Is It Time to Quit Your Job? The 4 Most Important Considerations

Is It Time to Quit Your Job? The 4 Most Important Considerations

Q – I’ve been with my company for 3 years now and part of me thinks it is time to move on to pursue new opportunities. I’ve become extremely frustrated with my boss lately and I don’t see a clear career path for me. That said, its been a great experience overall, I’ve got some awesome co-workers, and I’m really good at my job. How do you know when its actually time to quit?  

A – This is a really timely question for me. I had someone leave my team recently and it has me thinking a lot about this subject. We all think about it from time to time, and its one of the hardest questions we have to ask ourselves through the course of our careers. The stakes seem so high. The price for making the wrong decision is scary. To be objective seems impossible.

How do you really know when it’s the right time to quit?

When does it make sense to stick it out a while longer?

Is the grass really greener on the other side?

The challenge is, how do you think logically about a situation that carries so much emotion with it? It’s your job, your livelihood, your friends. How are you supposed to know, with any degree of certainty, that it’s actually time to leave?

I’ve worked at enough places to know that every company has problems. It’s unrealistic to think the mere act of moving to a new job is a guarantee that everything will be made better for you. That’s just not how things work and you need to be careful of taking on that mindset. I often think back to one job in particular I left because I thought it was unbearable, only to feel later like I’d given up too soon. Many years later I can objectively say I probably did in fact leave too early. How do you avoid making the same mistake I did?

Unfortunately, when I google “how to know when it’s time to quit your job” I get a lot of bad advice. Most of the advice in these articles ranges from obvious truisms e.g. you should quit if you’re experiencing physical abuse; to poorly conceived career strategy e.g. you should always quit when layoffs are coming; to just plain unhelpful e.g. you should quit because “life is too short” … thank you for that pearl of timeless wisdom. I highly suggest discarding the advice in most of these articles.

I’ve spent a lot of time over the last couple weeks asking myself the hard question – how do you know when it’s time to leave or time to stay? And for me, I’ve determined, it really boils down to four questions. One quick point before I share them – This isn’t one of those things where you have to answer yes to every question or you should quit – it’s more of a method for getting your perspective straight so you can evaluate your situation based on the things I think ultimately have the biggest impact on your long term opportunity and happiness. I hope they’re helpful for you in making your own career decision.

Does your boss genuinely want good things for you?

For me, this is probably the most important consideration. I would be very hesitant to leave a job where my boss was my biggest fan and a genuinely good person. Especially if she has a good reputation at work and strong growth potential herself. It’s just too rare to find a boss who cares about you and respects your work to give up on this without careful consideration. It can take a long time and a lot of hard work to create a situation where a senior person in the company is an active advocate for you. It can dramatically accelerate your career growth. To leave a situation like this for an unknown opportunity is very risky in my opinion. On the other hand, if your boss is not a particularly good person or isn’t one of your biggest fans or isn’t committed to helping you grow your career, I think you can be confident that leaving is a viable option for you.

Is there overwhelmingly positive sentiment for you in the organization?

It takes a long time to build a strong reputation and network in a company and you shouldn’t discount its value. If you’re in a situation where just about everyone in the organization thinks you’re great, I wouldn’t give that up lightly. When you start a new job at a new company you have to start the process of building your reputation over again, which can take years and is never a guarantee. So if you’re widely regarded as a star in your current company I’d think very carefully before giving that up for a new opportunity. Conversely, if you are a polarizing figure at work or you’ve done things, purposefully or not, to create some negative sentiment towards you, a fresh start might be good for your career.

Is the company growing quickly or benefiting from natural market momentum?

If I could go back in time and give myself career advice, the first thing I’d say is to pick your jobs based on the company vs. the role. There is so much to be gained from working at a high growth, well regarded company, that in my opinion, its actually worth taking a lower level role than you might want, just to be a part of it. Granted I am the first one to argue that you can find opportunities for career advancement even in the worst scenarios e.g. downsizing, restructuring, acquisitions etc. (A lot more on that subject in my book if you’re interested) But when you get into a company that is growing rapidly you can benefit immensely from the opportunities that creates. So if you’re considering bailing on your job at a super high growth company, my advice is to think very carefully about what you’re giving up and where you might be going to.

Do you have another job offer and how good is it really?

It should go without saying that unless you’re completely miserable at your job, and you simply can’t take one more day of it, you shouldn’t be considering leaving without another job offer in hand. This is just too risky. Assuming you do have another opportunity in hand, you also have to evaluate how good it actually is relative to opportunities at your current company. Does the new job offer more money? If so, how long will it realistically take to reach this level in your present situation? Years? Months? One benchmark I use when considering this is whether or not it will take multiple promotions to reach the level or compensation offered in your new potential opportunity. If it only takes you up one pay jump or one level, I’d at least consider staying on and talking to your boss about your career path. But if the new offer will take you up multiple pay jumps or levels, I’d give more consideration to leaving.

Each of us, at one time or another, have this existential career conversation with ourselves. The challenge is how to be objective when everything about the decision seems so subjective and emotionally charged. I hope these four questions help make this tough choice a little easier for you and give you the confidence you’re making the right call when you ultimately do.

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