A few years ago, I visited with a group of high school students to talk about my career path so far, and to participate in a few mock interviews. During the session, I followed the script, offered helpful feedback to each student on their pitch, and then moved onto the next.

But then, during some down time in between sessions, one of the students came back up to me and asked for more detail about what I'm working on now, so I shared a bit about my fractional work life. In passing I made some comment about how you could tell it's roach season in NYC because I keep seeing them all over my apartment.

That passing comment stopped him in his tracks..

"Wait," he said, eyes widening. "YOU have roaches?"

"Of course I do," I shrugged. "It's New York City, we all have them."

It was a little bit like a part of his brain didn't compute what I was saying. That he couldn't reconciles how some unattainable benchmark of career success could also simultaneously carry the gritty reality of icky critters crawling around your apartment. That I might also have to sometimes sacrifice my favorite shoes, or favorite books, for the good of killing a live roach on sight.

"I mean, I have roaches too.. but I didn't think that you..." and he sort of trailed off.

"Are you kidding?" I laughed. "I live in a basement apartment. I'm killing two roaches a day on average, it's disgusting."

After that, he opened up entirely, sharing a bit more about his home life, his family, and even felt a little bit braver telling me more about his own career goals and conflicting directions. I invited him into a bit more of the messy reality of fractional work, the highs and lows, the project-to-project hopping, the difficulty of explaining my wide ranging portfolio career to new people.

In the end, our conversation went much deeper than it had in our early, more scripted interview. It deepened because he found a relatable element, and we anchored ourselves in a shared, honest reality. From that moment, he was more open to learning what he could draw from my career path to shape his own. And I was more eager to share, because I could tell that he was genuinely interested in what I had to say.

Embracing the Critters Between the Walls

The reality is, for a lot of us, our careers don't fit inside of a neat little box that you can explain with one word, or even one line. That makes it hard to pinpoint a clear direction for ourselves, let alone to find proxy personas to emulate or look up to.

Even when we find ourselves in a room with someone more senior, it's easy to miss the bigger picture—seeing their success as unattainable rather than inspiring, as if they’ve unlocked something we’ll never catch ourselves. That's why it's important to talk about your roaches. It keeps us human.

If you don’t have literal cockroaches, metaphorical ones will do just fine. What are the tiny, annoying critters scuttling through your life or work right now? What’s going wrong, rather than right? What’s the boring, unglamorous stuff that quietly eats up your time but feels too ordinary to mention?

Another way "seeing roaches" shows up for me is in observing moments of visible learning when someone I respect or admire openly navigates unfamiliar territory. It can feel counterintuitive, but admitting what you don’t know actually demonstrates strength and self-awareness. It's a signal that you have a very strong understanding of where, exactly, the outer limit of your knowledge is. (Which in turn implies that you know, exactly, what you need to learn next.)

This is also why watching someone try something new for the first time (and have them not knock it out of the park) can be weirdly motivating. Or why karaoke is such a good leveling and team-building activity; it invites everyone to embrace imperfection together.

As a leader, you can seek out these valuable learning opportunities by actively learning from people more junior than you, or via experts in areas decidedly out of your domain of expertise. Sure, the classic example might be an older person asking a younger colleague for help with social media or pop culture references, but this idea goes far beyond that cliche.

Sharing your own roaches—or encouraging others to share theirs—humanizes the learning process. It reminds people that nobody is perfect or has all the answers. So go ahead, don't be afraid to look for a few of the critters in between the walls.