Times Like These: Notes on Creativity, Chaos and Reinvention

Times Like These: Notes on Creativity, Chaos and Reinvention

Must Be Nice? No—It’s Necessary.

Protecting Your PTO as an Employee and a Leader

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Jon Willey
Sep 10, 2025
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Every vacation starts with a choice: drag your inbox with you, or leave it behind. Pick wisely.

I’ve seen the whole spectrum.

I’ve had bosses who told me flat out: “Don’t bother putting in vacation with HR—just take what you need when you need it, as long as we’re covered.” That’s trust. That’s leadership.

And I’ve had the other extreme: every single minute off tracked, logged, and corrected if you didn’t take it exactly as entered. That’s control. That’s distrust.

Sports is brutal about this. People outside sports grind just as much if not more I’m sure, but in this business, 75-hour weeks aren’t rare. They’re normal. So when you’ve pulled that kind of week/weekend and want to take a Monday off, you shouldn’t be forced to drain PTO. Any leader with a shred of empathy knows that.

Baseball has unwritten rules. Don’t steal a base when you’re up by 10. Don’t bunt to break up a no-hitter. Don’t admire your home run too long (although these days…).

The workplace has unwritten rules too. Work your ass off, take the time you need. Cover your teammates, trust them to cover you. My entire philosophy as a leader can be summed up in one sentence:

I trust you as a grown-ass adult to make sure your work gets done and that you take the time you need.

Scripts You Can Actually Use

Here are a few things that have helped me. When you’re in the fog of the season, sometimes you need the words written down. Use these. Copy and paste them. Adjust them to your style.

1. Asking for PTO without apologizing

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