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.”

Blogging year 1: how I went from 0 to 66,029 readers and what I learned along the way


On March 14th, 2017 JasonConnell.co turned one year old.

In that time, readership has grown from a few hundred monthly readers to, 66,029 as of last month. Along the way I learned much more about life, writing, and marketing than I ever expected to. Here are the big takeaways:

The life lessons

It’s ok to have haters, what matters is how you handle them. The trick is to be thoughtful in how you deal with them. Personally, I try to avoid engaging. When the haters manage to get under my skin, which happens more often than I’d care to admit, I usually call my brother who is quick to comfort me and mock the offender.

While it’s tempting to engage with your detractors (including killing them with kindness), I’m not sure there’s a huge advantage in doing so. Both time and energy are finite resources; I’d rather channel mine into something more productive than arguing with people who think I’m an idiot.

If you can see the first step, take it – even if you can’t see the second. When I launched JasonConnell.co I only knew two things:

1) I was done being a professional speaker (at least for a while)

2) I really wanted to invest my time in writing

I had no idea where my income or readers would come from, I just knew I needed to do it. Rationally, that doesn’t seem like enough information to make a big life decision, yet, it felt right.

So here’s how it all played out:

  • Forty-four days after launching this blog my first coaching client came to me.
  • After about three months, I was making enough to support myself.
  • After six months, two partners approached me about consulting for authors and thought leaders who want to become professional speakers.1 Right around the same time coaching started to feel wrong,2 so I quit coaching to focus exclusively on writing and consulting.
  • Today, my life is better than it’s ever been. Had I not taken that first step because I was unable to see the second, I wouldn’t have gotten to this moment.

A very related lesson: sometimes you have to walk down the wrong path before you can find the right one. Though full-time coaching wasn’t right for me, I had been curious about it for a few years and needed direct experience with it before I could let it go.

Without good people in your life, success will feel meaningless and failure will feel crippling. If you have the audacity to chase your dreams, brushes with both success and failure are virtually guaranteed.  The question is, how do you handle them? Most people are quiet about their successes and even more quiet about their failures.

I’ve learned that both moves are mistakes. Success should be celebrated and shared with the people who contributed to it. Celebration makes everyone feel good and amplifies their energy, setting everyone up for an even bigger success in the future. Failure, too, should be shared – even if it’s only to help dilute the feelings of inadequacy and brainstorm a new approach.

Play the long game. Though it’s taken me a long time realize this, I’ve learned that moving slowly and thoughtfully is the fastest way. While it lacks the adrenaline of chasing overnight success (which is probably a myth anyways), it offers stability, abundance, and a calm sense of control.

The writing lessons

3rd draft of the article you’re currently reading

Writing well is much harder than I expected. When I started, I arrogantly assumed that I’d be able to crank out decent writing without much effort. Boy, was I wrong. In reality, it takes me 2-3 hours per page before I’ve produced anything worth reading.

Any given article will go through at least five drafts before it’s published. In most cases, the process looks like this:

  • Write a shitty first draft (and by shitty, I mean really, really shitty… most of the sentences will be rewritten in the next draft)
  • Edit the first draft on my computer
  • Print the new draft and edit it by hand
  • Type up the edits and then send them off to V* who looks at content, syntax, grammar, marketability, and usefulness to the reader
  • V* returns her draft to me
  • Finally, I print the article, read it aloud to myself – which really weirds the people in my coworking space out – make any final adjustments, and then publish it

After that I’ll take a few days off of writing and start again.

Before sitting down to write, I get neurotic and distracted. A creative ritual helps tame the demons. The ritual seems to act as a signal to my mind to be focused and creative, and it facilitates the surprisingly difficult transition from not writing, to writing.

Though the ritual changes every now and then, my current process is:

  • Put my phone in airplane mode and turn off the Wi-Fi on my computer
  • Go for a quick walk to clear my head and start brainstorming
  • Put on a pair of special, writing-only headphones and blast LCD Soundsystem on repeat.  My go-to choices are “45:33” or “Daft Punk is Playing at My House” on repeat.
  • Write (my favorite platform is WriteRoom)
  • After roughly 40 minutes of focused work, I’ll take a quick break to check my phone and email, and then resume writing

When writing about someone, assume that she’s going to read it. When writing about yourself, assume that everyone you know will read it. When I started blogging, I assumed that most of the people I know wouldn’t read my work and that I was free to write about them with minimal repercussions. That was a bad assumption. It caused fights with a few people close to me, and at least one friendship.

Do all my friends and family read my stuff? No, of course not, but assuming that they do prevents me from being reckless in how I portray them.

At a deeper level, I realize that when I write about someone, I’m forcing them into the public arena. It can be extremely uncomfortable to read about yourself if you’re not expecting it.

Get someone to look at your stuff before you release it to the world. V* has saved me from making an ass out of myself more times than either of us can count. She’s also improved my writing by leaps and bounds. Even if you don’t think you need a devil’s advocate it’s calming to have someone you trust look at your work before it goes live. The real trick is to give that person permission to candidly tell you that your work sucks.

The marketing lessons

A caveat: you may not want to take my marketing advice. While I’m proud of my readership (y’all are AMAZING!), plenty of other bloggers have built larger audiences in less time. What I’ve arguably learned to do better than most is appeal to a very specific demographic: people who are intelligent, cultured, and more influential than average.

Going micro-viral sucks. On January 8th, I was averaging about 900 readers per day.  On January 9th, I published this article and suddenly averaged 20,000+ readers per day for about a week.

The unexpected spike in traffic was much more destabilizing than I imagined. My inbox exploded, multiple people threatened to sue me, and the comment section was unmanageable. I became addicted to my phone, even waking up in the middle of the night a few times to check email, comments, and traffic.

At a deeper level, the success made me neurotic. I worried that my new readers would slip through my fingers. The pressure to produce another viral article nearly caused a panic attack, leading me to write and promptly delete sentence after sentence for well over an hour.

Pick a simple marketing strategy that makes sense for you, and then stick with it. Marketing is infinitely complex and runs the risk of consuming as much time as you allow it.

When I started JasonConnell.co I had to consider whether or not to run ads. If I did, Facebook or Google? Should I bother with SEO? Do I prioritize reader experience, conversion, or traffic? How frequently should I post? Do I use Aweber, Infusionsoft, Mailchimp, or something else? And we haven’t even really scratched the surface here.

In my case, I decided to prioritize the reader experience while consistently writing the best longish articles I could and nothing else. The bet I placed was that consistent, high quality work might be able to stand on its own, even in today’s hyper-saturated marketplace. Literally every reader and client I’ve gotten from JasonConnell.co came from that bet. To date, I haven’t invested any time in SEO, sales funnels, or social media advertising.

Could I get more traffic if I optimized my site, bought Facebook ads, and spent more time guest posting, syndicating, and interacting with online communities? Absolutely, but that sounds exhausting. For me, it’s not about maximizing success; it’s about building a life I love.

Reminders to myself part II: notes for the good times

“The proper response to life is applause” –William Carlos Williams

As I write, I find myself in an unfamiliar spot. All of the elements in my life that I really care about? They’re behaving beautifully. Work is going great, my social life is (almost) too much fun, I’m building a relationship with a woman I adore, and I’m in the best mental and physical shape of my life.

It felt like just yesterday I was trying to keep my head above water. I wasn’t sure if I could make a living as a writer and consultant. My social life was uninspired, and my sense of self was rapidly evolving (more on that in a future article). While coping, I made a list of 10 reminders to myself. These reminders acted like the eye of a storm, by creating the emotional and mental space I needed to stay on track.

Today, I find myself in need of a new set of reminders.  As before, I share these to cement my own understanding and in hope that they may also serve you. These new reminders revolve around time, impermanence, surrender, and the inner child.

1) Loosen your grip. While I certainly appreciate the joy and abundance that defines this phase of life, I know that everything ebbs and flows.

My instinct is to hold onto it all with a tight grip, lest it slip through my fingers.

I consider taking on as many clients as possible and staying neurotically organized so that I don’t a drop a ball. I’m tempted to say yes to every ski trip, party, and brunch I’m invited to. I think about saving as much money as possible and being extra disciplined with my diet and exercise.

But seriously, who am fooling? Trying to hold onto all of this will only prevent me from fully engaging with the amazing things happening right now.

Besides, a tight grip is an act of scarcity and paranoia. It’s a vote against my own ability to build a life I love and a denial of the flow that defines the human experience.

I’ll trust that when I drop a ball or say the wrong thing, it probably wasn’t that important to begin with. I’ll trust that the important stuff will resurface when I miss it the first time.

The real skill is learning to be ok with everything you love slipping through your fingers. Because whether you like it or not, all of this will eventually end. It’s important to enjoy it while you can. So right now, while I’m in the pocket of my own life, I’ll loosen my grip and use the extra energy to revel in it all.

2) Widen your lens. Loosening your grip allows you to celebrate the impermanence of everything that life offers. Widening your lens allows you to access and influence the entire arc of life.

If you actively shape your future from a moment when your life is already amazing, you gain access to a creativity, clarity, and confidence that’s otherwise elusive. (And if the present isn’t amazing, you can always do something small to improve the quality of this moment. Doing so will improve the quality of the next.)

When you work to shape your future, approach it with a bit of assumed power and playful humility. Your aim is to build something beautiful for yourself and the world.

3) Let love in. Countless people – possibly even most – struggle to feel the love that already exists in their lives. They’ve been trained to bat it away. I certainly have. We tell ourselves that we will be more lovable in the future than we are right now.

We behave as though we need to cross some invisible line before we can truly surrender to the joy already in our lives. We act like we need to make enough money, accumulate influence, start a business, travel the world, be more disciplined, or hit a target weight before we’re really worth giving a shit about. But that’s just not true. Doing so reinforces the delusion that you’re not ok as you are. It trains you to reject the love and respect that already exists in your life.  

In reality, you’re surrounded by love, joy, charm, and whimsy. You just have to let it in.

Doing so is strangely vulnerable. It requires trusting people and letting them see you, rough edges and all. It requires opening up. You have to let the compliments, praise, and smiles affect you. You have to remember what someone is really saying when they kiss you, hug you, text you, or give you a gift.

It requires surrendering to what is.

4) Spend some time playing with your inner child. Your inner child has been yearning to come out for years. It seems cruel to keep him caged up, pretending that you’re more mature, sophisticated, confident, and enlightened than you actually are.

Let the kid play a prank. Or have a Nerf war. Or stay in bed. Or delight in a dinosaur toy. Or drink too much caffeine. Or run wild, barefoot in the park. He’ll love you for it, and as far as I can tell, the more your inner child loves you, the better everything goes. Besides, I’m pretty sure he’s the cause of your current success anyways…

What happens when you’re completely honest for a year?

October 2016: M* is upset with me for a good reason. Two reasons, actually.

Reason number 1: I’m in town and I didn’t call her to hang out.

Over the course of our 12-year friendship, M* has come to visit me countless times. I’ve never visited her.

Even so, the lack of balance isn’t why she’s upset. She’s upset because she recently moved to Boston and learned – via a Facebook photo – that I’m nearby and didn’t let her know.  

She calls to ask, “Jason, why the heck didn’t you let me know you’re in town? That stings.”

Reason number 2: I answer her question honestly.

My mind races with excuses. I could tell her, “I’m not actually in Boston! That photo was taken ages ago,” or “I was going to surprise you,” or “I was actually just about to call you, OMG!!!”

But these would be lies

Instead, I tell her the truth: I forgot she lived in Boston.

For the past few years, she’s lived on the West coast; her move East slipped my mind.

She was hurt that I forgot about this huge life event.

Then, something crazy happened: I realized that even though she was upset with me in the moment, it didn’t change the fact that she still wanted to be my friend.

For many people, this wouldn’t be a profound realization, but for me, it was. The people pleaser in me is forever worried that if I upset someone, they’ll no longer think I’m worth their time.


My personal challenge for 2016 was to go the entire year without telling a lie, blurring the truth, or deceiving people.

This meant that I needed to be as honest as possible in both word and action. It also meant that I needed to prioritize speaking my truth over being agreeable.

The commitment to truth profoundly changed my life. In this article, I’ll cover how the challenge worked and how it affected my business, relationships, and sense of self. I’ll also explain how you can do your own honesty challenge and the results you can expect.

Lying is self-loathing (and we all do it)

Everyone lies.

We exaggerate our stories to make them better, claim to be busy to get out of commitments, and act like we love our friend’s shitty poetry.

We round up when discussing our height, income, and bench press, and we round down when asked about our weight, ETA, and time spent watching TV.

We lie through our actions by staying in dead relationships, taking calls from people we don’t care about, and pretending to give a shit.

We lie to ourselves too; claiming that we’re happy, confident, and just fine when really, we’re fucking miserable, misguided, and apathetic.

The question is: why do people lie?

We lie because we are afraid that we aren’t worthy of love. We lie because we fear that people won’t take us seriously. We lie because we are uncomfortable with our reality. We fear that if we show the world (and ourselves) who we truly are, it won’t go well.

So we pad the truth, blur the lines, omit a few details, avoid the hard conversations, and keep our mouths shut. The hope is that this fictional version of who we are will be worthy of love and that no one, ourselves included, can tell the difference between the two.

While lying offers emotional protection, it also makes it difficult for people to love the real you. You become suspicious of others’ affection because you can’t tell if it’s directed at you or the person you’re pretending to be.

When you commit to telling the truth, you create the opportunity for people to love the real you.

Blurry realities: the 2 ways we lie without realizing it

Telling the truth is more complicated than is immediately obvious. Whenever we blur our reality by providing vague answers (as opposed to giving crisp definition) we are being deceptive.

There are at least two ways that people blur reality without understanding they’re lying.

1) Allowing the truth to lead to false conclusions. You can easily deceive people without ever lying to them.

For example, the following is true: I make more money per hour than a doctor.

This statement should lead you to believe that I also make more per year than a doctor, but I don’t. I don’t even come close.

I spend about five hours a week doing billable work. Doctors spend 40+ hours/week doing billable work. They make way more per year than I do, even though I make much more per hour.

2) Lying through omission, false agreeableness, and avoidance. Lying through omission happens when we intentionally withhold information or misrepresent our reality.

We’re all familiar with obvious omissions, like failing to tell your accountability buddy that you ate half a pizza last night simply because she didn’t ask. But far more impactful are the subtle lies of withheld information that quietly define our lives. These generally happen through action or inaction, rather than words.

If you are pretending to agree with someone or avoiding hard conversations, you are lying through omission by withholding your truth.

For example, if you’re in a dead relationship but acting like everything’s fine, you’re lying to your partner. You’re avoiding the hard conversation the two of you need to have.

How the year of the honesty challenge worked

With all of that in mind, here are the guidelines I set out to follow for the year of honesty:

  • I am not allowed to lie, either blatantly or through blurred realities. If I do lie, I must correct myself as soon as I realize it. I was at dinner with a friend, and he was considering the kimchi soup, which I really wanted to try. I said, “I hear that’s really good. You should get it!” In reality, I hadn’t heard anything about the soup; I just wanted him to order it so I could eat some. When I realized I lied to my friend, I said, “Shit. Sorry. I lied to you. I haven’t heard anything about the soup. What I should have said is that it looks awesome, and I want you to order it so I can try some.”He ended up ordering the soup because he liked the idea of sharing.
  • No white lies. Many people believe that telling white lies is polite and compassionate. While I understand the logic, I think it’s flawed. When we tell a white lie we are shielding people from reality. If they already know the dress makes them look fat and we lie about it, we’ve undermined their trust. If they genuinely don’t know whether the dress makes them look fat and we deceive them, then we’ve held them back from the chance to understand themselves and improve their lives.
    Of course, frame and perspective should be taken into consideration. There’s a very real difference between, “Good lord you look fat” and, “Well, you look beautiful period, regardless of what you’re wearing, but yeah, that dress doesn’t seem to flatter you as much as the black one does.”
  • Speaking my truth is more important than being agreeable. Though I never had much of a problem speaking my truth on stage, where I was rewarded for it, it’s always felt risky in my personal life. I feared that if my perspective veered too far from my friends’, I might upset them, and they would grow uninterested in spending time with me. In order to remain fully in integrity, I needed to start speaking my truth even when it was uncomfortable.
  • I will not use “honesty” as an excuse to be unreasonable, anti-social, or a dick. When a clerk asks, “How are you today?” I will not unload my problems because I want to give her the “honest” answer.
  • It’s ok to say, “I’d rather not answer that” when people ask questions I’m not comfortable with.

As expected, following these guidelines became increasingly easy as the year went on. What I didn’t expect was just how profoundly they would affect everything in my life…

How honesty affected my business

Deals closed more quickly. As a consultant, I help people build six figure speaking businesses. Being as honest as possible forced me to set precise expectations during sales calls. I suspect that the high level of clarity differentiated me from my competitors.

For example, nearly everyone asks, “What sort of results are your past clients getting?” One honest answer is, “All of my clients are getting paid speaking engagements.” While this is accurate, it’s also vague.

The year of honesty forced me to offer a much more precise answer. Instead of saying, “I have a 100% success rate,” I started saying, “All of my clients have gotten paid speaking gigs. Most get gigs within 6-7 weeks, and several made over $100,000 in their first year. Still, I can’t promise results like that. Luck is a factor, as is how much time you commit to this. If you do the work, there’s a good chance you’ll land gigs within a few weeks. If you sit around expecting me to do everything, you’ll waste everyone’s time.”

This level of precision seemed to inspire trust in my prospective clients, many of whom signed within a week.

It forced me to close a very lucrative line of business. For a hot minute last year (well ok, six months), I worked as a life coach. I charged a lot for my time and my clients seemed happy to pay it.

It was interesting and engaging work. I enjoyed learning about my clients’ inner realities and helping them step fully into their lives. As time went on, I noticed that many of my clients were treating me like a psychologist, and I was allowing them to do it.

I realized that the issues my clients needed help with were better addressed by a mental health professional. Though I could have kept working as a coach, it would have been deceptive, because I knew I wasn’t truly qualified. So I closed my coaching practice despite the significant income it was generating.

Doing so opened up tons of space in my calendar and allowed me to focus on helping people build speaking businesses. I’m much better at working with speakers than I ever was as a life coach, and I enjoy it more. Perhaps unsurprisingly, the revenue from consulting is outpacing revenue from life coaching.

PSA: my personal opinion is that 99% of the life coaching industry is a crock of shit. Most “life coaches” use their practices as a way to avoid confronting their own demons. Their rough – if unspoken – logic is, “If people hire me to help them with their lives, my life must be awesome.”

If you’re thinking of hiring a life coach, I urge you to consider hiring a therapist instead. Yep, finding a good therapist is hard. I get it. But therapists have extensive training and ethical guidelines that they’re required to conform to while coaches don’t. More on why I think life coaching is a bad idea here.

How honesty affected my relationships

I got closer to the people who mattered. I used to have a nasty habit of holding grudges. I feared that if I had a hard conversation with someone, they would no longer want to be my friend or that their love for me would fade. So instead of asking for what I needed or expressing difficult emotions, I compartmentalized.

I realized that bottling my feelings was a form of dishonesty; it led people to believe that I felt differently than I did. I needed to start getting real, even if it scared me.

Doing so was – and is – hard. Sharing more of myself does create the opportunity for people to learn unappealing things about me. It may even shine light on undiscovered deal breakers between us, but openness also creates the opportunity for real connection. As I learned to be increasingly open with the people in my life, I ended up feeling closer to many of them than ever before.

I learned that raw, vulnerable honesty is the only path to true intimacy. This doesn’t mean you need to open up quickly, and it certainly doesn’t mean that you need to open up to everyone. It just means that if you want real relationships, you have to take the risk of showing people who you really are.

I finally let go of the people who I never liked all that much. There used to be people in my life who I didn’t enjoy spending time with. I’d return their calls and emails from a sense of obligation, not excitement. I realized that this too was a form of lying, and I slowly worked to reshape my circle so that it was filled with people I genuinely enjoy.1

How honesty affected my sense of self

“Live by the foma* that make you brave and kind and healthy and happy.
― Kurt Vonnegut, Cat’s Cradle
*Harmless untruths

When I started the honesty challenge, I assumed that the hardest part would be being honest with others.


The hardest part – by far – was being honest with myself.

Like many people, I unintentionally filled my life with gentle lies designed to protect myself from the harshness of reality.

Two of the more profound lies I was telling myself:

  • I love that I was a child entertainer – it made my life better
  • I have a healthy relationship to money

The truth about these issues is much more complicated:

  • My experience as a child entertainer was horrible. I hated it. It left permanent scars that I still feel today.
  • My relationship to money was toxic. Fortunately, when I stopped lying to myself, I was able to improve it dramatically.

Admitting these things to myself was disorienting. It’s weird to wake up and realize that I’m not the man I thought I was.

My life is messier now that I’m more honest with myself. The artificially clean lines and charmed personal narratives have fallen away. But in their place, I find myself. Happiness takes less effort and I don’t hold myself back or doubt myself as much as I used to.

Of course, it’s easier to keep casting illusions and denying your reality, but doing so disengages you from your life. It embeds pain and friction so close to your core that you don’t even notice it.

When you find the courage to be honest with yourself, life become expansive. You start to learn that in many cases you are already as talented, lovable, and capable as you’ve secretly hoped.

You also learn that sometimes you fall short, that you’re imperfect, and that not all of your dreams will work out. And that’s ok. That just makes you human. 

Through it all, you learn that you’re ok and that you can handle whatever is thrown at you. You learn that you have people – good people – to comfort you when you need them. You learn that people love you for you, not for the person you’ve been pretending to be.

So 2016 is over… am I still doing the honesty challenge?


Being honest has improved my life more dramatically than any other practice I’ve experimented with. It’s a fast and consistent (albeit difficult) path to self-love. It’s phenomenal for building intimacy. It makes life vivid.

I felt more alive and engaged in 2016 than ever before.

My recommendations to you…

Honesty has a weird habit of starting to feel like a super power when you practice it. It seems to draw the right people and opportunities to you, while speeding up the flow of life.

If you’re interested in doing your own honesty challenge, I suggest experimenting with the behaviors below. For most people, it will be easiest to tackle one change at a time. Once the new behavior becomes natural, move on to the next.

  • Eliminate white lies
  • Eliminate lies of omission
  • Answer questions precisely (as opposed to giving vague answers) or say, “I’d rather not answer that”
  • When forced to choose between speaking your truth and being agreeable, lean toward speaking your truth
  • Stop lying in entirety

Keep in mind that honesty can be more difficult and complicated than most people expect. We’ve all been conditioned to lie to ourselves and the world. Be sure to be forgiving and gentle with yourself as you evolve.