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August 25
Barbara Baskin spent 30 years convinced she wasn't very smart. School was academic probation and "needs to try harder" report cards. Then came an ADHD diagnosis at 30, followed by three decades of raising four kids (including triplets), caring for her mother with dementia, and running a business while being everyone's executive function.
At 60, Barbara made a decision that shocked everyone: she moved from a small town in Florida to a fifth-floor walk-up in New York City and started online dating.
Barbara is a writer, journalist, and author of The Ponytailed Guy from Last Night. She discovered that journalism was perfect for her word-loving, curious ADHD brain after struggling through university with brilliant workarounds—alternating "hard" semesters that put her on academic probation with "easy" semesters of ceramics and tennis. She learned she could master anything if she could touch it, which made her an excellent videographer and producer.
But decades of being the family's executive function while masking her ADHD took its toll. High functioning, Barbara realized, wasn't the same as being okay. When a psychiatrist asked what she'd done for herself that week, she couldn't think of a single thing.
In this episode, Barbara and Tracy explore how she built a successful career around her learning differences, survived the chaos of managing everyone else's life, and found the courage to reinvent herself in her 60s completely. They talk about why New York City feels like home to an ADHD brain, how online dating became an unexpected path to self-confidence, and what it means to choose adventure over settling.
Her motto: if they're not interesting, they better be damn interested in me.
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"If I can touch it, I can learn it."
- Barbara Baskin
"If I'm not with a partner that's driven... they're just gonna get left behind because I'm going and seeing and learning."
- Barbara Baskin
"You gotta walk through it. I was so scared on the first date... I thought, if I can just keep my feet moving forward... before I knew it, I was at the door of the pub."
- Barbara Baskin
"It's amazing when you find out that everybody's just like you... we're all the same. We've got different looks and different hobbies and different ways that we do life, but we're all the same."
- Barbara Baskin
"Signing up for a dating app takes so much courage. It's the hardest thing I think I've ever done."
- Barbara Baskin
"Someone that says the word retirement, I think I'd like to retire in two years. I'm like, you know, that ain't gonna be me... absolutely never, never."
- Barbara Baskin
- Barbara was diagnosed in her 30s after failing a computerized test she thought she "aced"—clicking when hearing specific numbers for 45 minutes while the psychiatrist passed easily.
- Despite studying more than anyone at University of Florida, she got report cards saying "makes careless mistakes" and believed she wasn't smart for the first half of her life.
- Created a workaround: alternating semesters of hard courses (going on academic probation) with easy courses like ceramics and tennis to bring her GPA back up.
- Discovered journalism after reading "if you love words, you're in the right class"—she'd always excelled at spelling bees despite failing academically.
- Learned she was hands-on during broadcast internship: "if I can touch it, I can learn it," becoming a successful shooter, writer, and producer.
- ADHD traits became strengths—natural curiosity made her excellent at interviews, and she could simplify complex topics for audiences.
[00:50:00 - 01:13:00] NYC Move and Online Dating Adventure
- After raising four kids, including triplets, and caring for a mother with dementia, realized "high functioning" wasn't the same as being okay.
- Moved from small-town Florida to NYC fifth-floor walk-up at nearly 60, inspired by Anthony Bourdain's show and seeking the energy the city provided.
- Started online dating despite being terrified, discovering it built self-confidence and taught valuable lessons, including memorable disasters like "The Wrong Barbara."
ADHD isn’t a productivity problem. It’s an identity problem.
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