The career ladder is broken

We were all told to pick a lane.
Choose a career. Commit to a degree.
Stick to one thing and climb the ladder.

But I think that today the world is too dynamic, technology is too fast, and most of us are too multi-layered to squeeze into a single title.

And earlier in my entrepreneurial career, I found that I was building my life around my business. Today, I’ve shifted to build my businesses around my life.

The journey is different for everyone:

You are more than one thing

Being “more than one thing” may just be a great future-proof strategy. I always say it in my personal branding workshops — and that’s not just okay, it’s a strength. Whether I’m speaking to a group of young students or professionals working in government, it resonates.

We often get defined by our title, our role or our LinkedIn headline.
But most of us don’t fit neatly into one lane.

That’s why this newsletter is called The Intersection. Because I operate at the intersection of multiple worlds — strategy, creativity, social impact, education, entrepreneurship…

Those intersections are where the most exciting things happen.

That’s not confusion, it’s clarity. It’s where innovation lives.

That perspective is huge for me, especially as a strategist. It allows me to connect dots between industries, understand audiences through multiple lenses, and adapt quickly as technology (especially AI) reshapes what “work” looks like.

Since I’m interested in so many things, doing only one at all times may not keep me interested for long. Being multi-passionate doesn’t mean being scattered, it means being deeply curious. It’s about recognizing that your interests connect — even if they seem unrelated on the surface. They often feed one another in ways that lead to new ideas, opportunities, and forms of impact.

As AI is automating tasks faster than ever, it’s the human ability to connect dots that stands out. Being multi-passionate is an edge here.

But today’s newsletter is NOT about AI or my work.

Let’s talk about the linear career.

The end of the linear career

This week, the algorithm served me a great piece by a guy named Toan Nguyen on how he no longer believes in the concept of a linear career, mainly because we live in a non-linear world.

For most of his early career, Toan admits he was focused on climbing the ladder — chasing titles, recognition, and all the external signals of success. But over time, he realized that these ladders often come with invisible costs: exhaustion, comparison, and relationships strained by the constant race upward.

I think that shift in thinking is big.
It moves us from chasing validation to building alignment.
From what do I do? to who am I becoming?

From ladders to portfolios

Toan illustrated this with this visual that you may relate to — a map showing the “main job” surrounded by a cluster of other roles that he personally has: podcaster, mentor, investor, teacher, advisor, speaker, creator.

It’s an example of what’s called a career portfolio.

We can, and often should, have multiple dimensions to how we work and create.

A portfolio career doesn’t mean juggling ten side hustles. It means intentionally curating your professional life around your skills, interests, and values, rather than one rigid path.

For some, that might look like blending a corporate role with creative projects or community work. For others, it might mean building a consulting business, teaching part-time, and launching a passion project.

The point isn’t diversification for its own sake — it’s integration (intersection).

There’s a writer and “Portfolio Career Mentor” out there called Anna Mack that I recently came across. She answered this submitted question: “How do I get from Point A (stuck in a stressful job) to Point B (going out on my own to build a portfolio career across a few areas; some I have experience in, and some that are just a pipe dream)” by showing the early trajectory of her own portfolio career in this great diagram:

Why this matters more now

What remains most valuable is perspective, creativity, and adaptability (what AI doesn’t do). Those who can connect ideas across industries, disciplines, and communities — those who live at the intersection can thrive. A nonprofit leader who perhaps has an MBA and applies design thinking is a perfect example.

An ability to move fluidly between worlds — and to make sense of the overlaps — is what will help us thrive.

A few reflections for you

If you’ve ever felt like your interests are “too scattered” or your path doesn’t make sense on paper, here’s what you can take away:

• Your career doesn’t have to be a ladder. It can be a web or a garden that you nurture and grow in different directions.

• Perspective is your superpower. The mix of experiences you’ve had gives you unique insight that others can’t replicate.

• Build around your life, not the other way around. Alignment and sustainability matter more than prestige or pace.

Does that sound like a career and life worth building?

It's not how high you can climb, but how diverse you go, perhaps.

If your career were a portfolio, not a ladder — what would be in it?
What mix of roles, passions, and pursuits make up your intersection?

Want to start or improve your own newsletter?

PS — I shared this brief video on social about the process of how I write this newsletter. There, I promised that the full steps would be shared in my next edition. So I wrote it all out for you, right here: The Weekly Newsletter: A Step-by-Step Guide

Thanks so much for reading! As always, I appreciate your time and attention. 🙂