Moving on, getting over, and choosing the work I want to do

I’ve been thinking about the difference between moving on and getting over. Moving on is the visible part: a conversation, a handover, dates, and a practical plan. Getting over is the internal part: the slow detachment from an identity, the urge to keep one foot in the old room, the desire to make the transition feel reversible. I’ve learned that you can do the first without really doing the second, and that’s usually where people get stuck. Still reacting to old dynamics, still scanning for signals, still needing the story to be validated by everyone around them.

What made this particular decision feel necessary is that my “Why” has become clearer than it has been in a long time. I care about helping founders make better decisions early, when the quality of judgment matters more than the quantity of capital. I’m drawn to the work of asking the right questions, seeing second-order effects, and connecting the right people at the right moment. My underlying belief is simple, and it’s only gotten stronger with time: early-stage outcomes are driven more by people and decision quality than by sector labels. Sectors matter, of course, but they’re not a substitute for judgment. And I want to build my work around that belief, with the discipline to say no to weak incentives and false certainty, even when saying no is inconvenient.

Once you can say that sentence out loud, you start noticing where your actual day-to-day does and doesn’t match it. That’s where the discomfort began for me, not as a critique of any one place or any one person, but as a mismatch between what I claim I’m optimizing for and what my calendar was quietly optimizing for. I found myself asking questions that sound abstract until you feel them in your body: am I spending my best attention on the highest-leverage moments for founders, or am I spending it on the parts of the job that are easiest to justify and hardest to refuse? Am I choosing stability because it’s truly the best path, or because it reduces the psychological cost of making a clean decision? Am I staying close to something because it’s aligned, or because being needed is a comfortable kind of significance?

The honest answer is that “comfort” was starting to compete with “alignment.” Not comfort as in ease—there’s nothing easy about serious work—but comfort as in predictability: known rails, known expectations, known identity, and the quiet relief of not having to reinvent yourself in public. Those rails have real value. They reduce variance, they protect your downside, they let you focus. But they also shape your incentives, and I’ve become increasingly protective of incentives because I’ve seen how they drive behavior even when people have good intentions. If I say I care most about judgment early, about the craft of decision-making and about being useful in the few moments that change trajectories, then I can’t keep outsourcing the shape of my weeks to structures that are optimized for other things. At some point, the only way to be honest is to align the operating system with the belief.

That’s where the risk tradeoff comes in, and I don’t want to romanticize it. It is riskier financially, obviously: less predictability, more variance, and a more direct relationship between the quality of my work and the outcomes that follow. It’s riskier professionally too, because you lose the halo effect of an institution and you have to stand on your own judgment; you can’t hide behind process, and you can’t borrow credibility from a logo. And maybe the most underestimated risk is psychological: you have to let go of an identity that was socially legible and replace it with one that is still forming. You become less easy to categorize, and that’s uncomfortable if you’ve been trained—implicitly or explicitly—to treat legibility as safety.

But when I list the risks honestly, I also see the risks I’m choosing to avoid. I’m avoiding the risk of drift; of doing objectively good work while gradually moving away from the thing that makes me feel most useful. I’m avoiding the risk of becoming dependent on structure for momentum. I’m avoiding the risk of telling myself I’ll “make time later” for the kind of work I actually want to be doing, because later has a habit of never arriving. In that sense, this is less a leap toward chaos and more a decision to make the incentives explicit: to accept more variance in exchange for more alignment, autonomy, and the ability to compound relationships and judgment in the direction I care about most.

A big part of the pull is also social, and I don’t mean that in the shallow “networking” sense. I want to work with my peers and build something alongside them. There’s a particular kind of seriousness that comes from being in the arena with people who are still forming their judgment, still iterating, still willing to be wrong in public and correct themselves quickly. I find that energy clarifying. It pushes me toward craft rather than performance, toward questions rather than posture. And it matches the kind of value I want to provide: not “advice” as theater, but judgment, directness, and useful connection.

This is also where “getting over” matters, because the temptation during any transition is to stay half-attached. To keep helping in ways that recreate the old role, to keep being the person who catches the overflow, to keep being needed because it softens the emotional edge of leaving. I understand that impulse in myself, and I’m trying to treat it as a signal rather than a command. If my why is to be useful in a specific way, then I need boundaries that make that usefulness sustainable and intentional, not reactive and always-on. A clean transition is not just respectful to the people you leave behind; it’s also respectful to the thing you claim you’re moving toward.

I don’t have a perfect forecast for how the next chapter plays out, and I’m not trying to manufacture certainty where it doesn’t exist. What I do have is a Why that feels stable enough to carry the variance of the how. I want to spend my best attention on early-stage judgment and decision quality, and I want to build around that with people I respect, in a way that compounds. If that’s true, then this move isn’t primarily about leaving something; it’s about choosing what to build, what to optimize for, and what kind of work I’m willing to be accountable for.

Let’s build.