You know what’s weird about coming to retro gaming late? I never had that Christmas morning Game Boy moment that every other gaming guy my age talks about. While kids in 1989 were unwrapping those gray bricks and discovering portable Tetris, I was… honestly, I don’t even remember what I was doing that Christmas. Probably helping my dad fix something that broke on the ranch, or splitting firewood. Different world entirely.
But here’s the thing about missing out on something the first time around – when you finally discover it, you get this unique view of the whole timeline at once. I didn’t experience handheld gaming as this gradual evolution where each new system was mind-blowing compared to what came before. I experienced it more like walking through a museum, seeing thirty years of progress laid out in front of me, able to compare a 1989 Game Boy directly to a 2022 Steam Deck without all that nostalgia getting in the way.
My daughter was the one who really opened my eyes to what I’d missed with portable gaming. This was around 2011, maybe 2012, and she was home from college for winter break. Brought her DS with her – the regular DS, not even the fancy 3D one yet – and was playing some Pokémon game during dinner. Now, normally I’d have told her to put the damn thing away at the table, but she was explaining how she’d been playing this same character for like 200 hours, had caught all these different creatures, built this whole team. The commitment impressed me, I guess. Reminded me of the patience you need for construction work, building something piece by piece over time.
She let me try it later that evening, and I’ll admit, the dual screens threw me off at first. Seemed overly complicated. But there was something appealing about having this entire world in your hands, being able to pick it up and put it down whenever you wanted. At home, gaming meant fighting for TV time or setting up in the basement. This was… portable. Independent. Made sense to a guy who’d spent his career working different job sites, never knowing where he’d be next week.
Started me thinking about all the times over the years when I’d been stuck waiting somewhere – DMV, doctor’s office, airport delays when I had to travel for work – and how I’d just sat there, bored out of my mind. These handheld things could’ve filled all those dead hours with something actually engaging instead of me just thumbing through old magazines or staring at my phone doing nothing productive.
So I bought a used DS Lite from GameStop, figured I’d try a few games, see what the fuss was about. The guy working there – kid couldn’t have been older than nineteen – was trying to sell me on all these newer systems. “You should really get a 3DS,” he kept saying. “Much better graphics, 3D effects, newer games.” But I wanted to start from somewhere closer to the beginning, work my way forward. Construction taught me that if you want to understand how something’s built, you start with the foundation, not the fancy trim work on top.
That DS Lite became my constant companion for the next year. Kept it in my truck, brought it into the job trailer during lunch breaks, played it at home in the evenings while my ex-wife watched her reality TV shows. The games were more sophisticated than I’d expected – not just simple time-wasters, but actual substantial experiences you could sink dozens of hours into. Fire Emblem was like playing chess, but with a storyline that actually made you care about the pieces. Advance Wars turned every lunch break into a tactical military campaign.
The battery life was decent too. Not like these modern devices that die if you look at them wrong. I could play for hours without hunting for an outlet, which mattered when you’re working job sites where finding a working electrical source isn’t always guaranteed. Simple pleasures, but they mattered to a guy who wasn’t used to having entertainment that didn’t depend on being plugged into a wall somewhere.
Eventually worked my way back to a Game Boy Advance SP – figured I should experience what came before the DS. Found one at a local game shop, along with a stack of games the owner recommended. Super Mario World, Link’s Awakening DX, some Pokémon game. The screen was tiny and the graphics were primitive compared to what I’d gotten used to on the DS, but there was something pure about these games. No stylus complications, no dual screens to manage, just simple controls and solid gameplay. Like the difference between a basic hammer and some complicated power tool – sometimes the simple version just works better for certain jobs.
Got curious about the original Game Boy after that, partly because I kept reading about how revolutionary it was, partly because I’m stubborn and wanted to see the whole progression for myself. Found one at a flea market, complete with Tetris and a few other games. The screen was barely visible unless you held it directly under a light, and the whole thing felt like holding a brick, but I’ll be damned if Tetris wasn’t still addictive as hell. Played it for hours that first weekend, sitting under the lamp in my living room like some kind of gaming monk.
What struck me most was how well these old games held up when you removed nostalgia from the equation. Tetris is still perfect – doesn’t matter if you’re playing it on a 1989 Game Boy or a modern phone, the core gameplay is timeless. Same with Super Mario Land, or the first Pokémon games. Good design is good design, regardless of the hardware limitations.
The whole handheld evolution made more sense once I’d experienced it backwards. Each generation solved specific problems with the previous one. Game Boy Color added color without sacrificing too much battery life. Game Boy Advance gave you console-quality games in your pocket. DS added touch controls and dual screens for more complex interfaces. Each step was logical, purposeful. Not just change for change’s sake, but actual improvements that made the experience better.
By the time I got to more modern stuff – picked up a 3DS around 2014 – I could appreciate how far things had come. The 3D effect everyone said was gimmicky? Actually pretty impressive when you’re seeing it for the first time without any preconceptions about whether it’s supposed to be good or not. The game library was massive, and everything looked gorgeous compared to those original Game Boy graphics. But I also noticed what we’d lost along the way – battery life wasn’t what it used to be, the systems were more expensive, games cost more.
Nintendo Switch was where things got really interesting for me. Bought one in 2018 after reading about how you could play full console games portably, then dock it to your TV when you got home. As someone who’d been fighting for TV time in relationships for years, this seemed like a miracle device. Play Zelda during lunch break at work, then continue the same save file on the big screen that evening. Game-changer, literally.
Breath of the Wild was my introduction to modern Nintendo games, and it blew me away. This wasn’t some simplified portable version of a console game – this was the full experience, running identically whether docked or handheld. The screen was gorgeous, the controls felt perfect, and I could play anywhere. Started bringing it on work trips, playing in hotel rooms instead of watching terrible cable TV. Made business travel actually tolerable for the first time in my career.
The Steam Deck, though… that’s where things got crazy. Heard about it in 2021, reserved one immediately even though the wait time was like eight months. When it finally arrived in early 2022, I couldn’t believe what I was holding. This thing could run actual PC games – games I owned on Steam, games that were designed for desktop computers with keyboards and mice – on a handheld device with decent battery life and good controls.
First game I tried was Stardew Valley, figured I’d start with something simple. Worked perfectly, looked great, controls felt natural. Then I got ambitious and tried Elden Ring. The fact that I was playing a brand-new, graphically demanding game on what was essentially a portable computer while sitting in my truck during lunch break… it felt like science fiction. Still does, honestly.
The ergonomics are what really impressed me about the Steam Deck. My hands aren’t getting any younger after thirty years of construction work, and the thing is designed like someone actually thought about how human hands work during extended gaming sessions. Compare that to the original Game Boy, which felt like holding a rectangular brick, or even the Switch, which cramps my hands after an hour or two. Progress isn’t always obvious, but sometimes it absolutely is.
Battery life is still the eternal struggle, though. My Steam Deck lasts maybe three hours if I’m playing something demanding, which is pathetic compared to that original Game Boy that could run for fifteen hours on four AAs. But that’s the trade-off – we get incredible graphics and processing power in exchange for constantly worrying about finding outlets. Keep a portable battery pack in my truck now, like I’m some kind of mobile gaming survivalist.
What’s funny is how my relationship with handheld gaming mirrors my broader experience with retro gaming in general. Coming to it late means you see things differently than people who grew up with this stuff. You’re not blinded by nostalgia or childhood memories. A game is either fun and well-designed, or it’s not. A handheld system either works well and has good games, or it doesn’t. Simple as that.
The social aspect has changed completely too. Back in the day, apparently, kids would link their Game Boys together with cables, trade Pokémon in person, battle each other directly. Now everything’s online, global, invisible. My Steam Deck connects me to players worldwide, but there’s something lost in that transition. Something to be said for having to physically be in the same room as someone to play together. More intimate, more communal.
These days, I’ve got examples of pretty much every major handheld generation sitting in my game room. Game Boy through Steam Deck, plus some of the oddball systems like Game Gear and PSP that I picked up along the way. Each one represents a different stage of technological progress, but also different approaches to solving the same basic problem: how do you make good games portable?
Some solutions worked better than others. Game Gear had amazing color graphics but terrible battery life. PSP was technically impressive but expensive and complicated. 3DS had innovative features but felt gimmicky sometimes. Switch nailed the hybrid concept but has limitations. Steam Deck is incredibly powerful but bulky and has battery issues.
Point is, there’s no perfect handheld, never has been. Each generation makes trade-offs, prioritizes certain features over others, targets different audiences. What’s remained consistent is the core appeal – being able to game anywhere, anytime, without being tied to a TV or a desk. That fundamental concept is as appealing now as it was in 1989, even if the execution keeps evolving.
Still haven’t experienced that childhood Christmas morning Game Boy moment, obviously. Never will. But discovering this whole world of portable gaming as an adult, being able to see the full progression without nostalgia clouding my judgment, appreciating the engineering and design decisions that went into each generation… that’s been its own kind of discovery. Maybe better than unwrapping a present when you’re eleven. Hard to say.
What I do know is I never leave the house without some kind of handheld gaming device now. Usually the Steam Deck, sometimes the Switch if I want something lighter. Always a portable battery pack because I learned that lesson the hard way. Thirty-plus years of handheld gaming evolution, and we still haven’t solved the fundamental problem of keeping the damn things powered up when you need them most.
Timothy discovered retro gaming at forty and never looked back. A construction foreman by day and collector by night, he writes from a fresh, nostalgia-free angle—exploring classic games with adult curiosity, honest takes, and zero childhood bias.
