In 1997, early in his career as a qualified civil engineer, Julian Pencilliah went through a crisis that would reshape how he thought about risk, planning, and what failure actually means. The instinct in a moment like that is to treat it as a verdict on yourself — proof that you aren’t cut out for whatever you were attempting. That instinct is almost always wrong, and it is also almost always unhelpful.
The more useful frame, and the one that eventually pointed toward a career in venture capital rather than engineering, is this: people don’t fail — strategies fail. A plan can be built on an assumption that turns out to be false, a timeline that was always too optimistic, or a structure that couldn’t absorb the shock it eventually met. None of that is a statement about the person who built the plan. It’s a statement about the plan.
This distinction matters because it changes what you do next. If you believe you failed, the only available response is to doubt yourself more carefully next time — which tends to produce caution, not better judgment. If you believe the strategy failed, the response is diagnostic: which assumption broke, and what would have had to be true for the plan to hold? That question is answerable. “Am I good enough” is not.
It’s also the reason a background in engineering translates more directly into venture capital than people usually expect. Engineering trains you to treat a failure as a structural question first — where was the load miscalculated, where was the tolerance too tight — before it’s ever treated as a personal one. Carrying that habit into capital allocation means a bad outcome gets interrogated for what it teaches about the next structure, rather than filed away as a reason to take fewer risks altogether.
One should always mitigate the risk of a decision before the decision is made, not after it’s gone wrong. That isn’t a guarantee against hard years — 1997 still happened. But it’s the difference between a hard year that ends a career and one that redirects it.
