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

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

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

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

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

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


I never spoke to her again.


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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

If neither of those techniques work for you…

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

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

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

6 Things to consider when evaluating a therapist

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

It takes a village…

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

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

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

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

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

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

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


The hidden agony of men and their mental health

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

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

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

On every count, these men were wrong:

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

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

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

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

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

The chasm between the inner and outer world

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

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

Externally, my life was perfect.

Internally… not so much.

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

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

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

In reality, that’s simply not the case.

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

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

Outdated concepts of masculinity

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

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

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

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

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

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

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

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

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

The stigma around men’s mental health

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

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

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

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

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

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

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

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

Advice for supporting the men in your life

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

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

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

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

What no one tells you about leaving the beaten path

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


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

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

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

I’m afraid.

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

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

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

So I did.

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


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

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

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

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

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

The amazing parts of leaving the beaten path

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The agonizing parts of leaving the beaten path

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

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

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

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

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

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

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

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

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

But of course, I didn’t.

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

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

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

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

The insane parts of leaving the beaten path

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

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

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

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

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

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

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

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

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

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

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

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

Well said my friend.

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

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

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

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

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

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

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

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

So, should you leave the beaten path?


Just simply yes.

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

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

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

Overcoming low self-worth

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

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

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

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

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


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

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

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

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

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

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

Before we begin…

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

Understanding self-worth (and dispelling a common misconception)

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

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

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

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

Your past, present, and future

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Leaning into the pain

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

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

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

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

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

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

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

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

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

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


The healing process looks different for different people.

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

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

Most fall somewhere between the two extremes.

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

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

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

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

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

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

Postscript: A note on false healing and false sickness

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

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

The true litmus test: do the positive feelings last?

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

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

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

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

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

What happens when you put life ahead of work for a year?

Someone once asked the Dalai Lama what surprised him most about humanity. He replied,

“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.”


Late April, 2016: I’ve never had to make this choice before…

I just quit my job as a professional speaker and launched my blog. My next move is to build a consulting practice. Just two problems left to solve: one, I have no source of income, and it’s unclear when consulting will start paying off. Two, my social life is pathetic and I’m not enjoying life as much as I’d like to.

There are two ways to approach these problems:

Option 1: Do the “smart” thing and focus the bulk of my attention on building the consulting practice until it makes enough money to live comfortably. As the practice grows, I’ll be able to invest my income into my social life.

This path seems safe and familiar, and I’ve been told it’s wise.

Yet, whenever I think about using most of my time to build a business, it feels like I’m suffocating myself. It’s not that I don’t love my work – I do – it’s just putting it as my top priority feels wrong, even though logically, I should.

Option 2: Build the life I want now, even if it means spending more than I’m making (which is literally nothing for the foreseeable future).

I dream of joining cool communities, attending live events, going on dates, and throwing dinner parties for the people I meet along the way. If I did this, I’d only be able to work on my business in the background, which feels irresponsible.

This path is exciting, but it feels scary. It seems like leaping without a net.

For several days, I’m stuck in limbo.

Eventually I screw up my courage to its sticking point and make my move. I decide to put my life first and figure out the details of my business later.

I sign up for a gym, an improv class, and a coworking space (I’m not completely neglecting my business…). I buy decorations for my apartment and a sweet bike. I email the few people I know in Denver about my first dinner party, and I cross my fingers as I hope to avoid bankruptcy.


Putting my life ahead of my work was a calculated risk. I suspected that the more I fell in love with life, the better my business would do.

It’s been just over a year since I placed that bet, and one thing has become clear: it worked!

In this article, we’ll cover why putting life first is a deceptively safe bet, how the path forward differs for entrepreneurs and employees, and how it played out in my life. I’ll also give practical examples that you can do this week to help you live more fully for yourself.   

To be clear, I’m not advocating hedonism, exorbitant debt, or ignoring your career. Instead, I’m encouraging you to create a life around the things and people you love before finding space for the stuff you have to do.

A note about inequity and the world we live in

I understand that many people are barely able to make ends meet and can’t consider whether it makes sense to spend less time working and more time living. To me, this is a sign of an ill society. It’s my belief that if you’re fortunate enough to have the option of prioritizing life, you should also use some of your resources to help the people around you.

The pain of putting work first

If you live in a Western culture, there’s a good chance that the timeline of your life was set before you were born. Roughly speaking, the sequence goes:

  • Get an education (which will likely require a loan)
  • Get a job
  • Save up to buy a house and a car (both of which will require loans)
  • Find a life partner
  • Try to get promotions
  • Scale your lifestyle to match your income
  • Squeeze in a few parties, trips, hobbies, volunteer projects, creative projects, long weekends, and side hustles whenever possible
  • Retire (at this point you’ll be old)
  • Finally, pursue your passions and start living on your own terms! (That is assuming that you’ve taken decent care of your body and still have the requisite energy and money left over)

Do you see the problem here? If you take this path, your life will only exist in the margins. Almost everything will be about work.  

Sure, there will be moments of beauty that take your breath away, but they’ll be more scarce than they should be.

A better approach is to start by building a life you love. Doing this requires courage and audacity. You have to assume that virtually everyone is approaching life incorrectly. That’s a difficult bet to make. Fortunately, there are strategies to make it easier.

How to put life first: the big stuff

Practice strategic minimalism while focusing more on experiences than stuff. Work to minimize your expenses. Doing so will increase your freedom, and it will allow you to be more selective about the jobs you take and the people you work for.

You’ll start to realize that happiness often comes from subtracting – not adding – things from your life.

Besides, the studies are clear. Spending your money on experiences produces more happiness than spending it on material items. Fortunately, many of the coolest experiences are free or inexpensive.

Next, figure out what actually matters to you. In most cases, you already know, it’s just a matter of doing it.

Have you had a burning desire to join the Peace Corps, work as a camp counselor, learn an instrument, go back to school, or travel the world? If so, it’s time to start making that happen. If you’re not in a position to completely overhaul your life (which I don’t suggest anyway), start taking consistent baby steps toward where you want to be. They’ll compound more quickly than you imagine.

Figure out where you want to live. This is one of the most important decisions you’ll ever make, and it’s one that few people ever put much thought into. Are there countries, regions, people, or settings that you really love? If so make it a point to (at the very least) spend as much time as possible there. If and when you can, move.

Moving is chaotic, so don’t feel the need to rush this one, but if there is someplace you’re truly yearning to be, honor that desire and figure out how to make it work at some point in your life.

Be thoughtful about how much of your life you can enthusiastically dedicate to work. How much of your life are you able to dedicate to a job without resenting it? Remember that unless you’re intentional you’ll end up spending more time with your coworkers than your friends and family. To the best of your ability, set boundaries around your work. You don’t have to be perfect about those boundaries, but the second your job starts to define you is the second you’re no longer living for yourself and the people you love.

The next step varies a bit depending on whether you work for yourself or someone else.

If at all possible (and I realize it’s not always possible), hold out until you find a job that excites you. You can always drive for Uber, work at a coffee shop, or bus tables in the interim. No, those jobs aren’t glamorous, but they will tide you over until you find a job that you love.

If you’re working for yourself, build your life before you build your business. Most entrepreneurs promise themselves rewards when their company hits a certain goal. Instead of waiting to give yourself those gifts (a watch, a vacation, a gym membership, a trip to the doctor, whatever), give them to yourself now.

Besides, in many cases, people never actually give themselves the rewards they’ve promised. Once they cross that illusive line in the sand they say to themselves, “Well, even though we just hit our revenue goals, I’ll put off taking that trip until we’re a bit more stable.”

Though it seems counterintuitive, the more you invest in the quality of your life, the better your business will do.

The next step involves looking at your day-to-day life.

How to put life first: the small stuff

While the plan above is ideal, it’s not realistic for everyone. If you’re a college student who’s just graduating, you’re in a terrific position to put your life first. If you’re a mother of three, making those changes is going to be prohibitively difficult.

Fortunately, putting life first isn’t just about the big decisions. It’s also about how you approach your day-to-day. Your aim is to fill your day with events both large and small that delight you. A few examples:

  • Call in “sick” and use the day to sleep, binge on Netflix, go for a walk, and catch up with your best friend. Better yet, get your best friend to call in sick too!
  • Every now and then screw eating salad for lunch and grab brownies!
  • Give yourself a little gift, not because you’ve “earned” it, but just because.
  • Tell your friends to keep tomorrow evening free, then drive to their house, kidnap them, and go mini golfing.
  • Take. A. Vacation. It’s been too long. And if not now, when?
  • Stop going to those stupid networking events.
  • Take 15 minutes to enjoy a hot chocolate and watch puppy videos.
  • Screw getting a promotion, instead work just hard enough to keep your boss happy and invest your extra time into something else.
  • Get yourself that sick leather jacket you’ve been dreaming of (or is that just me??).
  • Make the little things you truly love in life (like coffee and long walks or cheesy spy novels) non-negotiable. Schedule them into your calendar if you have to.

As you begin to put your life ahead of your work, you’ll notice something surreal: as your life improves, your work follows suit. The sad part is that the inverse isn’t always true. Those who put work ahead of their lives rarely seem to achieve the quality of life they’ve been looking for.

How all of this played out in my life and business

When I decided to put life first, I made a few decisions that would remove some of the financial pressure. First, I rented an apartment that cost much less than I could afford. Second, I promised myself that I would err towards cooking and inviting people over to my place, over going out for food and drinks. Third, I did my best to get books from the library instead of buying them (books are my weakness). Finally, I got a bike to minimize my dependency on Ubers and rented cars.

From there, I more or less lived as I wanted to live. When choosing a gym and a co-working space, I went with the ones that I loved, not the ones that were cheapest. If friends were going snowboarding, I’d join them. If I was exhausted or just didn’t feel like going to work, I’d keep any meetings I had scheduled, but push everything else off until tomorrow. Along the way, I tried to be as generous to myself and others as I could be.

Of course, I didn’t stop working on my business. It’s just that it got much less of my time and attention than most people think it should.

As expected my social and personal lives took off. Looking back, I realize that this was kind of the point anyway.

What did surprise me was how this affected my business. When I was working, the quality of work I produced was better than it had ever been. Because the work was better, I started getting referrals meaning less of my time was spent on sales and marketing. When I had a sales meeting, I felt more calm and confident which increased my close rate. Without realizing it, I started charging more for my services. If a client proved to be a bad fit, I simply let her go and refunded her investment, creating space for a new client to potentially appear.

In other words, my work adapted to fit my life. Though prioritizing my life over my work was never a strategic choice, it ended up being one of the most effective business moves I’ve ever made.

Postscript: on death and human nature

“The trouble is, you think you have time.” -Jack Kornfield

As I’ve mentioned before, three of my friends died when we were all in our twenties.

One lesson their deaths taught me is that tomorrow is never promised.

Our lives aren’t meant to be spent at work looking at spreadsheets, sales analytics, and TPS reports. They’re meant to be spent loving, exploring, laughing, crying, lounging around, fighting, embracing imperfection, leaving the dishes until the morning, traveling, art, playing pranks, watching movies, protesting corrupt governments and wars, seeing concerts and magic shows, playing with puppies, and worshiping whatever sort of god you believe in.

We aren’t meant to put these things off until tomorrow; we’re meant to do them now. For some of us, that tomorrow may not come. Even if you do make it to tomorrow, when you rest on your deathbed you’ll never think to yourself, “Thank God I pulled all of those 70 hour weeks instead of spending time with my kids and lover!”

To focus on work is to focus on security. Yes, security is seductive, but we both know that humans weren’t built to play it safe. We were built to be bold and playful risk takers who live as though life were a precious gift.


How to overcome the need to be a people-pleaser

A confession: I am a recovering people-pleaser. In no particular order, I’ve:

  • Stayed in friendships, business partnerships, and romantic relationships wayyy longer than I should have, resulting in uninspired, sluggish, and deadening relationships
  • Diluted myself in order to be a false peer to people I didn’t even like or respect
  • Offered thousands of dollars in discounts and free services without being asked
  • Committed to stupid shit that I had no desire to do in the first place (“Oh yes, I’d love to give you notes on your one man show about roast beef and flatulence…”)
  • Made countless other bad decisions simply because I was afraid that if I didn’t, people wouldn’t like me

My unconscious logic was that if enough people liked me, I would feel safe and secure in my relationships.

Though I didn’t realize it at the time, I’ve come to understand something simple: people-pleasing is a lose-lose. By catering to other’s needs before my own I was subtly lying about who I am. Since I wasn’t being sincere, I left little room for anyone to form an open and honest relationship with me.

People-pleasing is manipulative and self-loathing

People-pleasing is the act of putting other people’s needs (or perceived needs) ahead of your own.

Let’s say you’re looking forward to spending Saturday afternoon drinking black coffee and reading East of Eden. One of your friends texts asking if you’d go to a yoga class with him. Saying no makes you feel guilty, so you decide to go to the class even though you’d rather stay home.

This is people-pleasing. You’ve effectively decided that your friend’s need for a companion is more important than your need for rest. In agreeing, you’re lying to your friend about who you are while signaling to yourself that your needs are unimportant.

Putting other people’s needs ahead of your own from time to time is no big deal. The problem comes when you chronically prioritize other people over yourself. Doing so hijacks the best part of you. It leads to dictating your choices like when to stay in a marriage, where to live, what company to work for, who you surround yourself with, and countless other decisions that shape your life.  It forces you to play small and remain closed off.

At its core, people-pleasing is a denial and suppression of self.

8 Skills to Overcome People-Pleasing

Fortunately, it’s possible to overcome being a people-pleaser and doing so will dramatically improve your life. I know because it’s something I’ve been actively working on for the past year.

I’ve found the following eight skills to be disproportionately helpful. As always, experiment with the ideas that excite you and be curious about the ones that scare you:

1) Understand your needs and desires. Many people ensnared by people-pleasing aren’t even aware of their own needs. You feel that your job is to be liked by as many people as possible, while in reality your job is to be true to yourself.

Work to uncover the needs and desires you’ve been neglecting. What do you need to be the best version of you? Lots of sleep? Alone time? To play the flute every evening? To find a circle of friends? To spend less time with your family? There are no right or wrong answers here, only what’s right for you.

If you’re not sure what you need, experiment until you find it.  

2) Say no more often. As you start to recover from people-pleasing, you should say no as often as you can. In some cases, you can allow your actions to speak for you.

  • Your intimate partner wants to have sex, but you’re not feeling it? Don’t have sex with them. If they make a big deal out of it, consider whether or not this is the right person for you.
  • Your whiney friend is calling to bitch about her mom again? Send the call to voicemail and deal with it when you’re ready (if at all).
  • Your boss asks you to stay late when you’re really excited to go home? Tell her that you have other obligations.
  • Your children are begging to watch “Paw Patrol”1 but you can’t stand another second of animated dogs solving uninspired crimes? Tell them it’s nap time.
  • A friend of a friend proposes a coffee date so that you two can “network” and “get to know each other,” but you have zero interest? Ignore the email.

If needed, say no again and again and again until the person finally takes a hint. You’re under no obligation to go on a second date with that weirdo from OK Cupid, and you really don’t need to return your parent’s calls if you don’t feel like it.

3) Start asking for what you want. People-pleasers tend to feel that their needs are unimportant and unworthy of other people’s time. In reality, your feelings of unworthiness are nothing more than phantoms of your mind. To prove to yourself that you are worthy, get in the habit of asking for what you want. This can range from calling a close friend to vent, requesting a refund for a crappy product, or staying in even though you told your friends you’d go out.

4) When you are around toxic people be especially vigilant of your needs. The sad truth is that many of us have people in our lives who don’t care about us. There are a few ways you can detect these people, they:

  • Are unwilling to invest in you, even though you’ve invested in them
  • Never express any form of curiosity about you or your life
  • Leave you feeling drained, shut down, depressed, sluggish, small, or lethargic

When dealing with people like this it’s wise to consider keeping the relationship at arm’s length or letting go of it all together. However, there are times when doing this is either impossible or undesirable. In these cases, make a habit of simply giving yourself whatever you need when you’re around them.

Let’s say you’re having dinner with your relatives and their constant worrying, anxiety and nagging is starting to tear you down. You’ve already tried to change the topic a few times, but they won’t relent. Instead of sitting there politely (ignoring your needs), simply say, “I love you guys, and I’m going to get some air.” Then go for a walk to create distance between yourself and your family.  Return whenever you feel like returning. There is no need to explain yourself or apologize.

5) Treat yourself like the badass you are. One of the most fun ways to overcome people-pleasing is to turn the equation around and start using your energy and focus to delight yourself. Get a massage, drive with the windows down and the AC blasting, drink milk straight from the carton, whatever.

The more you honor your needs and desires, the better. Personally, I try to spend at least one evening a week doing exactly what I want to do.

6) Let go of the guilt that comes with prioritizing yourself. If you’re just getting the hang of prioritizing your needs, you’re probably going to feel guilty when you say no to people.

Your job is to let go of that guilt. It’s sabotaging you.

One way to let go of an emotion is to pause and allow yourself to really feel it’s presence. Feel the tension, anxiety, and fear rippling through you. When you stop fighting against reality – including negative emotions – you gain presence and power in the moment.

7) Retreat to comfort. If you’re accustomed to prioritizing other people’s needs, putting your needs first will require you to leave your comfort zone. Still, it’s important to return to your comfort zone soon after you’ve left it. Call your brother to talk, grab a beer with your friends, listen to a funny podcast, or whatever. Taking good care of yourself will make leaving your comfort zone easier in the future.

8) Understand that sometimes people’s needs clash and offer no clean resolution. A difficult reality: sometimes two people have needs that are in stark opposition to one another.  During a fight, one partner needs to be held while the other needs to be alone. During a meeting, one employee wants to take notes on her phone, but phones in meetings drive the boss nuts.

Heck, the more in touch with yourself you are the more you’ll notice conflicting needs within you. It’s entirely possible to desire an expensive leather jacket while also thinking it’s stupid to spend tons of money on a piece of clothing (not that I’m dealing with that exact situation or anything…).

We all have to accept that sometimes people have conflicting needs. One way of handling this is to consider which person’s need is stronger or more important. Unless it is 100% clear that the other person’s needs really are more important than yours, I urge you to prioritize your own.

Building your relationships around MUTUAL desire and excitement, not obligation

People-pleasing is a cold and difficult way to live. It results in the people-pleaser hoping that if enough people like her, she’ll like herself too. I’ve been there. It creates relationships that feel transactional. You spend time with people you dislike in hopes that they like you and will provide the sense of security and love that you’ve been craving.

It’s much better when relationships are built out of mutual desire instead of obligation or covert contracts.

Taking this stance in relationships creates a huge amount of fluidity and connection. It means that when you’re with someone, it’s because you want to be with them and not because you’re subtly trying to win their approval. Though it may not seem like a huge shift when you read about it, to live it is to change your life dramatically.

Of course, learning to prioritize your needs will change your relationships; it did for me.

Some people are less interested in working with me or spending time with me. Some people are disappointed because I don’t spend as much time with them or no longer engage in stuff we used to do together.

Though it’s difficult to accept that some people like me less, I realize something simple: I prefer to be around the people who want the best for me. Likewise, I strive to be the type of guy who wants the best for others. If people fault me for not sacrificing myself, we were never a good fit in the first place. I’m learning to be cool with that.

The trick to long-term change

If you’ve read this far you might be ready to let go of being a people-pleaser and start living more fully for yourself. That’s a beautiful thing.

It’s always tempting to make dramatic changes all at once. If that feels right to you, go for it, though it tends to be unsustainable.

A more gentle approach is to make small consistent changes across your life. Stop returning the calls you have no interest in. Say no twice this week when you would have said yes. Do something to delight yourself. When you’ve become comfortable with one new behavior, add another.

Many people find that it’s easier to create change when they have someone by their side. If you know someone else who may benefit from putting her needs first, call and see if she’d like to go on this journey with you. Hold each other accountable by checking in during the week and getting together for coffee over the weekend to trade stories and encourage one another. Change tends to be more effective and fun when it’s shared.


I don’t know how else to say it: you are the most important person in your life. You matter and your needs matter. It’s ok to prioritize them. The people worth loving will accept you as you are. Those who want you to be someone else? It’s best to let them go.

Post script: the problem with treating symptoms

I want to be transparent about something: this article, for the most part, addresses the symptoms of people-pleasing, not the cause. Treating symptoms is generally bad practice; it’s better to treat the cause.

For some, when you begin to prioritize yourself, your awareness will naturally increase and you’ll begin healing. You’ll start to untie knots that you didn’t even realize you were bound by.

As I understand it, people-pleasing is often the result of a tightly held insecurity that may have been caused by trauma or neglect. Addressing these deeper issues is beyond the scope of what any article can reasonably address.

If you’ve tried a bunch of personal development methods or experimented with a few of the suggestions here and you still feel stuck, get help. There is no need for you to endure more suffering than necessary.

While there are plenty of coaches who claim to be able to help you heal old wounds, I believe that this type of work is best done by a licensed mental health professional.

I know that getting help can be uncomfortable. I know that it’s easy to put off. I know that most of us are living under the delusion that our problems will one day fix themselves.

Instead of continuing to deprive yourself, I urge you to get the help you need. 

On relationships, awareness, and compassion

“I have just three things to teach:
Simplicity, patience, compassion.
These three are your greatest treasures.
Simple in actions and in thoughts, you return to the source of being.
Patient with both friends and enemies, you accord with the way things are.
Compassionate toward yourself, you reconcile all beings in the world”

-Lao Tzu in verse 46 of the Tao Te Ching


March, 2017: Angrily, I hang up the phone and ask myself, “Why the hell are you being such an asshole to the people in your life? She didn’t deserve that. You should have just been honest and said you were frustrated, confused, and more vulnerable than is obvious.”

I think to myself, “What the hell is wrong with you, man? Can’t you do better than that?”

The answer is complicated.

I didn’t want to be a jerk to the other person, but for some reason I was. It must have been a combination of my feelings about myself, her effect on me, the side of the bed I woke up on, and stress levels.

Strange as it seems, I think that in the moment, being a jerk was the best I could do.


How would your life change if you started giving everyone – yourself included – the benefit of the doubt? What if you start assuming that every single person is doing exactly as well as they can in any given moment?  What if you start accepting that sometimes people are incapable of truly expressing themselves, even if they want to? How would other people’s lives change if you started accepting them as they are, instead of wishing they were different?

I suspect that it would remove huge amounts of friction from your relationships while developing new levels of empathy, understanding, intimacy, acceptance, and connection with the people who matter.

With a bit of luck, you’ll become gentler with yourself, because the more you accept others, the more you accept yourself.


For the past few months I’ve been living with two assumptions about the people in my life:

  • Everyone is doing the best they can (even when it doesn’t seem like it)
  • People are not always capable of saying what they want to say. Sometimes they lack the verbal fluency, or they can’t access the required vulnerability, or both. Consequently, it can be a mistake to take people literally.

It’s difficult to express just how much these assumptions have improved my relationships. I’ve learned that giving people the benefit of the doubt serves as an act of compassion for both myself and the other person.


Are people truly doing the best they can in any given moment? Who knows? I think they are, but many of my friends disagree.  Either way, we’ll never really be sure.

What I do know is this: giving people the benefit of the doubt allows you to see them in their best light. It releases you (and them) from the fantasy of who you wish they were and creates space to love and connect with the person right in front of you.

More than that, you create space for a better version to emerge in the near future. If you stop resenting others (and yourself) for who they are right now, you free up tons of energy and focus to improve the present moment. When you improve this moment, the next will be ever so slightly better.


Day to day, an individual’s behavior can vary dramatically, making accepting  them deceptively difficult.

On a good day, I can delight my clients, string together new deals, work on article, hit the gym, meet my friends for happy hour, and get home in time to cook dinner with my girlfriend.

On a shitty day, doing anything besides binging on Netflix and cherry Pop-tarts feels intimidating.

But you know what? That day spent resting in bed gives me renewed energy for the next day. It draws an improved future a bit closer to the present.


Sometimes there is a chasm between what someone says and what they mean.

Even the most eloquent people struggle to verbalize whatever sentiment they’re trying to express.

Even the most emotionally fluent people struggle to find the vulnerability needed to open up.

And we all wear masks more often than we’d like to admit.

If you take people too literally, you run the risk of failing to understand them.


There have been countless times when words got caught in my throat. Times I wanted to say, “I’m afraid of losing you. Will you just hold me and tell me everything will be ok?” But the words never came out and instead, I said, “I need to go for a walk to cool down.”


If we accept that people can’t always express themselves, how are we ever expected to understand one another?

Good question.

Understanding other people – and ourselves – is an art. The truth tends to flow in a way that everything else doesn’t. You can generally find it in the intersection of action, sentiment, and word. It’s easier to detect when you approach people with love, curiosity, and compassion, instead of expectation and judgment.


Does the belief that people are doing their best and that they shouldn’t always be taken literally introduce deep philosophical and perhaps even moral problems?

Oh yes, many.

But I think that’s ok.

I believe I’m untamed enough (human, really) to accept the presence of conflicting thoughts and feelings. And I think you are too.

We’re all just beautiful messes anyways. Our lives aren’t meant to be drawn in clean lines or fit into neat little boxes. The loose ends aren’t supposed to be perfectly tied up.

As we learn to love people for who they are – imperfect, messy, confusing, difficult and beautiful all at the same time- we start to accept ourselves for who we really are.

We return to the simple truth that we are bound tightly together, united (or separated) by our (in)ability to cut through the illusions.   

My five best pranks

I still remember the first prank ever played on me. It was April Fool’s Day. I was 9 and my brother, Rob, was 6. The whole family was sitting at the dining room table when my Dad said, “Kids, we have a surprise for you… we’re going to DISNEY WORLD!!!!”

Rob and I screamed with excitement. We ran around the house and gave each other countless hugs and hi-fives. Breathlessly, we discussed which rides we’d go on, which characters we hoped to meet, and how amazing life would be in DISNEY!!

Then, our Dad looked at us and said, “Jason, Rob – we have one more exciting thing to tell you!! APRIL FOOLS! We’re not going to Disney World.”

I don’t remember how Rob and I reacted, but I do know this: my parent’s prank wakened a deep-rooted love of practical jokes.

In honor of April Fool’s Day, I want to share five of my favorite pranks. Also, if you’ve played or fallen victim to an amazing prank, please let me know in the comment section because I’d love to hear about it.

1: The, “Rooster in the Room” prank (2005)

After the infamous Disney World Prank, my parents became prime targets for Rob and I. In my opinion, the Rooster in the Room prank was our crowning achievement.

To preface, let me tell you about my family pet, Rosie. Rosie is a sweet little cockatiel and a true bright spot in my life. Cockatiels are the smallest breed of parrot measuring about 12 inches from beak to tail.

Rosie lives in a large cage, which is sometimes draped with a cloth at night to make it easier for her to sleep. Most of the time, the cage is kept in the living room, but occasionally, my mother brings Rosie into her room.

One of Rob’s close friends lived on a farm not too far from my parent’s house. I forget if it was Rob’s idea or mine, but we asked to borrow a rooster to put in place of Rosie.

On this particular night, Rosie’s cage was in my Mom’s room. Rob and I waited until the cage was covered, and I distracted my parents by taking them to get ice cream while Rob stayed behind.

Rob ran over to our neighbor’s farm to get the rooster. He then moved Rosie out of her cage and into my room where she happily went back to sleep. Finally, he placed the rooster in Rosie’s cage and covered it with the cloth. Miraculously, the rooster went to sleep and kept quiet.

Moments later, my parents and I returned with ice cream. Everything was set.

Before going to bed, my mom went to check on Rosie and lifted the cloth on the birdcage. When she removed the cloth from the cage, she woke the rooster who started making insanely loud cock-a-doodle-do noises. My Mom, expecting to see a small cockatiel, screamed and ran away saying, “What the fuck happened to Rosie?!?!?!?!”

Of all the pranks Rob and I have collaborated on, this is my personal favorite. It was also my Mom’s least favorite.

2: The, “Fake Menu” prank (2011)

When I lived in Washington, DC my close friend and roommates, W*, and I would go to our favorite dive bar, Red Derby, every Friday for Happy Hour.

In true dive bar fashion, Red Derby’s menu is extremely simple; it’s designed in Microsoft Word and uses size 12 Times New Roman font. The only design element is a few highlighted items. Here’s a photo of Red Derby’s menu:

One evening we stole one of their menus which W* used as a model to create an exact replica on his computer. He then took out two items, the “Fresh Veggies with Buttermilk Ranch” and “Foot Long Hot Dog and Fries” and replaced them with, “Buffalo Wings with Buttermilk Ranch and Blue Cheese” and a “BLT and Fries.”

We then printed 50 copies of our fake menu, highlighted and crumpled them, and splashed them with beer and water.

The end result? Our fake menus were virtually indistinguishable from the real menus. Here’s a photo of the fake menu. Notice the Buffalo Wings and BLT? They weren’t there before…

On the following Friday, W* and I posted up at the bar as usual. I used my, “I’m a former magician skills” to secretly swap our fake menus for their real ones.1

When the bartender, A*, came back, we asked her for food menus, and she – unknowingly – passed out the fake menus to W* and I.

W* studied the menu, and then proceeded to order the Buffalo Wings, one of the two fake items we snuck on there.

A* had a perfect reaction. She said, “You guys know we don’t have wings. What do you really want?” W* pointed out the new item on the menu. A* got really excited (she texted one of her friends to share the good news) and a bit annoyed that no one told her about the change.

When A* put in the order for Buffalo wings, the cook got confused and explained that they don’t stock wings. A* returned, now very confused herself, and apologized, explaining she had no idea was going on.

W* responded by saying, “Let me just get the BLT then [the other item we snuck onto the menu].” A* got overwhelmed, spoke to the kitchen and returned saying she had no idea what was going on, but they didn’t have BLTs either, even if they were on the menu.

As the evening went on, it dawned on her that the whole thing was a prank orchestrated by W* and I. In all honesty, it was the start of a beautiful friendship for A*, W*, and I. To the best of my knowledge, the owner still keeps one of our fake menus in her home as a souvenir.

3: The “Christmas Pecker” prank (2009)

Note: for those of you who have passed the point in life where penis jokes amuse you, you may want to skip this story. It’s a testament to the fact that, no matter how mature I may seem, my inner 17-year-old boy is still very much alive and well.

I used to spend my summers working at an amazing camp in Maine. On one of my days off, I wandered into a quirky store that had countless unusual gifts. One gift dubbed “Captain Pecker the Party Wrecker” was a six-foot tall inflatable penis. Obviously I bought it, even though I wasn’t entirely sure what to do with it.

A few months later, Rob and I were both home to celebrate Christmas with our parents. I inflated the ole’ Captain and put it in Rob’s room when he was out. When he came back he discovered the six-foot monstrosity and laughed. We then got down to business, brainstorming about how we can use this to prank our parents.

We waited until Christmas morning and got up at 4am. While our parents slept, we removed the decorations from the Christmas tree and hid it in the garage. We then put Captain Pecker where the tree had been and carefully decorated him with the ornaments and flashing lights from the tree.

Several hours later when my parents awoke on Christmas morning, they were greeted by a huge six-foot Christmas cock wrapped in twinkling lights and shiny ornaments. Fortunately, they both have great senses of humor and laughed. They did however make Rob and I return the tree and hide Captain Pecker before the extended family came over.

4: The “Breaking into Rob’s Room” prank (2007)

Rob’s bedroom is on the second floor of my parent’s house and has a big window. In fact, his window is so big that someone could easily climb through it and into Rob’s room if the window were open. Of course, the window has a lock for this exact reason.

One day, I was home from college, and Rob was at school. I snuck into his room and unlocked the window. I stayed up late that night, waiting until Rob was fast asleep. I then changed into all black clothing (including a black face mask) and quietly placed a ladder against the window.

I climbed the ladder and – making as much noise as I possibly could – proceeded to break into Rob’s room through the window.

From Rob’s perspective, a loud crash woke him from a deep sleep. When his eyes focused, he watched in horror as a cat burglar climbed into his room.

He screamed, “WHAT THE FUCK?!? WHAT ARE YOU DOING!!!” and sprinted out of his room, presumably to call 911 or wake my parents up.

I fell over laughing, took off my mask and went to find my brother. I then explained that his room wasn’t being broken into; I was just an asshole.

5: The, “Hi, I’m C*’s mattress” prank (2004)


As kids, C* and I hung out every day. When preparing dinner, our parents would often ask, “Should I make enough for Jason?” or “Should I make enough for C*?”

Like many families, C*’s hid a secret key outside in case someone got locked out. As an honorary family member, they told me where it was.

During senior year of high school, I decided to take advantage of their secret key. In the middle of my study hall, I simply stood up, left the school building, and drove over to C*’s house. I used the secret key to get into his house, take the mattress out of his room, cram it into my car, and return to school.

In order to get the mattress into the school building, I had to walk right by the principal’s office. Miraculously, no one stopped to ask why the heck I left school in the middle of the day or even why I was dragging a mattress around with me.

I left the mattress outside of C*’s locker with a note saying, “Hi, I’m C*’s mattress!” He had to deal with dragging his bed around school for the rest of the day.

Note: this prank leverages one of my favorite quirks of human behavior: no one questions confidence. If you act like you’re supposed to be doing whatever you’re doing, very few people will doubt you, even if you’re doing something eccentric. I was not supposed to leave school (or my classroom, for that matter), and I certainly wasn’t supposed to be dragging a mattress around the building. However, I acted like I was supposed to be leaving school and returning with a mattress. Because I behaved with (false) self-assurance, no one bothered to question the validity of my actions. For people unfamiliar with this particular form of con-artistry, it’s tempting to dismiss it. Before you do, I encourage you to experiment. It’s weirdly powerful.

Post Script 1: Before you feel too bad for the people in my life…

When you read about the pranks I’ve done to the people I love, it’s probably tempting to feel bad for them. You shouldn’t. My friends and family tend to be just as mischievous as I am. Here’s a short list of pranks that people have pulled on me:

  • C*, the same guy whose mattress I stole, spent four months growing a beard. He then shaved it, collected the clippings, and mailed them to me. To this day, I get nervous when a package arrives from him.
  • Years ago, a few friends stole one of my shoes while I was at a party. When I asked, “Where the heck is my shoe?” they said, “We put it in your car.” When I went outside I couldn’t find my car. Turns out the bastards had stolen my car too. When I finally found my car, it was filled to the brim with those annoying pink packaging peanuts which I had to wade through to recover my shoe.
  • My parents ended up getting Rob and I back for the Christmas Pecker prank. A few months later when Rob and I were home for dinner, they made an amazing pasta dish. Half way through the meal, we realized the noodles were shaped like penises. When Rob and I discovered what we had been eating we were surprised (to say the least).
  • To this day, my college friends have a game called “Bully Jason hour,” where the primary focus of conversation is (lovingly… it is loving, right guys?) teasing me and recalling the stupid shit I’ve done over the years. Most recently the focus of attention was an – admittedly quirky – decision to shave my chest in my mid 20’s.
  • There were a few months when every time I went out with a particular group of friends, they’d randomly rip my shirt off (like completely tearing it from my body) at whatever bar or party we were at. They took special delight in doing this when I was talking to woman. While it annoyed me at the time, I think it’s pretty funny now.

Post Script 2: The blue bird prank

The following prank is orchestrated entirely by my brother, and it’s one of the most clever practical jokes I’ve ever seen. Other than admiring it, I had no involvement.

I’ve already mentioned Rosie, my family’s pet bird. She’s white with flecks of yellow and bright orange. This is how Rosie normally looks:

Rosie loves to be sprayed with water from a hairspray bottle. She spreads her wings so you can mist her entire body.

At one point, Rob realized two interesting things:

1) Food coloring is entirely non-toxic

2) If you put enough food coloring into the bird’s spray bottle, it will dye the bird’s white feathers (I have no idea how Rob figured this out, but I admire his thinking).

One day, Rob was home alone, and he dyed the bird bright blue by spraying her with the water and food coloring mixture. Fortunately, the bird didn’t seem to mind or even really notice. This is how Rosie looked after Rob dyed her:

Rob then put a blue stuffed animal in Rosie’s cage with a note that said, “Which is the real Rosie?”

When my Mom came home, she only saw the stuffed animal and the note (Rosie was in a different room exercising her right to fly around the house), and my mom thought to herself, “Oh that’s a cute prank. Rob replaced the bird with a stuffed animal.”

Moments later Rosie – now bright blue – flew over to say hi to my Mom, who shrieked in confusion. She was screaming, “Why the fuck is the bird blue?!”

The funny part is that we all thought the food coloring would wash off the bird within a few days. Nope. She stayed blue for months.

A few years later, Rob reprised his prank and dyed the bird green to celebrate St. Patrick’s Day. Since then, my Mom has made Rob promise not to dye the bird anymore, but Rob’s only promise is not to “dye the bird any festive colors.”