After more than a decade in senior leadership, Rachel Barbaro is helping women rethink what they want from their careers, and what success can look like when they define it for themselves.

Rachel Barbaro spent more than a decade building a successful career in senior leadership. When she eventually stepped away from the corporate world to become an executive coach and entrepreneur, she found herself navigating a transition that went well beyond changing jobs.

Today, Rachel is an executive coach, advisor, facilitator, and founder of Empowerment Club. She works with women who are ambitious about what comes next, while also questioning some of the habits and expectations that helped them get where they are.

It is a tension Rachel knows personally. Her own move from executive to entrepreneur required her to reconsider how she thought about work, achievement, and her time, while learning to trust her own decisions without the familiar markers of advancement that come with a corporate career.

In this Five Questions With, Rachel shares what that transition taught her, why so many accomplished women reach a point where the way they have always worked no longer feels sustainable, and how they can continue to grow while making room for the rest of their lives.

1. You spent more than a decade in senior leadership before becoming an executive coach and entrepreneur. What did you have to unlearn about leadership when you stepped away from the corporate world and began building something of your own?

I had to unlearn that someone else would tell me I was ready.

In an organization, there are structures that hold you: a promotion, a bigger team, a more senior title. When you build something of your own, you have to decide what you believe, what you want to create, and what you are willing to stand behind before anyone else validates it – or buys it!

That is why I often say the transition from executive to entrepreneur is an identity transition as much as a business transition. You bring tremendous capability with you. Then you have to learn how to hold uncertainty, become visible in a new way, and trust your own decisions.

I also had to reconsider the relationship between effort and value, and my time and worth.
Building a business keeps inviting me to grow. You ask for expansion, and then you have to become the woman who can hold it.

2. You work with many accomplished women who have built successful careers but reach a point where the way they’ve always worked no longer feels sustainable. Why do you think so many women arrive at that moment, and what needs to change?

Many female leaders and high-performers have built their success around being exceptionally dependable. They anticipate what everyone needs, take responsibility and deliver.

Then there comes a moment when many women realize: “I can keep doing this, but I no longer want to.”

I see an opportunity in that moment. She is beginning to recognize that her capacity is valuable and that she gets to have a say in how it is used.

The change needs to happen at both the individual and organizational levels. Women need room to set boundaries, delegate, and stop treating someone else’s discomfort as evidence they are making the wrong decision. Organizations need to address workloads, unclear expectations, and cultures that depend on people continually overextending themselves.

In my work with leadership teams, I look at the individual, the team, and the organizational system. We need to understand what keeps producing the pressure if we want anything to change.

3. You talk about women defining success on their own terms rather than continuing to pursue someone else’s version of it. What does that look like in practice, especially when someone has spent years building a career around traditional measures of success?

I start with a question: “Do you still want this, or have you become very good at pursuing it?”
That question can open up a lot. Many women have spent years following a clear path of achievement without much space to ask whether the next milestone reflects what they actually want.

Defining success on your own terms means getting specific. What work feels meaningful? How much money do you want to earn? What do you want your days to feel like? What do you want energy for beyond work?

Then those answers need to show up in your decisions. It might mean negotiating your role, changing how you lead, starting a business, or protecting an afternoon with your children.

For me, meaningful work, financial success, travel, and time with my family belong in the same vision.

You can be proud of what you have built and ready for something different. You are allowed to outgrow a version of success you worked very hard to achieve. I definitely did!

4. Confidence, executive presence and visibility are often framed as skills women need to develop to advance. But you also focus heavily on self-trust and authenticity. What do you think we misunderstand about what it actually takes for women to become more influential leaders?

We spend a lot of time teaching women how to appear confident. I am interested in internal confidence, and what happens when a woman trusts that her perspective is worth contributing, regardless of how others react.

I teach congruence: the alignment between what you think, feel, say, and do. When those things come into greater alignment, your leadership becomes clearer. You spend less energy editing yourself and more energy creating.

That might look like naming an issue everyone is avoiding, offering a different perspective, or making a decision that you know will not please everyone.

Self-trust also allows you to listen without abandoning yourself. You can stay connected to your own values while remaining open to someone else’s experience.

Women also need equitable access to opportunities and environments where their contributions are respected. Individual confidence cannot resolve every barrier.

My work is about helping women become the fullest expression of themselves. Fear can coexist with belonging. You do not have to feel fearless to take your place in the conversation.

5. You describe sustainable leadership as being able to have greater impact without constantly pushing harder or burning out. For a woman who is ambitious and wants more from her career or business, how can she continue to grow without falling back into the idea that success requires doing more?

The first question I would ask is: “What actually requires you at this next stage?”

As your leadership or business grows, your role needs to evolve. You cannot keep adding responsibility while holding on to everything you have always done.

For a senior leader, that might mean developing the judgment of her team so every decision no longer comes back to her. For a founder, it might mean focusing on one strong offer, building simple systems, hiring help, and making time for the relationships that grow her business.

I talk a lot about sequencing. You can have a big vision without trying to build every part of it at once. Choose the few actions that matter, repeat them consistently, and give them time to work.

Recovery belongs in that plan, too. Your ability to think clearly, create, and lead deserves protection.

I want women to build businesses and careers that make room for their whole lives. You are allowed to want more, and you are allowed to enjoy what you have already built.

Published in