I came across the graphic from Anna Mackenzie on Substack the other day. Anna is a creator and multi-hyphenate who writes about portfolio careers.

It perfectly encapsulates the way we’re rethinking what building a career and finding success even looks like.

The career ladder was the version we were all raised on — one step at a time, up and to the right.

Many people who ended up becoming a solopreneur/fractional/etc. (myself included) realized at some point the career ladder no longer served them. Chasing more money or more impressive titles didn’t actually lead to what they want in life, whether that was more time, more freedom, more fun or something else entirely.

The corporate ladder worked during a time when work and companies were predictable… and we all know how that story goes now.

The ladder gave you status.
The web gives you freedom.

It’s not an update. It’s a new era for creators.

On November 13, beehiiv is pulling back the curtain on what the future of creating and publishing content online looks like. From creators to publishers to entire media brands, this is the moment everything changes.

At our Winter Release Event, we’ll reveal our vision for building, growing, and earning all in one place, with total control over your audience and your business.

If you make things on the internet, this is the day you finally see what the future holds.

RSVP for our free virtual event now.

RSVP today

As a first step outside the corporate ladder, you can experiment with the squiggly career (popularized by this book by Helen Tupper and Sarah Ellis).

You start with one skill — marketing, design, writing — and follow your curiosity to the next thing. You take a freelance project. You test a workshop. You start a newsletter. Suddenly your “career path” looks less like a line and more like a constellation of dots you’ve connected yourself.

The squiggly career became the first rebellion against the climb. A permission slip to pivot, experiment, and redefine success.

But for many creators and solopreneurs, even the squiggle isn’t enough anymore.
The call - and opportunity - here is much bigger: we can build entire ecosystems.

The web is what happens when your work starts to connect.

Each strand represents something different — your core craft, your side projects, your audience, your community. Some threads make money, others make meaning. Together, they form a structure that’s both flexible and strong. You realize that all the things you’ve done and experienced and the things that fascinate and excite you can all be a part of your work.

If the ladder was about climbing, the web is about weaving.

When I think about my own path from journalist to content strategist to creator, every move I made looked “random” from the outside.

But each new skill or experiment became another strand in the web: interviewing founders → storytelling → brand strategy → helping others clarify their own story.

That’s the beauty of the web model. Nothing is wasted. The dots eventually connect. I still don’t have a title or an elevator pitch that’s neatly package but I feel like my mission is clear to tell the stories of the creator economy and to show more people what entrepreneurship can look like. The work may take different forms but the web is what connects it all together.

And the creator economy is what makes this possible. We finally have the tools, platforms, and autonomy to build businesses around our mix of skills, not just the one that fits neatly on a résumé.

Your newsletter feeds your client work.
Your consulting informs your digital product.
Your writing builds your reputation, which opens doors you didn’t know existed.

It’s not about finding one path or following other people’s expectations of success. It’s about creating a network of opportunities that supports the life you actually want.

I’m continually reminded that building a business that you love is an active and intentional act (something Jenni Gritters and I talked about a lot in our conversation on sustainable solopreneurship!)

So in this week’s edition, I’m sharing a reflection on what i’ve learned from Ienni (and from my own messy, nonlinear path this year) about building a career web that actually supports your life, not the other way around.

The more I talk to founders and solopreneurs, the clearer it becomes: the web only works if the person at the center is steady. Every strand, like your offers, your clients, your creative experiments, depends on how well you know what you’re weaving toward.

Jenni’s reminder that entrepreneurship is a revolutionary act feels like the perfect note to end the year on. Choosing to build a business around what you love, and who you’re becoming, is radical in a world that tells you to fit in and stick to the ladder. It asks you to keep showing up, keep listening, keep rebuilding the web as you grow.

So that’s what I’ll be doing for the next seven weeks — looking back at what this year taught me, what threads i want to strengthen, and which ones it’s time to let go.

Here’s to weaving a 2026 that feels aligned, intentional, and entirely your own. 🕸️

I regularly share what tools I'm using, loving, and what's really making a difference in my business. I recently did a big cull of subscriptions and narrowed down the key tools that I am relying on most.

I realize that the key software that I'm using (and running a six-figure freelance business) costs me around $150/month. Not too shabby!

Here are some discounts for you to try: