Some Thoughts on How to Quit Your Job

It’s a paradox of the modern workplace: companies spend a ton of time thinking about how to treat employees who are leaving, yet almost no one teaches employees how to leave their company.

It is not taught in school. It’s not part of onboarding or employee training (probably should be). It rarely comes up in 1:1s or career conversations. Everyone is basically left to improvise through one of the highest-stakes phases with their employer. These are moments where trust is tested, egos flare, and reputations can flip quickly in either direction.

Here’s the part many people don’t fully understand: your exit — the moment, the mechanics, and the weeks after — often becomes the entire story of your time at a company. You can spend years doing great work and torch your reputation in the last week. You can also elevate it dramatically in how you manage your final days.

After seven years at Nextdoor, I recently stepped down as Head of People and Grand Poob-AI. Even after more than two decades (almost three!) of watching people define their legacy with their exits, I was surprised by how deliberate I was in managing my own choices and actions in those final weeks. I kept flashing back to all the missteps I’ve seen — career-limiting moves that could follow a person for years.

Somewhere in the back of my mind had been a memory from twenty years ago: a furious executive teeing off in a staff meeting over an employee who’d sent a multi-paragraph resignation goodbye to a distribution list with hundreds of people on it. He ended his tirade by declaring to no one in particular, “Someone should really write an article on how to resign.” I’ve been thinking about this post ever since.

So here is a guide I wish I could have handed over to dozens of smart, well-meaning people before they tripped over themselves on the way out the door.

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Rule Zero: Your Exit is the Story

Announcing your resignation is an emotional peak for you; for everyone else, it’s basically something that happened at work that day. This dynamic is compounded if you’re a leader. You’re thinking about dozens or hundreds of people impacted by this news, but each of them only might be thinking about what it means for their day to day. This mismatch can create weird behavior by the exiting individual: over-explaining, validation seeking, melodramatic goodbyes, “one last chance to tell you what I really think” energy, bursts of self-importance — all bad choices that can lead to resentment on either (or both) sides. 

One of the reasons this is so challenging is because upon exit, there is an identity crisis for all involved. By leaving, you are moving into the past tense. It’s over. Any future possibility of your impact is taken away and the record of your time there is now close to the final version. You are no longer formally responsible, you do not need anything from anyone and you don’t have any real sway. This is a vulnerable, volatile moment where any wrong moves can redefine you. A common trap is when people try to over contextualize or explain too much to protect the story about their time there or to justify why they are leaving. A terrible, terrible mistake is to engage in debate about how it might have been better, if only. Fight against succumbing to this.

This scenario was brought to life in The Last Dance, a documentary about the Chicago Bulls Dynasty in the 1990s. Episode Ten explores the challenging end to one of the greatest teams in basketball history. The Bulls had won their sixth (and third in a row) championship together but the general manager and owner of the team had made the decision to blow up and rebuild. In telling the story, Michael Jordan is enraged, knowing that the chance to extend his “greatest ever” legacy was taken from him, and unloads with all the reasons why the organization was making the wrong choices. This differs from the story from the owner Jerry Reinsdorf, arguing why they decided to blow it up early instead of waiting too long to start over (for the record, that decision was totally indefensible and I’m with Jordan!). But what struck me about this scene was the approach of the iconic coach of the Bulls, Phil Jackson (who would go on to win five more championships as the coach of the Shaq & Kobe Los Angeles Lakers), who expressed just a few measured and intentional words when asked for his opinion on his forced transition out of the organization while at the absolute peak of his craft...

”It was time to go”. 

In all my years of experience dealing with exits, this is the absolute best thing you can say about why you are moving on - and it works whether it is your choice or not. It is time to go. No one needs any other reason. If you’re really struggling with what to say and in particular if you are feeling drawn into a battle over the story as to why you are leaving — trust me, just go with “It’s time to go” and don’t say another word!

Rule #1: Tell Your Boss First

This is the first real operational step.

Unless it’s truly a disaster situation with your manager, they should hear it before anyone else. They’re the ones who have to stabilize the situation, manage communication, and reassign your work. Finding out through someone else destabilizes trust instantly — right when steadiness is crucial.

Every experienced leader has had the “I found out secondhand” moment. It’s not a good look for anyone.

You should have the adult conversation. There is no way to avoid how much influence your manager will have over how your exit goes. Better to start clean and set the tone for this final act together. Their needs are important. You should be flexible but firm in putting the plan together.

Some pro tips:

• Your manager shouldn’t find out you’re unhappy by your resignation. Starting with “I’m not happy/Ready for something new/in a rut/etc.” well before it gets to resignation carries some risk but it’s their job to try to help you. The mature thing to do is start there with enough time for them to make changes for your benefit.

• If you’ve done that, then be crystal clear with the resignation conversation. The best way to do this is have a conversation and then send a short, explicit email. You may think you resigned, but with no agreed upon end date (for example), the manager may be thinking they have a window to turn you around. Formalizing the last day on payroll (which needs to be confirmed by the manager to be formalized) is a crucial step that gets messed up all the time.

• The communication and email is best if it’s 100% logistical and 0% reasons why. Maybe 90/10 but do not write a book about why you’re leaving to your manager.

• You should be clear if you are resigning as leverage and are open to stay for better conditions (new manager, higher pay, new job) or if you are actually leaving no matter what. Many times I've seen someone skip the first bullet point of engaging maturely with their manager, decide they are leaving, then be offered a new role of some kind and then stay. It’s really messy and after the resolution you’re now at a company you quit from, which the leadership will never forget, because you didn’t start with an honest conversation. Trust goes two ways and you started with the nuclear option to get what you wanted. 

Rule #2: No Long Goodbyes

Once you decide to leave, leave.

Smart people routinely convince themselves that prolonged notice is a responsible act. It’s not. Team readiness for your departure is the responsible act and it matters much more than how long the runway is. A crisp 2–3 week handoff beats a meandering, rudderless eight week farewell every time. 

I’ve seen people frustrated that they were not given a lot of notice by people who resign. I believe that they were actually frustrated that there was not a good plan and also not a lot of time to deal with that. In my experience, once the team feels reasonably good about the plan, the time is no longer a concern. 

The best advice on timing that I ever got came when I transitioned out of my first manager role. I was genuinely distraught about what my team would do without me and thought I should stay in place for weeks, if not months. The HRBP that I shared an office with looked me dead in the eye and said, “Let’s say you’re literally the best manager in the world — and I’m being kind by starting with that — then they might still be thinking about this on Friday (it was Tuesday). By Monday they’ll be fine.” This has become an eternal truth for me and something I’ve passed on to many others. I’ve added my own line, “Their paychecks don’t come from your bank account. They have a new boss now and it’s selfish for you to hold them back from getting started.”

Once people know you’re leaving, they immediately orient toward the new reality. That’s what they should do. It can sting if you’re the one leaving, and that sting can lead to truly damaging reactionary behavior on your part: gloating about your next gig, clinging for recognition, bragging how great it is to be free, or over-sharing your decision process.

Get the team set up, execute the handoff, and move on. This is the only thing that you need to focus on once the timeline is agreed to. 

Another harsh truth: You should hope for the best and prepare for the worst. If the company wants to walk you out that day and turn off your access immediately, they can. Don’t take it personally if that happens. The appropriate mindset is that you are ready to help with the transition but you are leaving the company and as soon as they are ready to take it on — well, you wanted to leave, so leave. 

Rule #3: Your Reputation Is Made After You Announce

This is the operational window where most people take a hit.

After the announcement, people stop evaluating what you did as part of the team and start evaluating who you are as you leave it. They’re watching for…Are you consistent? Do you follow through on what your agreements were or hand them off in a productive way? Do you run through the finish line or pull up because you’re on to the next thing? Do you gossip and dump grievances or try to settle scores? Do you see your legacy as what you did or what the team can do going forward?

People remember how you act when the stakes feel low for you but remain high for them. That window can define you more than anything that came before it. How do you behave when you technically don’t have to do anything? I have been absolutely stunned — in both directions — in how people have made choices during this period. 

For those who think that the company holds no power once they've resigned, I cannot emphasize enough that references are how the company holds the final card. References are the Ghost of Christmas Past, Present and Future. No matter how great of a new thing you might be going to, people are going to call and ask around at some point in your career and how you left the company can dominate your actual track record. 

The last phase is everything. I’ve seen people terrible at their job manage their transition so honorably that the leaders who were their references went above and beyond to help them get to their next opportunity. I’ve seen people who were absolutely heroes at their company destroy all goodwill they had spent years accumulating with stupid choices in their final days. 

The final weeks can define you for years, I’m telling you!

Rule #4: Don’t Abuse Communication Channels

This is the one that triggers me the most, and it’s where the 20-year-old rant comes roaring back.

Do not announce your resignation to giant email aliases or Slack channels meant for real work.

Product-Team-All does not need to know you are “off to your next adventure.” All-fte is not a place for your TED Talk.

Maybe I’m old fashioned, but if you want to notify people yourself, take the time to contact the people you worked with. If it’s a lot of people, then the same email bcc’d to individual addresses is the acceptable cop out (and it is a cop out). I personally think if the person meant something to you, they deserve a 1:1 communication. 

Mass goodbyes create a weird “happy birthday thread” phenomenon where everyone feels socially obligated to respond if someone else does. Everyone hates this performative bullshit! 

100% of the people who disagree with me on this point are narcissists. Their arguments boil down to:

• “I don’t know who might want to know I’m leaving.”

• “Typing individual addresses takes too long.”

Both translate to: Other people’s time is worth less than mine. 

If you are a senior leader or otherwise important person (early employee, etc), then your boss or the CEO will tell the company on your behalf.  Don’t send your goodbye note to a large group alias unless that alias is literally the group of people who report to you.

You will be judged harshly for this type of alias abuse.

Rule #5: Don’t Take What Isn’t Yours

Your work product is not your personal scrapbook. You built it for the company, on company time, using company resources while being paid by the company to do so.

Decks. Docs. Research. Code. Strategy notes. Templates. Internal lists. Customer materials. Think twice about taking them — it’s all discovered by the IT team after you leave (which is so obvious I still can’t believe it needs to be explained). You won’t be there to defend why you are not a thief and so that’s how you’ll risk being remembered. If there are things that you really think you need (e.g a design portfolio, or presentation you’re particularly proud of) - ask. Do not assume. If it’s reasonable, you’ll take it with the company’s blessing. 

This is the one where you can permanently brand yourself as untrustworthy. This mistake travels. This type of behavior is discussed in circles much larger than you realize. I have seen this happen many times and never once has the material in question been worth the damage. 

Rule #6: Show Gratitude

Thank the people who shaped your experience. Don’t write a memoir, but share what your time at the company meant to you. People spent their time and energy with you — share with them how they made you feel and what gifts they’ve given to you. 

Gratitude lands best when it’s specific, proportional, and doesn’t require a reply.

Finally….The Actual Rule #1: Your Exit Starts on Your First Day

I’m ending here because it is how you really should start.

The best way to resign is to work in a way that allows someone else to step in without missing a beat long before you ever actually decide to quit. You should be creating systems that survive beyond your time. Build to last instead of just doing your job. Help your teammates get ready for whatever role they’ll need to play when you’re gone - even let them sit in your seat, so to speak, so they can talk to you about it. Sometimes you don’t get to choose when you leave — life intervenes — but you’ll still be judged by what you left behind so you should get to work on that on that the day you get started 

For many who leave, you may never meet the person who replaces you. Whether you know who steps in after you or not, you should strive for that person to want to thank you for what you left them to take forward.

 

That is playing the long game of How to Quit Your Job. 

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It’s counterintuitive to have to step up when you’re stepping down, but resigning is a  leadership moment. It’s one that arrives earlier and more often than people expect.

You don’t control every part of your career, but you absolutely control how you leave your team. It’s the final chapter your colleagues will remember, and those impressions compound. 

Leave with conviction. Leave with respect. Leave like a pro.

Leave it better than you found it.