From Corporate to CEO: Sustainable Entrepreneurship in Midlife

Have you ever looked around at your life and thought, wait — is this actually what I want?

For so many women, midlife is the moment when that question finally gets loud enough to act on. The kids are a little older, the career has been ‘successful,’ but something still feels off. In this episode, I’m joined by Judith Fine, a coach who helps women in midlife navigate one of the most exciting — and most emotionally complex — transitions of their lives: leaving what’s familiar and designing their next chapter on their own terms.

We start with the true self and false self — a concept from therapist Donald Winnicott — and why midlife is often the first time we feel ready to take off the mask we’ve been wearing since our twenties. Judith speaks beautifully about the confidence that comes not from certainty, but from finally knowing who you are and what you actually want.

One of the most powerful reframes in this conversation is the cost of not changing. Instead of asking ‘what if this doesn’t work?’, Judith invites us to ask: ‘what does staying cost me?’ That shift in perspective can completely change how you approach fear, risk, and the decision to leap.

From there, we get into the very real practical challenges of going from employee to entrepreneur — especially in midlife, when brain fog, energy shifts, and perimenopause can make even the most organized person feel like they’re working against themselves. Judith shares how she learned to stop fighting those rhythms and start designing her days around them: matching task types to energy levels, protecting boundaries like walking as a non-negotiable, navigating the loneliness of working alone, and building in accountability from the start.

We also touch on the ADHD piece — something many women in midlife are discovering about themselves for the first time — and how to harness that kind of mind rather than fight it. Because when you learn how your brain actually works, productivity stops being about pushing harder and starts being about working smarter, more sustainably, and with a whole lot more self-compassion.

This is an episode for the woman who knows something needs to change, but isn’t quite sure where to start. It’s practical, it’s honest, and it might just be the permission slip you’ve been waiting for.