Winning Doesn’t Mean You’re Okay
Some signals the scoreboard didn't show
This week I’m trying something new. At the bottom of this essay you’ll find three new sections: A Note on Practice is a post script describing what I was thinking as I wrote, In the Margin links to other material related to or adjacent to this piece, and What I’m Reading are other books and articles I enjoyed this week, no relation to this essay at all.
I invite you to check them out. If you think of something I should add or change, let me know!
Winning Doesn’t Mean You’re Okay
What the Process Required
I was on vacation with my family when the call came in. The kids were already asleep. I stepped out onto the balcony so I wouldn’t wake anyone. It was the investment banker representing the other side of the deal, and this was my first time selling a business to a large Bay Area tech company.
He didn’t ease into the conversation. He yelled. At one point he blasted “What kind of a man are you?!“ I could feel the spittle through the phone. All of it was delivered angrily as advice. This is how acquisitions work. This is what serious people do. If I wanted the deal to close, I needed to meet their expectations.
I remember trying to keep my voice steady while my heart raced. The contrast was jarring. Quiet Cancun breeze, and a pugnacious banker unloading on me as if that were the most reasonable thing in the world.
It took months before something clicked. This wasn’t a bad day. It wasn’t a personality clash. This was the job. He was, in a very real sense, being paid to be a professional asshole. His role was to apply pressure until something cracked. He was very good at it.
At the time, though, I immediately brought it to my board. The deal was coming apart.
I described the calls as plainly as I could. The yelling. The insults. The way each conversation left me wired and uneasy long after it ended. I wasn’t trying to dramatize it. I was trying to understand whether my feelings matched reality.
Their response was logical. Pressure was part of the process. Aggression meant leverage. If the banker was escalating, it meant the deal was still alive.
But it wasn’t reassuring. It landed as a contradiction.
They were expecting me to take their advice on faith, at the exact moment when every fibre of my body was telling me something was wrong. My instincts were screaming retreat. I understood their explanation. I just couldn’t reconcile it with the panic I felt after every call.
We were talking about the same events. They were interpreting a signal. I was absorbing the impact.
A few weeks later, the deal was signed.
Closing at a significantly higher value than the original offer, it was the largest acquisition the buyer had ever completed. By every external measure, it was a success. There were congratulations. Relief. A sense of having survived something difficult and come out ahead.
And yet, in private conversations, when there was no reason to stay composed, I found myself reaching for different words. I used the words abusive and traumatic without much thought. Not for effect. Just because they fit.
It was exactly the kind of outcome people point to when they say the process worked.
The System at Work
It took me a long time to stop personalizing these moments.
Nothing about that experience was especially unusual. Capital markets reward predictability and momentum. Boards exist to protect outcomes. Leadership culture prizes endurance, composure, and the ability to absorb pressure without becoming the story.
None of this is malicious. It’s functional.
These systems are very good at measuring what they were built to measure. Green when numbers are moving in the right direction and red when they are not.
What they don’t measure is personal cost. Not the kind that shows up slowly. Not the kind that accumulates in the body before it ever reaches a spreadsheet. From the system’s point of view, silence reads as strength.
We see this surface publicly from time to time. Someone at the top of their field steps away, or falters in full view, and the story becomes about bravery or weakness or resilience. What rarely gets examined is the system they were winning inside of, and what it had no way of seeing.
So when pressure works, it is reinforced. When endurance holds, it is rewarded. And when someone carries the weight without asking for anything back, the system learns that nothing is wrong.
What Stability Required
Nearly a decade later, at a different company, a restructuring had worked.
It had been painful and exhausting, but the company was on stable footing again. Cash runway extended and, for the first time in a while, we could talk about the future without flinching.
So we did. Growth returned to the agenda. We explored hiring plans, product design, and fundraising. It was all the familiar language of possibility.
Inside, though, I was done.
Not tired in the way a vacation could fix. Just hollowed out and raw. I was getting through the days on habit and obligation, not energy. Every new conversation about ambition felt slightly unreal, like it was happening to someone else wearing a convincing costume of me.
I called one of my board members and told them I wasn’t okay.
There was a pause, then a practical response. This was common and manageable. Everybody else was on medication. I should talk to my doctor.
They were offering a way to keep going, but what landed was the quiet confirmation that the system was working as designed. The company was stable again. Growth was back on the table. My internal state was something to address elsewhere.
The appointment itself was unremarkable.
A small exam room. A printed reminder about the new appointment booking system. The familiar routine of being asked how I was sleeping, how my appetite was, whether I was exercising. I answered carefully, the same way I answered board questions. Direct, accurate, and contained.
We talked through various medication options. The risks and side effects. Then she said, almost casually, “I like this one for you, it’s an antipsychotic“.
I don’t believe the pause that followed was intentional, but it perfectly punctuated the moment. To me, medication was a source of shame. To her, it was simply a tool. One more way to stabilize the system.
I left with a prescription and a strange sense of dislocation. Outside the clinic, life went on as usual. Emails waited. Meetings still mattered. The company still needed a steady hand.
What I couldn’t shake was the feeling that I was out of step with one of our core values: Honesty & Empathy. Standing in front of the team, talking about ambition and belief, I felt like I was withholding something essential. Not lying exactly. But not telling the whole truth either. What unsettled me most was that I couldn’t tell whether the discomfort was a real signal, or just an idea I’d absorbed about how I was supposed to feel.
New products shipped, and we closed the funding round. The company looked, from the outside, like it had found its footing again. There were congratulations and the familiar relief of momentum returning. I kept filling my days with meetings and the familiar work of keeping everyone else motivated.
What I didn’t do, though, for many weeks, was tell anyone what was happening underneath. That I was on a mix of antidepressants, or that getting through the day required more scaffolding than I wanted to admit.
I couldn’t see a clean way to reconcile the story I was telling publicly with the one I was living privately.
The win was real. So was the dislocation.
Learning the System
Over the years, I’ve noticed a pattern among the founders I’ve invested in, the executives I’ve mentored, and other high‑performing people I’ve had the pleasure of knowing.
They’re exceptionally good at learning systems.
They pick up quickly on how marks are actually awarded, how promotions really happen, what investors respond to, and which signals move decisions forward. They learn to reverse‑engineer incentives, often without being taught, and to adapt their behaviour accordingly. This isn’t cynicism; it’s competence.
The same people tend to be disciplined and able to bear unusual amounts of discomfort in service of an outcome. They notice what’s praised, what’s ignored, and what creates friction. Over time, they get very good at focusing their energy where it counts and muting everything else.
This skill translates well. It works in school, in work, and in environments where progress can be measured and rewarded. It’s also remarkably effective at suppressing signals that don’t register anywhere formal.
Fatigue, fear, and doubt don’t show up on a scorecard. So people who are fluent in winning learn, almost automatically, to process those costs privately.
Over time, I’ve come to recognize that, internally, this rarely feels like suppression. It feels like professionalism. Like maturity. Like doing what the situation requires.
Once I could see the pattern, it became harder to pretend I wasn’t complicit.
I noticed that I stayed quiet when naming harm might have slowed things down. I accepted reframes because they allowed me to keep moving. I told myself that endurance was part of the role, and that anything else was a distraction.
That adaptation wasn’t forced on me. It was chosen, again and again, often because it felt responsible. Because it felt like leadership. Because there were people counting on me to keep things steady.
Looking back, I’m sure there were moments where I rewarded the same silence in others. When someone showed evidence of strain, I helped translate it into performance. When I praised resilience without stopping to ask what it was costing. Not out of indifference, but because that was the language I had learned to speak.
There’s no clean villain here. Just a series of small, reasonable decisions that added up to something harder to see while it was happening.
The Question That Lingers
When I ask leaders how they’re doing, they often answer with how the company is doing. Revenue. Hiring. Runway. Whatever the most recent signal happens to be.
It usually takes asking again, with a slight change in emphasis, before the answer shifts. “How are you doing?”
There’s often a pause then. Not a dramatic one. Just long enough to notice. Long enough to suggest that the question isn’t asked very often. Or that the answer doesn’t fit cleanly.
I’ve come to think of that pause as information. Not something to fix or fill. Just a sign that the system we’re all fluent in doesn’t really know what to do with the question.
The system is very good at telling us when we’re winning.
It never had a way to tell us whether we’re okay.
A Note on Practice
I was tempted to end this with a list.
I didn’t, mostly because I don’t trust dashboards in this context. I’m good at turning almost anything into another way to perform, including self‑care.
That said, insight alone hasn’t been enough for me either. These days, I pay attention to a handful of quiet signals that don’t show up on a cap table: how I’m sleeping, whether my body feels braced or settled, how often I see people I don’t work with, and whether I’m still making time for things that don’t move anything forward.
This isn’t a system I’d recommend. It’s just what I’m experimenting with after realizing how long I outsourced the question of whether I was okay to outcomes.
If this piece landed and you want to compare notes, drop me a line. I’m always open to a conversation.
In the Margin
Here are a few things this piece kept brushing up against. I’m sharing in case you find them interesting as well.
Video: a successful gymnastics coach on how winning doesn’t always equal success
Article: a doctor debunking a viral claim that antidepressants don’t improve quality of life
Article: a famed athlete’s startling withdrawal from competition, and her triumphant return
Book: a more academic take on how measurement crowds out judgment and human cost.
What I’m Reading
Recent articles I’ve enjoyed and recommend
I really enjoyed this story and it made me think twice about my approach. I would have hung up as I refuse to deal with assholes. But I suspect if it were my deal, it wouldn’t have gotten done.
This resonated deeply. For a long time, I mistook suppression for professionalism. If something said or done to me affected my focus or engagement, I'd tell myself to 'grow up', 'move on', 'be professional.'
It took me much longer than I'd like to admit to recognize that wasn't maturity. That was just suppression with better branding