What I Already Knew
In 2007, I sat down and wrote out everything that was wrong. Not in conversation, not in my head. On paper, in a list. The conflict with the founder. The customers threatening to leave. The morale collapsing around me. The compensation that hadn't moved in six years. The equity I had earned but that had quietly stopped accruing. The offer to be acquired was substantial money, which the owner walked away from because he was sure he could get more.
I wrote it all down. Every word of it was true. And every word of it I had already known for years.
That is the thing Brianna Wiest names in 101 Essays That Will Change The Way You Think that I have never heard anyone else say plainly: the gap between the life you say you want and the life you are actually building is not an information gap. You already know. The gap is courage. Specifically, it is the courage to act on what you know, even when it is uncomfortable, and even when the familiar, however broken, still feels safer than the unknown.
I had known it was time to leave for longer than I admitted. But I stayed. I stayed because I had built something there, because the people felt like family, because I kept believing the next conversation might change things. None of those reasons were wrong. But none of them were the real reason either. The real reason was simpler and harder: I was afraid of what came next.
The Ceiling
Wiest draws on psychologist Gay Hendricks' concept of the upper limit: the internalized ceiling every person carries for how much good they will allow themselves to experience. When life starts to exceed that ceiling, the subconscious finds a way to bring things back down. You manufacture doubt. You stay too long. You pick the fight that derails the thing that was working.
I did not understand this about myself when I was living it. I understand it now.
At my first company, I had the vision, the relationships, the track record, and a clear path to ownership. I watched it dissolve. Not because I was outmaneuvered, but because some part of me kept expecting someone else to recognize what I had built and reward me for it. I was waiting for permission that I was never going to be given.
When I finally left and built my own company, I threw everything into it. Five years of hyper-growth. A team I was proud of. Partnerships across the US, Europe, Asia, and Latin America. And then my partner fell ill, priorities shifted, and I watched the same patterns emerge that I had lived through before: the short-term thinking, the misaligned values, the slow erosion of what we had built. I recognized it immediately. And I stayed anyway.
That's the upper limit at work. Not ignorance. Recognition followed by inaction. I had installed a ceiling above which I didn't quite believe I was allowed to go, and when I got close to it, I found reasons to stop.
What I Rerouted
Between 2007 and 2022, I carried something I didn't have a name for.
Two companies. Two exits. Years of being the person who showed up, managed, stayed functional, and held the line for the people around me. I did not fall apart. I considered this a success.
When I finally sat down with a psychologist in 2022, not in crisis but in a low-grade exhaustion I could no longer organize my way out of, she gave it a name: Good Soldier Syndrome. The tendency to over-function for others, to lead and serve while quietly burying your own needs, until the weight of what you have been carrying becomes indistinguishable from who you are.
Wiest writes about the feelings we most suppress: how anger becomes sarcasm, grief becomes busyness, fear becomes contempt, and longing becomes cynicism. The rerouting is so practiced that it stops feeling like a choice and starts feeling like a personality. I had been rerouting for years. I mistook my capacity to function for evidence that I was fine. I was not fine. I was just very good at not stopping long enough to notice.
My therapist said something that reoriented everything: my weariness was not weakness. It was the cost of carrying too much for too long without pause.
The Daily Vote
Wiest argues that what you do each day is not a series of choices. It is a continuous vote for who you have decided to be.
For a long time, I was voting for someone who stayed ready but never quite arrived. I was preparing, connecting, learning. All real activities, all genuinely useful. But organized around a future I kept not quite stepping into. I had enrolled in coaching certifications, mapped out a consulting vision, and rebuilt my network. I was doing all the right things in a way that kept the actual thing at a comfortable distance.
Then I committed differently. I applied for a leadership role at the company where I had spent nine years becoming exceptional as an individual contributor. I went through the process. I did not get it.
I applied again. I was not even considered.
I applied a third time.
Between the first and third applications, I did two years of deliberate work. I conducted informational interviews with every leader I could reach. The internal manager training program was completed in full. Scripted narratives. Refined stories. Honest conversations with people who had done what I was trying to do. Not waiting and not preparing in place. Voting differently, every day, for the version of myself I intended to become.
Why Do You Think You Were a Failure?
The question that broke something open for me came from my therapist. I had been cataloging, with some precision, everything I had gotten wrong. The business that didn't scale the way it should have. The equity that never materialized. The years that felt, in certain lights, like a detour.
She listened to all of it. Then she asked: 'Why do you think you were a failure? Seems you've done quite a lot to be proud of.'
Wiest writes about what she calls signs that you are doing better than you think, which most people miss because they are not the markers we have been trained to track. We track external validation. Achievement metrics. The approval of people who may not be paying close enough attention to matter. The real signs are internal and quiet: a steadiness you didn't have before, a comfort with uncertainty that used to undo you, a clarity about what you actually want that took years of wrong turns to arrive at.
At my first company, I had learned to sell. At my own company, I had learned what it takes to build one, and what I wasn't willing to sacrifice to keep it. At the company where I spent a decade in enterprise sales, I had developed a depth of craft, a set of customer relationships, and a reputation that had outlasted three CIO transitions and a bankruptcy. I had done it. I had just been measuring it wrong.
The Third Time
In October 2023, I got the leadership role.
The third time. After two years of showing up differently. After sitting with a therapist who helped me name what I was carrying. After reconnecting with the people who mattered and letting myself receive what they were offering. After long drives in the old Land Cruiser and mornings with a camera and the slow work of reclaiming what joy actually felt like when I stopped managing around it.
I am not sharing this as a story about persistence, though persistence was part of it. I am sharing it because of what the two rejections taught me. The first time, I was not ready in ways I could not yet see. The second time, I was closer but still reaching from the wrong place: from urgency, from proving, from a version of the heroic effort that had served me as a seller and would have eventually undermined me as a leader. The third time, I arrived differently. Not because I had finally solved something, but because I had finally stopped running from it.
Wiest writes that the life you keep avoiding is not out of reach. It is on the other side of the ceiling you installed when you were young enough to need it and old enough now to question it.
I had installed mine carefully, over decades, out of intelligence, self-protection, and a very human desire not to want things I might not get. Dismantling it was not dramatic. It was a therapist's question on an ordinary afternoon. It was a third application after two quiet failures. It was a Jack London quote my mother had framed on the wall when I was growing up, one I had looked at my whole life without fully understanding what it was asking of me.
“I would rather be a superb meteor, every atom of me in magnificent glow, than a sleepy and permanent plant. The proper function of a man is to live, not to exist. I shall not waste my days in trying to prolong them. I shall use my time.”
The question is whether you are willing to look up.