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

UPDATE AUGUST 21, 2020: Quick heads up – my thinking on some of the topics in this article has changed. A lot. Please see points 1 and 2, here, for my latest thinking on the importance of expertise and education. Spoiler alert, I’ve done a 180. I think credentialed experts are of extreme importance. I’m also really glad that I finished my undergraduate degree. 


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

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

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

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

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

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

More on that in a moment….


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

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

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

But you didn’t.


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

Those are lazy excuses.

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

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

What happens when you finally start trusting yourself?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

What. The. Fuck.

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

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

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

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

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

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

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

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

Ok, so how do I actually start trusting myself?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Why I wish I dropped out of college…

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

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

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

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

You don’t need a net

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

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

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

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

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


  1. Yeah, I know that pretty much all companies claim to value innovation and thinking outside-the-box. When you look at how companies behave though, it becomes clear that talk of innovation and creativity is mostly hot air.
  2. Estimating the reproducibility of psychological science
  3. Comment on ‘Estimating the reproducibility of psychological science
  4. I’m tempted to cite a source here, and you’re probably reading this because you’re looking for sources. But what good would that really do? The whole point is that science,“studies,” and citations are less reliable than we’ve been led to believe. If you really need a source, check out Antifragile by Nassim Nicholas Taleb. Better yet, research the issue yourself instead of trusting my research. Even better still, go out into the world and have a direct experience rather than losing yourself in endless contradictory studies.
  5. If you’re unfamiliar with “The Emperor’s New Clothes” by Hans Christian Andersen’s: two weavers promise the emperor a new suit of clothing. The clothes, the weavers promise, have a special property. They can only be seen by people who are intelligent, loyal, good, etc. But it’s a trick. There are no clothes at all. Since everyone wants to be considered a good person (including the emperor), they all pretend to see the imaginary clothing, except for a small child who asks why the heck the emperor is wandering around naked.
  6. I got my first clients not by using my credentials, but by using my network, cold calling, making myself easy to hire, offering a money back guarantee, and hyper-exceeding expectations.

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9 thoughts on “Don’t trust me. Trust you. A guide to overcoming self-doubt.

  1. I enjoy reading your stuff Jason. I am forever thankful you crossed paths with.. and took a chance on.. Anna!

    1. Thanks so much for the kind words Nancy. And honestly, I’m glad that Anna took a chance on me. 🙂 She’s my secret weapon!

  2. I loved this so much.
    I’ll start experimenting in restaurants! I always change my mind several times before ordering.

    I’m a college dropout, and at times I thought “hmm, if I persisted and got a bachelor’s degree in [completely irrelevant field], maybe getting into a master’s program of [field I was actually interested in] would be possible?” – but honestly, I don’t have the time, nor do I want to spend the money on going back to school. I’m done with that.

    I realize that every single thought of that nature was undermining my confidence in the decision that I made.
    You put it so symbolically, and now I want to honor that symbolism too.
    Quitting university was what lead me to this path of becoming an entrepreneur. Maybe I wouldn’t be here now if I stayed.
    I trusted myself, and I did well.

    1. Thanks, Nela. I’m jealous that you’re a real dropout. 🙂 So glad to hear the article resonated with you. Good luck on the path to trusting yourself… it’s a doozey in the best possible way.

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