I was 61 when I got hired into a regular job for the first time in 37 years.
I’d been an entrepreneur since 23. Goldsmith, business owner, financial advisor, online business builder, tech consultant. By 60 I was broke, driving Uber, and applying for a 401(k) account manager role with no US employment history and a resume that read like four people’s careers stitched together.
I got the job in two weeks. Started a week before COVID lockdown. The age never came up.
The part that surprises people
What surprises people more is what happened next.
Two years later, one of the firm’s clients hired me away. I became Chief of Staff to a NY company at 63. I’ve been with them over four years. The CFO told me recently that as long as he has a job, I have a job.
The reason he hired me wasn’t my financial background, though that helped. It wasn’t my problem-solving, though he said that mattered. Here’s what he actually told me, on a phone call early on:
“It’s like talking to a friend over coffee. I call you before my other calls because you put me in a good mood.”
He calls me before hard conversations. He runs his thinking past me before board meetings. He tells me what’s actually bothering him before he tells the people who need to hear the polished version. Somewhere in year two, the title stopped describing the work. I’m his confidant. Sometimes his life coach. The org chart hasn’t caught up.
What he was actually buying
He wasn’t buying my spreadsheet skills. Spreadsheet skills were the floor.
He was buying the ability to read what he wasn’t saying on a phone call. To know which question he was about to ask before he asked it. To make him feel less alone in a job where most of his peers can’t be vulnerable with anyone. He was buying judgment. Discernment. The kind of read on a person that comes from having been wrong about people enough times to finally get good at it.
None of that was on my resume. It couldn’t have been. There’s no line item for spent five years in my forties figuring out why I kept choosing the wrong men or survived two financial collapses and learned to tell the difference between someone who’s scared and someone who’s lying.
But that’s what he was paying for. He just didn’t have language for it until he was already on the phone with me.
The thing AI is making visible
There’s a piece of writing going around right now about Amy Porterfield closing her flagship course business and moving to a high-end mastermind. The argument is that AI is coming for the middle of the knowledge economy. Standard information, repeatable processes, anything you could turn into a course module — AI does it for twenty dollars a month now. The work that survives is the work that lives in a specific person with a specific history.
I think the writer is right. I also think the framing leaves something out for women my age.
We didn’t suddenly become valuable because AI got good. The value was always there. AI just made the rest of the workforce catch up to what hiring managers like mine already knew when they bothered to look.
For a decade I was told my zigzag resume was a liability. Five careers, three continents, two collapses, a pile of skills no recruiter knew how to categorize. I half-believed it. I burned through my savings trying to be more legible. I tried to hide the gaps. I tried to make the path look straight.
Then a financial services firm hired me at 61 because the founder wasn’t intimidated by my age. And then his client hired me away at 63 because what he needed was a person, not a process, and he could feel the difference on a phone call.
What this means if you’re 50 or 60 and reading this
You don’t need AI to threaten white-collar jobs for your experience to matter. It already mattered. The story that it didn’t was always wrong. AI is just removing the cover the story was hiding behind.
The thirty-year-old who can build a slide deck faster than you isn’t your competition. Neither is the AI tool that can build it faster than both of you.
Your competition is the version of yourself you’re still running — the one who learned, somewhere along the way, that her accumulated reads on people, her survived collapses, her decades of having had to figure things out without a map were too messy to monetize.
That version stopped fitting a while ago. Most people are just still wearing it.
It’s not too messy. It’s the only thing left that’s worth paying for.
The hard part
The hard part is that you have to be able to see it before someone else can.
My CFO read me through the phone in a way I couldn’t read myself. Most people don’t get a CFO doing that for them.
They have to do it for themselves first.
They have to look at the unrelated careers and the years that didn’t translate to a credential and the skills they built in the wrong order, and find the thread.
The thread is always there. It’s just that the people who have it have usually been told for decades that the thread is a liability instead of an asset.
The asset was always the asset. We’re just finally living in a moment where it’s getting harder to pretend otherwise.
If you’ve been reading my work for a while, you know this is the heart of what I do. I write for people who are done running a version of themselves that stopped fitting. The CFO read mine off me on a phone call. Most people have to do it for themselves first.