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I was chatting a few days ago with someone who is about to head out on a 3-month sabbatical. (Super jealous!)
“It’s not a great time” to be leaving, they said, “but I planned and booked it a year ago.”
I had a new employee almost miss their best friend’s wedding in India because they were afraid to ask for the time off.
Their reason? It wasn’t a good time. They had just started in the role and didn’t want to jeopardize their new job.*

How many times in your life have you thought ”it’s not a good time,” and didn’t do something as a result? You …
missed your child’s school event
skipped the gym, nail salon, masseuse, or whatever you needed for self-care
put off scheduling critical doctor’s appointments or routine surgeries
planned your vacation around work, even if it was inconvenient for your plans—or simply didn’t take a vacation at all
… all because of real or perceived conflicts with work.
For me, there are too many of these moments to count across my career, sadly. Some things have taken me a long time to learn.

There will always be something that makes it “not a good time.” Board meetings. Planning cycles. Quarter end. Offsites. Org changes. Project deadlines. Colleagues’ PTO. The list is endless.
The reality (of work) is that it’s never a good time.
Which is sort of freeing. Because if it’s never a good time, then there is no need to consider work in your plans—just make them.
Attend that wedding. Take that vacation. Schedule that appointment. Enjoy those kids. The best time for that [insert life event here] is now.
Work will go on forever, but you only get to experience life once.
Don’t miss out on it because it’s “not the right time.”
Bonus read: Leaders need to walk the walk and not just talk the talk. Encouraging your folks to take time off? You also have to practice what you preach, because ….
*This story has a happy ending, thankfully. They were encouraged by another colleague to ask—at the last minute—to go. Of course I said yes! But I would have preferred to have known and planned for their absence with more than two days notice.