Dear Waiting + Wondering,
The rule of thumb when it comes to “maybe” making career changes is to kind of be the one in charge of the changes being ‘maybe’ made to you. If you’re wondering about whether it’s time to leave, just make sure you’re the one doing the leaving, rather than floundering your way to getting fired (always the worst kind of sign to tell you to start looking).
With that little lecture behind us, let’s get on with the handy list you’ve been looking for.
Signs it’s Time to Throw in the Towel:

  • Take the high road and see where you might be responsible for your own misery. (I say this without judgment because it takes a former career masochist to know one.) If you’ve looked in the mirror, been honest about the stuff you need to do to bring the best version of yourself to work, and then brought that version, and your situation still doesn’t improve, then it might be time. If you can go home each night for a whole month straight and honestly say you’ve done your part to make work better, and it hasn’t made a dent in your crappy experience, you should start sniffing around.
  • When the tradeoffs just don’t work anymore, it might be time. We all make compromises to do the work we do, and sometimes the allure of our work just doesn’t tip the scales in favor of the things we were once fine to put up with. Someone I know talks about how the once mildly annoying tradeoffs of traveling during weird hours and wearing a suit (when he’d so much rather be wearing jeans) became intolerable, it signaled his need to make a change. (Like starting a company called Happy Spectacular.)
  • When you’ve stopped getting better at what you do and it’s not looking likely you’ll ever be challenged again, it might be a good time to find or create a role where you can learn something again. Learning is the oxygen of keeners!
  • Evaluate what you’re like to be around. What kind of a friend/ spouse/ parent/ human have you been like lately? If you’ve been complaining about your incompetent boss and your lame coworkers and your archaic computer and the impossible commute and your company’s shitty reputation and your unjust performance review all the time, then you’re probably a real joy to be around, friend. If you suck the energy out of the room with your work woes, be a better friend and just quit.
  • Fantasizing about other things? Are you spending a lot of time imagining yourself doing something else, like going back to work in finance? Or becoming a stay at home dad? Or going back to school to be a paramedic? Living somewhere else in your head might mean you need to live there in your body, too.
  • If you’re certain you’re going to get fired, then sometimes it’s better to bust out before you’re sat down with a sorry excuse for a severance package. (Debate the merits of that one at your leisure. Sometimes it depends on that severance package.)
  • Feeling cheated? If the deal doesn’t feel fair to you anymore (like if your coworkers are being paid more for the same work, and it just doesn’t sit well with you), renegotiate or move on.
  • If your energy takes a nosedive when you log into your computer each morning, but then strangely recharges when you log out, it might be a sign.
  • Psychopathic boss? No, really psychopathic? (Grandiose sense of self-worth? Lacking all empathy & emotion while lying & blaming others, wrapped in a superficially charming package?) Get out while you still have a shred of sanity.
  • If your company can’t make payroll and payroll really matters to you (&/or your mortgage lender), consider it a sign to look around for a financially viable job.
  • And some reasons are just obvious that it’s time to cast your net: if your IBS flares up like clockwork every Monday morning, if you’re making voodoo dolls in the likeness of >85% of the people in your office, if you’re starting to surreptitiously pour Bailey’s into your coffee at work just to handle the 9 a.m. meeting, if it’s likely your CEO might be indicted soon-ish, if you’re being transferred to a remote fishing village (and you don’t even eat fish), if you’re on the cusp of being busted for not really being a surgeon (like Leonardo DiCaprio in “Catch Me If You Can”), or if you were once a successful child actor and you haven’t landed a gig in the decade since you turned 21 (and you grew up to look really unfortunate), it might be time to give up the dream.
  • And the easiest one of all: if a new job finds you, and it’s everything you’ve ever wanted, and you’ve been forthright with your current company about what your needs are along the way, leave the old job in the dust (with utter class and grace, of course).

Have you had any of these scenarios happen to you? When have you known that it’s time to leave?

Jodi Wellman

Jodi is a co-founder of Happy Work Spectacular Life, loves red Skittles (maybe too much) and finally got a Happy Spectacular logo tattoo.