Notes from a Younger System

I wasn’t trying to look backward.
I was just moving files.

For most of my career, Microsoft wasn’t a preference — it was an environment. I didn’t simply use the ecosystem; I supported it, worked inside it, and depended on it. It was job security. It was responsibility. It was something you had to understand deeply, because when it failed, people didn’t get frustrated — they got stuck, delayed, or hurt. And they called you.

Technology, for me, wasn’t a lifestyle in the casual sense — it was infrastructure. It became a lifestyle because I lived inside the systems I was responsible for. I needed to understand them fully, end to end, because partial understanding wasn’t an option.

Apple products never interested me back then. I didn’t need to know them. I wasn’t curious about learning a second ecosystem recreationally. Technology wasn’t about taste or novelty — it was about control, predictability, and accountability.

At some point, that changed.

I no longer needed my personal technology to be a proving ground. I wasn’t trying to teach myself platforms at home anymore. I just wanted my tools to work — quietly, reliably, without asking for attention. So I switched to macOS, not as a statement, but as a boundary.

And that’s how this happened.

Moving years of files from OneDrive to iCloud meant opening folders I hadn’t touched in a long time. Old Word documents. PDFs with dates in the early 2000s. Filenames that made me pause before clicking, unsure whether I’d feel embarrassed, detached, or nothing at all.

What I found instead was familiarity.

Letters I wrote when systems failed people. Appeals where enforcement didn’t match reality. Complaints that weren’t really complaints, but attempts to reconcile how things were supposed to work with how they actually did. Job materials from the moment my career opened up. Technical write-ups written in the middle of live incidents, when clarity mattered more than comfort.

Different years. Different contexts. The same voice.

I’ve been told for most of my life that I’m intense. Too detailed. Too direct. Difficult. The implication is usually that these traits developed later — armor I put on after enough disappointment.

But reading these files in sequence, that story doesn’t hold.

In the early 2000s, I was already writing with certainty that bordered on sharpness. I didn’t yet know how to soften my delivery — only how to be exact. When a system failed, I said so plainly.

“Your safeguards triggered correctly — and still failed.”

Reading that now, I don’t feel defensive or proud. I feel tenderness. I can hear how much certainty I needed then. Precision was how I protected myself in environments where being vague meant being dismissed.

In another file from around the same period, I contested a fine I didn’t deserve. I paid what I had to, documented what I could, and drew a clear line around responsibility.

“I paid the original fine even though I did not deserve this ticket.”

That distinction mattered deeply to me. It still does. What’s changed isn’t the instinct — it’s the delivery. Back then, clarity came with edges. I didn’t yet know it could exist without them.

The same tone carries into my professional writing. Calm descriptions of systems in fragile states. Consequences stated plainly.

“If we lose one more drive during this rebuild, all data will be lost.”

No drama. No posturing. Just reality.

Those documents read now like early drafts of a skill I would spend the next twenty years refining: translating technical truth into language other people could actually act on.

And then there are the personal artifacts — the ones I didn’t write.

A post from a friend, written in 2004, realizing out loud that the loud, blunt, overbearing guy was also the one doing the connecting, organizing, showing up. That maybe being “the fun one” came with emotional cost they hadn’t noticed at the time.

Reading it now, I don’t feel exposed. I feel seen. It names something I didn’t yet know how to articulate for myself: that being useful, visible, and available can quietly turn into being taken for granted.

There’s a Christmas letter from the end of 2004, written just after I moved to Chicago. Professionally, everything had finally clicked. I had the job I wanted. I was trusted. I was traveling. I was free. And almost casually, I wrote this:

“Professionally my life is AWESOME… personally, it’s kind of dull out here in Chicago.”

I didn’t try to fix the feeling. I just named it.

Looking at all of this now — with three years of therapy behind me, a lot more life lived, and long stretches inside real corporate environments — what stands out isn’t how much I’ve changed. It’s how much I’ve softened.

The instincts are still there. I still care deeply about fairness. I still notice when systems fail people. I still believe clarity matters.

But I no longer need sharpness to make a point land.

Therapy didn’t remove precision from my voice. It taught me when precision was serving truth — and when it was serving protection. Experience taught me that you can be firm without being hard, and that clarity doesn’t require collateral damage.

A recent piece of work surprised me when I reread it. The argument was still uncompromising, but the tone was steady, almost quiet. It didn’t demand attention. It assumed it.

In that note, I wrote:

“This is no longer an IT inconvenience. It is a strategic disadvantage.”

Reading it back, I could hear the same instinct I’ve always had — the need to name risk clearly and without dilution — but without the urgency that used to sharpen everything it touched.

These files weren’t curated. They weren’t saved for reflection. They surfaced because I changed tools and took the time not to lose anything in the process.

What survived the migration wasn’t just data.

It was a younger system — earnest, precise, loud when it needed to be — doing the best it knew how to do at the time.

I’m grateful to that version of me.
And I’m grateful I now know how to be gentler without being smaller.