your life becomes.

Many people have learned to ease the moment-to-moment pain of life by telling themselves (and others) white lies, or what Kurt Vonnegut refers to as “foma.” You know those times when you’ve tried to convince the world that you’re doing, “Great. JUST GREAT!!!” when in reality you’re in a rut? Yeah. That’s what I’m talking about.

While the deception may feel good in the moment, it causes damage in the long run. The lies prevent you from knowing your true self.

If you want to form a stronger connection to you, it’s your job to cast away the white lies. The more vulnerable you feel during this process, the more effective it will be.

Your secret weapon: honesty.

How to interview yourself

Increasing self-awareness is as simple as holding space and using it to interview yourself. Though the exact process can be modified, here’s what I recommend:

  • Schedule four, two-hour blocks of time to interview yourself over the next month. Put these appointments into your calendar.
  • When you interview yourself, do it someplace you find inspiring. This could be a quiet lake, a coffee shop with a great vibe, the atrium of a gorgeous museum, etc.
  • Before you start, turn your phone and computer off. This is time for you to focus exclusively on you. If you’re struggling to create silence in your life, that’s a clear sign that you’ve become addicted to distraction.
  • Don’t just think of answers; write them down. Use pen and paper. Doing this will slow you down, draw you into the moment, and force you to crystalize your answers.
  • Make it special. Buy yourself a nice pen and journal for this project. Get a lavender latte and a chocolate croissant at the start of each session. Wear your favorite shirt. The trick is to signal that this is sacred time dedicated to focusing on you.

Even if you ignore all of the other tips above, be sure that you are unreachable during your time reflecting. At minimum, put your phone in airplane mode, turn off the wireless card on your computer, and resist the urge to jump online.

11 questions to spike your self-awareness

A good interviewer spends time preparing questions for her subject, while remaining open to spontaneity. She asks questions no one else has the audacity to ask.  She follows her subject down rabbit holes even when it’s unclear where they’re going. She accepts that some questions will have short answers.

The questions below are designed to aid in your preparation. I have found them to be important in my life. Feel free to answer all of them or only a few. The more time you invest in yourself, the greater your results.

Pay particular attention to the questions that excite you and the ones that make you nervous. The answers to those questions will provide important insight. Revisit the answers that feel incomplete at later sessions.

As you go through this process new questions will arise. Perfect! Add them to your list for future sessions. With each honestly answered question, you’re getting closer and closer to you. Here are eleven to get you started:

  • Your doctor calls. She informs you that you’ll be dead in six months. How does that change your life? How would you spend your remaining time on earth?
  • You’ve just inherited $100,000,000. Now that money is no longer an issue, what do you do with your life? Bonus: how can you start doing that – even just a bit – today?
  • Are you happy? If not, what do you think you need to be happy?
  • What lies have you been telling other people? What lies have you been telling yourself? Why?
  • What would your perfect day look like?
  • What do you hope people say about you at your funeral?
  • What’s missing from your life? What can you do to get it?
  • Have you ever felt fully loved by yourself or someone else? If the answer is no, what would it take for you to feel loved? Is something inside of you blocking that?
  • In what areas of your life are you underestimating yourself?
  • What gifts, talents, or passions have you been hiding from yourself and the world? What can you do to start engaging them more often?
  • In what areas of your life are you out of integrity? How can you fix that?

Where do you go from here?

By taking the time to interview yourself, you are forming a stronger sense of self-awareness. The next step is to translate awareness into reality. You do this by making the life you live a reflection of who you truly are.

Attempting to change everything all at once is seductive but unrealistic. A better approach is to consistently make small changes. Over time, the small changes will compound and become significant changes. You will become more you.  


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

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

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

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

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

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

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

More on that in a moment….


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

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

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

But you didn’t.


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

Those are lazy excuses.

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

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

What happens when you finally start trusting yourself?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

What. The. Fuck.

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

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

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

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

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

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

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

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

Ok, so how do I actually start trusting myself?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Why I wish I dropped out of college…

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

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

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

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

You don’t need a net

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

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

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

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

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

How to handle the emotional chaos of change

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

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

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


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Weathering the storm: 8 reminders for dealing with change

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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