The most genuinely successful people I know have résumés that a corporate headhunter would consider unremarkable: their CVs are full of unknown companies, strange gaps, or small boutique ventures you have never heard of. And I am the first like this: half of my career so far has been self-employment, and ironically that doesn't look good on a CV.
Viewed strictly through the traditional prestige lens, their careers look disorganized, maybe even like failures.
Look at their actual lives, however, and the picture flips completely. They travel year-round, spend quality, uninterrupted time with their partners and friends, and hold total sovereignty over their schedules. They don't report to a board, they don't submit PTO requests, and their net wealth belongs entirely to them. Contrast them with my friends in Milan who work 60+ hours a week at corporate advisory firms and investment banks: they earn just enough to cover an overpriced apartment (if a single room barely fitting a bed can be called that) and the drinks required to numb down the routine. Their net savings at the end of the month are virtually zero. Yet, when you point out that their effective hourly wage is lower than a bartender's, they shrug and hit you with the reflex response: "I'm in finance."
As if prestige were a currency you could hand to your landlord.
They are paying for status with their youth, mistaking institutional affiliation for personal fulfillment.
Prestige is not a neutral measure of human excellence; it is an institutional subsidy. Elite firms use prestige as a discount code on human autonomy. If an employer can offer a candidate social validation, an elite brand name, and dinner-party bragging rights, it doesn't have to offer them a manageable workload, real equity, or a path to independent capital. Prestige is the non-cash compensation that keeps overqualified people enduring high-friction lives.
They get a better CV, I give them that, but they are trapped as they treat that single-page document as an objective scoreboard. At first, they chase prestige because they want to be better than their peers; then, they chase prestige because they want to fit in with the new peers; and finally, in the end, they chase prestige because after an entire life doing so, they are now treating the logos they have been stamped on with as a proxy for their value. But a résumé only measures how reliably you fit inside someone else's machine. It records compliance under twentieth-century gatekeepers, not adaptability, taste, or life satisfaction. And optimizing for prestige means letting human resource departments dictate what a successful life looks like.
No wonder these people are all miserable.
After all, when you analyze how prestige operates, you quickly realize it functions as illiquid scrip: it feels powerful inside the ecosystem that issued it, be it colleagues, LinkedIn, or industry dinners, but it loses all purchasing power the moment you try to convert it into actual freedom. You cannot trade a corporate logo for a month of travel or an evening with your family.
And if you leave the ecosystem, your entire "prestige capital" disappears. In his book What It Takes, Stephen Schwarzman recalls the moment this became real. Inside Lehman, he had spent years building a reputation as "the rainmaker," and the easy move was obvious: stay, climb, maybe open a new division under the Lehman name, and cash in the prestige he'd already earned. Instead, he walked out with none of it. When he and Peter Peterson started Blackstone, nobody cared who they used to be. Their recognized value turned out to be a function of Lehman's letterhead, not their own judgment, and for years they fought an uphill battle with zero institutional prestige to lean on.
That friction wasn't a side effect of leaving: it was the price of it, paid in advance, before anyone confirmed they were allowed to charge it. And it's exactly what the safer, internal path would never have demanded of them, because it would never have offered what waited on the other side of it, either.
The ultimate goal isn't having a prestigious logo attached to your name, but understanding that the freedom on the other side of losing the logo is worth more than the logo ever was, and that you only find that out by giving it up first, not by waiting for permission to.