Why Overthinking Keeps You Stuck
Years ago, I was in a job I knew wasn’t aligned with me. The culture was... interesting.
I learned early that it was the kind of place where the loudest people got the shine. Not the people doing meaningful work. Not the folks thinking critically. Just the ones talking the most—even if what they said wasn’t valuable.
Still, I stayed.
Not because I was happy. But because I wasn’t sure what I wanted next. After years of job changes and gaps in my resume, I craved stability. Or at least the illusion of it.
Before I accepted that role, I told myself I wasn’t asking for much. And honestly, that was the problem.
Years of survival mode had made me think the bare minimum was enough. I was just looking for solid ground. Something that felt “safe.”
I’m definitely one of those “ask, believe, receive” types. So before I took the job, I made a list of what I wanted. I remember writing down:
“I want a job where I can do the job I was hired to do.”
That’s it. That’s what I wrote. And in hindsight? Whew. That should’ve told me everything I needed to know.
That list came from a place of fear and exhaustion—not alignment. No wonder the job didn’t match my values. But I forgive myself. I made the best decision I could with what I knew at the time.
Fast forward to the first time I went into the office.
My role was remote, but some senior leaders were in town and I thought it would be good to meet them. From the moment I stepped inside, I felt tense, uneasy, completely out of place. My smile was polite, but forced. My shoulders were up around my ears. I couldn’t relax.
By the time I got home—just 15 minutes away—I felt like all my energy had been drained. Like something had been taken from me. Looking back now, that was the beginning of the end.
But I didn’t leave. I was scared. The job market was rough. Honestly, it’s been rough since 2020—maybe even before that. And I kept telling myself, this is the job you asked for. Be grateful.
But the truth is, my needs had changed. I kept trying to justify my current choices based on an old version of myself.
Still, I tried to figure it out logically. I created a pros and cons list.
If I stayed:
Maybe things would get better.
Maybe I could make a bigger impact.
Maybe this was just growing pains.
Maybe this was an opportunity for growth.
If I left:
I'd have to explain more résumé gaps.
The job search could take forever.
What if the next place was worse?
I wasn’t even sure what I was looking for.
It felt like a tie. I kept saying I didn’t know what to do. But deep down, I knew—I just didn’t like the answer. I was scared to start over again.
So I made a deal with myself: Try everything. Exhaust all options. That way, if you leave, you’ll know you did your part.
Because in the past, I was quick to go. I had one foot out the door as soon as things felt off. That worked in my 20s—and I stand by it. But now, in my 30s? I had real goals. Financial goals. Life goals. Constant job hopping didn’t feel sustainable anymore.
And I TRIED.
I worked with my therapist. I worked with my life coach. I explored every angle. I looked for blind spots. I tried new approaches. I told myself, this is happening for a reason. It’s not about me—it’s for me.
And I still believe that’s true.
I didn’t take anything personal at that job:
The people who didn’t like me? That wasn’t mine to carry.
The teammates who tried to micromanage me without half my skills? Projection.
The biased “expectations” I supposedly didn’t meet? Small-minded. I did my job—and I did it well.
Maybe it’s because of my faith, but I believe every experience offers something:
A lesson.
A mirror.
A boundary.
A place that needs healing.
And I held on to the belief that something better was waiting on the other side.
Eventually, I got to the point where I said, There’s nothing else I can do.
It was no longer about effort. It was about misalignment. The rest was on leadership. On the environment. On the system. And I couldn’t control any of that.
So I started planning my exit. I gave myself a 4–6 month runway—enough time to make a strategic move without blowing up my life. I had a plan.
But I didn’t get to use it.
Because when I left the company, it wasn’t on my terms.
And sometimes, I wonder—if I hadn’t overthought it... if I had just trusted that first feeling in my gut... could I have saved myself the chaos that followed?
I don’t know for sure. But what I do know is this:
Next time, I’m listening to my body before I listen to my list.
Because sometimes, the list isn’t the answer.
Your gut is.
Ready to start trusting yourself again?
If you’re in a space that doesn’t feel aligned—but you’re overthinking your next step—my free transition guide can help you take the first step with clarity and confidence.