Breaks Don't Work the Same Anymore

For 28 years, Thanksgiving break meant one thing: exhale.

The fall sprint was finally over. Back-to-school nights, parent conferences, the relentless rhythm of early dismissals, and faculty meetings. By the time November rolled around, I was running on fumes. That Wednesday before Thanksgiving felt like crossing a finish line. Four days of not setting an alarm. Four days of eating leftovers, watching football, and hoping this is the year Ohio State will beat Michigan after four straight losses.

This week felt different, though.

I woke up Wednesday morning and realized nobody was giving me permission to stop. There was no Head of School sending the “enjoy your well-deserved break” email. No collective sigh in the faculty room. Just me, my laptop, and a to-do list that doesn’t care about the academic calendar.

Here’s what I’ve learned about holiday seasons as an entrepreneur: breaks aren’t breaks anymore. They’re opportunities.

That sounds hustle-culture toxic, I know. But hear me out.

When schools go quiet, inboxes go quiet. Decision-makers aren’t buried in the daily chaos of running a building. That head of school you’ve been trying to reach? She might actually have ten minutes to read your email. That proposal you sent three weeks ago? It might finally get the attention it deserves.

I’m not saying I worked through the entire long weekend. I didn’t. I ate too much pie and watched the Lions lose, just like everyone else.

But I also spent a few hours this morning doing the kind of deep work that’s impossible during a normal week. No Slack notifications. No calls to return. Just focused time to think about where the business is headed and what I want to build next.

The old rhythm is gone. I’m still figuring out the new one.

If you’re considering making this leap, know that the calendar you’ve lived by for years won’t matter the same way anymore. That’s disorienting at first. But there’s also freedom in it. You get to decide what a break means now.

Nobody’s giving you permission to rest. But nobody’s stopping you from working either.

You’re the one who gets to choose.