Over the last 5–7 years, I’ve found myself in many conversations with young colleagues, students, and friends — often during moments of transition or uncertainty as they reach out for guidance on certifications, referrals, or help in framing a career pivot. But as these conversations unfold, a deeper pattern emerges. Many are setting goals based on what’s visible, popular, or endorsed by the loudest voices — not what truly fits their temperament, values, or long-term aspirations. They’re choosing paths that sound impressive but feel increasingly hollow as they walk on that path.

In their urgency to “build a great career,” they often adopt generic advice — optimize for brand names, chase high-growth sectors, follow passion loosely defined — without realizing that these choices are quietly steering them in the opposite direction of the life they actually want. The tragedy isn’t that they’re lost — it’s that they think they’re on track, when in fact they’re sprinting down someone else’s path.

As I observe my own journey and how I navigated (learnt from all the usual generic mistakes that most of us commit) some patterns and learnings emerged.

Short-term optimization vs getting on a long term learning path

One of the most widespread traps is short-term optimization — choosing a job primarily for its salary, title, or brand. It feels rational. After all, we are taught to maximize. But research — and my own lived experience — suggests something different: early-career learning environments are a far stronger predictor of long-term success than anything else.

I learned this first-hand. I made a career pivot by moving away from hardcore commodity traders job to being a research associate at an academic institution, I didn’t have the flashiest role or the highest pay, but I was working alongside some of the sharpest minds in development finance. They held me to high standards, exposed me to diverse challenges, and helped me build what Cal Newport would later call “career capital” — rare and valuable skills that quietly increase your bargaining power over time.

While it was more of an impulsive decisions and realization that I wanted my work life to be in sync with my values and my craving for learning, this decision did wonders for me. But at that point of time, no-one backed my decisions as this was against most of the established templates: a massive salary cut; moving from a permanent role to a contractual role; and moving from a coveted brand name to an institution that was fledgling research institution at that point of time.

Reactive vs Intentional Career Choices

Another subtle but significant pattern I see is reactivity. Most people don’t choose careers. The careers that they are coveting for are shaped by family expectations, peer pressure, market trends, or mimetic desires (the unconscious imitation of others’ ambitions).

I made that mistake too. My first job was the best offer on the table and I wanted to get that because it was the most coveted offer. But once I stepped into it, I realized how little it resonated with who I was. I had ignored the quieter signals: what kind of problems excited me, what kind of team I wanted to be around, what kind of life I would lead if I continue to be in this role.

Being an introvert who spent all his free time reading and reflecting I was getting to know myself and my thought process better. Now, I strongly believe that intentional career choices come from self-awareness — an evolving understanding of your values, temperament, and curiosities.

Which brings up a connected point: most of us don’t choose our peer group or mentors. We inherit them. And while many mentors mean well, they may unconsciously project their own nostalgia — urging you to follow the path that worked for them, not the one that works for you.

The Role of Serendipity

There’s one more thing we often underestimate: the role of chance. We’re conditioned to think of careers as linear — choose the right degree, get the right internship, and get the right company…. But the real world doesn’t work like that. Careers unfold through serendipity — unexpected encounters, side projects, failed applications that open surprising doors. (The switch from a commodity trader to a researcher was made possible only because the research project for which I had applied expected the applicant to have deeper understanding of commodity trade!)

John Krumboltz’s Planned Happenstance Learning theory suggests that the most ‘successful professionals’ don’t follow rigid plans — they follow curiosity. They are open to small experiments (one of the experiments that I tried early in my career was to learn coding and started a blog-both had no objectives and just were driven by curiosity but blogging led me to know many fellow bloggers and exceptional individuals who just expanded exposure and learning), stay open to surprise, and treat uncertainty not as a threat but as terrain to explore.

Some of the most pivotal turns in my career — working with some of coveted global institutions did not come from a master plan, but from being open to (and paying attention to) what emerged when I followed the work that felt meaningful, even if it didn’t fit an established template.

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