Knowing when to quit

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!”

Me at WMHD
Me outside the WMHD studio in 2012. Some buddies and I painted that wall in 1988.

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.


29 responses to “Knowing when to quit”

  1. J P Cavanaugh Avatar

    Oh good – for a minute there I was afraid that hammering out a daily blog was going to finish out your list.

    I have always struggled with this. In many areas of life I tend to start strong and then have trouble finishing. So is it really time to quit? Or is this just something else that is I’m tempted to abandon when I really shouldn’t? My, but isn’t self-examination hard work before getting coffee. :)

    1. Jim Grey Avatar

      I’m a veteran navelgazer and I’ve learned that this pursuit is fruitless when insufficiently caffeinated.

  2. Jason Shafer Avatar
    Jason Shafer

    Wonderful synopsis of knowing when to quit – or move on. Currently facing the same sort of dilemma, this is so timely. You’ve got me thinking!

    1. Jim Grey Avatar

      My nefarious plan is working!

  3. teatimechic Avatar

    This is such an important message..thanks for sharing and for the reminder.

    1. Jim Grey Avatar


  4. Gary Tyrrell Avatar

    Quitting is underrated. Sometimes, you just gotta get the hell out of Dodge with handful of sweet, sweet, untraceable cash.

    1. Jim Grey Avatar

      If you find a source of that untraceable cash you let me know now y’hear?

  5. N.S. Palmer Avatar

    Wisely stated. Of course, it’s also important to know when not to quit. Two “quit quotes” always come to mind:

    “Quitters never win, and winners never quit. But people who never win and never quit are idiots.” —

    “You’ve got to know when to hold ’em,
    Know when to fold ’em;
    Know when to walk away,
    And know when to run.”
    — Kenny Rogers’s song, “The Gambler”

    I quit collecting typewriters because it’s expensive and takes a lot of space. I quit technical writing because it’s now almost entirely contract work and is a complete joke (e.g., $25/hour for 10 years experience and enough tech skills to work as a developer at Google). But the things I will never quit, I will never quit.

    1. Jim Grey Avatar

      Solid quotes there.

      Did you see my post on my software blog a couple years ago about tech writing and how it’s a dying career? It got picked up on several tech-writing forums and holy wow have I been excoriated on some of them. You know how sensitive we tech writers can be! :-) It’s the most read post on my software blog.

  6. lasousa2015 Avatar

    Jim thanks for your words. My philosophy is to control the things I can, understand that some things are totally out of my control, and do my best to understand the difference. And keep my side of the street swept by trying to do the right thing. When is it time to quit collecting old cameras? It is an obsession of mine now. If you get a chance read my post on about the Exacta Varex IIB. You might enjoy experimenting with one of these cameras. If you are interested in one I recommend finding the Ebay store of “cupog”. He restores them before selling. Mottled shutter curtains are the bane and he replaces them and calibrates shutter speeds. Great old Zeiss glass, and it’s all cheap. Keep up the good work.

    1. Jim Grey Avatar

      Thank you so much for the tip about cupog! I’ve stayed away from the former eastern bloc cameras because it all felt kind of risky, but having a seller who overhauls them before selling takes the sting out!

      I’m still interested in trying old cameras, but only keeping ones I fall in love with. I’ve paused on selling non-loved cameras from my collection because time doesn’t allow — eBay selling is surprisingly time consuming — but hope to resume this spring or summer. I must lighten my load!

  7. DougD Avatar

    Yes, good advice. I tend to be the stoic never quit until it’s far too late type of person. My 19 year Triumph TR4 project is a good example.

    Employment wise my record is mixed. I quit my engineering job in 2001 to work for a smaller company that I quickly realized was on the path to disaster. I stuck it out for almost a year, then got re-hired by my old employer. That was a good decision, folks at company #2 showed up one day to padlocks on all the doors. Now I’m still here, not terribly exciting but it’s a paycheck reasonably close to home. In these times is that good enough?

    1. Jim Grey Avatar

      I am driven by adventure in my work life. It’s led me to take greater risk than my usually conservative self would undertake. I’ve had nine jobs in my 28-year career as a result. Twice companies I worked for couldn’t afford to pay me anymore, and once I was fired and then un-fired. (Story here: Several times I’ve taken a new job because it meant a new adventure.

      I’m fortunate that software development has been such a growth industry most of my career. I’ve never lacked for opportunity.

  8. davidvanilla Avatar

    I have long admired your level-headedness, your successful management of your career, your humor, and your positive attitude. But I just may be a better quitter than you are. :-)

    1. Jim Grey Avatar

      Hah! In this context, it’s good to be an accomplished quitter!

  9. SilverFox Avatar

    Wise words and I have made those kinds of decisions myself. Pulling the plug on my marriage was the hardest but had been inevitable for longer than it should have.

    1. Jim Grey Avatar

      The hope the second time around (which is where I am now) is that your quit sensor isn’t too sensitive.

      1. SilverFox Avatar

        Funny you should say that I am embarking on a new adventure in this very area ;)

  10. Photobooth Journal Avatar

    I love the way some of your posts prompt self reflection. I enjoy learning more and more about you and your philosophy of life, Jim. I was very relieved that the title of this post was not referring to you stopping your blog, which was my fear when I first saw it.

    1. Jim Grey Avatar

      I’m spreading the gospel of navelgazing!

      1. Photobooth Journal Avatar

        He he he! ๐Ÿ˜€๐Ÿ˜€

  11. Lani Avatar

    Knowing when to quit is tough. Esp when you feel like you’ve invested all this time and effort into something, be it a job or a relationship. But quitting (despite its stigma in our culture) is perfectly okay. I wonder if we should do it more often, actually.

    1. Jim Grey Avatar

      I think inertia and self-doubt keep us stuck. Both are challenging to overcome!

  12. dmswriter Avatar

    “…you are not actually enslaved to the choices you made” is one of the best thoughts I’ve heard in a long time. Just because we make a choice doesn’t obligate us to follow it through until the bitter end.

    I found myself nodding to several of your situations: ran out of steam at a job – yep. Hanging in there when a marriage goes waaay bad? Yes. Yakking at the kids to do responsibilities they should be taking on? Oh, you bet. It’s so freeing to let this stuff go and open up to a better life. Good post, Jim!

    1. Jim Grey Avatar

      I think in these situations we are clinging to hope and not reality! Glad this resonated with you today.

  13. ellieslifejournals Avatar

    Wise words. Quit when all other alternatives are exhausted. Never really thought about it but you are right. Sometimes it takes a lot to quit, to give up on something.

    1. Jim Grey Avatar

      Heck, sometimes it’s right, or at least not wrong, to quit before all other alternatives are exhausted.

      1. ellieslifejournals Avatar

        I suppose it is too. In certain situations it even saves you wasting your time. But it’s good to know that exhausting alternatives is not such a bad thing to do.

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