Knowing when to leave may be the hardest thing that anyone can learn

By Jim Grey (about)

I leave jobs. It’s what I do; in my career’s 29 years I’ve worked for ten companies. My longest tenure has been just over five years and my shortest was 14 months.

(To my boss, and to my team, who are almost certainly reading this: no, I’m not thinking of quitting!)

Usually I’ve moved on to gain new experience or a higher position. A few times I’ve quit because the situation had become untenable — once for a relentlessly crushing workload; another time because of a micromanaging and mean-spirited boss. Twice I’ve been laid off when a company fell on hard times.

During my father’s era, loyalty to an employer was lauded. But today, and especially in our industry, spending too much time at one employer can make your skills look stale. That makes it harder for you to land a next gig.

But when is the right time to go? It’s often hard to know, but it’s hardest in the first job you take after college. It’s easy to form an attachment to the employer and your experience there, and stay too long. I did that myself.

It is easier the second time you quit, and the third. Soon you get a good sense of when it’s time to go. Here’s what I’ve learned.

Sometimes a company pushes you out:

You struggle to get behind major changes. Companies regularly adjust course, sometimes dramatically. When it happens, can you get behind the new direction? If you don’t think the new strategies will work, or if you find some of them to rest in a moral gray area, make your concerns known. But if things don’t change, or if you just don’t want to be a part of those changes, you should probably find a different company where you can be all in.

You are constantly frustrated with the way you have to work. If you’re comfortable in a high-process environment, low-process environments will feel too chaotic for you. If you enjoy high autonomy and low structure, you’ll feel strangled in a company with rigid hierarchy and lots of rules to follow. Or if you are highly competitive, an environment that values close collaboration and shared success will drive you nuts. Try to adapt to the environment, to grow through your limitations, and to influence change where you think things can be made better. But if you constantly have to be someone you’re not, find a company where you can be you.

The company seriously struggles financially. Every company goes through tough times, so don’t be quick to bail. But you should see your company making strong steps to bring good results back. Some companies aren’t transparent about their finances or strategies, so keep your eyes open. Look for new initiatives that gain traction. Watch your sales team — their growing happiness or deepening despair is a bellwether. But no matter what, persistently poor financial results will result in layoffs, or worse.

You don’t get along with the boss. Try hard to work things out first. Get some feedback from trusted colleagues about how you might be contributing to the difficulties, and fix those things. But sometimes you and your boss will just never be a good fit. And once in a while you will simply work for a truly awful boss. In both cases it’s time to go.

You see or sense moral rot in the company. I once worked for a company where the CEO was unable to not sexually harass his assistants. Finally one sued him; he got his entire executive team to lie about it in court and he got away with it. I worked for another company where the sales team would go to the annual user conference and spend their off hours, it was strongly rumored, drinking too much and sleeping with each other and with customers. It can be hard to separate hearsay from fact, and don’t spread rumors. But watch closely for signs of bad behavior, because moral rot will do your company in. It absolutely undermined the first company, and just the rumors in the second company seriously damaged the culture.

Sometimes your needs pull you out:

You aren’t growing in skills, pay, or title. Your career should progress. What that looks like depends on what motivates you. I like to get better and better at what I do, and if that’s not happening I get bored and leave. You might just want to make more and more money, be promoted to some level in your company, or move into a different kind of role. Your growth might stall for a while in any job. But if it stalls for too long, first ask trusted colleagues and managers what you might be doing to block your own growth, and fix those things. If that well is dry, perhaps you’ve gone as far as you can go and to grow you’ll need a new opportunity elsewhere.

You need a job that won’t challenge you. This might sound strange. But if your personal life ever goes seriously sideways you might need to put career aspirations on hold for a while. In my mid 30s my first marriage ended in an awful mess. I ended up working in IT for a large insurance company in a role where I could meet expectations with very little stress. I came home at night with the energy to focus on getting my life back together. Eventually my life restabilized and I wanted to grow in my career again, so I left.

You want to work for a company whose culture or product aligns with your values. Where I work now we build a product that aims to make the work life better for employees everywhere. We attract people who want to be a part of that mission. If you see another company with a mission that resonates with you, by all means, find a job there!

You want to work with more modern technologies. You might follow one tech stack through your career, or you might become a polymath and ride the cutting edge. If the latter appeals to you, get out when your company’s technologies become widely adopted, and find the next new thing.

You want to work for a company that is succeeding wildly. It might matter to you to be a part of the next big success story. If you sense another company is a rocket on the launch pad, and that excites you, what are you waiting for — get in over there!

In my next post, I’ll give some tips about how long to wait before you launch a job search, and how to manage your feelings about leaving.

Thanks to this song for giving me a great post title.