The "Remind Me Later" Button Is a Decision — Just Not the One You Think

By Jordan Polasek · July 20, 2026

I was helping a client in Sugar Land pull a report off her laptop last month when a little box popped up in the corner of her screen. An update was ready. She clicked "Remind me later" without even reading it — the way you'd swat a fly — and kept talking. I asked her, half-joking, how long that update had been waiting. She laughed and said, "Oh, that thing's been there since spring."

I hear this all the time, and I get it. Updates always show up at the worst moment — mid-sentence with a customer, right before a deadline, the second you sit down to get something done. So we click "later," and later becomes never. But here's the thing worth sitting with: clicking "Remind me later" isn't putting off a decision. It is the decision. You've just decided to run the older version a while longer.

Usually that's fine. Right up until it isn't.

Updates aren't mostly about new features

The reason we ignore updates is that we think they're about features — a new button, a redesigned menu, some setting we didn't ask for. And a lot of the visible stuff is exactly that.

But the updates that matter most are the ones you never see. When a company like Microsoft or Apple or your accounting software vendor pushes an update, a big chunk of it is quietly closing doors that someone figured out how to walk through. A researcher — or a criminal — found a way in, the vendor built a fix, and that fix is sitting in the update you keep dismissing.

Here's the part that surprises people: once that fix is released, the problem it solves becomes public knowledge. The bad guys read the same release notes I do. So the gap between "update available" and "update installed" isn't neutral time — it's the exact stretch where a known, published weakness sits wide open on your machine. Waiting doesn't keep things the same. It slowly makes you the easiest target on the block.

Why "later" wins every single time

I don't think anyone is genuinely against updates. The problem is a design one: the update always interrupts, and "Remind me later" is the one button that lets you get back to work right now. Of course we click it. We're humans with a customer standing in front of us.

So the fix isn't willpower — you'll lose that fight every time, because the interruption always comes at a bad moment and the reward is invisible. The fix is to take the decision away from your future self, so updates happen without you having to be disciplined in the middle of a busy Tuesday. That means two things:

• Turn on automatic updates wherever you can, so the machine handles the boring, critical stuff on its own.
• Give it a moment to actually finish. A lot of updates only fully install after a restart — and if your laptop hasn't been shut down since the Astros were last in the playoffs, that update is downloaded but doing nothing. A weekly restart is the quietest, cheapest security habit there is.

The stuff that quietly falls through the cracks

Here's where I see good intentions break down. People picture "updates" as the Windows laptop, and they turn that on and feel done. But your business runs on more than a laptop.

Think about everything with a little bit of software in it: your phone and its apps, the Wi-Fi router in the closet, your point-of-sale system, the security camera you set up three summers ago, the printer, the tablet at the front counter. All of it runs software that gets updates — and almost none of it nags you the way your laptop does. It just quietly ages.

The router and the camera are the ones that bite people, because they sit in a corner and get forgotten for years. You don't need to become the IT department overnight — you just need to know these things exist and give them a look now and then instead of assuming "no news is good news."

The rule of thumb I give clients: if it connects to the internet and you can't remember the last time it was updated, that's the thing to check first.

What to do this week

No project plan needed. Give this maybe thirty minutes:

1. Turn on automatic updates on your main computer and your phone. On both, it's a setting you flip once and never think about again.

2. Restart your computer — a real shut-down and power-up, not just closing the lid. Do it at the end of the day so any pending update can finish overnight.

3. Update your phone's apps. Open your app store, hit "update all," done.

4. Look at the forgotten box. Find your Wi-Fi router and check for a firmware update (search your model plus "firmware update"). If it's more than five or six years old and hasn't updated in ages, put "replace the router" on your someday list.

5. Make it a habit. Pick a slow afternoon each month and give your devices ten minutes. Ten boring minutes beats one very exciting afternoon later.

None of this is glamorous. That's exactly why it works. The businesses that get burned rarely do so because they lacked some expensive, fancy tool — they get burned because something ordinary sat un-updated for two years and someone found it.

If you're staring at a shelf of blinking boxes and have no idea which ones matter or when they were last touched, that's one of the most useful things a good IT partner does — keeping the boring, critical stuff current so you don't have to think about it. If you'd like a hand sorting out what's current and what's quietly falling behind, reach out anytime — no pressure.

And next time that little box pops up? Give it the five minutes instead of the swat. Future you will never know it mattered — which is the whole point.

— Jordan Polasek