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How to Know When to Quit While You’re Ahead

Whether to double-down or not can be a surprisingly introspective question

So things are looking up, huh? Your boss gave you an unexpected promotion, your career is on a whole new level and that side hustle you’ve been working so hard on is more profitable than ever. Basically, life is better than ever, and you plan on riding that wave for as long as you possibly can.

But then, as the wave comes to a peak, a scary thought crosses your mind: Sure, life is good now, but should I cash in and run before things inevitably crash and burn?

Because crash it almost surely will. It’s a phenomenon we see time and again, particularly with high-profile celebrities, musicians and athletes, who believe their careers are eternal before falling from grace because they run out of steam. Take, as an example pulled completely at random from a vast hat full of similar characters, singer-songwriter Natalie Imbruglia: In 1997, she blessed us with “Torn” and sold seven million albums worldwide. But alas, that was the high point for Imbruglia, and despite releasing several more albums, the world has barely seen her since.

Now, you can’t really blame anyone for trying to keep that ball rolling: Knowing when to gracefully make your exit in situations like this can be tough, since their positive nature can easily cloud your judgment — I just sold a bajillion records, so why the hell would I stop now? But looking beyond those clouds is the simplest way to know exactly when to jump ship before things fall apart. And it’s a lesson those in more regular jobs would also do well to learn.

“The most important thing is to always be aware,” says career strategist Daisy Swan. “This is one of the reasons why mindfulness has become so important, since it enables people to have more perspective on how they’re living. It’s always important to see what’s happening around you.” That means constantly staying aware of the general zeitgeist of your world or career, how things are changing, whether or not there are new competitors popping up and perhaps even how your company is doing.

Realizing that you might have more to learn — which can admittedly be hard to accept when you feel like you’re on top of the world — is also key. “As always, be aware if there’s something you need to learn that you’re not currently learning at your job, or that your company isn’t paying attention to,” Swan suggests. If things seem stagnant, chances are, it’s time to take your leave.

In simpler terms, while the sailing may be smooth, always keep your eyes on the horizon for anything that seems perilous.

Meanwhile, there’s also the question of whether you feel satisfied with where you’re at, even if you’re ahead, so to speak. “There’s a dilemma we all face when things are going well,” says psychologist Jeanette Raymond. “Just like with any other gamble, can we go further with the lucky streak, or are we going to lose it all?”

“The way to deal with this,” she continues, “is to tune into your satisfaction and fulfillment levels in your career. Have you achieved what you set out to do? Are you making enough money? Do you need more, or is this just a vanity thing to tempt fate and go further even though there’s no other reason? If you feel satisfied and have enough to let you do everything else you want in life, it’s time to move on. If not, then stay longer, but with a purpose in mind, not just for the sake of your ego to play with fire.”

Knowing yourself, and more importantly, how you deal with risky situations, can help you make the right decision as well. “Like any other gamble, if you’re the type to get a kick out of risking everything for the ‘high’ that you get from a winning streak, you’ll probably keep going, but not because you have a particular affinity for the career — more for the addictive qualities of gambling,” Raymond explains, which is obviously something you want to watch out for. “But if you’re not greedy and you’re content with what you have, rather than risking everything for the sake of your ego, you’ll probably get a good gut feeling about when it’s time to go without having to compromise on your initial goals and rewards.”

So then, the simple lesson here is to do what you set out to do and be happy with what you have. Because failure to do so may well leave you cold, shamed, and lying naked on the floor.