The false linearity of careers

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in

For the loser now will be later to win – Bob Dylan

At 18, I mapped out my life with the precision of a military campaign. Before even stepping foot in Oxford, I had a 10-year plan: the societies I’d join, the internships I’d secure, and the career trajectory I’d follow. I envisioned leveraging the Oxford Alpha Fund to become a finance wizard, joining an investment bank for two years, pivoting to private equity, and eventually launching into Harvard, Stanford, or Wharton. From there, I’d build a startup, make a quick exit, and retire early.

Fast forward to today, and the version of me who wrote that plan would barely recognise the person I’ve become. Some parts of the plan came to fruition—I landed my dream job in a country I once thought was paved with gold. But my experience has shown me that life doesn’t reward rigidity. After initial success, I grew complacent, believing I had earned my place and could coast on past efforts. That complacency, however, was a wake-up call.

A head start can indeed put you ahead of the curve, sometimes offering compounding advantages. Oxford, with its unparalleled resources and network, is an incredible head start. It’s a privilege that opens doors many don’t even know exist. But no head start is permanent; erosion inevitably sets in if you stand still while the world moves forward.

For those just beginning their careers, life is still profoundly malleable. Securing a coveted first job is significant, but it’s not destiny. In fact, life becomes more dynamic after school, when there’s no fixed curriculum or structured path. Career trajectories often take surprising turns.

Consider the people who struggled through university without landing a single internship but secured fantastic roles thanks to a lucky break. Or think of computer science students from the 1990s, who pursued their field out of passion, not profit, only to ride the wave of the internet revolution post-2001 into meteoric career growth.

Success and wealth manifest in myriad ways. Some people make fortunes selling carpets or patents, while others thrive in trades, trading, or riding waves of market trends. There are those who follow the herd to influence and wealth, and others who bet against the tide and win big. Even crypto millionaires often started by investing on a whim. One lucky break—be it timing, networking, or serendipity—can make all the difference between having wealth and having none.

The key is to avoid getting lost in comparison. While “comparison is the thief of joy,” it can also drive progress if approached constructively. Look to others not as benchmarks for your own worth, but as windows into opportunities you might not have considered. Stay in your lane, make your own luck, and let the success of others expand your horizon, not diminish your confidence.

A Parable of Perspective

This brings me to a parable that has profoundly shaped my thinking:

Once, in a small village, there lived a wise old farmer who tilled his fields with quiet dedication.

One evening, his only horse escaped into the hills. The villagers came to console him. “What terrible misfortune!” they said.

The farmer shrugged and replied, “Perhaps.”

A few days later, the horse returned, bringing two wild horses with it. The villagers were amazed. “What incredible luck!” they exclaimed.

The farmer remained calm. “Perhaps,” he said again.

Not long after, the farmer’s son tried taming one of the wild horses but was thrown off and broke his leg. Once again, the villagers offered their sympathies. “How unfortunate!” they said.

The farmer, unperturbed, replied, “Perhaps.”

A week later, soldiers arrived to conscript young men for war. Seeing the farmer’s son injured, they left him behind. The villagers congratulated the farmer. “How fortunate for you!” they said.

The farmer smiled faintly and replied, as always, “Perhaps.”

No Fixed Path

This story is a reminder that life’s twists and turns defy prediction. What seems like a setback today may be the foundation of tomorrow’s triumph, and vice versa. There is no fixed path, only the opportunities and choices we encounter each day.

Growing up, I believed success was governed by rigid predictors and preconditions. Oxford would lead to a bank, a bank to private equity, and so on. But life doesn’t work that way. Recognising this has opened my eyes to the countless paths branching out from where I stand now. This realisation has made life far more exciting—and far less deterministic—than I once imagined.


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