When is it time to leave your job?

November 16, 2022
Estimated reading time:
9 mins

“I try to change jobs every two years,” said Julie.

I thought it was a rather brazen statement for someone 18 months into their current role, sat in the middle of an open plan office, but there you go.

“Here’s why,” she continued.

“The first 6 months are for learning and figuring out what it is you’re supposed to be doing. The next 12 months are for doing an amazing job. The last 6 months are to coast a little while you look for your next role.”

I was 23 at the time, on a graduate trainee scheme, my first exposure to the Professional World of Suits and Ties. Up to that point, I’d never really done any career planning. I’d based my professional choices to date on the idea that finance and accounting was a skillset that you could use in many industries, in many roles — accounting is the language of business, after all — but that was as far as my formal career planning had gone.

By contrast, Julie had 20 years’ more experience than me, and had clearly put some thought into her career. She was accomplished, well-respected, and seemed to really enjoy her work.

Office Space at 20 - Gary Cole Was the Original Horrible Boss in Office  Space: "Didn't you get the memo?" - Screens - The Austin Chronicle
She was the opposite of this, thankfully.

I can’t honestly say that I deliberately took Julie’s advice from that point onwards. But if I look back at my career history to date, it looks like she was pretty on the money. Here’s how long I’ve spent at each company:

This peripatetic path hasn’t been because of any strategic career planning. In every case, I’ve moved on when I got to the point where I felt I was no longer growing and developing in the role (or in the case of company 2, when they decided to fire me).

Essentially, I’ve let boredom be my guide. Am I bored in this role now? If so, probably time to move on.

Knowing when it’s time to leave your job

I didn’t have much more of a framework for knowing when to leave my job except “Am I bored?” — until recently, when I discovered a wonderful post from Nick deWilde, helpfully titled This chart will tell you if it’s time to leave your job.

Nick’s argument is that everything we have to do in our job falls into one of the quadrants on this 2x2 matrix, depending on whether you are good or bad at the task, and like or dislike doing it:

Decide for yourselves if Nick’s penchant for 2x2 matrices is evidence of a former career as a mangement consultant (my guess is yes).

Ideally everything you do falls into the top-left quadrant: you like doing it, and you’re good at it. If so, congrats! You are a unicorn.

More likely, you have a distribution of work across these four quadrants. How happy you are in your role depends on that distribution.

I personally value professional growth and development — I’m still early in my career and want to keep getting better and better — so I’d also want to spend a big chunk of time in the top-right quadrant: things that I like doing and energise me, but I’m not good at yet because I’m still learning.

On the flipside, I understand that I also need to balance that against what my employer needs, so I know that I can’t spend too much time doing things I’m bad at, otherwise the company suffers (and in the long-run, my role becomes untenable).

We start to get into danger territory when we’re spending too much time in the bottom half, too. This is where we’ll either get so bored we leave (bottom-left) or it’s a toss-up whether we get fired or leave first (bottom-right).

(As an aside: the one and only time I’ve been fired was essentially because my role turned into something that was all bottom-right for me. It was work I both intensely disliked, and was bad at. I later described this as my “dream job”, but later realised that it was the company I loved. The actual role itself was a terrible fit for my skillset and personality. I just didn’t have the experience or the mental framework to recognise that at the time.)

Things change over time

The eternal challenge is that the distribution of work across quadrants doesn’t stay static. We develop, we grow, we change, and we want more. What was once a challenging stretch assignment, something that got you fired up, now becomes routine, stale, boring.

We start out in the top-right, not really knowing what we’re doing but excited to learn. Slowly we move left, as we become competent. And then as the novel becomes routine, we move downwards. Unfortunately, the company doesn’t really give a shit whether you like it or not: you’re good at it, so they want you to keep doing it.

This maps pretty nicely to what Julie told me early in my career:

So this leads us to a nice answer: it’s time to leave your job when you are both bored, and competent.

Importantly, at this point something must change: either a shift in responsibilities to give you something new and interesting to get stuck into, or you need to change the role.

Otherwise, Nick points out:

Things don’t end at the bottom left box.

As your share of tasks in the bottom left box climbs above 50% you’ll start checking out. You’ll get sloppy and miss things. Like that warning sign your biggest customer is about to churn or that one clause in the contract that could screw your company. At the very least, you’ll stop paying attention to best practices, and your skills will become outdated.

Now those things you were once good at have shifted into the dreaded bottom right box.

Not everyone goes through this transition. Some people are perfectly happy with a role they are good at, and quite like, and they can put up with doing the same thing day in, day out. I am not one of those people, and if you’re reading this, I doubt you are either.

What should I do about this?

Well, shit, if I knew that, I’d do it myself.

I’m somewhat wired to seek novelty and challenge, so my response has been to change roles every 2-3 years, most of the time accompanied by a change in both company and industry.

That works for keeping me interested, but it comes at the expense of not compounding my knowledge of a given company or industry, which is a shame.

Here’s what you shouldn’t do:

The answer I’m working towards: find a role and a company that has scope to grow with you, and a boss that will enable that growth.

As you learn and excel, you will need new opportunities for you, and people around you willing and able to push you and help you grow into those new opportunities.

And when that stops being the case, it’s time to leave.

Carve outs

A few things I want to highlight while I’ve got your attention:

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