jack of all trades

In my first mentoring session, I brought up something that had been bothering me for a while with her: I felt my profile was too generalist, and that this was a bad thing.

It was 2022. I was interested in a lot of things, I could move between different topics, but there wasn't a single one where I could say: I'm an expert in this.

So she told me about a phrase we've all probably heard at some point:

Jack of all trades, master of none.

But there's an extended version that adds:

...but oftentimes better than a master of one.

The phrase has stuck with me ever since. And lately I've come back to it a lot.

Because I think AI is changing, among many other things, what it means to be a generalist.

Until not that long ago, stepping into a new discipline came at a fairly high cost. If you were a PM and wanted to better understand a technical decision, you needed someone to explain it to you. If you were a developer and wanted to explore a design solution, you probably depended on a designer. If you were a designer and wanted to test how an interaction actually behaved, you needed someone to build it.

Obviously, those specialties still exist, and depth is still valuable.

What changed is the distance between them.

Today you can ask Claude to explain a technical concept from scratch, to walk you through building something you've never built, to critique a design, to help you analyze data, or to give you enough context to take part in a conversation that until recently felt completely foreign.

It doesn't mean a PM suddenly becomes a developer, or that a developer becomes a designer.

It means the gap is much smaller.

And when the gap shrinks, many more opportunities to step in show up.

I was talking about this with Gonzalo recently and an image came up that I really liked: sometimes the generalist works as a translator, or as glue.

They can understand enough of two worlds to connect them.

When design and engineering speak different languages, they can translate. When someone from the business side needs to talk to someone technical, they can help build the bridge. When something important is falling through the cracks because formally it's "nobody's job", they're probably one of the first people to notice.

That kind of value is hard to put in a job description. And maybe that's why, for a long time, it was hard to recognize.

We're used to defining our contribution by our role: I'm a PM, so I do these things; I'm a developer, so I do those other things; I'm a designer, so this one's on me.

But that question interests me less and less. I'm much more interested in another one:

What is this team missing that I can contribute?

It's not about having seven developers and deciding that now I want to be a developer too. It's about understanding what that team needs to work better, and asking myself whether there's something I can do to get it closer to that.

Maybe it's understanding enough about technology to ask better questions. Maybe it's prototyping an idea instead of discussing it across three meetings. Maybe it's noticing that two people are trying to solve the same problem from different places. Maybe it's learning something that, technically, wasn't part of my role.

That's where another skill shows up, one I think is going to matter more and more: judgment.

Because if we have tools that let us do more and more things, the question stops being only what we know how to do. We also have to know what's worth doing.

And judgment doesn't appear magically: it's built with experience, with curiosity, with exposure to different problems and, above all, with focus. When that direction isn't clear, you can have a huge amount of knowledge and be perfectly solving the wrong problem.

Maybe that's one of the most important responsibilities for those of us who lead teams: not telling each person exactly what they have to do, but giving them enough context to figure out where they can create value.

Because the more capable the tools become, the less sense it makes to lock people inside a rigid list of responsibilities.

That doesn't mean we all have to do everything. Nor that specialization has stopped mattering. It means our role can be a starting point, not necessarily a boundary.

And that maybe being a jack of all trades was never simply knowing a little about a lot of things.