When It's Time to Quit

The individual point of action of the Great Resignation is quitting.

But how do you know when it’s time to go? If your place isn’t completely toxic or you’re not deeply unhappy, it can be hard to tell when giving up an “alright” thing should yield to a better opportunity, and the effort and risk of moving.

For any job you have, even a great one, you should have a proactive system for evaluating at regular intervals whether consider a change every quarter. There’s also a more reactive “gotta go now” checklist where hygiene issues or changed conditions are a consideration to pull the ripcord.

AIGCC - the Proactive checklist

People often are more loss averse than they focus on gain. Having a system for objectively evaluating your role and company on a quarterly basis helps avoid stagnating and staying too long. Think of it as you evaluating your company’s performance with regard to you, rather than your own performance reviews.

The AIGCC checklist idea I picked up in a blog post read (apologies if you’re the author, I could not find the original link again to give credit), though felt the tone of the original post was way more mercenary than an even-handed approach to the trade-off between your and a company’s interests.

Why should you regularly evaluate your complacency in a role. As an example, the vast majority of my career advancement has come from moving jobs. Internal promotions can be slow, political, nepotistic, and often have little to do with value you provide rather than your boss’s personal biases. Also, internal pay increases at most companies increase much slower than market through inertia - I find few firms have proactive approaches to market changes or inflationary pressures (and in some places, anti-poaching agreements or tacit agreements have frozen market rates for years since competition does not exist.)

AIGCC is a mnemonic for Am I Getting Completely Complacent? I have a reminder in my GTD app to check this one off quarterly to make sure I am understanding I can answer an unqualified Yes or No to the Clash’s eternal question of Should I Stay or Should I Go? Of course the actual meaning of the letters is different, but it’s a good checklist as a starting point for you. Figure out what’s important to you category-wise to you and riff to a similar acroynym. The idea is the same. Firms should be nourishing and growing your career. When they are not, you should start considering looking at other opportunities.

How do I use this? I have a small text table and I simply think back on the quarter and mark each of the categories below with a Y or an N. Add up the Y’s and divide by 5. If you are below 50% for too many quarters, and you can’t fix it despite raising issues with your manager, it’s a strong sign you should move.

AIGCC stands for:

  1. Accomplishments
  2. Impact
  3. Growth
  4. Challenge
  5. Community

1. Accomplishments

Did you complete or start something in the last quarter? Is your Work in Process constrained and good? Did what you work on that you feel good about add to value for both your employer and yourself (ie. can you humblebrag it on your CV?). For this past quarter, do you feel accomplished in some way or are you digging out from other people’s messes and finding ways to cope with internal factors and bad processes?

2. Impact

Many people’s sense of job satisfaction derives from Impact. Has what you’ve done in your role contribute in a meaningful way to you, the company, and has an effect on the world (not if it’s appreciated. That’s a different topic entirely.). If you feel you’re shuffling things from place to place, pushing stuff into new and different looking piles, or putting cover sheets on TPS Reports on time, these are bad signs. You can also fold whether you fundamentally find the work you do, or the company’s mission, meaingful into this factor.

Keep in mind, impact is regardless of if the position you hold is impactful merely by where it sits in the organization. It needs to be relative. If you’re not being impactful, and this is somehow out of your control, it’s not going to lead to longer term warm fuzzies about the job. And again, being able to point to unambiguous impact in a metrics-driven way is something you can add to both your CV and performance reviews.

3. Growth

Did you grow in the last quarter? What did you learn? A new skill or business competency? Increasingly honed an old one further? Has your manager discussed growth or career progression with you? A bad sign is if you have not had a growth or career conversation in the last two quarters with your manager (or worse, you’ve tried to raise one and they’ve said it’s too early, deferred indefinitely, or have no idea how to grow you or what you need to work on). An additional danger sign is growth that is compensating for organizational dysfunction or your manager’s preferred engagement methods rather than more general skillsets. I’d also advocate if this is No in 3 consecutive quarters no matter what the rest of the scores come out at, you should consider it time to go.

4. Challenge

Challenge is intimately connected with growth. Why? You need challenge and stretching to grow. Growth happens at the limits of comfort. Of course, much like Growth above, if your big challenge is simply getting on top of the mess, or the fact your organization has no idea how to prioritize, and your boss is not able to clarify or resolve critical issues that you’ve repeatedly raised, that’s not challenge, that’s coping. I find Challenge a big personal thing for me. Even for roles I feel are not quite what I wanted, a really big challenge, thorny problems (particularly ones others have failed at), or other distillable amorphous problems that need solving end up being big drivers of why I stay in roles. YMMV.

5. Community

You spend a lot of time at work. Do you like the people in your team? Your customers and stakeholders? The people you interact within in other teams? Your boss and other higher ups? Having a good friend at work, for example, is a very accurate predictor of job satisfaction and happiness and, well… only sociopaths want to be working with toxic people. Also, think about the communities that your job may allow you to access that you feel good about. For example, at my old company, we were deeply embedded and a part of the open source and entrepreneurial communities in our country which often made people feel part of a bigger whole. Do not underestimate how a sense of belonging can make a difference to a role.

Reactive checklist

If you found this post because you’re conflicted about your current role, a proactive system is not what you need right now. We all worry about whether leaving a role is the right thing, even for jobs you don’t like.

But how do you know it’s time to leave a job, even if it’s not bad?

First off, assess objective facts versus your contribution. Leaving does have effects to the company, and possibly even your reputation, so it’s important to separate out the transitory from the problematic. Society is built on trust and reciprocal arrangements. For example, a lot of people are PTSD after 18 months of COVID and fatigued. You may just need a proper break or a better way of managing seemingly always-on WFH.

Second, respectfully speak to your manager and try to resolve issues first that get raised in this checklist. If this isn’t met with action for changes (or worse, apathy or even hostility), you have a pretty clear answer.

Third, be sure what you want. A lot of people have re-evaluated what is important to them during covid and found that their job situation is not one of them. Take an honest account of how downshifting may affect your life, are willing to give up to get it, and consider if it’s time to make that move.

What are the signs after you’ve taken the above steps that your work is no longer working for you?

Coping, not Learning

If you’re interested in growing and mastering, you need to be learning. If no next growth opportunity is in sight and your manager is unable to even talk about what learning and growth opportunities may look like, that is not a good sign. There’s a difference between improving at a role and stagnating and it’s easy to see in interviews where people have been floating along and not growing.

Raise this with your manager. Or better yet, put together a plan on what you think you want to learn and go to them with it. If they’re unable to give you any sort of input in this regard after raising it (gently) a few times, then you have a problem. Of course, you need to performing well in your role already. You do need to show that you are ready and capable of taking on more.

A worse sign is that with organizations that are overly bureaucratic, have onerous processes, are political, lack clear direction or decision making, or similar, you’ve probably been learning coping mechanisms to get around internal dysfunction. This is not true learning, this is investing in the organization and coping mechanisms for it.

Learning coping mechanisms rather than skills is insidious because it may tie you to an organization’s way of doing things as the right way rather than creative ways to solve the same problem. Furthermore, toxic coping mechanisms you learn can be actually counter productive in a healthier job environment somewhere else.

Do separate out problems with toxic individuals, rather than a company culture, since they do differ. Often, it can be harder for companies to do things about toxic people in an organization (I find even good organizations with perforamnce cultures often have a hard time firing toxic individuals despite them being an acknowledged problem.). Though ultimately, tolerating them too long can affect internal culture disastrously as it passes the wrong message on what behaviours are encouraged and rewarded and what is tolerated.

Would Not Recommend

A key danger sign for me is I would hesitate recommending someone good coming and working with us. If I’m morally conflicted about hiring or recommending my workplace to someone, I should leave.

All companies have issues, so it’s important to put things in perspective and objectively assess whether this feeling is more a transitory thing, or something baked into the company’s DNA or management philosophy that is causing these reservations.

A good question to ask yourself to cut through the subjective clutter, “knowing what you know now, would you actively apply to this company and the role you have?” If your answer is coming up wanting, you have a fairly good barometer that perhaps it’s time to start looking around.


If a job is affecting your confidence, you need to go.

This is not simply having something go wrong or bad and realizing you should have done better, made a mistake, or screwed up.

Especially if you have plenty of evidence you are competent and capable from other roles, but for some reason the company has strange ways of doing or rewarding things that undermine your confidence, has a culture of blame, or simply a toxic Disneyland that somehow has some internal calibration mechanism that don’t square with reality, these things will start undermining your confidence in yourself (if not your sanity).

Stress effects

A little stress is a good thing, but a lot is fundamantelly detrimental to your life. Too much stress is seriously bad for health and can proceed from simple anxiety to physically somatic effects.

If you are chronically losing sleep and not getting proper rest, waking up anxiously thinking about the job , or can’t get to sleep because work is rattling around your head, you already have a problem.

If this proceeds to full on physical problems from chronic stress, if it’s not something you can fix immediately (or worse, require medication for), you should start looking for another role immediately.


In review, you need to be looking out for yourself. Firms often talk about loyalty, but most like to extract loyalty while not believing it’s a two-way street.

The proactive AIGCC check makes sure that you’re not simply settling over time for a paycheque versus looking out for your career.

The more reactive checklist is for strong signs you need to leave. Now. Where a firm has serious problems that make it fundamentally a bad place to be and that will not get fixed.

And hey, if you’re smart, get stuff done, have integrity, and play well with others I am always looking for great people to add to the teams I run at the companies I work for. I aim to make everyone who works with me have the most challenging and productive time of their career. You can see more about my philosophy on growing people in this framework blog post. So, if you’re an engineer, data scientist, analyst, or PM drop me a line. We’re hiring aggressively at the time of writing.

Let me know what you think about the post on Mastodon @awws or via email hola@wakatara.com and if it actually made a difference for you. I’d love to hear feedback about your own thoughts, processes, or approaches and what may have worked for you or tweaks to the above. Reasoned opinions on why I might be wrong and what might be even better always welcome.

You should always have a framework about when its time to move on from a job you have. Here's both a proactive one and a reactive checklist.

Daryl Manning


2290 Words

2021-08-04 14:14 +0800