Knowing when it's time to leave your job

Leaving a job is such a massive change in your life, so how do you know when it’s time to finally make that move?

Knowing when to change jobs is an incredibly difficult decision. Despite the average tenure in software engineering being only a handful of years, it can be a struggle to know when it’s the right time to leave a role. What’s more, even when you do know it’s time to pursue a new challenge elsewhere, inertia can be an incredibly strong force.

While this may seem like a privileged decision to make right now as the industry is rocked by waves of layoffs, the process of figuring out what your next move is should still be the same.

The catalyst

Most of us don’t wake up every morning thinking, “Today is the day I start looking for a new job.” Instead, it’s the sort of thing that comes up when something changes – a coworker leaves, your team changes, or a friend gets a cool new job. 

When something causes the question to pop up, it’s good to check in with yourself. In some cases, you’ll find that thoughts of leaving are just temporary flare-ups. This can be a spike of fear when someone leaves the team, or a bout of jealousy when a coworker gets a promotion elsewhere. But the real question is whether or not that feeling sticks around.

Sometimes, the idea that it’s time to leave isn’t caused by a specific event. Instead, it’s a gradual growth of the feeling that your current role isn’t right for you anymore. Some people have explicit career trajectories planned, and others are more improvisational, but whichever way you operate, it’s important to consider if this feeling indicates that your job has deviated from your career aspirations.

For instance, I regularly take a step back to see if I’m getting as much out of a job as I’m putting into it. While everyone’s ideals are different, you should have a good understanding of how to weigh the balance of compensation, growth opportunities, interesting work, and anything else that factors into your calculation.

Regardless of whether the realization comes from a catalyst event or a slow build-up, at some point, you’ll begin to question if now is the right time to leave your job.

Preparing for your career transition

Internal considerations

First off, you need to know what you’re leaving for. This could be anything from growing your skills in a particular area, financial independence and early retirement, starting your own company one day, or something else entirely. There are ample reasons to make a change like this, but make sure you have an idea of where you’re going, otherwise, you won’t be able to adequately assess your next opportunity. It’s a cliche, but it’s always better to be running towards something than running away from something.

Aside from having an idea of where you’re going, you need to know the narrative for your time in your current position. The story of your successes, failures, learnings, and how it all ties together is a useful tool in deciding if your story arc at your current company is at an end. Beyond that, it’s also helpful for informing the next arc of your story. Having both of those arcs in mind is a benefit when you’re going through the process of interviewing and evaluating offers.

Another important thing to consider is your current situation. Do you have enough squirreled away to be able to quit now and figure things out over the next six months? If not, do you have the capacity to practice and prepare for the application process while still maintaining your day job? The process of interviewing is a stressful one, and you should think through what you’ll need to set yourself up for the best chance at success.

External factors

Even if all of your internal considerations are telling you that it’s time to move on, you need to be aware of the broader market, as you don’t exist in isolation. With the global economic market being in the shape that it is, and the knock-on effect that has had on various industries, including tech, it’s prudent to think more extensively about what this might mean for you. For example, if you were interested in joining a startup to work on crypto, your prospects are very different in the autumn of 2023 than they were in the autumn of 2021.

Beyond that, companies are still figuring out their various policies when it comes to office presence. If you have strong preferences regarding work-from-home vs. in-office, you need to make sure you’re evaluating what the opportunities are.

Remember your reasons for leaving 

Even after you’ve gone through the whole thought process outlined above and decided that it’s time to move on, there’s still a lot to be done. You still have the interview gauntlets, offer negotiations, notice periods, and more. And even through all of that, you should continue to think about what made you want to leave your current role as this will help you evaluate your next potential position.

This needs to be part of the interview process – you need to be interviewing companies as much as they’re interviewing you. To gain some insight into a corporation you may join, look to your network. Even if you’re only a few years into your career, you’ve likely worked with people who have already moved on that you could reach out to. Knowing someone inside helps you get a better sense of what it’s actually like working for a given company, and depending on the circumstances, they may be able to help you with referrals or references.

Along with any inside connections that you already have, small interactions in interviews are going to be your best signals into the company. And because you already know what you’re leaving for, use the interview process to make sure that a prospective company meets your needs.

You’ll never have as much information about a future company or role as you do about your current one, but you should still be evaluating it as best as you can. If a job offer doesn’t address your specific wants and needs, then you should think twice before accepting it. Just because it’s new doesn’t mean it’s better, and hastily moving to greener pastures could result in starting this process over sooner than expected.

Final thoughts

We’re in a privileged position in this industry to be able to expect more from our jobs than simply enough to survive.

Understanding what you expect to get out of your career and reflecting on how your current role supports those goals will help you make better decisions when something starts to tickle that part of your brain that says, “Maybe I should quit?”