July 21, 2026

Unconventional Career Paths and “Am I in the Right Career?”

FILED IN: Uncategorized

I googled “am I in the right career?” at midnight. More than once.

I remember laying in bed, when I couldn’t sleep, typing that into the search bar (poor sleep hygiene and all). The piece I remember most is the desperation and loneliness of those moments, the quiet of the rest of the house being asleep, and just feeling like I was alone with my thoughts and alone in my experience.

On one of those occasions in particular, I burst into tears. For two reasons.

First, I finally felt seen. Like maybe I wasn’t the only person who felt like they’d made all the right choices, tried to do the responsible thing, go to university, work hard, get an adult job, move into management, and still felt empty, like the career still wasn’t the right fit.

But that relief was fleeting. Quickly replaced by the second reason for those tears. Even though I felt less alone in those thoughts, I just felt defeated. So many of the posts I was reading came from a place of pain, from that messy middle, and nothing was giving me any sense that things could actually change. I was so afraid that this is just what being an adult meant. That you picked a career, worked for 40+ years, and hoped that the career you picked didn’t make you lose yourself before you retired.

And I’d already made multiple career changes at that point. So I felt extra behind, and honestly like I was stupid for not picking something and sticking with it.

It felt like so many people had decided what they were going to be when they grew up as kids and just followed that path. And from my perspective, they were happy with that choice. Meanwhile, all through school my career aspirations changed time and time again. In my last two years of high school, when everyone around me was planning to be a lawyer, an engineer, a doctor, a nurse, or a teacher, I felt like the odd one out because I still had no idea what I actually wanted to do. Multiple well-meaning adults told me to just pick something I was interested in and I’d figure it out, because I had lots of time.

So that’s what I did. Then spent most of my undergraduate degree debating between law school and grad school, before landing on grad school and the desire to be an academic. But during grad school, I saw the cracks in that system and realized it wasn’t for me. And then I landed in places where I still didn’t know what I really wanted, but I was good at my jobs and they were stable, so I stayed for a while, and then got too antsy and left.

I tried to trace my career path and found something that, if I hadn’t lived it myself, felt wild and confusing and completely unrelated. And I kept comparing it to the people in my life who picked a career and stayed there.

Then something clicked. Not in some dramatic lightning-bolt moment, actually, it happened recently, while I was trying to figure out exactly who my audience is and what I’m building and who I’m actually building it for. I was going back over my own story, thinking through the advice I’d received over the years, trying to understand what had landed and what hadn’t and why.

And I realized something.

There are lots of careers with clearly laid out paths, a map that takes you from point A to point B. And then there are unconventional career paths, which most people treat as one category. But they’re not. There are people who take a winding, scenic route through unexpected places and eventually arrive at a career that already exists. They took a detour. They still found the destination.

And then there are the rest of us. The ones where the destination doesn’t exist yet. Where the map doesn’t exist because the thing you’re navigating toward hasn’t been built. And well-meaning people, even those who took unconventional paths themselves, keep saying things like “you just need to follow this map” or “maybe you just need time to find your way to a path that exists.” And it’s beautiful that they’re speaking from their experience. But their map was never mine to follow. Because I wasn’t looking for a path to something that already existed. I was trying to find something that didn’t. Yet.

The hardest part of that isn’t the uncertainty itself. It’s what you quietly tell yourself about wanting it.

Overlaid on a picture of a river path and a climb in a forest is the text "I was trying to find something that didn't exist. Yet."

I spent a long time blaming myself for wanting something that doesn’t exist. Telling myself it made me stupid. Selfish. Delusional. That I just needed to suck it up and figure out how to be happy with something that was already there.

So the first thing I needed, before any framework, before any methodology, before any map, wasn’t strategy. It was permission. Permission to want the thing that doesn’t exist. To not have that be evidence that something is fundamentally wrong with me.

You’re not delusional. You’re not selfish. You’re not broken for wanting the thing that hasn’t been built yet. And the loneliness of it isn’t just “I don’t know what to do.” It’s “I’ve been quietly telling myself I’m the only one who wants something no one else seems to want.”

You’re not.

I don’t think my purpose is to build a new path for people to follow so they can follow my path. I think it’s to build something that is so fundamentally me that I can help people find, craft, or build the thing that is so fundamentally them.

That’s what I’m working on right now. It’s called Make Your Map, and it’s still being built. I’ve been on an untrodden path for most of my career, and I’ve built supports to navigate it along the way. But I’m genuinely not sure yet which parts of that would actually help someone else, and I’d rather ask than assume.

So here’s what I want to know from you, if you’re one of those people. The one who tried to do everything right and still doesn’t have a path to where you’re going, other than a strong internal knowing that you can’t stay on your current path for the next 20-plus years.

What was the thing you needed? What’s the thing you need now?

Not what you think you should need. The actual thing.

Leave a comment or send me an email at rebecca@rebeccafoleyaskew.com.

I’m listening.

Disclaimer

The views expressed on this blog are solely my own and do not reflect the views, positions, strategies, or opinions of any current or former employer, employee, client, customer, or affiliated organization. My commentary is based on general professional experience, education, publicly available information, and knowledge and skills acquired throughout my career and is not based on confidential, proprietary, privileged, or non-public information belonging to any current or former employer, employee, client, customer, or affiliated organization.
 
Any examples, scenarios, or observations are intended for general informational and educational purposes and may be presented in a generalized or hypothetical manner. Nothing in these posts is intended to identify, criticize, disparage, or comment upon any specific current or former employer, employee, client, customer, individual, or affiliated organization. The opinions expressed are personal in nature and should not be interpreted as statements made on behalf of any other person or entity.

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