Reinvention, Midlife Magic, and Building a Business That Feels Like Home
Dec 04, 2025
There are certain conversations that stay with you long after the recording stops — the kind that remind you why women in midlife are such a force. My chat with Heather Bolt was one of those moments.
Heather is the founder of Dotty, yes — but what struck me most wasn’t the clothing. It was her: her reinvention, her humour, her willingness to tell the truth about life, motherhood, aging, and following the kind of nudge you can’t ignore.
This episode isn’t really about fashion. It’s about what happens when a woman decides she’s not done yet.
A Story of Listening to the Clues Life Leaves You
Heather didn’t grow up dreaming of running a clothing company. In fact, she fully expected to end up in law school. But life has a funny way of showing you who you are before you’re ready to claim it.
For Heather, that moment came from a roommate casually pointing out:
“You know you spend all your time sewing, right?”
It wasn’t a lightning bolt. It was a breadcrumb — and she chose to follow it.
Her story is a reminder that the things we’re meant for aren’t always loud or dramatic. Sometimes they’re quiet, familiar, almost too obvious. And they keep tapping you on the shoulder until you finally say, “Okay, fine. I’m listening.”
Midlife Isn’t an Ending — It’s a New Beginning
If there’s one thing Heather embodies, it’s the idea that midlife isn’t a slowdown. It’s a deepening.
She talks about her 50s with this blend of playfulness and certainty that made me want to stand up and cheer. She’s lived enough life to know who she is. She’s made enough mistakes to know what matters. And she’s confident enough to do things her way.
There’s something magnetic about a woman who’s not performing, not pretending, not polishing — just being.
And that’s where her story becomes universal.
You don’t need to be a designer to feel the pull toward something new. You don’t need a business plan to start evolving. You don’t need to be in your 20s to change direction.
You just need the courage to trust that your life isn’t behind you — it’s unfolding.
The Confidence to Show Up Exactly As You Are
One thing I love about Heather is how she shows up for her community. Not as a brand. As a human.
She talks about parenting teenagers, divorce, body changes, aging, joy, frustration — all of it. And she does it with this “here’s the real deal” energy that women in midlife crave because it feels like permission.
Permission to be imperfect.
Permission to take up space.
Permission to evolve.
Permission to remember the parts of yourself you’ve tucked away.
At one point she said, “I want women to remember who the F they are,” and I felt that in my bones.
Because how often do we forget? Between the carpools, the deadlines, the grocery lists, and the never-ending mental load… we drift away from ourselves.
Heather’s story feels like a hand on your shoulder saying, “Hey, come back. You’re still in there.”
What Her Journey Teaches Us About Being a Woman in Business
This isn’t a story about hemlines or fabric or design techniques. It’s about:
- starting something before you feel ready
- pivoting when the path you’re on doesn’t feel like yours
- being bold enough to take up space
- bringing humour into the hard moments
- trusting that midlife can be expansive, not restrictive
- building a community through honesty, not perfection
Heather didn’t build her success through strategy alone — she built it by being unapologetically herself. And that’s the part that’s actually relatable for every entrepreneur listening.
My biggest takeaway from Heather’s story?
That reinvention is available at any age. And sometimes, the most powerful thing you can do for your business is to reconnect with yourself.
Her journey is proof that you don’t need a flawless plan — you just need to trust the pull toward the next version of you.
If you’re in a season of questioning, shifting, or starting again… this episode is your reminder that you’re not late. You’re right on time.
