2025 — 2026

Hi! You and I may be friends or family. We might be Twitter Bluesky Mastodon buddies (and we should be). We could be neighbors across the street or across the cities. We might be passing acquaintances or going way back. It's really nice for you and me, for us to chat again, even if it's just with this letter.

Who am I again? Well, aside from the blatantly branded card that brought you here today, there's absolutely no way to know that I am Ryan Rampersad. I might be that weird Pokémon-enthusiast or that quirky branding guy with long hair and red ribbon, or that Twitter Bluesky Mastodon-enthusiast or that trusted technical advisor. You bet. That's me.

OK, what's up with this card? These cards have been delivered to fine folks everywhere since the famously fabled year of 2016. Why was 2016 renowned? Well, the best way I can put it is: "I don't know, I think I became an adult." Back then, I felt this overwhelming urge to send a heartfelt thank you. That's for all of you, collectively, but also for you—the person holding this card right now. Whether you're pulling late nights with me on the grind, wandering the park with Roxy and me, or out there across the globe making the dazzling magic happen, thank you. You're amazing. Seriously. I'm beyond lucky to have you in my life, and I'll say it here: the world is better because of you.

And who's that cute little dog? That's Roxy! She's the star. She's the best dog. We have a whole section dedicated to her too.

If this is your first card, a heartfelt hello world to you—welcome to what I hope will become a cherished custom. If you've received a card before, welcome back, and thank you for being part of this increasingly long legacy once more. Your continued curiosity and kindness mean the world to me. These cards are my small but sincere way of staying connected, and I hope to carry this cozy tradition far into the future.

Let's continue into my ramblings and musings!

Everyone's first question is: what kind of dog is Roxy? Here's how the story goes: she comes from my mom's cousin's farm where two dogs went into the barn and puppies came out. Allegedly, she is a terrier and beagle mix. A few years ago, we ran some box-kit rudimentary DNA tests on Roxy (which is fine, because she's a dog; nobody knows you're a dog on the Internet unless your owner submits your DNA), and we found out she might be part Lhasa Apso. To be honest, whenever someone asks me now, I still say terrier beagle because that makes sense, and Lhasa Apso feels like I'm speaking nonsense. Either way, she's very much made by her own personality and how cute she is.

15

Roxy is 15 years old this year! It's a major milestone. That means if you quint, Roxy is half my age. Roxy is in pretty decent good health. Sure, she's no stranger to old age. She can't jump as high. She used to hop up the steps in the backyard from the yard level to the deck level, but she gave that up in winter a few years ago - it was just too scary. She uses a ramp I built her. It's an 8-feet long and 30-inches wide ramp. She loves that ramp. She goes up and down all day with it. She also kinda slides down the ramp when there's snow and ice. The friction strips I added a few years ago are starting to get old. She likes to jump off the ramp towards the end prematurely, so I have since added soft rubber tiles to cushion her jump fall. She used the steps for 12 years, so occasionally she forgets about the ramp, and tries to use the steps. She ends up realizing: "ooooh there's a ramp!"

Despite good overall health, she's also had her share of catastrophes in the past few years. Last year it was all due to chasing a cat in the backyard. Roxy loves her two cats (Jack and Tango). Rarely her two cats have escaped the house (wandered the backyard a bit), and Roxy has been very vocal and proactive to get them back in. She thinks all cats are her cats. When she saw an unknown cat in the yard, she thought it was her duty to find it immediately and ask it to return to the house. She went way too fast down the ramp and sprained her hip. For about a month, she couldn't really use her left back leg. She would hobble from room to room, but outside walks were too much. I would bring her to the park in the wagon so she could see somewhere different than the yard, and she would try to walk around and smell the trees. Since then, she's recovered just fine. She's getting daily "cosequin" chews for her joints, and from all signs, that's helping. She's back to her usual self again.

This year, her old-age ailment is something more akin to a wheezing or hacking. She's doing fine with it, though it does wake her up during the night occasionally. It sounds worse than it actually is.

She will accept our usual neighborhood walks in desperation, but she loves going on walks outside of the neighborhood and she's always up for an adventure, especially in the woods. Since she can't walk as far as she used to, I bought her a push-pull wagon. In summer, I would load her into the wagon so she could get further before overheating, and if she did get too hot, she could make it back home in the wagon too. Her feet sting in the cruelly cold winters. Using the wagon is a bit trickier in winter, especially when it's recently snowed. She rejects the entire concept of a sled. When we go on a longer destination walk, Roxy can stay in the wagon for a little while, then get out and explore, and when she's tired again, she can hop back in. It's also nice so I can carry extra snacks and water. Everyone loves to see her in the wagon.

Despite being 15, she still gets bursts of energy too. Roxy only plays stick-fetch when she's in the shallows of the lake or river. She'll make two or three fetches before getting distracted, but she is so into it for those three rounds. Similarly, she's always watching for me to come home after work or running errands. She'll wait outside on the deck studying every car passing by, waiting for me. Then when it really is me, she'll run to the door as fast as she can; sometimes too fast.

Roxy's a good eater. Maybe too good. When she was 8 years old, I thought that, well you know dog, you're not going to last too many more years—so you can eat whatever you want. Within reason. Since 2020 and roughly working from home regularly, she really does get her fill of food. To break up her dog food, I'll also cook her her own shredded chicken. That's her favorite.

Even dogs need vacations. She's had two vacations this year. We typically vacation in the fall as it starts getting cooler (though not yet outright cold). Roxy easily overheats. This year, as most years, we went to our rental cabin in Garrison, MN in September. This year we had to stay in a different cabin since our usual was already taken. That ended up just fine—Roxy was even closer to the lake and had the time of her life going in and out all day. In October, we visited Duluth and stayed at PierB, a hotel that allows dogs on the second floor. Roxy loves hotels—the elevator is magic and roaming the main floor and getting attention is a highlight. Roxy was not convinced by Lake Superior, she wasn't sure why it was superior compared to a lake without waves.

I saw a sign a few years ago at the Minnesota State Fair. You know all those signs people buy and put in their houses? Like “Live Laugh Love”? I saw a sign I thought was funny, and that was accurate. “I work hard so my dog doesn't have to.” I think that's really fitting for me and Roxy.

What were you doing on March 28th, 2016? That was the day I started working.

Not formally my first job—but the first real job of my career.

When I started, I was incredibly lucky. I worked with thoughtful, generous people and was given something that's hard to name but easy to recognize: permission. Permission to make mistakes, to learn in public, to grow, to have autonomy and agency, and eventually to lead. I stumbled into a place that trusted me before I fully trusted myself.

A couple years later, I was invited to speak briefly at the infamous HackerX recruiting event. In just a few words. I summed it up like this:

“I can't believe they pay me to do what I love doing.”

Computers—bicycles for the mind. I get to ride them every day. Sure, it's hard sometimes. Maybe it's harder now. Nothing is perfect. But it's also wonderful.

In just a few months, I'll reach the ten year mark: ten years of being a productive member of society. Maybe even growing into some approximation of an adult—finally.

That was 2016. That was (almost) ten years ago.

Recently, on December 11th, I was chatting with a coworker I hadn't worked closely with in a few years. We were reminiscing, as one does. As certified Minnesotans, we were of course talking about the weather—specifically, the blizzard that was about to roll through. That of course made me wonder: "What other huge winter storms do I remember?"

Everyone here knows the Halloween Blizzard of '91. The one that allegedly altered the state's history, and now we're stuck hearing about it forever. I hear we're still digging out, thirty-four years later. Just a rumor. I wasn't there for that, so it's all hearsay at this point.

In April 2018, the Thunder Blizzard rolled through—right over Minnebar weekend. 15-inches of snow fell, high winds in the morning. It rarely snows that much in April, but as they say, sometimes it snows in April.

When I was in college at the University of Minnesota, classes were canceled due to extreme cold. No storm—just wind and temperatures plummeting to -50°F. Our Twin Cities campus rarely yields to weather. This time, it did.

And I remember when the Metrodome collapsed. I was a senior in high school, sitting in AP Calculus. I remember the room, the moment, the strange disbelief of it. Stadiums don't implode. There was a lot of snow, and that was quite a blizzard. Somehow I had already made it to school, which was impressive enough. Even more miraculously, I made it home.

And to think, I was just finishing highschool a few months after that.

That was 2010. That was fifteen years ago.

If I haven't told this story in one of these letters before, I'd be surprised. But my local robots can't seem to parse my prose right now, so you'll have to indulge a repeat.

During winter break in sixth grade, my mom took me to the Borders bookstore in Midway. A wonderfully literal name—halfway between Saint Paul (the capital city) and Minneapolis (where things exist). That part is a joke. Mostly.

In hindsight, it was also a fitting place for me: a midway point. Before and after knowing code. Because once you know how to code, once you understand how to articulate an idea to a machine and watch it follow along—you're ruined. You know it's all mechanically constructed and you can figure it out, eventually.

Inside that Borders, I did what I'd seen my dad do countless times and wandered into the technical books section. I don't think I had real interests yet, beyond games and curiosity. But something happened anyway.

A wild HTML book appeared.

HTML—the world's most effective gateway. For some reason on that day, I fell for it and started reading that book. Eventually, it was time to leave. I'd somehow convinced my mom to splurge on this (right after the holidays, no less). I remember sitting at the kitchen table with the family laptop, writing my first web page. An improper Hello, World. And then came the rest: PHP, memory editors, ASP.NET, Flash, JavaScript (MooTools!), then Java, Rust, Go… the list keeps growing.

It all started that one afternoon in Borders, with a to-go cup of hot chocolate and an HTML book.

That was 2005. That was twenty years ago.

Have you heard about the robots? I call them that, though most people call them "AI." Often that means "GenAI," which is itself a loose umbrella term for "LLM," or "Large Language Model." You've certainly heard about them. Maybe you're even asking your robot to summarize this very letter because it's too long.

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Jargon aside, these tools can be surprisingly fun. You give them a rough prompt in plain English and, after a moment of theatrical thinking, and then they return relatively reasonable text. That's all it is—it's just text. It's not actually thought. It's not necessarily true, and it's not always accurate or precise. But are you?

When you look in the mirror and distill things down to the question, "How do you know what to say next?" it starts to feel a little similar to what's going on inside these tools. They're called models for a reason; they're only approximating what we do with language. But what, exactly, are we approximating?

I can make things up just as confidently as any robot these days.

Originality and authenticity are often heralded as prime human traits. If, in the end, we're copying our own training data and plucking the next sensible word out of the word salad corpus—with a bit of internal entropic jitter and some weights thrown in—who's to say we're not robots too?

As an uncertified philosopher, I find it important to get some perspective on the robot behind the curtain. Look, we've been writing to machines professionally for years, in code. That's felt fine, even enchanting evidently. Writing to a stochastic parrot machine and watching it return something coherent can feel uncanny, even sentient. It isn't. But it's understandable why it sometimes feels that way.

Related to all of this is a strong sentiment floating around the industry: that these robots are bad, dangerous, or even evil. And to be fair, those concerns aren't coming from nowhere. There are real, plausible disruptions ahead—for work, for the economy, for society at large. As a card-carrying millennial, I've lost count of how many economic upheavals I've had the privilege of living through already. It's reasonable to feel tired, cautious, or skeptical.

I was skeptical too. In 2022, I mostly watched from the sidelines and laughed at the monkeys on the keyboards attempting to quote Shakespeare. In 2023, I tried one of these tools for the first time, cautiously, with low expectations—and you know what? It actually worked. In 2024, I was given broad access at work, and somewhere along the way I started paying for it personally at home. It's displaced some Google searches. When voice chat was working, it was nice to speak naturally, unlike a dragon, in a conversation. None of it was perfect, but it can certainly retrieve some information or get some tasks done. (Ironically—Google's Gemini is the one I do not pay for; yes, I'm a Claude and ChatGPT shill now. 👋)

Now, all that said, if you're not giving them a try because, from your high horse on top of your ivory tower, they seem remarkably less [fancy word for human proficiency], well—grab that mirror again and look closer. Are you actually that good at literally typing? Are you actually that good at being accurate and precise? Are you really that good at crawling your own mental index for obscure references? Typing was never the differentiator. Human's are notoriously inaccurate and imprecise. Memory is increasingly fallible. It was always how you framed the problem, how you reasoned about it, and how you decided what mattered.

A computer can never be held accountable, therefore a computer must never make a management decision.

These tools are not a panacea. They won't think for you, and they certainly won't replace judgment. We wouldn't let them make decisions, but they can help get you there. You can dislike specific inputs. You can dislike specific outputs. You're allowed to be annoyed by their tone, their confidence, their mistakes. You're allowed to dislike their caricaturization and inane sycophancy. You're absolutely allowed to shudder in disgust at the obtuse investment required to make sand pretend to think. (The robot suggested I end this paragraph with "That's not failure—that's discernment." That's just such a robot way of writing, see? That "It's not X, it's Y" quirk is everywhere. That's human discernment: we can pinpoint the robotisms. And we evolved from mud too!)

And then there's today. There is no moat here. You can just try these tools. There's nothing special sauce, no extra permission necessary. You have my permission at least.

In practice, there are usually two reasons people haven't given the robots a try. One is environmental: the tools, time, or incentives simply aren't there. The other is personal: you haven't experimented on your own yet. (You can draw conclusions about things either way.)

If it's the former—your job is busy, your ridiculous KPI and OKR metrics are relentless, and exploration isn't rewarded or encouraged—that's unfortunately understandable. That's the industry these days. And if it's the latter, nobody is asking for heroic moonlighting at 1AM. An occasional hour spent reading, tinkering, or testing a tool when it pops up can be enough to form an informed opinion. Casual curiosity scales surprisingly well.

Either way, I'll encourage your job to give you the broccoli, and I'll give you permission and encouragement to try it. Broccoli isn't delicious on its own; it's valuable because of what it gives you. You might not crave it, and you don't need it at every meal, but dismissing it without tasting it is mostly a choice about comfort. You might even learn to love it. Just give it a try. Try your broccoli.

The barrier to entry is gone. There is no moat.

Warning: the following section is neither original nor authentic. Proceed accordingly.

Originality and authenticity. They're complementary, but not interchangeable. You can have originality without authenticity; it might be clever, novel, impressive, and yet still feel hollow or performative. You can also have authenticity without originality; it might be familiar to the point of exhaustion, repeated ad nauseam, but still feel honest, grounded, and true. One isn't a substitute for the other, and neither is guaranteed just because the other is present.

There's a Japanese term: Kintsugi (きんつぎ / 金継ぎ). "Golden joinery." That's the literal translation. Historically, it refers to repairing broken pottery using lacquer mixed with gold powder. The damage is not hidden, the joints are laced with gold after all. Let's connect the dots between originality and authenticity with Kintsugi.

In the pottery example, when a pot breaks and is repaired with golden joinery, it's still a pot. It still holds water. It still does what it was made to do. But now it comes back together with visible seams, with history traced in gold. Is it original? In some ways, no, it's not the untouched, unblemished object it once was. In other ways, yes, absolutely. It's no longer reproducible. You can't rewind the break, or replicate the exact lines where it separated, or fake the specific way it came apart and was brought back together. Is it authentic? It's truly a pot again, it's no longer broken pieces. Maybe even more so than before. It isn't pretending nothing happened.

What I like most is that the repair doesn't try to overwrite the original form—it works with it. The object doesn't return to what it was; it becomes what it is now.

I enjoy the thought of something becoming differently original and differently authentic than it once was. Not in spite of change, but because of it. Because it carries evidence. Because it has context. Because it has been handled, dropped, repaired, and kept.

I've been baking a lot recently, and I've found myself admiring the ridiculous stains on my sheet trays. You know, the ones that are effectively impossible to clean off? That's polymerized oil. You only ever see perfectly pristine sheet trays garishly glistening in show kitchens. No one who cooks regularly actually wants a pristine one. The discoloration isn't neglect; it's the same expansion of originality and authenticity. After that change, sheet trays heat more evenly, release food more easily, and do their job with less effort than they ever did when they were new. What made them useful hasn't been lost; it's been reinforced. Yes, you might see rorschach shapes on your sheet tray, but it'll bake better than ever. (Unless you're making cookies—then it just makes the cookies taste funny.)

Originality and authenticity aren't qualities that disappear when something changes. They can grow through use, repair, and continuation. What remains isn't a diluted version of the original—it's something more specific, more capable. Shaped by use, space and time.

As always, you are my honored guest here. Writing this letter is no small endeavor, and taking the time to read it is no small gesture either—thank you for that. Whether or not this years letter has an overarching theme is a mystery that only a full read (or a curious robot) could uncover. And yes, if you asked one of them, it would undoubtedly begin with, “Certainly!” But truly, thank you once more for being part of this tradition. I hope it brought a smile to your face, a moment of reflection, or maybe just a bit of joy. Heres to a year well-lived and an even better one ahead.

If you are adventurous and fastened your awesome card featuring Roxy the dog somewhere decorative or festive, please snap a photo and share it with me.

Thank you, and have a good one.

あなたは読んでくれてありがとうね！じゃね！
See you!

Thank you, and have a good one.