Like me, you’ve no doubt seen loads of posts and articles about portfolio careers – the idea that instead of having one full-time job, you build a career (and income streams) across different types of work: traditional employment, freelance gigs, contract work, short-term projects, advisory roles, board positions, and so on.

I’ve been intrigued by the Portfolio Career concept for a while. And while I wouldn’t say I’ve gone full portfolio, I’ve definitely been circling the edges.

Over the past year, I’ve done a mix of work – all in and around associations:

• Ongoing contract work for a marketing agency
• Long and short-term, project-based consulting
• Ongoing / retainer based advisory and consulting
• And an active search for an in-house, perm leadership role

It started out as a practical (and unplanned) decision. We had a family situation that made flexibility more important than consistency for a period of several months, and freelance and project work gave us the breathing space we needed.

Now, I find myself with a few regular gigs, a few ad hoc ones, and the growing sense that this might keep evolving in ways I didn’t expect.

It’s been great in many ways – the work is often stimulating and purposeful, and I get the chance to focus on bigger-picture work without getting buried in day-to-day minutiae.

But it also raises a question I keep circling back to:

Is this kind of work compatible with leadership in associations?

We say we want modern thinking in this sector. Innovation. Fresh perspectives. Strategic minds.

But I’m not sure we’ve caught up to the fact that modern thinkers often don’t have traditional CVs anymore.

Instead of neat, linear progression, you see:

• Deep experience built across diverse projects
• Short-term roles with long-term impact
• Advisory and consulting work that doesn’t slot neatly into job titles

It doesn’t always look like stable, ongoing employment. But it often reflects exactly the traits we want in leaders: expertise, adaptability, and a high tolerance for ambiguity.

So where does that leave those of us whose recent career history looks a bit… squiggly?

Can we bring that kind of path into a GM or Exec role?

Will boards and selection panels recognise the value in project-based experience?

Or is the association sector still wired to reward linearity over diversity of experience and thinking?

Because working across different organisations, with different teams and challenges, builds a kind of transferable insight that’s hard to develop inside a single structure (wood, trees, etc).

Associations champion innovation in their sectors. So why is leadership within so often the exception?