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ReAmbitioning

Nick Cakebread

Ambition, Reimagined. Exploring how ambition, success, and purpose are being redefined in a changing world, and what it means to live and lead with meaning, clarity, and freedom.

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Substack
PricingOnly free issuesPublishesWeekly
Issues8Foundeda year agoLast Issuea month ago
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Latest Issues

What deserves your ambition now?

It’s a question I’ve found myself coming back to a lot this summer.

I’ve been taking a little time away from work, travelling around Europe, catching up with old friends, and creating some space to think.

During that time, I came across a...

a month ago
6

Sometimes the Pause Is Part of the Ambition

I haven’t written here for about eight months. Time really does fly as we get older!

At the beginning, I felt guilty about that. I had started ReAmbitioning because it was something I genuinely cared about and enjoyed. After exiting my bu...

3 months ago
3
2

It’s Okay to Dream Small(er)

I was listening to a Mel Robbins podcast recently (maybe this one) and she said something about dreaming bigger.

I love Mel, but that topic stuck with me. Not because she’s wrong, but because it reminded me how deeply we’ve all absorbed th...

a year ago
2

Is This the End of the Permanent Home Base?

For years, ambition around “home” meant permanence. You worked hard, bought the house, and planted roots. It wasn’t just shelter, it was proof you’d arrived.

But maybe that story has expired.

We’ve all heard about Gen Z and millennials ma...

a year ago
5
2

Are Slashers the Future of Ambition?

Editor’s note: This story was first published on Beehiiv in 2024. I’m republishing it here as part of the ReAmbitioning archive, because the shift toward portfolio careers feels even more relevant today.


Two years ago, after leaving...

a year ago
1

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  • Nick Cakebread

    Exploring how ambition, success, and life are being redefined. Signals, stories, and gentle guides.

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