When it's time

When an impulse hits you that it’s time to move on, what do you do?

Your next impulse might be to suppress and put off the feeling. If you’re naturally given to fighting and “making it work”, the thought of leaving may be so unpleasant and unwanted that it’s all around just easier to kick it away for another day.

Yet delaying the right decision has its costs. I probably don’t need to tell you that staying in a bad situation will often negatively affect one’s creativity, growth, and even mental health. And at the very least, it will delay reaching your future potential.

Instead of kicking away the feeling, take a deep breath and ask: what’s causing it?

Good reasons to move on

I’ve agonized over & ultimately made my own departure multiple times, and supervised or reviewed tons of other farewells. It’s difficult to think of a departure that was not rooted in at least one of the following reasons.

• You’re much more excited about something else. Probably the “best” reason to move on is to leave for something you’re just much more excited about¹. My management team would triage new departure notices by classifying them as either “running from something” (i.e. leaving a shitty situation, which we’ve still got to fix), or “running to something” (i.e. leaving for and excited about something different, which we just can’t be). It’s hard to say no to passion. Sometimes you must just follow it.

• You’ve been offered an upgrade. A big comp bump, title or role upgrade, or both, are common reasons to jump ship. I separate this from the previous reason—perhaps it’s not quite passion that’s pulling you away, but cold hard pragmatic factors that are unquestionably better for you & imprudent to ignore.²

• You have a bad boss. There are so many kinds of bad boss. Toxic and disrespectful bosses are the easiest to identify. An absentee boss, whether because of overload or incompetence, never has time for you. Perhaps the most subtle and mundane variety is the boss who is friendly enough but who does not inspire or create high-impact opportunities. Great bosses can have a profoundly positive impact on your career, your creativity, and your sense of self-worth. Getting away from a bad one can & should be reason enough to leave. Don’t let your loyalty cap your potential.

• You have a bad team. When your profession is a team sport, it means that your personal success depends quite a bit on the performance of (and your relationships with) your peers. A team where some members routinely leave messes for the others to clean up, for example, is going to burn out and drive away the more conscientious and respectful performers. If your team doesn’t share your values, professionalism, or ultimately help you do better work, “voting with your feet” is always an option.³

• You’re no longer learning. When you a came to a job excited to develop new skills and ways of thinking, and you’re no longer doing that, it might be time to seek something new. Sometimes we choose a job because of a specific mentor, but that mentorship reaches a plateau or the mentor leaves. Or, maybe there just isn’t an appetite for you to be spending time learning. And, let’s face it, that attitude can be totally appropriate for the company: companies exist on different planes of success, and a struggling company is going to have a harder time prioritizing anything besides staying alive. If your learning has stopped, and you want it to continue, your best option may be elsewhere.

• The work sucks. Maybe you have a great boss and a great team, but you can objectively say that the role is not what you thought it would be—and your day-to-day is miserable. This could be a flavor of “no longer learning”, or it could be you were oversold to begin with; ultimately, the job itself is not a fit for what you want.

• You’ve lost trust in the company and/or leadership. Even if your immediate boss is great and the work is fun, sometimes a pop up to the bigger picture shows something much worse. An old colleague of mine described how, after one “final straw” situation, he had “flipped the bit” on our leader: he decided that leadership was incompetent beyond redemption, and would depart soon after. Even if leadership is respected, a dramatic change to mission can also provoke departures, especially when the new set of goals is not accepted by those hired under the previous regime. Whether because of shattered trust or misalignment with the mission, if you’re not confident in where your leaders are taking you, it’s natural to seek something different.

• You’ve accomplished what you set out to do. You might wake up one day and feel like you’ve hit your own personal “mission accomplished” milestone. Perhaps that was getting the company to certain stage; getting that Nth promotion; or finally shipping the product you originally set out to build so long ago. Many entrepreneurs are great at the “zero to one” stage (building early) but are not good, or not excited by, later-stage challenges. This feeling hasn’t happened often for me, but I absolutely consider it a gift when it does. If you accomplished what you set out to do, and even if you can see there are still some genuinely good opportunities available staying put, it can be a fine time to make a change.

• You’ve made major changes to your own goals. When your goals change, a role that was perfect for you yesterday can be no longer worthwhile today. Maybe you’re an engineer who wants to get become a manager, at a company that has no such roles nor mentors available. Or maybe you decide a very different working environment (e.g. the stability of a big company instead of the tumult of a scrappy startup) is better for your non-work needs right now. Just as it could be a deal-breaker if the company suddenly pivots to a mission you object to, changing your goals to something the current company cannot provide can result in the same mismatch.

• Your motivations to stay are all negative. When you ask yourself, “Why am I here”, if all you can summon is fear, that’s a sign it’s time to change things up⁴. Staying because “it looks better”, “I don’t want to interview”, “I think it might be different in a year”, and so on, are weak reasons to commit to an environment where you won’t be at your best.

You have a good reason to move on when you at least one of those reasons is true for you. You have a great reason to move on when it’s several. If you’ve exhausted alternatives and can otherwise afford the leap, what else are you waiting for? It’s probably time.