I think you just know when it’s time to quit. Quit anything, really. Look back at your life, at the things you’ve quit. I’ll bet that you can pinpoint the moment when you knew. Even if you didn’t recognize it at the time.
It was 1992. I had graduated from engineering school almost four years before and had a job with a local software company. I’d even picked up part-time work in pro radio thanks to my experience at my alma mater’s station, WMHD. But I was still doing a weekly show there, too. I had been station manager while I was a student, and was well known and liked by staff and listeners. And so when I asked the next station manager if I could still do a show even after I graduated he was thrilled. “You’d do that? Really? Well, of course you can!”

It was exciting and weird to keep playing records on that little 160-watt pea shooter. Thursday right after work I’d drive over to the station and park in visitor parking, a clutch of records from home under my arm as I headed into the basement studio. Students who remembered me, themselves now about to graduate, would come by to say hello. The phone would ring with longtime listeners on the other end telling me they were glad to hear me and hey can you play a song for me?
For a couple years it was great fun and I felt like a local celebrity. And as the coaching I got in my pro gig made me a better disk jockey, my work on WMHD sounded better and better too. Here’s 45 minutes from a show on a late-January day a quarter century ago.
But it was about this time it started to feel different, like it was time to move on from it. I had the time to do it. It was still fun. And management told me that I could keep doing it for as long as I wanted. But I was just playing the same classic and progressive rock I’d always played, even as the youngest students were starting to introduce hip hop on the station. Students from my era would have had none of that nonsense! But I was about to turn 25. I couldn’t even pretend to feel like a college student anymore. My world had moved on, even if I hadn’t from here yet.
So I quit. I don’t remember when my last show was; probably in February at the end of that academic quarter. I wish I had recorded that show. But I remember telling listeners that this was it, and getting their very kind phone calls telling me they enjoyed hearing me and wished I’d stay. But then the time came, and I played my last song, and walked out of the studio for the last time. And while it felt odd to know it was over, it didn’t feel bad. I could tell: it was time, and this was right.
There have been other times I knew it was time to quit and I didn’t honor it.
I knew it was time to quit collecting coins, a hobby I’d had since childhood, when checking my change stopped being an exciting hunt and started feeling like an obligation. I hung on anyway for years, hoping it would become fun again. It never did.
I knew it was time to quit that first career job when one day the controller, who was kind of a friend, stopped by my desk to tell me that I should go straight to the bank and deposit the paycheck I had just received, as not everybody’s check would clear that day. I made a beeline for the bank. Yet I had been comfortable there, and I hoped in futility that it would become comfortable again. And so I hung on for two brutal years as the company circled the drain.
I knew it was time to quit being a technical writer when I grew weary of writing things like, “Open the File menu and choose Print,” over and over. Yet I did it for a couple years more as it took me that long to push through fears that I couldn’t successfully shift my career into something different.
I knew it was time to quit my first marriage one afternoon when my wife did something particularly ugly to me, something I don’t particularly feel like sharing. There are two sides to every story anyway. Yet I hung on for a couple more years for a whole bunch of complicated reasons, and it about put me into a rubber room. I quit only when she filed for divorce.
I knew it was time to quit riding my youngest son’s butt about doing his homework when I recognized that homework was all we ever talked about. It drove a wedge between us. Yet my fears that he would fail to launch kept me at it for months after I recognized that. I finally forced myself to quit, regardless of my fear. Our relationship rebounded quickly. And then he figured his focus challenges out on his own.
Sometimes even when you know it’s time to quit, you can’t. Not just yet. Maybe it’s a job, and you can’t live without that income. Maybe it’s a marriage, something not to be quit lightly, something to be quit only after all alternatives are exhausted.
Or maybe you simply forget that you have agency, that you get to choose your life, that you are not actually enslaved to the choices you made. Even if you feel enslaved, because you’re addicted to something, there is help out there for you.
Because you can lay plans. You can get help if you need it. You can keep trying to make the changes necessary so that you can quit. And move on into the phase of your life you’re meant to be fully living.