The most successful people I know are by far the poorest

When self-made fashion insider Stacey Duguid broke from behind her glossy Instagram persona a few weeks ago, revealing that she’d been out of work for 16 months and was struggling emotionally and financially, she was met with an outpouring from people in the same boat. While Duguid has since focused her campaign on the way midlife women in particular are hobbled by the current job market, the truth she tapped into is increasingly a universal one. In 2026, success simply doesn’t equal financial security, whether you’re talking about high wages or even just the expectation of grasping the next rung on the ladder. For millennials in particular, that pill has been a bitter one to swallow. Sold a dual-pronged dream as kids – hard work pays off; do what you love and you’ll never work a day in your life – we entered the workforce bright eyed and bushy tailed only to collide with the financial crash, Brexit and Covid. Now, AI threatens to demolish the world of work all over again, with job hunters and recruiters locked in a robo-arms race that rejects genuine applicants in favour of CVs wrought from its own homogenised LinkedIn drivel. Clinging to survival by the skin of our teeth, very little seems clear to my generation, but one thing’s for sure: the steady careers we were raised for are gone, if they ever existed in the first place. Call it the gig economy, or side hustles – truth is, nowadays many of us need more than one job to survive, let alone thrive. Nowhere is this truer than in positions that seem the most “successful” from the outside – and while that might sound ironic, I promise it makes a weird kind of sense. All my friends are clever and wonderful in absolutely equal measure – but it’s undeniable that the ones with the most glamorous résumés (international symposiums, publishing deals, magazine profiles) are by far the poorest and most precarious, when all is said and done. Meanwhile, the ones with less glitzy gigs are much more stable – and as we enter our mid thirties, they’re much better paid, too. The stuff that looks cool tends to pays terribly, I guess because the kudos is supposed to compensate. As for 9-5 jobs, with managers and payslips and HR departments, they have to actually compensate you with, you know, money and a pension. But while you could lay our precarity at our own doors, my fellow freelancers and I are arguably insulating ourselves from a different kind of insecurity. After all, solid jobs are only solid until they’re gone, which, as per the example of Duguid, can happen in a flash. On the other hand, multiple income streams – whether via a side hustle, or having lots of clients as a freelancer – means spreading your eggs across more than one basket. Clearly, it’s an idea that appeals: the number of 16–24-year-olds in the UK freelancing is at an all-time high; meanwhile, 57 per cent of US Gen Zs report having a side hustle compared to 21 per cent of boomers. It’s worth paying attention to all these enterprising young-uns, because while we’re tearing our hair out as we come to terms with the new workplace reality, they’ve been born into it. They might be famously demanding as employees, but that’s because Gen Z see jobs as opportunities from which to wring everything they can, rather than wells to pour as much energy into as possible – and if there’s no guarantee of the well being there tomorrow, who can blame them? I promise that all this is liberating as well as devastating, if you squint. Detaching our concept of worthwhile work from the promise of financial security stops us labouring under an illusion, enabling us to shake off the self-reproach that creeps in when slogging away doesn’t necessarily produce prosperity. Other corollaries are positive too – because if doing what you love doesn’t result in buckets of cash, then you have to tap into other motivations for keeping at it, like, I don’t know, artistic integrity, or genuine joy. And at the risk of making myself sound even more like someone with a raging case of Stockholm syndrome, at least this new status quo requires us to get creative when it comes to the question of “how am I going to make a living?” As such, you’ve probably got the era’s inbuilt precarity to thank for not only your favourite Uber Eats deliveries and OnlyFans accounts, who may well have started freelancing on online platforms to supplement their income, like one in seven UK adults — but also singer-songwriters, stand-up comics and designers, many of whom fund their creative lives by clocking in to an office five days a week (so quaint!). Once, we had jobs to pay the bills and hobbies to keep us happy. Now that so many of us use hobbies to pay the bills, it’s surely not too much to ask that if jobs don’t literally bring us joy, they’re not actively deleterious to our wellbeing. Without the landmark of a stable career to sail towards, it’s easy to feel untethered. Which, it’s worth remembering, can entail the thrill of freedom as well as the stomach-lurch of freefall.