You’re a high-achieving woman who’s navigated countless challenges throughout your career. You’ve built something meaningful, raised a family, or both. But now, somewhere in your 40s or 50s, you find yourself at a crossroads.

The old playbook is no longer practical. The goals that once motivated you feel hollow. And you’re ready for something different, even if you’re not entirely sure what that “different” looks like yet.

Coaching can be powerful during this stage. I’ve watched women completely reclaim their lives through this work. However, I’ve also noticed that even the most capable and intelligent women make predictable mistakes when they first start. These mistakes slow you down, drain your energy, and leave you wondering if coaching actually works.

The good news? They’re fixable. And recognizing them is the first step.

Mistake #1: Overthinking Every Decision Instead of Taking Aligned Action

You’re analytical. Strategic. This has served you beautifully in your career—but in midlife transformation work, it can trip you up.

Here’s what it looks like: You’re not just overthinking the big decisions like whether to leave your job. You’re overthinking everything. Should you reach out to that contact? Should you take that course? Should you have that conversation? Should you post about your transition on LinkedIn?
It’s a hundred small, incremental decisions—and you’re analyzing each one to death. Meanwhile, that quiet voice inside that already knows what you need? It gets completely drowned out.

I see this all the time. Women spend weeks researching before sending a single email and months of preparation before having a single conversation. They’re waiting for perfect clarity on all the mini-steps, and nothing moves forward.

The Fix: Practice making small, aligned decisions quickly. Give yourself permission to take imperfect action on the little things.

Try this: When you’re facing a small decision, pause for five minutes. Put your hand on your heart. Ask yourself: “What does my gut say?” Then do that thing within 24 hours.
Transformation doesn’t happen in one big leap. It happens through many small, incremental decisions made from your inner knowing, rather than your analytical mind.
You don’t need perfect clarity on every step. You just need to start taking them.

Mistake #2: Fearing Vulnerability and Staying Surface-Level

Success has taught you to have answers. To appear confident. To solve problems on your own. That armor that served you in the boardroom? It can get in the way in coaching.

You show up talking about strategy and systems, but you avoid the deeper emotional stuff that actually creates change. You’re comfortable discussing what you want to achieve, but uncomfortable exploring why certain patterns keep showing up.

I get it. After decades of being the competent one, the one with answers, it feels scary to say: “I’m lost. I don’t know what comes next.” But here’s the thing: The real breakthroughs happen when you’re willing to look at what’s actually been running the show.

The Fix: Start small. Share one thing with your coach that makes you feel a little uncomfortable. Maybe you’re scared of starting over. Or you sometimes feel like a fraud. Or you’re just exhausted from pretending you have it all figured out.

Those things you’re afraid to say out loud? They’re usually the keys to your freedom.

Mistake #3: Expecting Instant Results Instead of Trusting the Process

You’re accustomed to setting goals and achieving them quickly. So when you invest in coaching, you expect quick returns. You want to know exactly when you’ll feel clear about your purpose. Precisely how long will this take? When transformation doesn’t happen on your timeline, you get frustrated.

I’ll be honest: Midlife transformation isn’t a project you can manage. It’s a process you have to trust. Real change happens in layers. You might have a powerful insight one week, then spend three weeks living into it before the next shift happens. That’s not slow—that’s how it actually works.

The Fix: Notice the small stuff. Did you speak up in a meeting where you usually stay quiet? Did you say no to something that didn’t feel right? Did you choose rest without feeling guilty about it? Write these down. There’s evidence that things are shifting.

Trees grow roots before branches. The same goes for you.

Mistake #4: Trying to Go It Alone Instead of Embracing Community

Independence has been your strength. You’ve built success by figuring things out on your own. But that approach can actually work against you in midlife. You might book coaching sessions, but resist joining group programs. You consume content but avoid connecting with other women on similar journeys. You keep your struggles private and miss out on something powerful: realizing you’re not alone.

Here’s what I’ve learned, facilitating groups of high-achieving women: When you’re isolated, every fear and doubt gets louder. Community doesn’t make you weak; it makes transformation actually sustainable. When you watch another woman have a breakthrough, something in you recognizes you can too. When someone names exactly what you’ve been feeling, the shame begins to lift. When women share how they navigated their transitions, the path becomes visible.

This is precisely why I’ve created safe group spaces for women navigating this stage. I’ll share more about this at the end; please keep reading.

The Fix: Take one small step. Share what’s really going on, not just the polished version, with one friend you trust. Or consider group coaching where you can witness what’s possible.

Asking for support isn’t a weakness. It’s smart.

Mistake #5: Focusing Only on External Changes While Ignoring the Internal Work

You’re action-oriented. So, when you decide to change your life, you immediately start taking action. Update your resume and research new careers. Start a side project. This action matters. But if you only focus on the external stuff and ignore the internal work, you’ll end up in the same patterns, just in a different setting.

Your mindset, the stories you tell yourself, and the beliefs you hold create your reality. If you don’t address what created your current situation, you will likely recreate it somewhere else.

I see this constantly. A woman leaves a demanding job for a “better” opportunity, and six months later, she’s just as exhausted because she brought the same patterns with her.

The Fix: Spend 10 minutes each morning on the internal work.

Notice what you’re telling yourself about what’s possible at this stage of life. Are you thinking, “I’m too old to start over”? Or “I have wisdom and experience that make this the perfect time”?

Pay attention to which voice is loudest: The one saying you “should” stay where you are? Or your inner compass, calling you toward something that actually fits? Your external changes will only stick if you also do the internal work.

Your Next Step

Here’s what I want you to know: Midlife isn’t a crisis. It’s an invitation to reclaim who you actually are under all the roles, expectations, and “shoulds” you’ve accumulated.

You don’t have to figure this out alone. You don’t have to keep making these same mistakes. And you definitely don’t have to settle for a life that looks good on paper but feels empty.

If you’re reading this thinking, “This is exactly where I am,” let’s talk. I’m opening The Reclamation, a 6-month group coaching program for high-achieving women at midlife in February 2026. It’s limited to 8 women, and early registration closes December 15th.

But before you even consider the program, let’s have a conversation. I offer complimentary clarity calls where we explore what’s true for you right now, where you want to go, and whether this work is right for your journey.

Your transformation is waiting. The question is: Are you ready?
The woman you’re becoming is already there—she’s just waiting for you to get out of your own way.

Ready to talk? Reach out to learn more about The Reclamation.