In my notes for a mentoring course I’m taking, there’s a line I wrote almost as a confession. The prompt asked what I do beyond teaching that shapes students into professionals. I wrote that I advise a student program, and then this: my path is so different from theirs that I have trouble relating. What I offer them is technical opportunities. But I don’t connect the way another advisor does.
I meant it as a weakness. The kind of thing you admit quietly and then hope to fix.
I’ve been sitting with it, and I think I had it backwards.
The thing I labeled a liability
My path here was not a straight line. I had a kid at nineteen. I dropped out of college. I didn’t go back until my late twenties and I finished the road I’d walked away from years earlier than I was supposed to.
For a long time I read all of that as distance. My students are nineteen and twenty, right on track, doing it the way you’re supposed to. I wasn’t. Their road looks nothing like the one I took. Surely the advisor whose path maps more neatly onto theirs is the one who really reaches them.
But here’s what I finally noticed. Nineteen is not an age I’m looking back at from across a gap. It’s the age I was when everything came apart. I’m not a stranger to where some of these students are standing. I’ve stood there. I know what it feels like to be that age and have the plan stop working — to walk away from school not knowing if you’ll ever find your way back.
That’s not distance from my students. That’s the closest thing to common ground I could possibly have.
Relating isn’t about looking alike
Our roads don’t match on the surface. I got to where these students are standing by a completely different route — years off schedule, from the wrong direction, after walking away and doubling back. If connection depended on our paths looking the same, I’d have nothing to offer.
But that was never the part that mattered. What I share with a stuck nineteen-year-old isn’t the shape of the road. It’s the feeling of the plan falling apart and not knowing what comes next. I’ve felt that one all the way down.
And the way I let them see it now is by being openly, imperfectly in progress — still learning things in real time, still falling behind and catching up, still choosing to actually understand something instead of just getting through it. I’m not relating to them by pretending to be where they are, and I’m not relating to them by pretending I’ve got it all figured out. I’m relating to them by being honest that I’ve been lost too, and that being lost at nineteen was not the end of my story.
A student who’s scared they don’t belong here doesn’t need to see someone who always did. They need to see someone who wasn’t sure either — who actually walked away once — and found the way back anyway.
Two kinds of mentor, and you only have to be one
Here’s the part I want to say plainly, because I think a lot of people who come to teaching sideways need to hear it.
You do not have to become the other advisor.
My connection with students runs through opportunity and through modeling — here’s a competition, here’s a tool I built, here’s me learning the thing right alongside you. It may never look like easy personal rapport, and honestly it may never feel like connection to me, because I measure it against a version I’m not built for. That’s fine. It still counts. The students who need exactly what I offer are being reached, even on the days I can’t feel it.
The mistake was thinking there’s one correct shape for reaching a student, and that mine was a broken copy of it. There isn’t. There’s the version that fits who you actually are — and for people like me, and maybe like you, that version is built out of the very path we thought disqualified us.
Why this is the whole point
Everything I do here — this site, the work in rural classrooms, the push to get real technology into the hands of people the traditional pipeline skips — rests on one idea. A non-traditional path is not a deficit you overcome before you’re allowed to belong. It’s often the exact thing that lets you reach the next person who also doesn’t fit the mold.
I spend a lot of time telling students to stop selling themselves short. To trust that where they come from is an asset, not a thing to apologize for.
Turns out I needed to take my own advice.
If your road into this work was unusual — if you got here late, or sideways, or by a route nobody would recommend — please stop treating that as the thing standing between you and the people you’re trying to reach.
It might be the bridge.
Tasha Penwell teaches business and information systems at Ohio University and is the founder of Bytes and Bits, a platform working to expand access to technology education across rural America. Her own path was anything but traditional and that road shapes how she mentors students today. She builds AI tools, enters coding competitions for the fun of it, and is pursuing a PhD in Instructional Technology. She writes about teaching, technology, and the case for the non-traditional path at bytesandbits.org.
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