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How to Know When It’s Time to Leave Your Job (and how to do it)

Most people make the mistake of staying too long. Here’s what I’ve learned about the art of saying goodbye.

There was once a job I held where every day (frequent times a day), over weeks and weeks, I thought about quitting.

I weighed the pros and cons over and over again, stuck in analysis paralysis.

I felt stuck.

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If that’s where you are today, I’ll share a few questions to ask yourself that can help you break out of that paralysis.

These questions have helped me as I’ve contemplated taking on ‘extra’ tasks at work, staying in jobs, seeking new ones — basically, anytime I think about whether I should take on or start something new:

1. Do I like the work? (what are the problems we’re solving and/or agenda ahead)
2. Do I have the chance to learn something I think will be helpful for me in some way? (will I grow as a person)
3. Do I have the chance to work with someone(s) I want to get to know better? (will I grow new relationships or deepen the quality of an existing one)

Whether it’s a new opportunity or a continuation of my current role, the answer to at least two of the questions above has to be YES — and ideally, it hits all three.

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For example, I’m willing to do work that I hate…if I am learning something and getting the chance to work with someone I’ve always admired or looked up to.

Or, I’ll say ‘yes’ to something where I know I won’t learn anything materially new…but I love the work and I love the people involved.

If something is only hitting on one (or none!) of those questions, it’s a no for me.

It’s hard to walk away from a current situation, the “bird in the hand.” But sometimes, that’s a risk worth taking. And if you’re thinking about making that change, here are a few things that can prepare you to do so.

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Step 1: Re-evaluate your current state.

It’s almost always worth exploring whether something about your current circumstance can change — whether it’s the role you’re in and what you’re working on, or the people you’re working alongside.

Be specific about what you’re looking for and give your manager or others at your company a chance to see if there’s something they can do to scratch that itch. (this way, it’s also not a total surprise if you do decide to leave)

Step 2: Think about your future.

Generally, finding a path outside the one you’re on within your company falls into one of three buckets:

1. A job change (similar job to what you’re doing today, at a company)

2. A career change (totally different job/career path, at a company)

3. Going out on your own to do something similar to your job today(see this post for specific tips about carving your own path)

4. Going out on your own to do something totally different than your job today

Preparing financially and emotionally for each of the above changes will be different. Some of the options above may take more time (#4 is the option that probably takes the most time) — so it’s helpful to narrow down what you want to do.

Step 3: Contribute Towards a Smooth Transition

Some people are “burn it down” people when they leave an organization, but I swing the other way.

No matter how much you’re ready to leave or never intend to return to an organization, the value of preserving your reputation and network is likely worth more than the satisfaction you might feel in a moment of self-expression. (plus…I never say never!)

It’s also likely that folks you know and consider friends, will be left to carry on the work — so try not to leave them in a bad position, to the extent you care about them as people.

Your transition doesn’t have to be overly prolonged, but take some time to ensure basic business continuity:

• Consider who might be able to carry on all or parts of your duties, thinking broadly about folks’ previously expressed interests, readiness (like a mini-succession planning exercise)
• Write-up a brief status for anything you own — business-as-usual work, or project initiatives, along with FAQs likely to come up in your immediate absence, and provide links to any important files or documents
• If possible, spend time with the folks taking over your responsibilities before you leave. They’ll value the chance to ask questions before you head out the door. If you’re willing and the organization is open to it, you may be able to set up a paid agreement to be available for questions and counsel following your departure.

These questions have served me well, and have helped me to make decisions to stay or leave more quickly, with a lot less spinning.

You may have a set of different questions that align to what’s important for you.

Find a question framework that works for you, because once you can commit to a decision (should I stay or should I go?) — it frees up your mind to live and embrace that decision fully, in a way that will likely lead you to more success in whatever you do.

Good luck.