I was on a blind date, sitting across from some guy I’d met on Match.com, when he asked what I did for a living.
You would have thought I was a street walker, the way I started hemming and hawing. I was so mortified to tell him I was a chemical salesperson—selling industrial chemicals across a multi-state territory—that I kept trying to dodge the question.
Obviously, he was confused. Why wouldn’t I want to tell him I sold chemicals? What was the big deal?
“Because I feel like I’ve outgrown it,” I finally blurted out. “I’m embarrassed that I’m still in chemistry when I’m not meant to be in chemistry.”
That moment of raw embarrassment? It completely changed the trajectory of my life.
I talked about this turning point on Jules Wyman’s podcast “Coming to Your Senses,” and if you want to understand how I see the world—and more importantly, how I stumbled my way from chemical sales into writing and building a business—you should give it a listen.
Here’s what I’ve learned: those negative emotions we want to run from—the embarrassment, the shame, the jealousy—they’re not bugs in the system. They’re features. They’re harbingers telling you there’s something not working in your life, something you’re not pursuing, some shift you haven’t acknowledged yet.
That blind date guy (not Walt, by the way—although I met him on Match.com, too) asked me what I’d always wanted to be. “I think I always wanted to be a writer,” I heard myself say.
Then he said something that sounded absolutely insane: “Well, why don’t you go back to school and study writing? You could go to Harvard.”
Harvard. At 37. With two kids, a full-time job, and living back home with my mother after my former husband had died. Everything in my life screamed this was the wrong moment to make a change.
But I did it anyway. Drove two and a half hours each way to take evening classes. Got home at 11 or 12 at night. And within the first two weeks, I absolutely knew I was in the right place.
What I love about Jules’s question—how did I walk away from full-time employment into writing—is that it assumes there was some master plan. There wasn’t.
The path from that first Harvard class to building a business helping people write books was so ridiculously non-linear it’s almost embarrassing to admit. I flirted with the idea of teaching Vietnamese (there are maybe two people in America with a burning desire for basic Vietnamese conversation). I put up a website about drawing healthy boundaries while having the sketchiest boundaries on the planet.
It was all yes, yes, yes to opportunities I had no business saying yes to. Hearing that I ran a local writing workshop, someone I ran into asked me, “Can you teach people how to write a book?” Sure, I’ll figure it out. Shortly thereafter, one of those students asked, “Can you work with someone one-on-one?” Yeah, I can figure it out.
The key phrase here: I can figure it out. That wasn’t something I was saying at 20 or 30. Back then it was more like “I hope somebody else is going to take care of it for me.”
I have to be honest about something most people don’t talk about: I had a financial safety net. Whether I made $360 every six weeks or $3,600, it didn’t matter because I had support underneath me. I could say yes without knowing how things would work out because I wasn’t worried about the kids not eating.
Not everyone has that luxury, and I’m not going to pretend otherwise. If you’re driving Uber or waiting tables while trying to build something, your trajectory might be different. You might need to be more strategic about your yeses and nos.
But here’s what I think applies universally: the willingness to start before you know how it’s going to pan out.
In the podcast, I talk about growing up in a household where one minute everything was falling apart and the next minute everyone was sitting around the breakfast table acting like nothing happened. On and off switches, no obvious fixing.
I had to learn that everything worthwhile—whether it’s training for a marathon, building a business, or figuring out who you are—involves process. Sticking with something when you’re completely unsure how it’s going to turn out. Beginning anyway, even when you don’t know if it’ll be worth the investment of time, money, or energy.
You’re aiming for Everest Basecamp in Nepal and you end up in Tibet. But the journey to Tibet changes you in ways you never bargained for.
What fascinates me most—and what comes through in my conversation with Jules—is how people think. I’m endlessly curious about why people do what they do, what’s driving them, what need they’re trying to meet.
Part of this comes from being completely puzzled by myself for years. I was a hot mess through my teens, twenties, and probably into my early thirties. Not the girl you’d bring home to mother. I’d do crazy stuff and then wonder, “What the hell was I thinking?”
So I started asking other people: What do you think? Why are you doing that? What do you see when you look at this? Because I realized I was this interpretation chamber, seeing things in ways that confused everyone around me, including myself.
Working with people on their books, they’ll start telling me their stories, and three stories in I’m like, “Actually, let’s go back four stories because that’s where everything really starts. That’s your why, your driving force, the power behind everything you do.”
If you’re in your twenties or thirties thinking you’re a complete and utter shit show and don’t know what you want to do, here’s something Jules pointed out that I want to echo: I’m in my sixties, she’s in her fifties, and we’re only just feeling like we understand life a little bit.
It’s okay. It’s absolutely okay.
The embarrassment, the shame, the feeling like you’re supposed to have it all figured out by now—pay attention to those feelings instead of running from them. They might just be pointing you toward something you need to pursue.
And remember: it’s not going to be a straight line. It’s going to be a squiggly mess that somehow gets you where you need to go, even if that’s not where you originally planned.
You can listen to my full conversation with Jules Wyman HERE—it’s called “Coming to Your Senses”].
Trust me, it’s worth the listen if you want to understand how saying yes to things you don’t know how to do can completely change your life.
