Lisa Steadman was twelve years old, playing with Barbies in her bedroom in Saudi Arabia, when her mother walked in and said, “Your dad doesn’t love me anymore.” Lisa cried. Then she started solving her mother’s marriage.
She’d never kissed a boy. She had zero business being anyone’s relationship counselor. But that’s where it started — forty years of studying why relationships work and why they don’t, long before she wrote five bestselling books about breakups, long before she picked up a camera and made a short film that premiered at Cannes.
I brought her on to talk about friendship. We ended up talking about all of it.
Making Friends After 40 Is Its Own Kind of Hard
Nobody tells you that the friend-making machinery you had in your twenties just… stops running. You’re not in a dorm. You’re not at happy hour with coworkers every week. If you work from home, you might go days without a real conversation that isn’t with your dog.
Lisa’s answer wasn’t a hack. It was a habit: go where you already light up. Pilates, a hiking group, the coffee shop you keep meaning to try. Her husband texts a group of friends every Thursday — “this is where I’m going tonight, come or don’t” — and if nobody shows, he talks to strangers. That’s the whole system. Show up on purpose, often, and let some of it not work out.
The Friendships We Never Learned to End
Here’s the part that stuck with me. Lisa had a trio of close friends — people she worked with, socialized with, trusted. One of them needed her during a divorce, and Lisa, buried in a stressful house purchase, blew her off. She knew it. She sat with the shame of it for years before she finally reached out and apologized. They’re close again now. They went to Paris together.
The other friend in that trio, she never got the chance to repair. Radio silence, then a voice memo dripping with anger, then nothing. Lisa doesn’t know exactly what she did wrong. She reached out twice, got no real answer, and eventually understood: some things don’t get fixed just because you want them to.
Both of these are real. Both of these happen to grown women all the time, and almost nobody talks about them out loud. We show up with a casserole when a friend gets divorced. We don’t have a script for when a friend just disappears.
That disappearing act — the ghosting, the slow fade — is the one Lisa can’t stand. “I would rather you tell me to my face,” she said. Not because it doesn’t hurt. Because at least it gives you something to work with.
When You Change and Your People Don’t Come With You
Lisa also told me about an old friend who circled back twenty years after a nasty falling-out, needing a favor. When she turned him down, he came back swinging — this time about her body. She’d lost weight. She’d gone on GLP-1s, on purpose, for her health. He framed it as her thinking she’d “made it.”
She hasn’t spoken to this person in two decades. It still stung. Because that’s what happens when you make a change — quitting drinking, losing weight, leaving a marriage, leaving a job — and the people around you don’t know what to do with the new you. Some of them take it as an insult. A lot of them just miss their old drinking buddy, their old eating buddy, their old excuse not to change too.
You don’t owe anyone the old version of yourself.
Advocating for the Woman You’ll Become
Midway through our conversation, Lisa said something that stuck with me: it’s like finding advocacy for your future self. Not in a vague, manifestation-poster way. In a practical one—how you eat, how you move, whether you’re saving anything, and whether you’re honest with yourself about your health.
I told her about a habit of mine: I journal most mornings, and sometimes I write as if I’m talking to my 80-year-old self. One entry hit me hard. She told me, on the page, that she’s not guaranteed. That the choices I make today don’t just determine whether her life is good—they determine whether she has one at all.
I know how that sounds coming from two women with the resources to make these choices. Lisa said it herself: choosing to leave a corporate job in her 50s, choosing to sink savings into a short film, choosing to prioritize her health—none of that happens without privilege. She was upfront about that, and so am I. But the tiniest steps toward taking care of yourself aren’t reserved for people with a safety net. Loneliness alone is as dangerous to your health as smoking a pack of cigarettes a day. That part isn’t optional for anybody.
The Leap
Lisa left her corporate career last year — the steady paycheck, the bonus, the matching 401k — to make a movie. It premiered at Cannes. She still doesn’t know if she’ll get another traditional job. She’s not sure that matters to her anymore.
Her advice to any woman standing at the edge of her own leap, wondering if she’s brave enough:
“You’re braver than you know. And the woman you’re going to meet—your future self—she already exists. She’s holding her arms out, and she’s gonna catch you when you take the leap. But it’s up to you to take the leap.”
Getting clear on what you want sounds simple. It’s not. It’s just that the hardest part was never the leap itself — it’s the long stretch of time before it, where you already know, and you keep pretending you don’t.
About Lisa Steadman:
Lisa is a writer, director, and producer who has spent her career examining modern relationships — from five bestselling books on breakups and dating to television pilots, romantic comedies, and her most recent project, a short film that premiered at the Cannes Film Festival. Find her at @lisasteadman.
If this episode hit something for you — a friendship you’ve been avoiding, a change you keep putting off, a leap you haven’t taken yet — send it to the friend who needs to hear it. And if you want more conversations like this one, hit subscribe wherever you listen, and come find us at @grownasswoman.guide.
COMPLETE TRANSCRIPT
Lisa: “You’re braver than you know, and the woman you meet — your future self already exists. And so she’s holding her arms out, and she’s gonna catch you when you take the leap. But it’s up to you to take the leap.”
[JACKIE INTRO]
You know that feeling when you already know something but you’re just not ready to deal with it yet? Maybe it’s a friendship that’s been on life support for two years, or maybe it’s a job that is slowly killing you inside. Or maybe it’s your health, and you keep telling yourself you’ll get serious about it next month.
Here’s the thing: you already know, and you’ve known for a while.
Lisa Steadman has spent her entire career studying why relationships work and why they don’t. She’s a USC film school grad who wrote five bestselling books on breakups and dating before she went back to screenwriting and directing. Her latest short film just premiered at Cannes. But this conversation isn’t about any of that. It’s about what she’s built in her 50s once she started actually listening to what she already knew — in her relationships, her career, her health — and what she’s learned about herself through her work.
PART 1 — ORIGIN STORY & FRIENDSHIP
