Field Notes · by Kristen Tolbert
People study entrepreneurs like we're zoo animals. Something to be observed, analyzed, maybe even envied. A curiosity. A puzzle to solve. What makes someone choose this life?
It's true, we're wired differently. Our drivers, our non-negotiables, our definitions of success — they don't line up with most people's.
And if you're wondering whether we're broken, traumatized, or running from something: yes. Always yes. But that's only part of it. We build because we have to. We solve problems obsessively because building isn't optional for us. It's lifeforce.
Here's the better question, though.
Why are you so curious?
What are you trying to understand about yourself by studying us?
Because whatever fascinates you about hard-charging types is telling you something about what you value, fear, or secretly want. And you ought to know what that is.
Hold onto that. I'll come back to it.
When people try to understand high-stakes leadership from a distance — no matter how closely they watch — it comes through their lens. Without the visceral experience of owning the complexity, the nuance disappears. Complexity gets flattened into comfortable narratives. Tidy explanations that feel clear and miss the gravity entirely.
Which is why simple advice rarely lands on someone leading at this level. Take a vacation. Take a break. Have you tried meditating? It trivializes what's actually being carried: the responsibility for keeping the thing alive, for everyone getting paid, for the whole system continuing to exist tomorrow.
What outsiders don't see are the waves of unseen problems just past the horizon — visible only from inside the loop, where the intellectual and the emotional collapse into the same survival-level decision.
It's like telling a pregnant woman mid-contraction to take a spa day. Or suggesting she deliver early so she can cross it off her list and move on.
It's asking a boxer to call a timeout seconds before the bell so he can visualize winning and get his mindset right.
It's telling an attorney to step out for a bathroom break mid-sentence during closing arguments.
Timing is not a detail. Context is not a detail. The weight of the thing you're holding is not a detail.
There's a finding that cuts against everything I've just written, and I've made my peace with it.
People reason more wisely about other people's problems than about their own. Not less. More. Standing outside a situation, you recognize the limits of what you know. You weigh other perspectives. You allow for the possibility that things will change. Step inside the same problem and those capacities shift — and the researchers who documented this found that deliberately taking a distanced perspective on your own life restores them (Grossmann & Kross, 2014).
So the outsider isn't wrong to think they're seeing something. They are. What they have is better reasoning and worse information. Less entangled. Less informed.
Which means the person who can actually help you is neither of the obvious candidates. Not the one who has never carried it, watching from the stands with a clear head. Not the one so deep inside their own version that they can only see yours through it.
It's the rare one with both. Enough distance to think clearly. Enough immersion to know what they're thinking about.
Those are hard to find. That's the entire problem.
They're sharp. They think at a high level, constantly, about hard things. Basic advice won't do, and not because they're too proud for it. It's that they aren't struggling with intellectual sophistication and they don't need productivity tips.
They need someone who knows how to think — not to hand over a solution, but to ask the question that opens the problem, and then to stay in it while it gets worse before it gets clearer.
They need to be around other people who can do that. It's rarer than it sounds.
Whatever fixates you about another person is usually about you. That isn't a figure of speech. It's how the mind works, and I've written about it elsewhere.
Your fascination is data. It's just not data about me.
If you're smart — if you're honest — you won't only wonder about us.
You'll work out what you're actually looking at.
—kt
Grossmann, I., & Kross, E. (2014). Exploring "Solomon's paradox": Self-distancing eliminates the self-other asymmetry in wise reasoning about close relationships in younger and older adults. Psychological Science, 25(8), 1571–1580.
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