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A professional mentor helped me launch my tech career. Here’s why it was essential for me

Software developer Benjamin Kostenbader's advice to aspiring technologists: Find people who will coach you and teach you, and have a vested interest in your success.

Mentorship can make a big difference in an aspiring technologist's career. (Pexels/Mikhail Nilov)

This guest post is a part of’s Pathways to Tech Careers Month. See the full 2024 editorial calendar.

This is a guest post by Benjamin Kostenbader, a software developer and the founder of Pittsburgh design collective Dot Foundry.

I’m not a savant. My journey into tech didn’t start with phreaking or breaking into the Pentagon’s mainframe. I learned to type by messaging friends on AOL Instant Messenger. I learned Windows administration by locking my grandmother out of her new XP.

My early career brushed up against tech in many ways, but it never fully immersed me in it. I troubleshot computer issues for my coworkers. I administered a cloud server with educational and administrative programming. I never quite classified myself as a super user, but I was often the guy who set up computer systems. I enjoyed using them.

But I wanted a long-term, lucrative tech career. Many people told me, “You’re good at languages and you’re good at computers. Why not become a developer?” The idea resonated, but I couldn’t seem to crack it on my own. Every code-learning website didn’t quite grab me. I tried and I tried, but I couldn’t connect deeper concepts to real-world examples.

How I found a technical mentor

I first considered going back to school or entering a bootcamp. Things were expensive! And I was a new father, with a full-time job. I needed something flexible. So I listened to the many speakers in my life who told me to reach out to people who already did what I wanted to do.

My cousin was a QA engineer at the time, working for a B Corp in Virginia. She introduced me to Max. Max had nearly three decades of experience in software engineering. His expertise went far beyond the usual abstraction and tooling. He knew networking, OSI layers and machine code. And he was managing teams that used Agile methodologies and test-driven development to maintain and improve enterprise software.

Max’s mentorship was transformative. He didn’t just hand me a fully loaded software project or guide me through a tooling setup. He taught me how to build a server, fix things myself when they broke, and understand the underlying flow of technology. One of his most impactful lessons was that “it’s never the computer’s fault” — a mantra that challenged me to flex and continues to remind me that in our industry, the only limitation is our imagination.

My journey was neither quick nor easy. It spanned four years, intertwined with full-time work and parenthood. But encountering and solving problems at my own pace provided a more profound and comprehensive understanding than any accelerated program could offer.

What makes a good mentor-mentee relationship

The success of the mentor-mentee relationship hinges on trust and honesty. By being transparent about my aspirations and challenges, I was able to make the most of Max’s guidance. I dictated the tempo and, when applicable, chose the lesson flow. I learned what I needed to learn, and I never burned out. He had all the fuel I needed, and I could ask him for it any time.

Another key to a successful mentoring relationship is ownership. Sometimes I was able to bring my knowledge back to Max. I was always savvy with design, and I spent countless hours perfecting CSS. It wasn’t because he asked me to, it was because it was my journey. We briefly learned to compile in C. We later tinkered in machine learning with TensorFlow. It wasn’t his specialization, and it wasn’t directly related to my final goals. It just made us better.

Even now, the fundamentals I developed manifest in surprising ways. We recently found that Dot Foundry can make fully featured WordPress websites with perfect mobile Google Lighthouse scores. It’s a very difficult and technical accomplishment, and it still astonishes me. I attribute a significant part of that success to the guidance and support I received from Max.

Mentorship as a way to give back

I see mentorship as a continuing part of my journey in tech. The principle of open source software is pretty key to all we do. We need to remember that every dollar we make comes from the public knowledge of volunteer contributors. Participating in community projects, speaking, contributing, and mentoring are something that every developer should do.

Every year, as time permits, I take on one to two mentees of my own. It’s not as lucrative as software development, but it’s very rewarding. I aim to pay forward the knowledge and insights I’ve gained, just like Max did for me. I also try to be the good I want to see in our community and the world. This is software, not coal mining. Everybody can succeed here!

For those embarking on their tech journey, my advice is the same as those speakers in my early years: Seek out industry leaders you can trust. Find people who will coach you and teach you, and have a vested interest in your success. Mentors like Max and myself are out there. That momentum can carry you far through any imposter syndrome you might face.

Series: Pathways to Tech Careers Month 2024

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