- My dad worked a job he hated and planned to retire at 55.
- He died at 52, before he could enjoy the life he was saving for.
- That changed how I live — I stopped waiting and started taking risks.
The image of my father that lives most clearly in my memory is this: a man in a suit, on a train platform, me, a child in my PJs, staring out the windows of our car as my mother picked him up.
On reflection, I feel really sad that the standout memories of my dad now were those of a man who looked like he was always either just arriving from somewhere he didn't want to be, or about to leave for it again.
He commuted every day from the city to our small suburb. He worked in banking. He was, not infrequently, angry. He also saved carefully, spent carefully, working in a role he hated, but it was OK, I understood why; he planned to retire at 55.
But then he died at 52.
I dropped out of fashion school
When he died, I left fashion school. There was no big conversation, no dramatic announcement, no plan. I just left. Which, looking back, was probably the first honest decision I'd ever made, the biggest, smallest choice, because the plan I'd been following wasn't mine to begin with. It was the plan that I inherited by default: finish school, accumulate credentials, enter a system, and work my way up it. Be responsible. And wait to retire.
My father had waited. He was still waiting when he died. So I stopped waiting. I decided to just live, almost nihilistically at first.
I said yes to things I had no business saying yes to. I walked into rooms I hadn't been invited into and stayed until someone asked me to leave, and sometimes then went to the after-party. I was married twice before I was 30, which I mention not as a confession but as evidence. Evidence that I was someone who ran toward things rather than hedging against them. It didn't always work. That's not actually the point.
I moved from London to New York
At 22, the Daily Mail named me "London's most invited." By 25, I moved to New York alone. No close contacts, almost no money, a level of confidence that was almost certainly disproportionate to my actual situation.
People thought it was reckless. I thought the alternative, staying somewhere safe and watching a version of my father's life slowly take shape around me, was the riskier move by far. I had fun.
By moving there, I was to become the Fashion Director at one of the largest women's media companies in America, running a site with 500 million monthly visitors. Anna Delvey was, briefly, my intern.
None of this is what a financial advisor would have recommended. None of it looked responsible on paper. I made a documentary with no filmmaking experience because women were dying, and I needed people to know, and I also knew it would probably not make any money for that exact reason. But that never really mattered to me.
I never thought of retirement
I have never obsessed over a retirement account. I have never once made the choice that looked safest; I have always chosen the ones that would help get what, deep down, might actually be my life goal. Not chasing a title, a promotion, or some tidy, résumé-friendly milestone. Really, I was chasing the idea of an exciting life. The kind of life that, if I play it right, might one day warrant a New York Times obituary. The girl who lived.
We don't talk honestly about the risk that financial advisors never bring up. The risk of the life you defer and never get to. It doesn't fit neatly into a financial planning conversation. It doesn't show up in a spreadsheet. But it is a risk, and for a lot of people, it is the one they are most exposed to, because it is the one they never think to calculate.
My daughter is 9. I think about what she sees when she watches me work; my parenting is actually one of the areas where I'm careful, and I think about the life model I'm showing her. Not the titles or the decisions or the specific bets. But whether she sees someone who understands, early and without ambiguity, that time is the real asset. That you don't get it back. The train platform is not where you want to be when you run out of it.
My father's plan was 55. He never made it.
I don't have a plan. I have a life I've already lived, and I'm not done. In many ways, I expect to never retire.
In a world where everything feels unstable, I've found that showing up, fully, prematurely, imperfectly, turns out to be almost the entire battle. The rest is just staying on the train long enough to see where it goes.
