THEĀ PODCAST

What Can't Come With You? A Lesson in Letting Go to Level Up

betting on yourself business systems midlife reinvention women entrepreneurs Sep 10, 2026
Penny Fitzgerald and Andrea Engstrom smiling under the text What's Weighing You Down
 

There's a version of "getting to the next level" that most of us default to without ever questioning it: add a system, add an offer, add an hour, add a habit. Level up means more. And so we keep stacking things on, quietly wondering why we feel further from freedom instead of closer to it.

I see this constantly in the women I coach. Somewhere along the way, we started believing that growth only moves in one direction. More responsibility. More on the calendar. More we're carrying for everyone else, right alongside the business we're trying to build. Nobody hands you permission to subtract anything, so you just keep adding until the whole thing feels heavier than it should.

Andrea Engstrom, who joined me this week, described a hot air balloon. It rises two ways. You add hot air. Or you drop bricks. Most of us only ever reach for the first option, because it feels like progress, like doing something. Dropping a brick can feel like giving up, or falling behind, or admitting you can't hold it all. But Andrea built a business doing six-figure months while working three days a week almost entirely through the second option: relentlessly asking what could no longer come with her.

That question is bigger than business. It's old stories about who you're allowed to be. It's responsibilities that made sense five years ago and don't anymore. It's the identity of being the one who handles everything, the one who's easy-breezy, the one who doesn't need systems because systems feel restrictive. Andrea had to let go of that last one specifically, and what she found on the other side wasn't chaos. It was more time and more income, because she'd finally stopped spending her best hours on things that didn't need her at all.

I think about this with the mental load piece especially. So much of what women carry never makes it onto a business plan or a to-do list, because it's not a task, it's a background hum: keeping track of everyone's needs, managing the house, being the one who remembers. If you're in a season of trying to grow something, that hum has to get quieter somewhere, and it usually means letting go of the belief that it all has to run through you.

Andrea shared a journaling prompt: write "wouldn't it be cool if..." at the top of a page and just keep going. Not what should I do next, not what's realistic, just wouldn't it be cool if. It bypasses the part of your brain that's already listing reasons why not, and gets you back to wanting something in the first place, which is its own kind of clarity.

Not what do I need to add to get where you're going. What can't come with you. A habit, a story about yourself, an old version of "helpful" that's actually just exhausting. You don't have to figure out the whole balloon at once. Just find one brick, and see what it feels like to set it down.

HAVE A QUESTION?

Or idea for a guest?

CONTACT ME

SUBSCRIBE FOR WEEKLY LIFE LESSONS

And the occasional cocktail recipe.

We hate SPAM. We will never sell your information, for any reason.