CAREER: The rise of the portfolio career

And why corporate stability is no longer a thing.

Does this sound familiar: You grew up more or less conditioned to go to school, get a good degree, secure a job at a big prestigious company and that was it. Settled for life. One clear identity, one path, set steps to follow.

And then something shifted. In the economy, in technology, in society.

By force and by choice.

Short term contracts and project based work became the norm, and the advanced degree became less of a differentiator and more of a prerequisite just to be considered.

You needed experience to get your first internship but could not get experience without one.

You got in but on a fixed term contract. When the budget ran out the juniors were cut first. And just like that, così, you were back on the street looking for the next role.

At some point you cannot help but ask: what is the point of chasing a corporate career when you have no control over it, you are required to almost beg for roles below your level, and in the end you are basically forced to take whatever lands on your lap just to survive?

When is the infamous stability actually supposed to arrive?

I have seen this happen over and over, to others and to myself. And it has led me to one conclusion: we need to change what we expect from a career and what progress actually means.

That shift, I think, brings a lot of relief.

Because once you see each job or project as a standalone piece of a portfolio rather than a step on a linear ladder, everything looks different.

Each role served a purpose. Each one taught you something. On each, you were in control. It does not matter how disconnected or unrelated they seemed at the time.

And when you see the value of each period on its own terms, you stop explaining yourself. You stop justifying gaps. You stop questioning whether it all makes sense. Because it does.

The power law career

If that still does not convince you, think about a venture capitalist.

VCs operate on the assumption of the power law. Returns are not distributed evenly across a portfolio, and most investments return nothing. But then there is the one that returns 100x the initial capital and covers everything else.

Applied to a career and projects, the same logic holds.

Not everything you ever do will bring enormous payback. But when you are not betting everything on one single path, the chances are that one project, one role, one side bet will return tenfold what all the others combined ever did.

That is where the beauty of the power law lies in careers, skills, and side projects.

And this is also why trying many things is not scattered. It is a risk management strategy.

But yes, easier said than done

Maybe this feels too radical. Maybe you do not know where to start or how to get rid off the conditioning of the linear path model.

Nonetheless, the over-explaining and self criticism has to stop as each phase and decision had its purpose.

And it is good to remember, even the most serious serial entrepreneurs question their efforts at times and whether getting “a real job” would be the right option, which just shows how difficult it is to do something that goes against the common expectation.

But when there is something you want to do and create, and which is beyond the linear expectations, you should go for it.

And equally, when there is no other option than doing something beyond your proven path, you should go for it.

In the end, choosing your approach to career is really about choosing which challenges you are willing to deal with.

The challenge of searching for that one perfectly matching next job for months with no guarantee of finding it, with no other proof of progress in the meantime. Or the challenge of stepping into the unknown, doing something unconventional, learning fast and on the go.

Don’t get me wrong: A linear career that just makes sense is a genuinely good thing. When you have it and you enjoy it, that is perfect. It is just that there is no guarantee of keeping it, which is the problem.

So, in the end it is about risks and rewards.

Where do you want to play it safe and where do you want to take the bet.

But one thing is certain: the rules have changed and there is no going back.