A high school student recently reached out to me, looking for guidance. It was quite open ended but they reminded me so much of myself — curious, driven, staring out at the vast, intimidating world of tech and wondering how to get started. I was impressed that they had the gall to cold call me via LinkedIn DM. This is what I told them. I hope it helps.

Fan the Flame

When I was in middle school, I taught myself BASIC on a hand-me-down IBM PC Jr. It was the start of something I didn’t yet have a name for — a lifelong journey in technology. I wrote little “choose your own adventure” text-based games using rudimentary logic and endless chains of GOTO statements. These weren’t elegant or groundbreaking, but they were mine. They were problems I could solve, stories I could control.

Later, I discovered HTML. It was the dawn of the internet, and learning HTML felt like unlocking a secret language that opened doors. One of those doors led me to a mentor starting up an internet company. They introduced me to classic ASP, then a cutting-edge server-side rendering technology. I didn’t realize it at the time, but I was standing at the edge of a new era.

Get Lucky, Make Your Own Luck

Eventually, I landed an internship at Bank One, which would later become part of JPMorgan Chase. The work wasn’t glamorous — I racked and stacked servers, installed Windows 2000 Professional on desktops, and set up Windows NT 4.0 on servers. Though I had already built my own gaming PCs on a shoestring budget for LAN parties with friends, this was my first exposure to enterprise-scale hardware. I was blown away by machines that cost upwards of $50,000.

At the bank, I was introduced to Oracle and Sun Microsystems. I fell in love with Sun, and with Solaris. UNIX was my next mountain to climb. I began learning Java, though the journey wasn’t easy. I asked a senior developer for help, and he handed me a book and sent me on my way. It was frustrating — I wanted mentorship, but he was there to do a job, not to guide me. At the time, I didn’t understand. Now, I do. Don’t expect anything from anybody. If help is offered willingly, accept it with great thirst. Recognize they didn’t have to help you and be thankful, you received something most never will.

Solve Problems You Want To Solve

So I learned Java the hard way. With a foundation in BASIC, HTML, rudimentary JavaScript, and some VB, the jump to Java was a massive leap. The learning curve was brutal. I spent six painful months trying to understand why javacand java.exe wouldn’t work as expected. I wrote command-line tools that organized my MP3s from Napster. I built Swing apps to help me randomly select movies from my DVD collection. These were small, arguably silly projects, but they were real to me. They were manageable problems that gave me confidence.

As I got more comfortable, I began forking open source projects. One of my favorites was an abandoned game I loved — I rewrote it in Java. That project taught me 2D graphics programming and deepened my understanding of rich client development.

Grab a Shovel, Even Dirty Jobs Teach You A Lot

At work, I moved beyond racking servers. I joined a development team, writing VB6 and COM+ backends, paired with HTML and raw JavaScript on the front end. We used classic ASP, and even though I didn’t know it at the time, we were pioneering AJAX techniques years before the term existed. It was an exhilarating time to be a developer, even if I didn’t fully appreciate how advanced we were.

The VB6 and COM+ was unattractive to me. I wanted to write Java — all I cared about was Java. However, this taught me another valuable lesson: sometimes you have to do the work you don’t want to do. It’s not all hitting home runs and running the bases, there is a field to rake, base paths to measure and bases to stake, not to mention a lawn to mow, a trash can to empty. It’s not all glamorous, but it all has to get done.

Recognize Your Own Naivety, Find the Right Help

With an old classmate, I started building what was essentially a prototype social media platform. I hosted it on my personal workstation tucked under a desk in my small basement apartment. Users could create profiles, connect with classmates, chat, and share photos. It was, in essence, Facebook — before Facebook. But I had no concept of startups, no vocabulary for entrepreneurship. I was a middle-class kid from Ohio. My parents were supportive, but we didn’t talk about venture capital or business models. I didn’t even know those words.

My friend and I still joke about how we were so close to beating Mr. Zuckerberg to the punch — but we really weren’t. Successful businesses are 10% the idea and 90% the execution, the rest is timing and luck. We had a great idea — but we had no idea how to scale it. We were two naive kids who could barely scrape twenty bucks together for lunch at Chipotle. We had a full load of college course work to tackle and full-time/part-time jobs to help pay for gas money. With the right mentors, things might have been different.

Why I’m Telling You This

I’m telling you this because that student reminded me how important it is to hear these stories when you’re just starting out. I wish somebody would’ve told me when I started out. I learned a lot of valuable lessons. I had a lot of great mentors. I wish I would’ve broaden my mind earlier. Perhaps if I had made other choices, I would have had the opportunity to be in different environments where other pathways were better curated for young people such as myself.

For kids today, the technology may be different. The world sure is different. But the path? It’s still full of forks, false starts, opportunities — and missed opportunities. Today, there are more technical disciplines, more access points. Cloud computing has erased the barrier to entry for infrastructure. You don’t have to run the next big thing from your crappy self-built desktop PC. You can deploy to the cloud, leveraging world-class infrastructure with a credit card and an idea.

AI is about to change everything — and yet, in some ways, nothing. You still need people willing to put in the blood, sweat, and tears to learn a domain, pick a problem, and solve it. AI can accelerate your progress, but only once you’ve reached a level of understanding where you can direct it. Until then, treat AI like the tutor I never had. Let it be your teacher, your sounding board, your co-pilot. But don’t mistake it for a substitute for mastery.

Finding Your Path

Seek out mentors. Build a “mentorship ring” — someone in enterprise, someone in consulting, someone building a startup. These perspectives will help you figure out which ladder you want to climb — or whether you want to build one yourself.

If you’re going to do a startup, do it young. But don’t go it alone. Find someone with age and experience who can stress-test your ideas and turn your hobby into a viable business. Many startups die not because the tech is bad, but because no one thought through how it would make money.

Final Words

Looking back, I don’t regret the head-banging frustration, the nights of trial and error, or even the rejection from that senior dev. It made me who I am. I learned how to learn. I learned how to build. I learned that no one is coming to hold your hand (or wipe your ass), but if you keep showing up, if you keep solving problems — however silly — they stack up into something real.

Good luck on your journey. The tools are better now. The paths are more visible. But the work? That part hasn’t changed. Dive in.

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