The Software That Raised Me

Coming of age in the wilds of Windows 95.

Editor’s Note: This one came together in bits and pieces.

Watching my nephews play chess at a family get-together reminded me of the old computer game we used to learn the rules—back when tutorials came shrink-wrapped in CD-ROMs. Around the same time, my group chat started swapping notes about our first AIM handles and favorite away messages. Then someone dropped a 3-second nostalgia bomb that blasted me into the past so intensely that I knew I had to write about it.

I’ve spent so much time thinking about tech through the lens of work, output, optimization. But this piece is about something earlier. Before strategy decks, before content calendars—before the word “interface” meant anything to me—I was already learning what it meant to feel powerful at a keyboard.

I'm curious: What was the first piece of software you remember playing with as a kid, and how do you think it influenced how you interact with technology today?

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The Software That Raised Me

It started with a cartoon blast.

A friend dropped a three-second YouTube relic of the dynamite effect from Kid Pix into Slack, and just like that, I was no longer thirty-something, sitting in my second-bedroom-turned-office. I was seven years old in the computer lab at Mason Heights Elementary, watching as the explosion pulsed outward in perfect circles across the screen, vaporizing my neon forest while a beige Mac wheezed in the background.

Within minutes I’d binged a twenty-minute super-cut, every stamp, splat, boing sluicing nostalgia straight into my bloodstream. I could smell warm CRT plastic, feel the too-slick mouse, hear the case fan struggling to keep up with my delight. In that flash of sensory time travel I realized: this wasn’t a footnote to my tech origin story—it was the prologue.

I write about technology for a living now, but I usually narrate my way into the field as a post-grad fluke: needed work, took an unpaid internship, followed the current where it led. But the video reminded me the current started long before paychecks and product-market fit. Tech raised its hand in second grade, spelled its name in concentric shockwaves, and waited for me to catch on.

If you, like me, were born around the turn of the ’90s—too analog to be a digital native, too online to be anything else—this may feel familiar. The bomb icon. The chat handle. The fanfic page, the pixelated landscapes, the Top 8 betrayal. We were raised by interfaces before we had the language to describe what they were teaching us.

This essay is a walk back through the software that shaped me—and maybe, shaped you too. It’s an excavation of early agency. A look at what it meant to learn power through prompts and pixels. And if you’re from a different generation—older, younger, somewhere orthogonal—I hope it nudges you to trace your own interface inheritance. What tools taught you how to think, to make, to be seen? Where did your sense of control begin?

Kid Pix and the Birth of Interface Instinct

I wasn’t a prodigy. I wasn’t making masterpieces. My primary aesthetic was “ugly forest.” I loved the tree stamp—big, neon green, dropped in clusters like I was trying to simulate foliage or signal distress. I layered in the barbed-wire crackle effect for drama, dabbled in the textures that made your lines look like brick or wicker. I don’t know what story I thought I was telling. But I remember the feeling of telling it: total control, total immersion, total chaos.

There was no saving, no sharing, no gallery of finished works. Just action and response. Input and explosion. I clicked, and something happened. The software made noise. It obeyed. It sparkled. It broke things on purpose. That was the magic.

That loop carried a secret syllabus: you can touch technology first, interpret it later. Mess around, break things, learn the edges by feeling for them. Nothing disastrous happens when a pixel forest burns.

The habit calcified. I took it to Mavis Beacon, Word, PowerPoint, Excel; to MySpace profile tweaks at midnight and, years later, to no-code dashboards and AI playgrounds. I still freeze in Figma, but hand me any new tool and a baseline certainty kicks in: I can figure this out by doing. All because once, a long time ago, I made a very ugly forest and blew it up, and the computer said: Good job.

Sim Town and the God Mode of Vibes

After Kid Pix’s cartoon anarchy, Sim Town felt methodical—city planning shrunk down to a tiny grid of pixel-perfect streets. School let out, Dad graded spelling tests, and I claimed a student desktop in the back row. Click → grid unfurled. Roads snapped to right angles like they’d been waiting all day for my cursor.

Haunted house beside a mock-Tudor, takeout pagoda next to the precinct, a perfect perimeter of trees because shade mattered more than zoning laws. I assume there were characters whose lives I was meant to be managing, but I had more pressing concerns. If the streets looked coherent—if the screen gave off the right hum—my citizens could eat air for breakfast.

What I didn’t realize then is that I was learning a new kind of aesthetic authorship. I couldn’t control what happened once I placed the buildings, but I could design the world they happened in. I was experimenting with how space shapes behavior, how arrangement becomes argument. I didn’t need the system to make sense—I just needed it to respond.

What sticks isn’t the sims themselves, it’s the clunk when a building locked into place, the hush of an empty classroom turning golden in late-afternoon light. I could conjure a world, watch it breathe, rearrange it on a whim, then bulldoze the whole thing without consequence. Order, risk-free.

If I had to psycho-analyze this eight-year-old version of myself, I’d say that Sim Town appealed to me because it let me impose my own order and rules on a world, digital or otherwise. Placing parks, roads, and homes was my way of testing how structure shapes life—seeing how a tidy street grid could guide behavior just as much as the sidewalks outside my house. In that tiny city, I learned that design isn’t decoration; it’s a blueprint for how things move, connect, and grow.

Treasure Galaxy and the Joy of Structured Wandering

The “Treasure” series—MathStorm, Galaxy, Mountain—marketed themselves as math drills. But as much as that thrilled my blossoming little over-achiver heart, it wasn’t the arithmetic that hooked me. It was the movement.

Each game unspooled like a miniature quest: climb the ice cliff, hitch a comet ride, duck into a pixelated cave. Progress wasn’t measured in grades—it was measured in access. Solve the problem, get the key, open the door. The world expanded if you played well.

This was the next lesson in my digital Bildungsroman: learning how systems work—and how to work within them. You couldn’t brute-force anything. Gates opened only when answers arrived in the right order. That cadence, once internalized, became a kind of power: not just knowing the rules, but navigating them with style.

And it wasn’t just contentment—it was flow. I didn’t have that word at the time, but I had the feeling. Total absorption. Puzzle-solving as propulsion. A frictionless loop of effort and reward. It taught me how to stay curious inside a structure—a trait I now recognize as core to how I work.

Of course I loved it. Child of two public-school teachers, the kind of kid who was gutted to learn the Library of Congress wasn’t an actual lending library. But these games weren’t homework in disguise. They were systems you could stretch. Linger long enough, poke every corner, and the software would reward your curiosity by letting the map breathe outward.

Roller Coaster Tycoon and the Capitalist Sublime

Evening routine: descend into the carpet-glue chill of our half-finished basement, flip on the boxy PC, and watch the screen bloom like midway lights after dark. Homework could wait; the park needed a CEO.

Roller Coaster Tycoon was Sim Town with a spreadsheet tucked under its arm. I could still fuss over tulip beds for ambiance, but now the world pushed back. Budgets hemorrhaged, food stalls stalled, guests hurled and thought-bubbled complaints. God-mode had evolved into ops-mode. I wasn’t just placing things—I was running them.

And in that shift, I learned a new kind measurable control. Want to test a pricing strategy? Adjust the cost of umbrellas in the rain and watch the revenue skyrocket. Want to build a killer coaster? Balance the thrill-to-nausea ratio or risk empty queues and a PR disaster. The rules were knowable, the levers visible. Input led to output, and the system kept score.

It was my first real taste of optimization as creativity. Every slider told a story. Every path placement carried consequences. I learned to experiment, tweak, iterate. To watch what worked and do more of it. It’s a lesson that’s followed me into pitch decks and pricing proposals, into strategy calls and scope changes.

I didn’t know it at the time, but the game was training me to think like a marketer. To build an experience people wanted—and to notice when they didn’t. Every time a guest bought an umbrella during a rainstorm, it hit me: beauty might earn a smile, but utility moves the needle.

And when I raise my rate by a few hundred bucks now and the client still says yes, I hear that same in-game cash register ping in the back of my mind.

Away Messages and Elvish: The Inflection Point

Childhood ends the moment the interface starts staring back.

Kid Pix, Sim Town, Treasure Galaxy—those were tools for doing: detonating canvases, laying roads, solving snow-math in exchange for pixel keys. But AOL Instant Messenger slid onto the taskbar and swapped action for exhibition. Suddenly, the game wasn’t about what I could build. It was about how I wanted to be seen.

First came legolas4ever89. Seventh-grade me, spinning a self out of Elvish quotes I’d memorized phonetically, mood-boarded with lyrics from Evanescence and Michelle Branch. I imagined classmates checking my away messages, decoding the tone, reading between the lines. It was early social theater—messy, cryptic, and intoxicating.

I didn’t have the chutzpah to message any boys, but this episode of Pen15 still hits a little too close to home. [Source]

This was a new form of agency: narrative control. Not control over a system, but over perception. Over which version of myself got to be visible. Over how vulnerability could be aestheticized, encrypted, made legible only to those fluent in the code.

Xanga took that instinct and ran wild with it. I treated it like a public diary—but without the guardrails. Every post was a low-key dare to be perceived: longing for crushes, cryptic sadness about friend group politics, whole paragraphs of emotional subtext disguised as song lyrics and scrollbars. I was learning to write for an audience I couldn’t see, but desperately wanted to imagine. The feedback loop wasn’t built into the software, but it was implied—someone might be reading. That was enough.

Then came MySpace—a brief stint, but a meaningful one. I didn’t know how to trick out my page with HTML like the cool girls, but it didn’t matter. The platform itself was a choice. No teacher told me to sign up. No adult oversaw my profile. I picked a username, set up shop, and for the first time, felt the freedom of selecting a platform to express myself.

Taken together, AIM → Xanga → MySpace marks the pivot from instinctive play to intentional self-construction. These weren’t just tools for connection—they were tools for authorship. I wasn’t simply reacting to software anymore. I was collaborating with it. Testing personas. Managing perception. Writing myself into being.

Raised by Interfaces—and Still Being Raised

I keep repeating the tidy origin myth: post-grad scramble, copywriting gig, a stumble into tech that somehow stuck. But scrolling back through Kid Pix detonations, Sim Town grids, the “greetings and incantations” from a cartoon wizard in the CD-ROM I used to learn chess, I see the plot hole.

I wasn’t hired into technology; I was raised by it.

Not by venture-backed APIs or oat-milk laptops, but by public-school Macs and shrink-wrapped CD-ROMs. By interfaces that trained me—gently, playfully, sometimes manipulatively—to expect response. To believe that if I pressed the right button, the world would move.

Each piece of software gave me a slightly different version of digital autonomy. Kid Pix taught me to click first and learn later. Sim Town taught me to make order from instinct. Treasure Galaxy taught me to feel out a system’s internal logic. Roller Coaster Tycoon taught me to tweak for outcome. AIM and Xanga taught me to shape how I was seen.

And now—now I use tools that don’t just respond, but anticipate. Interfaces that finish my sentences, propose my next move, polish my thoughts before I’ve fully had them. It’s still a feedback loop—but one that runs ahead of me sometimes. The thrill of fluency remains. But so does the question: whose hand is really on the mouse?

Self-determination hasn’t vanished. It’s just gotten harder to locate. More collaborative, more ambient, more obscured. But I still believe it’s there. That the rules can be felt out. That the system, however slick or inscrutable, still has edges—and I can still find them.

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Notes and Errata

LARPing as a Tech Reporter

Every let me go deep on Gemini 2.5 Pro and 2.5 Flash—the models powering more workflows than you might think, at least among the devs. Sundar Pichai shared it on X, so I’m considering updating my LinkedIn to say “writes content that reaches key decision makers.” Read the piece.

Tackling the TBR:

I’m trying to pull myself out of a reading slump. My shelf of shame is around 40 books long at the moment, so I’ve got my work cut out for me. Current pick for fiction is North Woods by Daniel Mason, and I’m toggling between A Swim in the Pond in the Rain and Careless People for nonfiction. Would I make more progress if I picked one and committed? Absolutely. Am I going to do that? No.

Ava update:

The dog park is finally open in Columbus, and Ava is thriving.

Stay curious (and remember to touch grass),

Katie P.