After 18 years leading tech transformations at Stanford, I’ve learned that success doesn’t come from titles or being the loudest voice in the room. It comes from knowing when to trust yourself — even when it means letting go of everything you’ve worked so hard to build.
If you’ve ever asked yourself, “Is this really it?” — today’s story is for you.
When the Dream Job No Longer Feels Like the Dream
I had everything I thought I wanted.
I’d earned the title. Built a team from scratch. Led big, strategic initiatives that actually moved the needle. For years, I loved the work and felt proud of what we were building.
But overtime, something shifted.
The work became more about managing complexity than creating impact. My days blurred into a rinse-and-repeat of meetings, different flavors of politics, and constant managing up. I was still getting things done, but I wasn’t solving real problems anymore.
And while nothing was technically “wrong,” I found myself quietly searching for something more.
I missed learning. Building. Stretching into the unfamiliar.
I missed being a little scared - the kind that meant I was growing.
The Fork in the Road
Around that time, a senior leader I respected approached me with an offer:
“Come work for me. I’ve got a massive transformation effort underway, and I want you to lead one of the initiatives.”
It was a chance to pivot into the IT organization — a team I’d long admired — and work on something bold and high-impact. But there was one catch: I wouldn’t be able to keep my title. Their org structure didn’t allow for it. They asked if I’d be open to making the move - without it.
That one detail gave me pause.
Could I really walk away from the team I built, the credibility I’d earned, and the comfort of everything I knew?
But here’s what I realized: staying would have meant continuing to shrink. And if I wanted to grow again, I had to make space for something new — even if it didn’t come with guarantees.
So, I said yes. And walked away.
Letting Go to Make Room
The decision wasn’t easy. Saying goodbye to my team was the hardest part. Trading prestige for possibility felt risky. But almost immediately, something shifted:
- My blood pressure dropped.
- I felt lighter.
- For the first time in years, I looked forward to Monday morning.
And that’s when it hit me: walking away wasn’t giving up. It was choosing myself.
The Biggest Shift Wasn’t My Job — It Was Me
Stepping out of my old role gave me space to reflect. For so long, my approach to work had been centered on performance — proving my worth through output, results, and recognition. But in this new season, I started focusing less on me, and more on we.
And something powerful happened:
That email that used to keep me up at night? It didn’t trigger the same spiral.
Those meetings that drained me? I approached them with curiosity, not defensiveness. That voice in my head saying “you’re not doing enough”? A little quieter.
By creating space, I started showing up differently — not just more calm, but more impactful.
And with that space, I also started giving back. I began coaching others — people who felt stuck or unsure of their next step — and saw how much it mattered. That felt like a real impact.
Redefining What Success Means (For Me)
Here’s what I know now: I used to chase the wrong metrics. Success, to me, used to mean: titles, recognition, getting invited into the room.
Now, it looks more like:
- Being excited to start my day
- Knowing I’m helping people grow
- Having the energy to show up fully for work and life
This isn’t the story of a perfect pivot. It’s the story of choosing growth over comfort — and redefining what a “winning” career move looks like.
Lessons I Learned (That You Can Steal)
1. Your health is non-negotiable.
If your body is telling you something, listen. Stress and burnout aren’t the price of ambition. They’re signals.
2. Trust your gut.
Even when the path is unclear, your inner voice knows when something isn’t aligned. Don’t wait for certainty to take action.
3. Invest in your network.
Building genuine relationships isn’t just nice — it’s essential. It’s how new opportunities show up. The people around you can open doors, and offer perspectives. Invest in that community.
4. Letting go isn’t a setback - it’s a set up.
Real growth often starts outside of your comfort zone. Sometimes, the boldest move isn’t pushing forward - it’s letting go. That role, that title, that familiar path? When you stop clinging to what’s “good enough”, you make room for what’s possible. You never know what’s waiting until you make space for it.
5. Reinvention isn’t failure — it’s courage.
You don’t need a perfect plan. You just need the willingness to bet on yourself.
What This Means for You
Too often, we stay in roles that look “successful” on paper but feel empty in practice. We tell ourselves that walking away is quitting — when really, it’s one of the bravest things you can do.
If you’re at a crossroads — wondering whether it’s time to leave, change roles, or even just set a boundary — ask yourself:
Is this job helping me grow, or am I just enduring it?
Titles and promotions are temporary. But your growth, your values, and your well-being? Those matter more.
Today’s Reflection Question:
If someone were to describe your impact today, what would they say? What do you want them to say a year from now?
Ready to Step Into Your Next Chapter?
I help leaders in legacy organizations navigate politics, build influence, and step into roles that feel more aligned. If this story resonated with you, I’d love to hear from you.
Send me a note — janet@janet.kim.
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