A few years ago I met a fellow backpacker in the Cyclades. While waiting to catch our boat over a few beers we swapped stories. As anyone knows who’s ever waited for a Greek ferry, we had time for plenty of stories and more than a few beers. Eventually conversation got around to life back home and the usual three questions. Where’ve you been? Where are you going? How did you wind up flying across an ocean to meet strangers at a dockside bar on Naxos?

It’s that last one I always find particularly interesting.

“I quit my job,” she said, “after a friend gave me some great advice. She told me, ‘if you’ve had three bad days in a row, you’re doing something wrong.’ I had bad days all the time working in finance and decided she was right. So here I am.”

Swapping a banker’s desk for a taverna on the waterfront? Pretty good deal if you can get it. More importantly, she raised an interesting point. Changing careers is a pretty huge step, and traveling the world with an uncertain future is an even bigger one. Whether changing jobs or building a whole new life, how can you tell when it’s time to walk out the door?

Bangkok Palace

When a writer is acting like an idiot? Quite possibly…

The Deadline

Deadlines are a good plan. Quitting your job isn’t a step to take lightly even when necessary. Just as much as no one wants to trudge away in misery for 40 years, impulse quitting because of an argument over the lunchroom fridge is also probably unwise.

A black and white test is a pretty good way of sorting out the bad days from the bad jobs.

The tough part is picking the right test. Three days, for example, seems rushed to judgment. Even great jobs can have a lousy week. A better idea is to build the deadline around your goals, both personal and professional. For example, “I’m sick of sitting alone in front of a computer all day” or “I’d like to like my coworkers.” Maybe someone else sits down one day and says “I’m just sick of waking up unhappy.” That’s a good place to start. Decide to fix that by the end of the month, then on the 30th be honest about how it’s gone.

The Future

My test was to consider the future. When I practiced law neither I nor any of my coworkers were particularly happy. Working in Big Law was tedious, unfulfilling and demanded almost every waking hour. Even that still might have been manageable if the job came with a future worth working towards.

After all there really is such a thing as putting in your dues. Ask any actor or novelist about the parade of lousy jobs they did while breaking into the profession. Then ask about the parade of lousy jobs they did once in the profession. Most will still tell you it was all worth it.

For me the time to leave was when I realized the job would never be worth it. My best case scenario was a partnership (unlikely these days, but for the sake of argument) that would mean even longer hours, higher stress and a staggering 80 percent divorce rate. In law school we called it the pie eating contest: first prize is more pie, and I’d had enough banana cream.

Sighisoara Stairs

A light waaaaaaay at the end of the tunnel…

The Present

It works the other way around too. Even if you like the job today, sometimes it’s worth changing to avoid stagnation.

Personally I’ll always vote for adding a little adventure to life, but that’s not what I’m talking about. Sometimes the best trigger that it’s time to up stakes and do something new is when you’ve fallen into a rut and just need something new. You might not be unhappy, but are you actually happy? At you developing as a person or a professional? What are your odds of advancement, or having something better in five years than you have today? If the best I can say at 2:00 pm on a Tuesday afternoon is that I’m not miserable, it might be time to find something better.

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