The Art of Starting Over Part 7: Redefining Success Beyond the Corner Office

She remembers when it was easier to tell who was for you and who was against you. This new-age way of climbing the corporate ladder was wearing Gina out. She doesn’t mind the truth. She’s not offended by it, and now she has a new CEO who has a trail of people behind him that he screwed to get to his position. She knew it was only a matter of time before it was her turn.

She’d been planning an exit in her mind but hadn’t taken any action. Gina always had a plan. She came from a family where planning was proof of discipline and discipline was proof of worth. She was the doer, reliable, measured, and focused.

Even as a kid, she organized the neighborhood spelling bees and kept score during family Monopoly games. She never lost. If she did, she wanted to know why. That was Gina: curious, sharp, and allergic to phony. She was as real as they come. People always wondered how she made it so far without being fake.

By the time she graduated from her HBCU, her résumé already looked like a career — student council, sorority, internships, glowing recommendations. HR was a natural fit. She understood people and policies. She could read a room, calm a storm, and somehow make management comfortable with it being her idea.

The money was good, the title was solid, and for a long time, that was enough. She married, raised three kids, and built a home where everything had its place. But slowly, something in her started to shift. It wasn’t loud, just a faint hum of discontent she couldn’t name. She felt a storm brewing.

The work changed first. When the new CEO came in, her HR projects became less about people and more about metrics. Spreadsheets replaced conversations. Words like efficiency and compliance took up space where growth and care used to live. She was writing policies she didn’t believe in and watching good employees disappear through doors labeled “restructuring.”

It all started to feel familiar, like the same corporate ache she’d seen break her brother Frank years earlier.

She remembered the day he called, saying, “Gina, they let me go.” She’d tried to talk him through it, remind him of his value, tell him it was temporary. But watching him rebuild a life around his true rhythm left an imprint she didn’t talk about.

Years later, her own children would hold the mirror up.

One evening at the kitchen table, her daughter said, “Mom, you know my friends don’t know how to do half the things you taught us?”

“Like what?” Gina laughed.

“Like how to budget, or interview, or even handle decision-making. They don’t know how to bounce back either.”

It stopped her. She’d spent her whole career developing people for companies, but what about developing people for life?

The idea started small, a few lessons written out for her daughter’s friends, some worksheets, a Saturday meetup. Then a colleague at a charter school asked her to come speak. Then another asked her to help train their staff. Before she knew it, she was spending more time after hours building something that felt alive again.

And then it happened. It was her turn to get thrown under the bus. Her CEO made a few mistakes that he didn’t have enough integrity to own, so he blamed her, and the board voted to hire a new HR Director. When she heard the news, she knew it was the end.

At first, she tried to fight. She had great points and even some supporting documents, but he had friends on the board. That’s how he got the job in the first place. So she put down her gloves and took the exit they offered. She left her corporate job, but because she had a side hustle, she still had her dignity intact. It wasn’t paying the bills, but it was fulfilling her.

She decided not to go for another HR job. Just as she made that decision, one of the charter schools she worked with recommended her to the head of the charter network. It was a step down for her financially and even prestigiously, but it felt right. Her friends and colleagues said she was brave. Some of them called her crazy behind her back. The truth is, she was terrified.

She took the job as HR Director for the charter school network. She was juggling speaking, consulting, and running the HR team. Even though she had to work harder to make less money, she felt more aligned. Within three years, her curriculum was complete. It became a pilot program across a few of the schools in the network. They shifted her to a consulting role, and she found her replacement for HR Director.

She still had quite a few years before she would be retiring, and now she felt like she had a second wind. Now she’s speaking to educators around the world about how to prepare students for real life, not just standardized tests.

She says it’s about transfer — transferring wisdom, skills, and self-worth from one generation to the next. She appreciates all the success tactics her parents taught her to put in place, and she teaches those too. But the life skills seem even more valuable to her now.

Gina still keeps a calendar, still loves her spreadsheets, still plans everything. But her definition of winning has changed. She’s more authentic and more herself, even though she didn’t think that was possible. She thought she was herself; turns out winning didn’t make her who she was — wisdom did.

Winning is no longer in promotions or plaques. It’s in seeing a young girl or guy who once felt confused find confidence. It’s in hearing a student talk about saving for their first car. It’s in watching teachers cry during her workshops because someone finally put language to what they’ve been trying to do all along.

Her parents would have been proud. They wanted her to aim high. They just didn’t know what high looked like beyond the office walls. She hasn’t just started over. She’s started something that will outlast her — even if she never gets a trophy for it.

Sleep Better, Live Better

Maybe you’re like Gina. Maybe you’re lying awake some nights thinking about who you used to be and who you’re supposed to become now. Maybe other nights you crash hard because life wears you out, yet you still wake up tired. Either way, your mind is doing overtime and your body is paying for it.

You don’t have to solve everything tonight. You don’t need a big strategy or a new title or a perfect plan to earn rest. Start simple. Try my free sleep meditations. 

They’ll help you fall asleep, stay asleep, and awaken at the right time feeling refreshed. I’ve helped more than 6,000 people restore their peace, and my goal is to help 10,000.

Will you be one of them? It’s free, easy, and could be the first real step back toward rest you don’t have to earn and a life that fits who you are now.

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