5 Ways Therapy Makes You A Better Entrepreneur (and Human Being)

“Plan on seeing 12 different therapists before you find one. It’s important. As my friend Todd Glass said, when people say like, ‘Oh, I can’t afford therapy.’ Get a shittier car! It’s important! I like growing and changing with new information. I think it’s important.” — Sarah Silverman

It’s Thursday. That means, for me, that it’s therapy Thursday (well, for me it’s every other Thursday — good therapists cost $$$ and if I could afford to go weekly I would, but for now I go every other Thursday).

If you’ve followed me for a while, you know I’ve struggled with my mental health. You know I’m willing to explore myriad ways to address my mental health, including psychedelic drug therapy. You know I’m always looking for ways to use entrepreneurship to find more joy and fulfillment in life, for me and others.

My efforts and self-explorations are all in service of the ultimate goal: to become a better human — and in the process a better husband, a better father, a better entrepreneur, a better friend, and better leader. And many other betters.

Engaging in therapy and other practices of self-exploration helps me uncover hidden patterns and the many ways my past and patterns control my behavior and how I view and relate to the world.

It’s work that’s difficult to do on my own; it requires a degree of self-awareness that I currently lack without a professional’s guiding hand.

I have zero shame in talking about seeing a therapist.

I have no shame in talking about my mental illness.

It’s time for us all to get over that bulls@#$. Being a good human is hard: we’re all — every one of us — layered with so many years of trauma, guilt, shame, pain and expectations that it’s often a struggle just to show up as a half-decent, let alone good, human being.

Therapy helps us peel back those layers, heal our wounds, and rediscover our true selves. I wish therapy were a million times more accessible, a million times more affordable (or free).

I wish everyone could have someone to talk to on a regular basis: someone qualified and strong enough to hold up a mirror to them and point out where those hidden layers and wounds are causing pain to themselves and others.

We’re getting there… slowly. One day we’ll reach a point in the conversation where we can talk freely about our mental health struggles and the work we’re doing with our therapists, and it’ll become so normal our politicians will talk about how we can make it freely or affordably available to everyone who desires to do the work.

Until then, all I can do is my part and get on my soapbox.

Because so much of what I write about is, as I put it, at the intersection of entrepreneurship and fulfillment, I want to talk about the ways that therapy makes you a better entrepreneur and human being.

So without further ado…

[note: when I mention ‘therapy’ below, I mean therapy provided by a good, qualified therapist. They’re not always easy to find, and even a good, qualified one may be a bad fit for you. Don’t get discouraged if you don’t have a great connection with a therapist or get breakthrough results in the first 2 or 3 sessions.]

5 Ways Therapy Makes You a Better Entrepreneur (and Human Being)

1. Therapy makes you a more compassionate human.

Doing the deep work of self-exploration helps you uncover your own pain and trauma, and discover the ways in which they guide and control your behavior, especially in relation to other humans.

In so doing, you begin to open up to the idea that, lo and behold, other humans carry pain and trauma, and their behavior just might not be because they’re a@#holes, or lazy, or whatever other labels you’re tempted to put on them.

Then, through this process, maybe — just maybe — you become a more compassionate human being.

And let’s face it, the world could use more compassion and understanding these days.

2. Therapy makes you a better leader.

“Leadership grows like tall trees. It needs both toughness and flexibility — toughness for accountability — flexibility to adapt changes with a compassionate & caring heart for self and others.” 
Amit Ray

Dealing with your s@#$ will inevitably make you a better leader. For starters, you’ll become more compassionate and understanding (see above).

Companies need compassionate leaders, and your staff want an understanding boss. One of the deepest human needs is to feel seen and understood and if you can address this need, the more your staff will want to go the extra mile for you and the company.

And being compassionate to yourself will ultimately lead you to make better decisions as a leader.

You’ll also show up freer and happier, and the ripple effect of that throughout your company can’t be overstated.

3. You focus on what’s important.

“Without self-awareness we are as babies in the cradles.” — Virgina Wolf

As you peel back the layers, therapy inevitably helps you discover where those layers contain subtle and not-so-subtle messages of what your life ‘should’ look like and which path your life ‘should’ take.

These messages come from often-well-meaning-but-nonetheless-damaging parents, teachers, friends, family, mentors, and others. Without self-reflection, these messages can dictate the entire course of your life (how many doctors and lawyers are miserable because they entered those fields to please their parents?).

As you continue to explore and peel back layers, eventually you will discover some kernels of truth — beyond all the shoulds and dictates of family and society — that resonate deeply with you. These kernels are the vestiges of your true self, before the world got hold of you and covered you in bullshit.

Listen to those kernels. Then focus on what’s important to you.

4. You feel more aligned with your work.

Once you being listening to those kernels of truth, you’ll feel more aligned. Your decisions will come more easily. You’ll learn how to use your company in service of your truest self, and in service of others.

I can tell you that feeling aligned with your work — in other words, feeling like your work resonates with who you really are, what you want in life, and what your values are — is one of the most freeing and wonderful feelings in the world.

When you feel aligned, others feel it too. They’re drawn to you. They want to discover their own alignment. They want to do business with you, spend time with you, and be in your orbit.

Taking the time to get aligned doesn’t necessarily mean selling your company so you can solve global hunger. Within your company there are myriad ways to find more alignment. Sometimes it can simply be showing up as a better, more compassionate boss and a champion for your staff, no matter what product or service you provide.

5. You get more comfortable not wearing a mask at work.

Let’s face it — we all wear various masks throughout our day, based on who we think other people want us to show up as: the confident leader, the visionary, the badass, etc.

Sometimes those masks are necessary: you probably don’t want to show up to an investor meeting being super-vulnerable and open.

But if you show up to work every day wearing a mask (and by ‘mask’ I mean hiding your true self), it’s:
a) exhausting (like really exhausting)
b) you lose opportunities to truly connect with people.

Through the work of therapy, you’ll learn to get more comfortable dropping the mask and being more vulnerable and authentic. You’ll develop less self-criticism and more compassion for those more vulnerable aspects of yourself, and more bravery in showing them to the world.

And I guarantee that will help you develop stronger and deeper connections with others, and be less exhausted in the process.


I’d love to hear from you…Are you in therapy? Have you thought about it? What have your experiences been like? There’s a ‘response’ feature down below, and I’d be honoured if you used it.

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P.s. I hope you’ve enjoyed this post and found value in it. If you’re interested in exploring topics like this further, there are a few ways I might be able to help you:

1. Join me and your fellow entrepreneurs at one of my upcoming Mastermind Adventures events, where we explore topics such as these and where you can connect with, learn from, and have crazy adventures with your fellow entrepreneurs.

2. Join my weekly mailing list and let’s talk about the entrepreneurial journey and how to find fulfillment and joy along the way.

3. I create a bit of space in my schedule to coach overwhelmed entrepreneurs (typically leading companies from $500K to $5M) on how to get out of their team’s way, free up their own time and have self-managing companies that create less stress and more joy in their lives.

4. If you’re in Toronto, join my event list and get notified about upcoming events I put on for entrepreneurs, like workshops, dinners and get-togethers.