What No One Tells You About Career Pivots at 40 (Spoiler: It's Terrifying)
Episode 109. From Federal Leadership to Starting Over: Career Pivot at 40 with Yaa-Hemaa Obiri-Yeboah
You know that feeling when you're sitting in a meeting, nodding along, maybe even leading the discussion—and something in you just whispers, "Is this it?"
Not in a dramatic, mid-life crisis kind of way. More like a quiet, persistent knowing that there's something more. Something different. Something that actually lights you up instead of just checking boxes on someone else's definition of success.
If you've felt that, you're not alone. And if you're scared to do anything about it because you're over 40, have kids, a mortgage, and responsibilities? Yeah, that's the part no one really talks about.
After recording an episode with Yaa-Hemaa Obiri-Yeboah, an episode that gave me chills, I realzied that she wasn’t running away from a bad situation, but towards alignment.
Yaa-Hemaa is a Rhodes Scholar, who spent 19 years climbing the federal government ranks to executive level, and then walked away from it all to start completely over at 40.
The Thing About "Successful" Careers
Yaa-Hemaa had everything that looks good on paper. Rhodes Scholarship? Check. Federal executive role? Check. Passing intense exams and interviews while on maternity leave with a 3-month-old? Check, check, check. But she kept saying this one phrase throughout our conversation:
“I want to operate from my power.”
And I think that's the thing about career pivots at 40 that nobody warns you about. It's not usually about escaping a toxic workplace or fleeing a terrible boss. It's about that slow realization that you've gotten really good at playing a game you never actually wanted to win.
The Scary Part No One Mentions
Here's what terrified Yaa-Hemaa (and what terrifies most of us): What if I'm just scared? What if I'm resisting the next level because of fear, not because it's the wrong path?
So she decided to do something brilliant, testing herself first.
She deliberately stepped into those leadership roles. She passed the exams. She proved to herself—and everyone else—that she COULD do it. That she had the talent, the judgment, the capability.
Only then could she walk away with confidence, knowing: "I'm not leaving because I failed. I'm leaving because I choose something else."
That's the part nobody talks about. Sometimes you have to succeed at the thing to know for sure it's not what you want.
When the Pivot Comes with Kids
The other thing that makes career pivots at 40 so complex? You're not just thinking about yourself anymore.
Yaa-Hemaa made her leap with two young kids. Two kids born a year apart, during the pandemic. And she still found a way to build The Y Variable—a business focused on helping Gen Z navigate early career transitions and bridging generational workplace gaps.
She didn't wait for the "perfect time" (spoiler: it doesn't exist). She didn't wait until her kids were older. She didn't wait until she had it all figured out.
She just knew. And she moved.
What Actually Makes It Possible
Throughout our conversation, Yaa-Hemaa kept coming back to a few things:
Community → She had people who believed in her before she fully believed in herself. A professor who encouraged her to apply for the Rhodes Scholarship when it wasn't even on her radar. A support system during the pandemic. People who had her back.
Testing the "what ifs" → She eliminated doubt by actually trying the thing. No more wondering if she should have stayed, could have made it work, or was just running away.
Listening to the knowing → That internal voice that kept saying "there's something more"? She didn't dismiss it. She didn't ignore it. She honored it.
If You're Reading This and Nodding Along
Maybe you're in a career that looks successful from the outside but feels hollow on the inside.
Maybe you're scared that pivoting at 40 (or beyond) with kids and responsibilities is too risky, too selfish, too late.
Maybe you're wondering if you're just afraid of the next level, or if you're genuinely being called toward something different.
I won't lie to you—the pivot is scary. It's uncertain. It's messy.
But honestly, staying in something that doesn't align with who you are, it’s a lot scarier.
Yaa-Hemaa's full story—from surviving a political coup as a baby, to her "public servant by day, singer-songwriter by night" era, to the exact moment she knew it was time to leave—is one of the most inspiring conversations I've had on the podcast.
Listen to the full episode with Yaa-Hemaa
Because sometimes the best career advice doesn't come from someone who has it all figured out. It comes from someone who had the courage to admit they didn't—and started over anyway.