What I Learned After Leaving My Job (You Don’t Have to Leave to Learn This)

In the month before I quit my job, I woke up every morning thinking, “This is it. Today, I’m quitting.”

And yet—every day—I’d sit at my desk, staring at my laptop.

I had a great boss. The company was thriving. I’d even been promoted from contractor to full-time based on the strength of my work—a moment I’d once dreamed of.

But instead of feeling like I’d made it, I felt like someone had slowly turned off the lights in my mind.

When I started as a contractor, I didn’t feel like a “professional.”

I felt like a stray dog someone let inside to clean up scraps. My job wasn’t to climb the ladder—it was to keep my head down and survive.

And yet, something strange happened: I thrived.

They handed me a big project, and because I had nothing to lose, I stopped caring about the “right way” to do things.

Not in a lazy way—more like:

“What are they going to do, fire me? Let’s just figure it out.”

🚀 I pinged people I wasn’t “supposed” to ping.

🎨 I tried things I wasn’t “qualified” to try.

⚾️ I took swings I had no business taking.

And then—like a kid playing truth or dare—I blurted out something insane:

“I heard your Chief of Staff just left. I wanted to throw my hat in the ring.”

Pause.

The Chief Growth Officer didn’t laugh. He didn’t tell me to stay in my lane. He tilted his head (virtually) and said:

“Let’s set up a 30-minute chat.”

A few months later, I got promoted to full-time.

You’d think this would’ve been my victory lap—It should have felt like crossing the finish line of a marathon, arms in the air, lungs burning, but proud.

But instead, it felt like someone handed me a blank map and said:

“Good luck figuring out the territory.”

There were no swim lanes. No guideposts. No “here’s what success looks like.”

And here’s where it all went wrong.

As a contractor, I was bold. Curious. Free.

As a full-time employee, I became obsessed with doing it right.

I started looking for the playbook:

❌ What’s the “right” project to take on?

❌ Who are the “right” people to work with?

❌ How do I make the “right” moves to prove I deserved this seat?

I didn’t want to step on toes. So I hovered at the edges of conversations, waiting for someone to invite me in.

I didn’t want to say the wrong thing. So I said nothing while others said the wrongest things to me.

Every day, I made myself smaller and smaller until the voice in my head whispered:

“They’re going to realize you don’t belong here.”

I stopped taking shots. I stopped asking questions. I stopped trying.

And instead of climbing that ladder I’d worked so hard to reach, I sat frozen on the bottom rung, watching as people walked over me to climb higher.

It was like the walls were closing in.

The version of me who’d boldly pinged the CGO? Gone.

The version of me who’d figured things out on the fly? Gone.

In her place was someone exhausted. Someone paranoid. Someone who could barely breathe under the weight of trying to “do it right.”

And one morning—after months of shrinking into myself—I realized I couldn’t do it anymore.

I didn’t quit because the company was bad.

I didn’t quit because the people were mean.

I quit because I’d stopped being me.

Here’s what I learned:

I’ve built my career by trusting myself.

From building out a new function at UserTesting, to landing a role at Google, to becoming an executive at a $100M valuation startups—every win I’ve had came from one strategy:

✅Running my own race.

I trusted what I was good at and let curiosity lead me. I trusted that showing up, asking bold questions, and figuring things out as I went was enough.

And it worked—over and over again.

But this time? I lost.

Not because I didn’t have the skills. Not because I wasn’t capable.

I lost because I stopped trusting myself.

The moment I weighed more on being right and playing by the rules, I shrank. I let other people decide how much space I could take up. I let their doubts drown out my own voice.

If you’re feeling stuck—if you’re frozen at the bottom rung, waiting for someone to invite you higher—here’s what I want you to know:

You don’t need a playbook. You don’t need permission.

Trust yourself.

➡ Show up.

➡ Ask the questions.

➡ Take the swings.

Because the truth is, you’ve done it before.

And you’ll do it again.

You just have to trust that you are enough.

It’s how I got here. It’s how I’ll keep going.

And it’s how you will, too.