Careers Are Not Ladders

We inherit a picture of a career as a ladder: one field, a fixed set of rungs, up and up. But many real careers look more like a lattice, moving sideways, changing fields, doubling back, and combining things that did not obviously fit. Shiv's path, from Princeton mathematics to Wall Street to building companies across the United States and India, is one example of a career that did not climb a single ladder.

Seeing careers as non-linear is not an excuse for aimlessness. It is a more accurate map, and a more forgiving one, especially early on when you cannot yet know where you will end up.

Titles are how organisations label you; skills are what you can actually do. Over a long career, the skills, relationships, and reputation you accumulate, your career capital, tend to matter more than any single title, because they travel with you when circumstances change.

This suggests spending your early years building rare and valuable skills rather than chasing the most impressive-sounding role. What you can do compounds; what you were once called does not.

There is real value in exploring across fields before narrowing down. Trying different industries and problems teaches you what you are good at and what you actually enjoy, information you cannot get from the outside. Generalists who have seen several worlds often spot connections that specialists miss, while specialists go deeper on one.

Difficult experiences, including failures and detours, are frequently where the most durable learning happens. A hard year in the wrong role can teach you more about yourself than an easy year in the right one.

Most career decisions involve trading off money, meaning, prestige, and fit, and different people weight these differently at different times. Prestige is especially worth watching: it is easy to chase what impresses others rather than what suits you.

One idea worth keeping is optionality: choices that keep future doors open. Early in a career, decisions that build broadly useful skills and relationships tend to preserve optionality, while decisions that lock you in narrowly tend to spend it. Neither is wrong, but it helps to know which you are doing.