Leaving Corporate Midcareer: How to Know It's Time and Build What Comes Next Before You Go
Erica Anderson Rooney is an ex-CPO turned executive coach and AI educator on a mission to get more women into positions of power and keep them there. She is the author of The AI Gap (2026), host of the Glass Ceilings & Sticky Floors and AI Voice or Victim podcasts, and NC Chapter Lead for Women Applying AI. Her SNAP and AI Continuum frameworks are taught to thousands of women through CHIEF, WICT, and Fortune 500 leadership programs. She is the sought-after speaker at the intersection of women, AI, and leadership.
A few years ago, when I was a Chief People Officer in tech, I started to feel that "growth" itch. You know what I'm talking about? That feeling where you know you are made for more, but you don't necessarily know what that is. I have a track record of feeling that feeling, and when I do feel it, my typical move is to jump on a certification. That's why I had an HR certification before I was in HR, and I was a certified Project Management Professional (side note - I’m not a project manager, nor have I ever been.) This time, I jumped to take an executive coaching certification. I figured that it would at least help me with my current role as Chief People Officer. Now, in order to earn the certification, I had to do some pro bono coaching sessions, for which I decided that I would coach women only. Here's where it gets interesting. Because I was a Chief People Officer, I was already working 50 to 60 hours a week, and I really didn't have time for these pro bono sessions except late on a Sunday. If you know me, I don't like working on the weekends or late on a Sunday. But after my coaching sessions, I could not ignore how lit up I felt. It was almost as if these coaching sessions showed me how miserable I was in my current role. It really illuminated the contrast of how I felt in corporate and how I felt coaching women.
Leaving corporate midcareer was nowhere on my to do list. And yet the best part of my week kept happening after the work I was paid for was done.
If you have felt that, you know how confusing it is. You are good at your job, and you worked hard to get it. So why does the thing you do for free on a weeknight feel more like you than the thing printed on your business card?
For a lot of us, that feeling shows up right after we reach the level we were working toward, when a small voice starts asking whether this is it.
When the Work on the Side Lights You Up More Than the Job
My whole why has always been helping people. It is why I was a personal trainer back in the day, and it is why I went into HR. But I am also an achievement chaser, and when I got to the top of the corporate ladder, I started asking myself, "Is this everything I should be doing? Is this what I want to be doing?"
So I started a coaching practice on the side, helping women get into positions of power without sacrificing their sanity, their sleep or their success. It gave me energy and it filled my cup, and it showed me that you do not have to quit your job or start your life completely over to find out what lights you up.
Sometimes all it takes is one small thing on the side and the honesty to notice how you feel when it is over.
When the Room Where It Happens Turns Out to Be a Puppet Show
My recent guest on my Glass Ceilings & Sticky Floors podcast, Stephanie Davis Smith, Chief Marketing Officer of The N2 Company, ran into that same question at the top of her own career, and she described it better than I ever have.
She spent 25 years in luxury magazines. She helped set up GQ and Self, she worked for Modern Luxury, and she sold the latest Dior collection to people who could afford the latest Dior collection. She told me she was so ambitious to get into that executive room that she could not see anything else. Then she got there, and this is what she found:
"I was trading my 40-hour workweeks for 60. I was expecting this flexibility and prestige as I got into the VP world, only to realize it was just more work, in a colder room."
A few breaths later she said the line we named the episode after, the one about what happens "when you're a woman and you get to the room where it happens and you realize it's a puppet show."
I finished her sentence for her on the episode, because I knew exactly where she was going. Nobody in there knows what they are doing. I have sat in those rooms as a Chief People Officer, and I have exited people from those rooms. So many of the people running them were in the right place at the right time and were never trained on how to be a leader.
Her turning point came in the middle of an office power struggle. A friend one rung below her on the ladder told her to march in there and remind everyone who she was. And Stephanie heard herself ask a different question entirely: "Am I just gonna lead with ego the rest of my life like I'm watching men and other people do?"
She did not want to do that anymore. So when she got headhunted to The N2 Company and they told her in the interview, "We don't hire brilliant jerks, so if you're a brilliant jerk, we don't want you," her answer was simple. "Check. That's what I want."
When you finally get the seat and the room feels colder than you imagined, that feeling is information about you, and you get to use it.
Why So Many Women Are Asking the Same Question Right Now
Stephanie and I are in very good company. McKinsey and LeanIn.Org published Women in the Workplace 2025 in December 2025, and for the first time in that study there is a notable ambition gap. Eighty four percent of senior level women say they want to be promoted, compared with 92 percent of senior level men.
I could already see the headlines saying women just do not want it as badly. I call bullshit, and so does the report. The same study found that when women receive the same career support that men do, that gap in ambition falls away. Those women looked at what the next rung costs and how little support comes with it, and they started doing the math out loud.
My own story mirrors this one. I was doing that math long before anyone put it in a chart, the minute I started asking myself whether this was what I wanted to be doing.
And then there is the ground shifting under everyone. Challenger, Gray and Christmas reported in September 2026 that artificial intelligence was the most cited reason for announced US job cuts so far this year, at 116,175 cuts. The job you are being loyal to is being redesigned while you are sitting in it.
I said it on the episode and I will say it again here. Times are tough, y'all. If you have been hit with a layoff, or your clients froze their budgets to pour the money into AI, wanting a second income stream is plain good sense.
Nobody Hands Women the Ownership Part of the Plan
This conversation matters to me because of who owns the businesses in this country. The Census Bureau reported in November 2025 that women owned 22.9 percent of US employer firms in 2023. For all the talk about women starting businesses, the companies with a payroll, the ones that hire people and build real wealth, are still mostly owned by men. My mission has always been more women in positions of power, and that means more dollars in our hands.
On the episode I told Stephanie that I like to make sure people know what is out there. We've got real estate, we've got coaching practices, and you can run a magazine. I did not know that last one, to be quite honest. I had no idea people could run a magazine on their own if they did not come up through the journalism world.
Franchising is one of those options. Franchise Business Review published a survey of women franchise owners in March 2026, and the women who had owned their franchise for at least two years reported average annual revenue of 1.2 million dollars.
That is the AVERAGE. I share it so you know ownership is a real option for women who have spent their careers building skills someone else profits from, and franchising is only one road to it.
A second income stream does not show up on its own. Someone builds it, and the easiest time to build it is while you still have the first one.
Is Leaving Corporate Midcareer a Mistake, or Should I Build Something on the Side First?
Build it on the side first. That is what I did, it is what I see the women who do this well do, and Stephanie told me some of her franchise owners run theirs as side revenue next to everything else. Here is how to run it.
1. Run the energy test before you run the numbers
I want you to pick one small thing outside your job that sits close to the work you love. One coaching client. One consulting project. One board or volunteer role where you get to do the thing you are best at. Then pay attention to how you feel when it ends. Do you feel the way you feel after the Thursday budget meeting, or do you feel the way I felt after those early coaching sessions, with more energy than when you started?
The reports tell you what is happening to women as a group. Your own energy tells you what is happening to you, and you are the only one who can collect that data.
2. Write down what you want to stop doing
Stephanie's decision started with that question about ego and a version of herself she was done being. So grab a notebook and write down the specific things your boss, your peers or the politics in your office expect from you that you are done doing. Maybe it is walking into a meeting ready to remind everyone who you are, the way her friend told her to. Maybe it is the person you become on the Sunday night email check. That list becomes your search criteria for whatever comes next.
3. Do the ick check before you sign anything
I will tell you what I told Stephanie. Whenever I hear "woman" and "franchise" in the same sentence, I get a little immediate judgment, and then I get the ick at myself for being judgy. She had the same reaction. Before she said yes to the job, she asked, "Is N2 Company a scam?" Then she did her homework. On the episode she walked me through it: no down line, you earn only from your own sales, and franchises come with regulations and a disclosure document you sign.
Whatever you are looking at, whether it is a franchise, a consulting practice or a product, ask the ugly questions in writing. Where does the money come from? What do I have to buy, and from whom? Who makes money when I join, and who makes money when I sell? If the answer is anything other than your own customers paying you for something real, walk away.
Then be clear eyed about the work itself. When I asked Stephanie about the sticky floors she sees in the women who struggle, she said "it's almost like you have to have grit. That's the only thing I can think that is the thread that I see through all these women, is grit". I added bandwidth, because I know myself. I love being out in my community, and I still told her I can't do it at this point in my life. Both of those answers are allowed.
4. Use your title while you still have it
People return your call faster when your email signature says vice president at a company they have heard of. Use that while it is yours. Start having conversations this month with women who already do the thing you are curious about, and ask them what they wish they had known in their first year. Those conversations are a lot easier to get while you still have the title.
5. Learn how to talk to the machine before you go
When you are building something small on the side, your time is everything. The woman who knows how to talk to the machine has it drafting her proposals and organizing her follow ups, and the woman who does not is doing her invoices by hand at eleven at night. That skill is learnable, and it is a big part of what we work on inside HER Collective.
What Lit You Up This Week?
That lit up feeling after my coaching sessions was the first clear answer I ever got to the question of whether this was what I wanted to be doing. I listened to it, and I kept coaching.
So I want you to notice what lit you up this week. Write it down. Then go do a little more of it.
When Stephanie decided she was done leading with ego, she told me she wanted to be "in a space where women are supporting women". You deserve that space too while you figure out your next move.
If you are in the middle of asking whether this is it, my second book, The AI Gap, was written for exactly this moment. The Awareness Gap section helps you map your next move in a system that was never designed for you, and the Compounding Gap section is all about turning income into leverage and building walk-away power. You can get your copy at ericaandersonrooney.com/the-ai-gap.
If you would rather work it out with other women beside you, we built that room. Come see it inside HER Collective at joinhercollective.com.
You are allowed to outgrow the room you fought so hard to get into.
I am cheering you on as you build what comes next.
Erica
Frequently Asked Questions
Is it a bad idea to leave corporate midcareer?
Leaving with no plan is the risky part. The women I watch do this well build the second thing while they still have the first job, so the paycheck funds the experiment and the title still opens doors. Test the new work on the side first and watch what it does to your energy and your bank account. If it earns nothing in the margins, it may be a hobby you love, and that is allowed too.
Why are so many women starting businesses instead of chasing promotions?
Many of them weighed what the next rung costs against the support that comes with it. McKinsey and LeanIn.Org found in December 2025 that 84 percent of senior level women want to be promoted, compared with 92 percent of senior level men, the first notable ambition gap in that study. The same report found the gap falls away when women get the same career support men get. So the gap is a support problem, and support can be fixed.
What should I check before buying a franchise or joining a business opportunity?
Ask where the money comes from. In a legitimate franchise you earn from your own customers, there is no down line, and there is a disclosure document you read and sign. Ask what you are required to buy and from whom. Then talk to women who have owned that business for at least two years and ask what they wish they had known in their first year.
Erica Anderson Rooney is an ex-CPO turned executive coach and AI educator on a mission to get more women into positions of power and keep them there. She is the author of The AI Gap (2026), host of the Glass Ceilings & Sticky Floors and AI Voice or Victim podcasts, and NC Chapter Lead for Women Applying AI. Her SNAP and AI Continuum frameworks are taught to thousands of women through CHIEF, WICT, and Fortune 500 leadership programs. She is the sought-after speaker at the intersection of women, AI, and leadership.
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