Living in the Messy Middle

This is a state that many of us live in sometimes more than once. I'm in one now.

I've had the privilege of several career chapters. I built a successful career in technology, traveled the world, raised three amazing children, and wrote a book published by a major publisher. I’ve poured my energy into creating impact.

Five years ago, I co-founded a business to help women entrepreneurs thrive in the digital economy. We raised capital, won state and federal contracts, served women around the world, and became profitable. We were doing the work. And then, political winds shifted. Support for women-owned businesses was discouraged and in some cases, outright banned. Contracts were canceled. Invoices went unpaid. We had to lay off our team.

Since then, I’ve been trying to move forward. But the truth is my efforts haven’t landed. I’m not ready to start from scratch again. I’m still passionate about supporting women, not just because they are women, but because it is a proven and powerful economic strategy. Still, I find myself neck-deep in the messy middle unsure of what comes next.

Friends say, “Take time, relax.” But time for what? I’m not ready for retirement. And patience isn’t something that comes easily to me. I’m standing at an intersection with no road signs. It’s disorienting. Uncomfortable. And yes, hard to admit publicly.

But maybe that’s the point. Maybe we need to talk more about these middle moments—the parts that aren’t wrapped in a bow. I’m sharing this not because I have answers, but because I know I’m not the only one navigating what’s next.

If you’ve been here or are here what helped you move through the middle?

- Kate Isler, CEO of TheWMarketplace