In October, I opened my calendar and had a mildly horrifying thought:

“If I took a screenshot of this and hid the Zoom links, it could be 2015.”

Back-to-back meetings. Thirty-minute “quick syncs” that were neither quick nor synced. A workday packed from nine to five, plus a few heroic replies after dinner to “stay on top of things.”

I’d rebuilt the office inside my laptop.

Meanwhile, the headlines kept screaming: CEOs calling people back to downtown towers, AI threatening to automate everything, four-day workweek pilots making the rounds. Lawmakers in different countries debated “right to disconnect” laws. It felt like the whole world was renegotiating work.

But none of that changed the simple truth: my calendar owned me.

So this year, I treated flexible work as something I actually had to practice, not just passively enjoy. Three experiments changed everything for me.

Experiment 1: Unclogging the calendar

My first move was embarrassingly simple: I stopped letting other people design my day.

I set a hard cap on meetings, added one protected "focus block" every day and another short block to unplug for a bit each afternoon.

At first, it felt selfish. But nobody minded. The people who had to wait an extra day for a meeting got a more prepared and engaged version of me when we actually connected. 

The people I met with most often, the ones I thought would be most inconvenienced by my new boundaries, were not only fine with it… they liked it. It gave them permission to build some boundaries of their own. 

If your remote day still looks like your old office day, this is the gentlest place to start: protect one block next week like it's a doctor's appointment you can't miss. 

Start as small as you need to and set any kind of constraint you like. 

Experiment 2: Letting AI actually give me time back

Like everyone else, I spent 2025 hearing about AI “giving us hours back.” For a long time, I used it in the most boring way possible: speeding up writing, summarizing docs… but even though I knew I was gaining efficiency, I didn’t find myself getting a lot of time back.

This year I made a rule: at least half the time I saved had to go somewhere meaningful.

Sometimes that meant a deep-focus sprint on a project that actually mattered. Sometimes I’d give Claude Code a particularly difficult task and then take the dog for a walk while it worked. The specifics don’t really matter. The important thing is not letting any of the precious time you earn back in your day fill with more work. 

The tool isn’t the difference. Your rules are.

Experiment 3: Being seen without being in the room

The biggest fear I hear from remote folks is, “If I’m not in the office, I’ll be forgotten.”

This year, instead of trying to be everywhere, I started a simple visibility ritual: once a week, I send a short update to the people who matter most to my work, what shipped, what I learned, and what I’m tackling next.

It’s not bragging; it’s narration. In a distributed world, people can’t always see the hours you’re putting in. If you don’t tell that story, no one else is going to.

Looking back, 2025 was loud: RTO battles, AI hype, four-day headlines, policy debates. But the biggest shift for most of our work lives didn’t come from any top down mandates.

It came from realizing that flexibility isn’t a perk your employer “gives” you. It’s a skill you practice.

If you’ve spent the last few years remote but still living a rigid 9-to-5 life at your kitchen table, here’s my invitation for 2026: protect one focus block, bank one saved hour, and send one visibility update.

That’s how flexible work stops being a promise in a job description and starts becoming the way you actually live.