How Do You Know When It’s Time?

I’ve long been fascinated by the question: How do you know when it’s time to move on?

For example, my dad spent over 20 years—my entire childhood and into my college years—working at a state university. When he decided to leave, I asked him how he knew it was the right time. There were several factors at play but mostly, he said, it was because he didn’t feel like there was anything new to learn there. Every year, there had been something new to do, something new to learn: a new position, a new committee or task force of some kind, a new challenge. But after 20+ years, he’d gone as far in the organization as he could go. There was nothing new.

I thought about this when I made the decision to leave theater. I’d gone to college with the goal of working professionally in theater in a big city. I did that for over a decade. But I knew when it was time to stop. There were several factors at play—the manual labor of tech work was taking a toll on my body, nonunion freelance work meant I had no health insurance or retirement plan—but mostly it was because I’d reached a point where I needed to take the next step on the career ladder, and move up into technical director and production management roles. But I didn’t want to. In truth, I was a few years past the point when I should have made this transition but those jobs had no appeal for me. In part, it was because TDs and PMs don’t typically run shows, and running shows was what I loved. But if I’m honest… The thought of taking on that much responsibility, the idea of being in charge, filled me with dread.

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