So I Asked... Laurie Flynn About Giving Yourself Permission

Five questions about reinvention, taking up space, and finally letting go of the need for approval

One of my favorite parts of writing on Substack has been discovering other women whose words make me stop scrolling.

That’s the idea behind “So I Asked...”—a series where I invite writers I admire to answer a handful of questions about midlife, reinvention, and the things we’re finally giving ourselves permission to want. I love seeing how different women, with different stories and different life experiences, arrive at completely different (and often surprisingly similar) truths.

This month’s guest is Laurie Flynn, author of My Menossance.

Laurie and I stumbled across each other here on Substack a while ago, but I knew we were going to get along after she published an essay in April titled “Where Did All My Fucks Go?” (I’ll let you connect the dots on why that one caught my attention.)

Laurie is fifty-three, recently divorced, and in the middle of doing something that sounds equal parts brave and terrifying: moving to Boston and rebuilding her life from scratch. Alongside leading an elementary literacy nonprofit and working as a certified life coach, she writes with remarkable honesty about reinvention, female friendship, and what it actually looks like to start over in midlife. Her work doesn’t romanticize change—it tells the truth about how messy, uncomfortable, and ultimately worthwhile it can be.

What are you not waiting for anymore?
Approval! I spent decades basing my choices on what other people might think of them. Would they understand? Would they agree? Would they still love me if I changed? It’s taken me 53 years, but midlife has finally taught me that I no longer need to wait and ask for permission.

What’s something you’ve stopped trying to prove?
That I can handle anything and everything for everyone at all times. For a long time, being capable was a huge part of my identity. I was the strong one. The reliable one. The one who could carry it all. And I did. But strength without boundaries is just exhaustion in disguise. I don’t need to prove my worth through overfunctioning anymore.

What does reinvention actually look like in real life—not the Instagram version?
Messy. Awkward. Uncertain. Reinvention is rarely glamorous. It looks like taking leaps without guarantees. Trying things that don’t fit. Missing the mark. Starting over and not knowing if you’re building toward something better or just wandering. After my divorce, I moved to Boston and had to build a life from scratch. New routines, new friendships, new places, new versions of myself. There were days it felt exciting, and days it felt profoundly lonely. But that’s the part no one talks about: sometimes you have to get lost to figure out what feels like home.

Where are you taking up more space lately—even if it still feels a little uncomfortable?
In my own voice. In my writing. In my wants. In saying what I actually think instead of softening it to be more palatable to others. In asking for what I need. In letting myself be seen more fully, even when it feels vulnerable. Especially then. And yes, often it does feel a little uncomfortable. But I am learning to sit with that discomfort a little better than I did when I was younger. To acknowledge it and to investigate it a little bit, but I’m done shrinking to avoid discomfort entirely.

What’s something you want more of right now—and aren’t apologizing for?
Connection. Real, in-the-flesh, deep connection. Maybe it’s a remnant of the pandemic isolation. Maybe it’s the strange disorientation of living in a world where so much feels filtered, curated, or hard to trust. But I want more time with real people. Old friends, new friends, family. More travel. More art. More shared meals and long conversations and spontaneous laughter. More moments that remind me I’m alive while I’m living them. Because at the end of the day, those are the things that truly make a life meaningful.

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There’s a lot to love in Laurie’s answers, but one sentence keeps bouncing around in my head:

“Strength without boundaries is just exhaustion in disguise.”

That feels like one of those sentences you read once and then catch yourself thinking about three days later.

By the time I got to the end of the interview, I realized every answer was really about the same thing: giving yourself permission. To stop waiting for approval. To stop shrinking. To ask for more.

Which, now that I think about it, feels like a pretty good definition of giving fewer F’s.

Thanks, Laurie, for the reminder.

You can find Laurie at My Menossance, where she writes candidly about midlife, reinvention, and the messy, beautiful process of starting over.

And if there’s someone you’d love to see featured in a future installment of “So I Asked...”, let me know in the comments.