The Portfolio Career

A few years ago, if someone had told me they'd eventually be a consultant, advisor, board member, entrepreneur, and corporate executive during the same chapter of their life, I probably would have thought they were unfocused.

Now? I think they might be ahead of the curve.

And I don't think it's because people suddenly have more ambition.

I think it's because more people are waking up to a question that didn't exist for previous generations:

What happens when the company, title, or career path you've built your life around no longer feels as secure as it once did?

Not wrong. Not bad.

Just... less certain.

I've been thinking about that a lot lately.

Especially after the conversations I've been having with women in tech.

Because while the headlines are talking about layoffs, hiring freezes, and AI, the conversations I'm having sound very different.

They're asking:

"Do I still want this?"

"What else is possible for me?"

"Have I made my career too important?"

And that's where I think the real story is.

WHAT

Here's what I can't quite shake. For years, we were told that focus was the answer.

We were told to specialize.

To become known for one thing.

To stay focused.

And for a long time, that made sense.

But I'm starting to wonder whether what looked like focus was actually dependence.

Dependence on a system that felt a lot more predictable than it does today.

Maybe that's why portfolio careers are becoming more common.

Not because people suddenly want more on their plate. Because fewer people want all of their eggs in one basket.

We're not defining portfolio careers. We're examining a belief.

WHY

I don't think this is happening because people suddenly want more freedom.

Or because everyone wants to become an entrepreneur.

I think people are responding to what they're seeing.

Five years ago, it was easier to assume that being good at your job was enough.

Today, I'm not sure that's the bet as many women are willing to make.

People with impressive resumes are finding themselves unexpectedly back on the market.

That's enough to make anyone question some long-held assumptions.

And for a lot of women, that's creating a realization that can be uncomfortable to sit with:

The thing that once felt safest may no longer be the safest bet.

And I think we're only at the beginning of that shift.

HOW

Three years ago, while I was still at Microsoft, I decided to do something about it.

I wanted to be known for who I am, not just the logo next to my job title.

At the time, I couldn't have imagined where that decision would lead.

I wasn't thinking about leaving Microsoft.

I definitely wasn't predicting what was coming.

I just knew I wanted to build something that would come with me wherever my career went.

Three years later, that decision has changed far more than my LinkedIn profile.

Here's the proof👇

When people look at that screenshot, they usually notice the 43M+ impressions.

What I notice are the conversations.

The opportunities that came from being known for more than a job title.

The reminder that building your reputation is very different from building your resume.

So here's the question I'd leave you with:

If your title disappeared tomorrow, what would still come with you?

Or have you been relying on the company to carry more of that than you realized?

Because I think that's the real cost of waiting to build something beyond your title.

In September alone, six women joined me inside Legacy By Design™.

All of them recognized the same thing:

The chapter that got them here isn't the chapter they're trying to build next.

They're not trying to figure out their next title.

They're trying to figure out who they want to be beyond it.

If that's the conversation you've been having with yourself lately, let's talk.

Until next week,

Jaspreet