On Shame
Welcome, Entrepreneurs. I’m so glad you’re here.
I’m writing this while jamming out to Rufus Du Sol, who I am shocked it’s taken me 38 years to find (10/10 recommend. And, if you like similar music, please send recommendations).
It’s funny, there’s a part of me that almost didn’t want to write that, lest people judge me for my musical tastes. That very slight feeling of shame might have previously stopped me from saying anything, and robbed me of the chance to connect musically with you all.
But I’ve learned to be skeptical, each time I feel any type of shame.
A widely miscalibrated emotion, shame stops us, like a governor throttling the scope of our lives. And if we’re interested in living big, fully-expressed lives, it’s worth taking a microscope to it, and our relationship to it.
Especially when the shame feels much bigger than musical tastes.
On Shame
Shame evolved to help us collaborate with our fellow humans. On the African savannah, way back in the day, you died if you deviated too far from your tribe. Our strength was in numbers, so shame played a vital role in helping us survive.
Today, to be successful and live your own life (not the one that society has handed to you), you must stand out. You must be different than others, a fact which creates some obvious and interesting tension with the conformity that’s been so important to the survival of our species up until now.
Suffice it to say, it’s really important how you deal with the emotion of shame. I’d go so far as to say that the life you want is on the other side of your shame. Hard stop.
So how do you work with this complicated, important emotion?
Shame and Risk: Understanding the Connection
Shame can be understood as a proxy for risk. In other words, when you feel shame about something, it’s your body’s way of telling you there’s a risk in sharing that thing with others. Often there’s a risk of social ostracization.
This is real. If you’ve murdered someone and nobody yet knows about it, your shame plays a critical role in you staying out of jail. It’s communicating to you that you should keep that part of yourself to yourself, or bad things might happen. You may have a less extreme example, but the point is the same, whether you’re a criminal or a CEO who’s made the wrong decision.
What isn’t real is the idea that shame itself is shameful. There are no “bad” emotions, in and of themselves. Shame is neutral, useful even. Granted, for most people it’s wildly miscalibrated (remember the stakes on the African savannah), so it ends up doing more harm than good – for example, when you decide that you’d better just deal with that crappy boss or job, because who are you to want better? But even in those cases, trying to get rid of or ignore our shame isn’t the answer.
Instead, the key is to recalibrate your shame to better match the actual risk of the situation.
Recalibrating Shame: Strategies for Overcoming
You’ve probably been inside one of those skyscrapers that have a glass floor near the very top. Consider the feeling of first stepping on that floor, if you’re afraid of heights. In spite of knowing it’s safe because of the hundreds or thousands of others who’ve stepped there before, our internal risk sensor misreads the situation and tells us we’re in extreme danger.
The process of recalibrating our risk sensor in those kinds of situations is one of testing the waters. First you step a foot onto the glass platform, and you don’t die. Then two feet. Then you walk for a little bit. And after some amount of time walking on the platform, the sublogical part of your body finally relaxes.
It’s the same with recalibrating your sense of – or “metabolizing” – shame.
Metabolizing shame requires going beyond the feeling of shame and sharing that part of yourself that you keep hidden. You first do it as an experiment. Once. And then assuming you don’t die, it’s slightly less scary to do it again the next time. And then again and again, and eventually, the fears in your head of what might happen are replaced with actual data from having shared yourself with real people, and that thing you were so ashamed of doesn’t trigger shame any longer. You can own that part of yourself that you have kept hidden.
Shame and Success: Breaking Free from Limitations
Shame not only appears in relation to our past. It also stems from our future. Specifically, shame is a key inhibitor of performance toward what you want.
That’s because most of us are ashamed of what we want.
We’re told from an early age what is ok to want. You can want to be successful in school, but you can’t want to be a racecar driver. It’s ok to want to win the big game, but it’s not ok to quit college to become an artist. These filters on what we allow ourselves to want are inherited from our family of origin and our peers growing up, and again, they are designed to keep us small. Keep us the same.
Shame prevents us from acting on what we really want. Maybe you want to be a singer. But you don’t do the work, because what if you failed and someone laughed at you? Our risk assessment of singing in front of people is way out of whack, because the real risk of singing in public is actually incredibly small. We know that intellectually, but our shame isn’t logical and is miscalibrated.
So we get a desk job instead. Just like everyone else. And we wonder what would have happened if we’d been brave enough to go beyond that shame. To sing anyway, to take the risk, and live the life we want, not the one that our tribe tells us we should want.
The process of metabolizing future shame is the same as dealing with shame from your past. It takes reps. If you want to be a singer, you start by singing. First alone, but then with one other person. If you don’t die, then you broaden it to a few friends. Then you join a band or choir and so on. Chasing your dream, what at first feels terrifying, over time becomes just who you are and what you’re doing. You’re no longer ashamed of what you want. You’ve metabolized your shame.
Metabolizing Shame: Steps to Personal Growth
When I talk to someone for the first time, I usually tell some version of my story. And usually, it includes the fact that I did a ton of drugs and drank a ton and went to jail for a minute. It’s always interesting to see how people react when I talk about that part of my journey. To me, it’s a key piece of context as to how I see the world (I’ve been to the bottom, so I feel more free to take risks because I properly understand what’s really at stake when I talk to an investor — not that much), so I include it. Some people raise their eyebrows. Some people tell me their own addiction stories. But nobody has ever disowned me over that information.
But I didn’t always share that part of myself. For most of my early career I guarded the story of my addiction like I was guarding the nuclear codes. I still remember the first time I raised money, and the angel investor told me they were going to do a “routine five-year background check.” All at once, I felt the shame of what I’d done, and the terror of losing everything when someone found out.
If I hadn’t been forced to reveal my past through a thorough due diligence process, I might still shy away from talking about it. But I was fortunate enough to have no choice at the time. I told the investor that I had two DUIs and had spent some time in jail. We talked about it for a minute, and he said he was glad I told him. Once the background check was done, he wired the money, and it never came up again.
And that experience, scary as it was, was what opened the door to me metabolizing the shame I felt from my past with addiction. I began telling more people, bit by bit. And finally, I talked about it on stage in front of 100 people I knew. At some point during that process, it started to feel much easier.
I’ve come a long way from then to now when it comes to the way I relate with that part of my life. But my journey with the emotion of shame continues.
When I tell my story today, I talk about drugs without a second thought, although it sometimes makes a strong impact on others. But during the past three years, I have often conveniently left out the fact that when I left the company I founded after 10 years as CEO, I didn’t really “leave” so much as I was “fired.” I can feel a little twinge of shame even when I write that now, and a part of me wants to explain away the circumstances and how it was because of insubordination toward the CEO I hired and subsequently vehemently disagreed with (as if that matters). I don’t hide the truth completely – I’ve often talked about it openly during the second conversation with someone – but the fact that it’s not a part of my intro story speaks to how differently I relate to being fired, versus having a history with addiction.
When I finally realized this late last year, you know what I did?
I announced it on stage to hundreds of people. And I didn’t die.
And then I announced it on Twitter to 150,000 people, which I can tell you is uncomfortable as hell, and is a tremendous accelerant to this whole process.
And I didn’t die.
It still feels new, today, talking about this here. But much less so.
Now I’m mostly curious to see how it turns out.
Why would I want to metabolize my shame?
Two reasons.
First, from a practical perspective, metabolizing shame, whatever form yours may take, will make you a significantly more powerful and effective communicator and leader. No matter how good you are at what you’re doing, if you’re hiding something out of shame, all it takes is something adjacent to that thing coming up to throw you off your game. All of a sudden the nerves take over and you clam up. Or some people get super aggressive. Whatever your response, you are no longer consciously in control of your communication, so you flail. On the other hand, once you metabolize your shame, when you fully own who you are and have been, no reservations, there’s nothing to trigger that emotion in you. And so the full force of your skills, talents, and passions can come through without kinks.
And second, related to shame around what you want, you are not meant to live the same life as everyone else. You do not live in the African savannah. The opportunity that you’re given in this life is, quite simply, to figure out who you are deeply, and then express that into the world honestly and faithfully. Your power, your influence, your edge…for fuck’s sake, your life. They’re all depending on you being the specific kind of different that only you can be.
You are meant to sing (metaphorically – that may not be your thing but you get what I’m saying).
Miscalibrated and unmetabolized shame is blocking you from the life you’re meant to live. It is keeping you small, in an effort to keep you safe. Only, you’re not really in danger.
And now, the next time you feel that familiar feeling, that shame in who you are, what you’ve done, or what you want, you can no longer say you don’t know how to recalibrate.
Clients of mine often push back quite a bit against the idea of metabolizing shame, and for good reason. It can be incredibly hard work.
But it’s worth it.
A Reflection, if you’re feeling brave
If this article resonates, I invite you to journal on the following prompts, to get a sense of where you are on your journey to metabolize your shame:
What parts of my life do I talk about freely, that others might not?
What parts of my life do I hesitate to talk about, or only talk about with a trusted few?
What parts of my life do I never talk about?
What am I scared would happen if people knew about these things? (List for each item)
How might I test whether that fear is grounded in reality, or not?
From a fellow traveler, good luck.
Want to dive deeper?
If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.
Here are a few of my favorites:
The secret to leadership (why authentic leadership is simply more effective)
How to pitch a big vision to investors without setting yourself up to let people down
Executive Coaching for Entrepreneurs
There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.
I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency that supports entrepreneurs to step fully into their lives, and transform their companies into their masterpieces.
Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.
I coach leaders how I want to be coached:
Focused on the person, not the role.
Focused on results, without the fluff.
To learn more about working with me, click here.