There is a story about someone who changed jobs ten times in ten years, helping them reach the career they wanted. I read it twice. The first time, I wanted to cheer that grit, and grit deserves applause. The second time, a quieter question crept in and wouldn’t leave: whose ladder were you climbing all that time?
Because here’s the thing nobody says out loud. Ten jobs in ten years require a remarkable amount of stamina. But at the end of each ten moves, the income still belonged to someone else. A better rung, yes. A bigger salary, often. But still a rung on a ladder propped against a wall you don’t own and someone else gets to decide, on a quiet Wednesday morning, whether that wall stays standing.
The ground is moving under all of us
I’m not saying this to frighten you. I’m saying it because it’s true, and because pretending otherwise helps no one. AI is quietly rewriting job descriptions across whole industries, not in some distant sci-fi future, but in the actual month you’re reading this. Even the BBC, the very outlet publishing cheerful career-change stories, announced plans to cut up to 2,000 jobs to save around a tenth of its budget. Read that twice, because it’s the whole point: the ladder-provider is sawing off rungs while telling you to climb faster.
And yet this is the part I find genuinely hopeful: workers are starting to feel it and move. In one recent survey, most people said they felt positive about their opportunities, and about half said AI was actually building their confidence to learn new skills and make a change. The mood has shifted from “job hugging”, clinging on for dear life, to something braver. People can smell the change in the air. The only question is what you do with that instinct once you’ve felt it.
Changing jobs is relocating. Building is repurposing.
Let me draw the distinction that took me years to understand. Changing jobs ten times is relocating, same arrangement, better postcode. You’re still trading your hours for someone else’s money, on terms you didn’t set. Building something of your own is repurposing: taking everything you’ve learned across those ten roles and pointing it, finally, at a life that’s yours.
I know this exchange intimately, because I was on the wrong end of it. Early on, I was stuck in a role I quietly hated, watching the clock, certain there had to be something else on the other side of all that effort. I loved finance but knew almost nothing about investing, and my impatience cost me early, silly risks that lost real money and taught me an expensive lesson about doing my homework. What I’d give to tell my earlier self one thing: the way out isn’t a better version of the same deal. It’s a different deal entirely.
You don’t have to leap. You have to start.
Here’s where people hear “entrepreneurship” and picture quitting on Monday and betting the house by Friday. Please don’t. That’s not courage; that’s a coin toss. What I actually did, and what I’d gently point you toward, is smaller and far less dramatic: build the thing on the side, while the salary still covers the bills. A skill you sell. A small product. A service ten people pay for before a hundred do. Let it earn its keep before it becomes the whole plan.
This is also where owning your own opportunity meets the boring genius of not putting everything in one basket. A job is a single income stream you don’t control. A life you’re building can hold several: a bit you earn, a bit you own, a bit that grows quietly in the background while you sleep. That’s not just a portfolio strategy; it’s a resilience strategy. When one wall wobbles, you’re not standing on it alone.
The real prize was never the job title
Strip it all back, and the ten-jobs story isn’t really about careers; it’s about a person refusing to accept the deal handed to them. I understand that refusal in my bones. But I’d nudge the ambition one step further: don’t just chase the career you wanted. Build the life you wanted the rounded one, with room for your people, your health, your Tuesday afternoons, and the sense that what you’re building can’t simply be taken away on someone else’s whim.
Ten jobs in ten years is impressive. One life that’s finally, unmistakably yours? That’s the version worth the climb.
If you want a place to start thinking it through, I keep the resources I wish I’d had at the beginning the map I never got handed. None of this is financial advice; it’s simply the view from someone who took the long way round and would love to save you a few of the wrong turns.
The Jacqueline Brand: knowledge builds confidence, and confidence builds wealth. This is editorial commentary for information and education only. It is not financial, investment or professional advice, and nothing here is a recommendation to buy or sell any investment. The Jacqueline Brand is not authorised or regulated by the Financial Conduct Authority. The value of investments can fall as well as rise, and past performance is not a guide to future returns. Figures were correct at the time of publication. Always do your own research and consider speaking to a regulated adviser. Where cryptoassets are discussed, they are high risk and largely unregulated in the UK, and you could lose all the money you invest. The Collection
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