"Should I specialize or stay generalist? Where should I be in five years? What should I focus on?"

I get asked this often by younger colleagues — people 5-6 years into their careers, trying to figure out their path.

Here's what I tell them.

(Caveat: I'm sharing what worked for me across a few situations. I can differentiate correlation from causation only 50% of the times — so take this with appropriate salt.)

When someone asks this question five years in, the problem isn't the question. It's that they haven't tried enough things and persisted long enough to actually know.

They're confusing learning discomfort with natural inclination.

Everything is hard when you're learning it. The initial friction of adapting to any new environment, any new function, any new skill — that's universal. It's not signal about whether you're a specialist or generalist. It's just the tax of being new.

Even the thing that will eventually feel "effortless" requires grinding through that initial phase. And when we say effortless later, what we really mean is: you enjoy doing it. The effort is still there. You just don't mind it anymore.

If you jump too early — switching because something feels hard — you're not learning about yourself. You're just avoiding the learning pangs that everyone goes through.

So how do you actually figure this out?

Part 1: The Exposure Test

Have you done 2-3 cycles in genuinely different functions? Not different companies doing the same role. Different charters. Different skill sets.

Operations, then marketing, then HR. Or engineering, then product, then sales. Genuinely different challenges.

If you haven't, you don't have enough data. The question is premature.

Part 2: The Self-Awareness Test

After that exposure, can you separate the joy from the environment?

It's easy to love a job because of great colleagues, a good manager, or a company that's winning. The question is: would you do that work again, even with different people and a different place?

Where did you feel genuine joy — not just comfort, not just success — but the kind of engagement where you'd happily do it again?

Part 3: The Pattern Recognition

Watch for these signals:

Here's a simple diagnostic for whether you're confusing learning friction with genuine misfit:

Benchmark yourself against others in the same role. How long did they take to settle in?

Most roles take about six months to learn, and about a year before you can meaningfully judge fit. If you're asking "is this for me?" in month three, you're not evaluating the role. You're evaluating the discomfort of being new.

Give it a year. Then ask.

Here's what most people don't realize: both paths lead to similar outcomes. The curves just look different.

The Specialist Curve: Slow in the beginning, then exponential. Think surgeons. Years of narrow focus, limited early growth, then suddenly you're irreplaceable. The payoff is back-loaded.

The Generalist Curve: Fast early growth, then tapers. You move quickly across functions, rise rapidly, then hit a ceiling where you need to specialize — in managing scale, in strategic judgment, in leading leaders. The payoff is front-loaded, but the later game still requires depth.

The insight: For people with similar drive and capability, the area under the curve is roughly the same. A driven generalist and a driven specialist reach similar career and financial outcomes. A mediocre generalist and a mediocre specialist both underperform.

The path doesn't compensate for lack of grit. And the path doesn't determine the destination — it determines the shape of the journey.

So don't compare yourself to someone on a different curve. They're not ahead or behind. They're just on a different trajectory.

Here's something for mid-career professionals — people 10-20 years in, making bigger bets.

You might think there's a 2x2:

But in practice, only the diagonals work:

The off-diagonals are rare and hard:

The path and the vehicle come as a pair. Choose accordingly.

The caveat: This 2x2 is for mid-career (10-20 years). Beyond 20-25 years, the diagonals converge. A large corporate leader needs generalist judgment — cross-functional thinking, strategic breadth. An early-stage founder needs deep specialization in at least one domain. At the senior-most levels, you need both. I wrote about this transition in The Syllabus Changed — when you move from managing ICs to managing managers, expertise stops being the job. The syllabus shifts entirely.

Here's the thing most people miss:

Most successful people never consciously chose specialist or generalist. They just kept doing the work.

They pushed through the learning pangs. They fell in love with what they were doing. They got good at it. And the identity followed.

The question "specialist or generalist?" only matters if you're stuck. If you're not stuck — if you're enjoying the work and doing well — don't overthink it. Just keep going.

Clarity comes in hindsight, not foresight.

I only saw my own pattern in retrospect.

At Practo, I stayed the longest I've ever stayed anywhere. Operations head, then founded and led marketing, then moved to HR for a year and a half, then took on P&L responsibility. Every two years, completely different challenges.

Anywhere I was boxed into managing one set of things? I got restless. I typically left within four years.

Looking back, the pattern is obvious: I'm a generalist. I thrive when the challenges keep changing.

But I didn't plan it that way. I was just too busy looking at my feet to look at the map. The pattern only became visible after I'd walked it.

If there's one thing to take away, it's this:

Don't compare yourself to people on different curves. They're not ahead. They're not behind. They're just on a different path.

Don't carry pre-baked biases. Somehow we've absorbed the idea that generalists are sexier, that being good at "everything" is better than being good at one thing. That's movie logic. In real life, rare specialists become irreplaceable. Both paths have dignity.

Don't confuse learning pangs with self-knowledge. Everything is hard when you're new. Give it time.

And if you're enjoying the work and doing well? Don't overthink the question. Just keep going. The answer will reveal itself.

Not the only way. Probably not even the best way. Just one practitioner's version that worked.

What's your pattern — generalist or specialist? When did you figure it out? Let me know in comments.

~Discovering Turiya@work@life