Taking off the Ring of Power

Why founders resist the very things that will heal them

Mar 22, 2024

Welcome Entrepreneurs. I’m so glad you’re here.

The other week, Jason, Micah, and I were having a conversation about change, and we noticed something: each in our own way, on the precipice of making a profound shift toward our own health and sanity, we hesitated.

“If I actually heal myself from my anxiety/fear/depression,” we each found ourselves asking, “Will I lose the superpower that has made me successful?”

Jason told his story here. Micah told his here.

Today I’m going to tell mine.

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Taking Off the Ring of Power

Once upon a time, I was sure I would write the next great American novel. Because of my major influences – Hemingway, Bret Easton Ellis, Chuck Palanhiuk, Hunter S. Thompson, and Irvine Welsh – what that meant to me boiled down to four key practices:

Write every day
Read every day
Do interesting shit
Drink a ton and experiment with drugs

While I haven’t finished a novel (yet), during that time, I wrote some very affecting essays and short stories, one in particular that made people give me a look like “holy shit this is good” combined with “this is also a bit insane.” I dug that.

Unfortunately, in addition to the writing, those practices took me down the very deep elevator shaft of addiction, culminating in alcoholism and a cocaine/Adderall (we called it “Diet Coke”) habit. I hit bottom, and I thought I’d never be able to crawl my way up to the light.

I did. Eventually. With a ton of work. But I remember during those early days of recovery – walking, biking, or hitching rides to meetings every day (losing your license is the worst), brutally fighting the addict inside me to stay in the house each night and away from trouble – this little voice inside me said that maybe I shouldn’t do all this work to recover. Maybe I should go back to drinking.

“If we don’t drink,” it said, “we won’t be able to write anymore.”

Once you get stuck in this paradigm, I found, it makes it hard to get clean. It feels as if it might be better to be sick and productive, than healthy and devoid of creative power.

But ultimately I knew better. And you know better. Whatever you’re addicted to, you know what it’s costing you to continue the way you are, and yet you pay that price, often hurting not only yourself but those around you, because you think the alternative will be worse.

It takes heroic sacrifice to do the work to heal yourself, even when you know it’s for the best.

Healing from the startup drug

Once I got sober, I thought I had escaped all that. But after fifteen years of building and leading companies, this same dynamic reared its head during my startup journey.

After leaving the company I’d built and scaled, I told Laura: “I’ve been running my ass off my whole life, thinking I was going to catch something that would make me feel better. But I’ve caught so many of these things I can’t convince myself anymore that there’s anything I can catch that will actually fix me. The way I figure it, if I’m not running toward something, I must be running away from something. So I’m going to stop running, let it catch up, and see what happens.”

I hit the brakes on my manic pursuit of achievement, and in the stillness, I found out what had been driving me all along. I saw the belief, the certainty, deep down, that I was worthless. And the conviction that, if I only achieved enough, I could fool everyone else into thinking that wasn’t true. I saw the way I’d been chasing the admiration of everyone around me for my whole career, like a true addict, and I was disgusted.

As with alcoholism, the path to recovery starts with hitting your “rock bottom.” What they don’t tell you is that rock bottom isn’t an event. It’s a choice. And I chose to make that moment my startup rock bottom.

And as tends to happen, at the moment I finally let go, the perfect resources began to appear.

Around this time, I read a book that laid out the score. Gifted kid learns at an early age that they can control others’ perceptions of them, and therefore others’ reactions to them, based on their performance. They tell good jokes, their mom laughs. They play sports well, their dad smiles and tells them they did well. And as Alice Miller writes in The Drama of the Gifted Child, the kid learns to become what she needs to become in order to receive the love she craves. Because of this talent to adapt, gifted kid also learns that who they are at their core is not worthy of love. That they must change/grow/evolve/strive to be ok.

Oof.

In that blessed stillness between companies, I committed to doing the work to break free and earn the right to live my own life. But then, that voice again.

“What happens when you’re finally ok and you no longer need to prove yourself? Why would you even get off the couch? Why would you be motivated to do anything?”

Fortunately, I recognized it. And like two decades before, when I got sober, the stakes were high enough that I was willing to make the sacrifice. I took off my Infinity Gauntlet. I dropped my Ring of Power into the volcano. I surrendered my striving and trusted that I would be ok.

And it was. It was better than ok. For the first time in my life, I felt free.

And, in the wildest of all surprises, I felt excited to create.

A note on resistance

In my work with founders, when a person is ready to do the work to free themselves of the core belief that drives them – many times the familiar I’m not good enough, but also other permutations like I’ll show them, they’ll never beat me, and the like—founders hesitate. They think that once they heal, they’ll lose their superpower.

I understand the hesitation. Now twice over. Is it really better to be healthy if you lose your ability to create?

I can promise you that it definitely is.

When I first got sober, my instinct was to discount the work I’d done drunk or high. To make it out to be somehow bad, or wrong.

But like any time you find one part of yourself resisting another part, this resistance itself causes tension inside your system that will slow down the transition process.

I looked back at my writing, and saw the echoes of a time I was desperate to move on from. And so, for fifteen years, I didn’t write anything.

It wasn’t until I went back and reread my old pieces, and actually appreciated them for what they were – great pieces of writing – that I felt ready to start again.

Similarly, once you see the possibility of powering your accomplishments through something else, it can easily make fear-powered effort seem bad by comparison. Like something you should be ashamed of doing, and should actively try to stop. And this perspective can create resistance in your internal system, and slow the process of finding a better motivation.

The reality is that you’ve needed that type of dirty fuel to power you through life. To power you through however many accomplishments and setbacks and teach you what you’re actually capable of. You wouldn’t be here without it.

On the way to a cleaner motivational future, one characterized by actions taken from love, purpose, and presence, far better to thank your fear and your anxiety for their help along the way.

Because on the other side lies a motivation, an energy – a muse, for the artistically inclined – that feeds on something different. It’s equally powerful, but without the same cost.

What it looks like to move beyond fear/anxiety based motivation

These days I like to think of those fear/anxiety/anger based motivations as diesel fuel. They work, for sure, but they pollute the hell out of your environment (both internal and external). When you’re first driving a diesel truck and creating industry, you’re getting everywhere you need to go, and it’s a revelation. It’s hard to imagine an alternative, or that there needs to be one.

But eventually you see the costs, and you look for an alternative. And there is an alternative. In fact, according to the Conscious Leadership Group (and my own lived experience) there are at least five.

Purpose
Play
Partnership
Presence
Love

Each of these emotions are just as motivating as anxiety without any of the cost. In fact, like nuclear fusion, they are self-replenishing. And the surprising fact is that most of my clients have already experienced one or more of them.

Purpose, they’ve experienced at the birth of their company. When they identified a worthy goal, and set themselves to achieving it. When they began their journey, not to satisfy their own egos (or not exclusively), but because the goal itself was worth it.

Play, they’ve experienced through music or band, Dungeons and Dragons, or high school improv class. When they found reserves of stamina, resourcefulness, and creativity needed to play a great song or a great game. Not to win anything. Simply for the sake of the game.

Partnership, they’ve experienced with their teams, either in business or sports. When everyone was working toward a common goal, and their individual role was clear. When they found those reserves to keep going and hit a deadline, or make a tackle, not because there was an existential problem, but because of a commitment they’d made to their partners.

Presence, they’ve experienced in moments of stillness, when they saw, really saw, a tree they just had to sketch or heard, really heard, a song lyric in their head they just had to write down. When the moment itself asks them to step up, to contribute. To play the one missing note in the symphony.

Love, they’ve experienced when they picked their kids up from school early. Or bought tickets to their spouse’s favorite band. When there was no occasion, simply an upwelling of caring for another person that had to be expressed.

Effort from each of these places creates tremendous action and results. They are responsible for great works of art, great feats of athletic achievement. For mobilizing millions toward a worthy goal or having the perfect sales conversation. Actions coming from these alternative forms of motivation don’t carry a tax on your self worth or safety. They are self replenishing.

When a client does the brave work to learn to let go of fear of failure, their worthlessness, all those wonderful, Faustian sources of motivation, and allow themselves to feel ok, it’s normal to feel a bit unmotivated. To feel disconnected from the juice that used to drive them. And that can be scary.

But rest assured this is temporary. A momentary disorientation, a liminal space after letting go of one sense of direction before finding another.

And then we begin the work of experimenting with these other, cleaner sources of motivation. We identify the areas in which we might already be acting from love, or presence, or partnership, or play, or purpose. We become intimate with the parts of ourselves that already know how to act in this way, and why. And we practice saying yes, with our entire selves, to these sources when they arise.

It takes time. More than that it takes practice. But soon enough, if you’re committed to going all the way, you will find a new, cleaner form of mojo. Of juju.

A mojo of play, like the one that wrote this essay. Or a mojo sourced from purpose and presence, like the one that builds this important organization, Inside-Out Leadership. A mojo that is capable of reaching higher heights, because it’s no longer weighed down by the burdens of shame, fear, or anger.

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