Why you should leave your job when it’s going well

You agonize over it for weeks. You make covert phone calls in the bathroom. You’re extra careful with your computer and phone when other people are around. You make up ever-so-obvious excuses as to why you’re showing up 2 hours late (I mean, how many dentist appointments can one person have in a month) and overall exhibiting all the pathologies of a cheating spouse, shame included. But you’re not cheating - you’re just someone who found themselves in one of the more absurd situations in this our modern world - looking for a new job while still very much employed.

Let’s hover over those bodily sensations. Obviously, there’s the fear of “getting caught”, which, depending on how valued you are in the organization, can have consequences ranging from the awkward to the catastrophic. If you’re extremely lucky, it can even invoke a sense of urgency to preserve you.

But there’s something else. The contemporary workplace (specifically in tech) is defined and showcased using terms like Culture, Vibe, Perks and Human Capital. Top HR functions are being rebranded as Head of People, Chief Culture Officer and Director of Fun (true story…) This is made a priority in part by companies looking to better their stand in the talent arms race that is constantly afoot, where an extra brand of craft beer in the fridge can apparently sway a star developer to sign with you and not the competition. However, it strikes a much deeper, emotional vein - if you’re bound to spend ? of every weekday (and often more) at work, it and the people who make it needs to have as large a cross section with your identity as possible. If done right, this in turn will make it so that you're more committed, loyal, and downright evangelical to your workplace.

So let’s assume all the above applies. You fit right in with the culture, you’re in love with everything the company does, recite their mission statement in 7 languages and half of your wedding guests were coworkers. If everything is so cherry blossom and cotton candy unicorn clouds - why are you hiding in the toilet feeling like the last of the adulterers? Why even look elsewhere if, seemingly, nothing is wrong?

For me, at least, as I made the decision to leave my job at Wix, it was the realization that you don't need to wait for things to go wrong in order to move forward. The majority of us are hopelessly change-aversive (present company not only included, I'm on the goddamn board) and will only spring into action when in some sort of (hopefully figurative) pain. This is understandable - most unmade decisions have their share of unforeseen consequences and inherent risks, and most people would choose to stick to the devil they know, so long as they can stand to be in the devil's company (and at times, you're actually quite fond of it)

But the truth of the matter is everything is finite, and every experience can only last as long as it provides you with value. It doesn't take a fatal error for things to go "wrong". Plateauing could be just as detrimental on one's feeling of self worth as being berated by your superiors for not doing your job right. There’s nothing quite as devastating as realizing, often too late, that you’ve overstayed your welcome.

Your next workplace will need you at your energetic peak - you will have little to no time to prove yourself not only professionally, but how your character fits in the larger fabric of the new team you landed in. If your transition is marred with disgruntlement, lack of enthusiasm and under-appreciation, then that’s what you’ll be talking about during those first critical days. That’s the story you’ll be telling your new colleagues, and you’ll be at risk of treating the new workplace, that spent quite a bit of time and money hiring you, as a refuge rather than the opportunity that it is.

Now obviously I'm not suggesting you quit your job right after a promotion or a significant raise. If you're in a position where you impact the organization at the highest level - stick to your guns and do some mountain moving. But if it's all going just well - maybe it's time to muster some momentum and leap upwards. You'll seek new opportunities with more confidence, be at the liberty to be choosy about where you're headed next, and when the time comes to give your notice - there's a greater chance you'll be remembered for your best and brightest, and hell, maybe even with a bit of legacy.