When the Path You Planned Doesn’t Work

There have been many times when I thought I was f’ing up in my career.

Four or five years into my career, I had a plan—or at least what I believed was a plan. I was going to get my MBA. It felt like the logical next step, the thing that would give me direction, credibility, and a path forward in my career.

So I did what you’re supposed to do. I took the GMAT, but I got a low score. I had studied so much. Feeling so deflated, I enrolled in a Kaplan course, and took the GMAT again, convinced that effort would change the outcome (effort is what had provided success previously).

It didn’t.

I got the EXACT same score.

That was confusing. I was driven. I was willing to put in the work. And yet, I couldn’t seem to produce the result that was supposed to unlock the next chapter of my life. I questioned my capability - maybe I wasn’t as capable as I thought I was.

Still, I applied to five or six business schools. I told myself that maybe my experience, work ethic, references, or something else would carry more weight.

I was rejected from all of them.

I didn’t know what to do next. I didn’t feel like I had a clear direction anymore. I had been counting on this to provide that clarity, to tell me I was on the right path.

I felt untethered.

I now know, I wasn’t lacking direction, I was looking for it in the wrong place.

Not long after, I found myself working for startups. It ended up being the environment that changed everything for me.

There was no structure in the way education would have provided. Roles were often loosely defined, priorities shifted ultra-quickly, and many of the decisions we had to make came without perfect information or clear answers. It was ambiguous in a way that would have made classroom learning unsatisfying, for me.

I thrived in the ambiguity.

I didn’t need everything to be fully mapped out in order to move forward. I could think through problems in real time, make decisions, adjust, and keep going. I wasn’t waiting for someone to hand me the “right” answer—I was learning how to navigate without one.

That experience became my version of an MBA.

Not in a classroom, but in the midst of messy, evolving situations where there wasn’t a clear playbook. I learned how to use judgment instead of relying on perfect information, how to lead without full alignment, and how to stay grounded even when things around me were constantly changing.

Looking back, I realize how much energy I had spent earlier trying to force myself into a system that didn’t actually fit how I learn or operate. I thought the path to success required a certain kind of validation—test scores, acceptance letters, structured programs. And to be clear, that works SO well for SO many.

But what actually moved me forward was finding an environment where my natural way of thinking and working wasn’t a limitation—it was an advantage.

We don’t talk enough about how often we mistake misalignment for failure. How easy it is to assume that if something isn’t working, it must mean something is wrong with us. If you have a high locus of control like me, this can exasperate this.

If you’re in a period of time where you feel like you’re doing everything you’re supposed to do and it’s still not clicking, it’s worth asking a different question. Not “What am I doing wrong?” but “Is this the right environment for how I operate best?” and “What was at play when I felt the most satisfaction in my career?”

Because the thing that makes you feel stuck in one place might be the exact thing that allows you to excel in another.

I didn’t get the MBA I thought I needed.

But I got an education that propelled me forward in my career because I found purpose and joy in my day-to-day.

No matter where you are in your career—figuring it out, in the middle of it, or feeling settled - there’s value in hearing how others have navigated their own F’ing Up moments.

🎙️ That’s exactly what we talk about on The F’ing Up Podcast.

If you’re personally in a moment of uncertainty and want help working through it, 👉 I offer coaching for people navigating exactly that.

And if you want more of these reflections, ✉️ subscribe to The Art of F’ing Up Newsletter.