Is Entrepreneurship Knocking at your Door? 5 Questions to Ask Yourself… Before You Take the Leap

You didn’t leave corporate to recreate burnout with a better view.

The women I work with aren’t beginners.  They are successful business women who left the titles, the bonuses, and  the org charts to build something that finally felt like theirs.

They’re smart, they’re seasoned, and they’re often the go-to person when things go sideways.

But even with all their experience, there’s a quiet question that creeps in behind the scenes…

“Am I actually cut out for this?”

Because entrepreneurship asks something different of you… something corporate never prepared you for.

Less structure, more visibility, fewer roadmaps, higher stakes. And no manager to tell you, “you’re doing great!”

If you’re still in corporate and thinking about entrepreneurship… this is the part no one talks about. 

And if you’ve already made the leap and feel like you're quietly spiraling, you're not broken, you’re just building something real.

Let’s talk about what this transition actually looks like… and how to know if it’s time, or if you’re on the right path.

First, the stats…

According to a 2024 Women in Entrepreneurship report by the Kauffman Foundation:

• More women over 45 are starting businesses than ever before, many leaving corporate careers to create more flexible, meaningful work on their own terms.

• But only 1 in 3 feel they had enough support, mentorship, or guidance in that transition.

• And the #1 regret of those who struggled? “I waited too long to get clarity.”

Sound familiar?

So how do you know if entrepreneurship is right for you?

Here are 5 questions I ask every woman who’s thinking about leaving corporate and stepping into something new:

1. Are you chasing freedom, or running from burnout?

There’s nothing wrong with wanting more freedom. But if your decision is driven solely by exhaustion, resentment, or the fantasy of never having a boss again… hit pause. Burnout isn’t a business plan, and entrepreneurship will ask you to show up with more clarity, not less. Instead of escaping something, ask yourself… “what do I actually want to build toward?”

2. Can you handle uncertainty without crumbling your confidence?

In corporate, clarity often comes from above (deadlines, org charts, performance reviews).

In business? You have to create that clarity yourself. That means making decisions without guarantees, pitching before you feel “ready,” and trusting your gut when no one’s giving you a gold star. It’s vulnerable, yes… but it’s also where you reclaim your power.

3. Do you want to do it your way, or do you still need permission?

Entrepreneurship asks you to define success on your own terms. And sure, that sounds empowering, until you realize how many of your definitions were handed to you by someone else: your industry, your parents, your past self. One of the hardest (and most beautiful) parts of this work is learning to hear your own voice again.

4. Are you willing to build before you feel bulletproof?

Most women wait too long. They wait for one more certification, one more financial milestone, one more nod of approval from someone who’s never built a business themselves. But entrepreneurship isn’t about being fearless. It’s about acting with fear, and moving anyway. The most successful women I know didn’t feel bulletproof when they started… but they said yes anyway.

5. Are you ready to be seen in a whole new way?

Corporate rewards fitting in, entrepreneurship requires standing out. That shift is disorienting at first, but it’s also deeply healing. Because when you stop managing perception and start building from your truth, everything changes. But first… you’ve got to be willing to be seen.

So… are you cut out for this?

Only you can decide that. But if the thought of building something that’s fully yours makes you light up (even if it also makes you nervous), it might be time to listen closer. And no, you don’t have to have it all figured out today. You just need to get curious, get honest, and take the next right step.

Want some help making that decision?

I’ve got a curated collection of free tools and resources waiting for you right here, designed to help you get clear, focused, and moving in the right direction.

👋 Or, if you’d rather talk it through, book a free 30-minute coffee chat. No pitch. No pressure. Just perspective.

This is your life. Let’s make sure it feels like yours.