Why I'm launching Ollie on Work

What I've learned after 6 months of hard conversations

Five years ago, I had no bloody clue what I was doing.

I'd just negotiated my exit from the digital agency I'd built and was contemplating the same question you're likely pondering now - what happens next when everything's changing?

So I started exploring. Interviewing the smartest people I could find. Reading everything.

At the time, I was just trying to work out what the hell was going on in my work and life, but in the years since, I’ve become obsessed with helping others ask the same question.

Here's what I've learned - most people are sleepwalking into a career trap.

Not dramatic failure. Just a slow slide into irrelevance while the game changes around them.

The writing's on the wall

Since ChatGPT launched, UK graduate job vacancies have dropped 31.9%.

Major companies like Meta, Amazon and IBM are laying off big chunks of their workforce – tens of thousands of people. Klarna and Salesforce have focused on expanding the AI workforce while reducing the number of humans. Goldman Sachs and Morgan Stanley are exploring AI for all their entry-level work.

I could give you 50 more examples, but you get the point.

And it's not just about AI. What skills will make someone valuable at work in the future? It’s become increasingly difficult to nail that down.

But, for sure, the old approach - build expertise, wait for instructions, follow the established path - isn't working anymore.

What I've figured out

Over the past six months, I stepped back to speak with hundreds of people - founders, laid-off workers, leaders, skeptics.

One thing became clear: if you're not thinking entrepreneurially about your career, you're storing up a big problem.

I don't mean we should all start businesses. I mean building the skills that matter when the rules keep changing - spotting opportunities, taking calculated risks, operating without clear instructions.

And I've also revisited the ideas I shared in Work/Life Flywheel.

Despite having moments of disillusionment with something I'd spent so much time talking about, I now believe in the principles I shared more than ever. Because when there's no clear and easy answer to what to do next, creating and sustaining momentum is the next best thing.

Why I'm optimistic (despite everything)

So, I'm definitely not some doom merchant - I'm genuinely optimistic about what's possible.

Yes, work is fundamentally changing.

Yes, that's disruptive and sometimes scary.

But I also believe we all have agency to take control of what happens to us.

I've been building and running businesses for 15 years. I've had the conversations, done the research, made the mistakes.

Those recent conversations with people in the thick of it have reinforced what I believe is going to happen over the next five years and I feel prepared for it.

And I'm determined to help you feel the same.

To position yourself so you're in demand, not desperately trying to prove your relevance.

What comes next

Well, a change is as good as a rest. And five years on from starting to do this stuff, Future Work/Life is becoming Ollie on Work.

I'll still be knocking out this weekly newsletter and the podcast, but I'll also be regularly sharing videos that will give you practical ideas to help you build and sustain momentum, including:

This week: A video explaining why this matters so much

Next week: The Momentum Starter Kit videos (three simple actions to spin your career flywheel) plus my podcast with Eric Jorgensen on how to create career leverage

End of July: How to nail the sweet spot of skills + passion + market need and, yes, some AI (useful shit, though, not fluff and foolery!)

I'm focusing on what I've learned the hard way - how to avoid the career expiration trap.

Not waiting and seeing what happens, hoping we’re still relevant when everything changes.

I'd love for you to contribute – by sharing the things you care about, or maybe struggling with.

And keeping me on the straight and narrow!

Thanks for reading,

Ollie