There are many important goodbyes in life.
Saying goodbye to a relationship. Saying goodbye to a city. Saying goodbye to a huge phase of your life.
But one of the most fraught — and most significant — is saying goodbye to a job.
Whether it’s a job you love or a job you hate, quitting is never easy. And yet it’s one of the most important conversations we’ll ever have.
Knowing how to resign is a talent, and it’s both an art and a science. Leaving a workplace gracefully can make the difference between having strong relationships and struggling with weak ties, between generating opportunities down the line and fighting to scrounge up work.
It doesn’t get talked about as much as it should, but quitting your job the right way is actually a core life skill.
And the need to master that skill has never been more urgent. The Great Resignation is witnessing millions of Americans quit their jobs during the pandemic, driven by greater demand, higher negotiating leverage, and a buildup of burnout, hiring freezes, and other economic pressures. If those viral rage-quitting videos are any indication, we’re living in the Golden Age of peacing the f*ck out for greener pastures.
The thing is, very few people know how to quit well. (Those rage-quitting videos, as hilarious as they are, are basically a master class in how not to quit. Although that story about the flight attendant who slagged off his passengers, popped the emergency side door, and jumped down the evacuation chute is pretty legendary.)
That’s because we don’t teach quitting as a set of skills that will allow you to leave on the best possible terms, and even strengthen your reputation and relationships along the way.
So that’s what we’ll be talking about in this piece: how to quit your job like a pro.
But if you’re thinking about making a professional change, there’s one crucial step to move through before you start drafting that “I’m out, suckas!” email.
Decide if you’re really ready to quit — and why.
There are tons of reasons to leave a job. Some reasons are better than others. And some aren’t actually reasons at all — they’re just unresolved thoughts and feelings about your colleagues, your organization or yourself that are driving you to fantasize about leaving.
So how do you know when you’re quitting to improve your life, and when you’re just running away?
The answer is to investigate your reasons for leaving, using a simple exercise I call “Getting to the Bottom.”
To know that quitting is really the right move, you have to be an interrogator of your own motives. I recommend carving out a couple of hours for this exercise, and maybe even doing it several times over a period of a few months. Put pen to paper if you can — that’ll make your insights even more real.
This exercise has three steps.
1. Take stock of the thoughts and feelings driving you to quit.
Start by asking yourself a few basic questions.
- Which thoughts do you notice cropping up regularly?
- Which feelings are you finding it difficult to deal with?
- What’s your opinion about your colleagues and workplace?
- What’s the general tone/quality of your career?
- How is your mood most of the time at work, and how does that differ (or not differ) from your mood in your personal life?
Write down your answers, being as specific as possible. Don’t edit yourself; no one will see this list but you. Don’t feel obligated to only write down your positive feelings, but don’t exclusively harp on the negative ones, either. Make an effort to tell the whole story.
(If you find yourself holding back or self-censoring, give yourself permission to be totally honest about how you see things. If you want, you can burn these pages after you write them down, like a cheesy villain in a bad spy thriller. It might even feel kinda good.)
Then take a step back and study your observations.
What’s the overall charge of your thoughts and feelings? Are they largely positive or negative? Hopeful or bleak? Inspired or disillusioned? Or are you looking at a mixed bag?
You might find that this exercise confirms your feelings about work. Or you might be surprised to find that you didn’t appreciate the full picture — things aren’t as overwhelmingly crappy as you thought, or they’re not as completely sunny as they seemed. That’s very useful information, too.
2. Trace the thoughts and feelings back.
The next step is to figure out the root causes of these thoughts and feelings (again, the good and the bad). Take each observation and emotion, and identify 2-3 sources for each one, going as deep as you can to the roots.
For example, let’s say you wrote down that you often feel excluded and ignored at work — a common negative feeling among people wanting to quit. From there, try to identify the sources of that experience. Don’t just limit it to external factors, like colleagues and policies. Try to include a few that are closer to home, if there are any.
For example, maybe you write down:
- “Tom from Compliance dominating meetings”
- “My boss Clare not empowering me with my own projects”
- “My own fear of making a mistake or sounding dumb”
Again, be as honest as you can when you do this exercise. It’s actually fascinating to notice how easily your mind pins the blame for negative experiences on other people, other situations. Those people and situations play a role, of course, but our personalities interact with those variables to produce the overall experience. So really try to identify your own behaviors and qualities here — that’s super important.
Do this exercise for all of the thoughts and feelings you wrote down, including the positive ones.
For example, let’s say you realized that you actually have a lot of fun at work toward the end of the day. For your sources, you might write:
- “Charlie from Marketing telling hilarious stories”
- “Clare not being in the office after 4”
- “Just letting loose and allowing myself to have a laugh at work”
Those might seem like trivial realizations, but they’re actually just as important as the negative sources. We’re trying to figure out what’s going on beneath the surface-level experience that’s making you want to jump ship. Which means appreciating the good and the bad, the inspiring and the frustrating.
Pinpointing the sources of your unhappiness at work points the way to growth. Pinpointing the sources of your happiness at work points the way to gratitude.
You can’t have total conviction in your decision to leave until you’re in touch with both.
3. Come up with a plan.
The final step in this exercise is to create 1-3 specific, practical, achievable things you can do to address the root causes of your dissatisfaction (or make the most of your satisfaction).
So let’s go back to our examples above.
For “Tom from Compliance dominating meetings,” you might write:
- “Talk to Tom privately about making a little more room for me to speak in meetings”
- “Speak up even when Tom dominates or interrupts, create that room for myself, explicitly ask for a moment to speak if no one gives it to me”
- “Ask my teammate Eileen if she’s noticing the same thing in meetings or if it’s just me, study how she handles Tom, give that a try”
For “Clare not empowering me with my own projects,” you might write:
- “Book 15 minutes with Clare to talk about this feeling, get feedback, understand her management style better”
- “Propose two new projects that I can run and manage on my own”
- “Find more ownership of existing projects even if Clare doesn’t explicitly give it to me”
And for “my own fear of sounding dumb or making a mistake,” maybe you write:
- “Schedule time in calendar to do my homework before I speak up in meeting so I’m more confident about what I’m saying”
- “Take a chance and speak up even if I’m afraid, see what happens”
- “Google this problem and personality type and learn some techniques for handling them”
You get the idea. For each source, there’s always at least one thing you can do to change it.
The same process applies to the positive thoughts and feelings.
For example, your action items for “having fun at work at the end of the day” might include:
- “Write Charlie an email telling him how much I appreciate him as a colleague, work with him to find a project we can collaborate on together”
- “Invite Clare into our conversations so she doesn’t feel left out”
- “Schedule my work better so I can finish a little early and enjoy 20 minutes of downtime with my teammates every day”
With the positive action items, you’re basically finding a way to capitalize on the upsides of your job and appreciate them even more. Sometimes we don’t realize how much happier we can be at work until we actually recognize the bright spots.
With the negative action items, you’re basically converting the downsides of your job into productive behaviors. You’re not settling for your initial response to a tough situation, but using that situation to up your game and show up as the best possible colleague.
In other words, you’re taking accountability, being intentional, and choosing how you manage your environment, rather than letting your environment manage you.
From there, your job is to actually pursue these action items.
Schedule time in your calendar for them. Review them at the end of each day or week, and see if you’ve made progress toward them. Update them in light of new information. In many ways, this action plan is your job now.
This practice is extremely powerful. This is what allows you to push past the knee-jerk story of “I’m miserable at work, it must be time to leave” to the more helpful story of “I can change this miserable situation by showing up in a different way.”
(Or at least try to work on it and see what the results are. If nothing changes, then you’ll know that leaving is the right decision.)
This, by the way, is how you also avoid a common trap of serial job-jumpers: recreating the same dynamic in every workplace.
People who move around a lot tend to think that their problems are all about their environment. They don’t recognize how they’re contributing to that environment, how they’re processing it, how they’re responding to it. Then they jump to another company, and the same problems crop up all over again, and they start to tell a new story: that work in general sucks, that other people are the problem, that things would be different if they were in charge, etc., etc. And that’s why they spend every evening scrolling job postings on LinkedIn, counting down the days till they can bail again when that energy would be much better spent doing this exercise.
My advice is to spend at least a month — maybe two or three — genuinely giving this action plan a try.
In most cases, no matter how bad things are at work, we can all afford to give things one last shot for a month. It’s not a huge investment. You don’t even have to believe that it’ll work — just be willing to find out if these new approaches change your experience, even a little.
After a month or two, go through this whole exercise again, and see how your thoughts and feelings change.
If they do, then you’ll realize that your dissatisfaction at work was actually a sign that it was time for you to make some changes on your side of the equation. Which is actually super exciting, and very empowering. And then you’ll know that the answer wasn’t to jump ship, but to better steer the ship you’re already on.
If your observations don’t change, though, then you’ll feel a lot more secure in your instinct that it’s time to quit. Which is a totally fair decision — but far more reliable if you know you’ve put in the work to fix a negative situation before you run away from it.
Know Your “Why”
If you do the Getting to the Bottom exercise over a period of a few months, you’ll have all the data you need to decide whether it’s time to leave. At that point, you should be in a good position to know why you want to make a change.
But like I said, there are good reasons and bad reasons for quitting, so it’s crucial to be able to articulate your motivations.
Good reasons to leave a job include:
- Wanting to chase an opportunity that’s more exciting, meaningful, or lucrative
- Being inspired to take what you’ve learned in your current job to a new product, role, or market
- Feeling stagnant or uninspired despite putting in real time and energy to get more out of your job
- Hungering to learn and grow as a professional
- Not feeling connected to the mission of the company anymore
- Realizing that a job is at odds with your core values, interests or lifestyle
Bad reasons to leave a job include:
- Struggling to get along with a small number of colleagues
- Being uninspired without actively investing much effort or working on your relationship with the company
- Feeling underappreciated or being passed over for promotion for only one or two cycles
- Being unhappy for reasons that are not directly caused by the job, such as major life events, mental health challenges, recent loss or disappointment, etc.
- Not knowing what you’d rather do, but feeling like it isn’t this job
Of course, you can have several reasons for leaving a job, like wanting to chase an exciting opportunity and not loving the mission of the company any longer. And sometimes your reasons will fall into both categories — for example, if you land a new job at a company that speaks to your core values and you really can’t stand Trish in HR. (Friggin’ Trish.)
In those cases, take a moment to pinpoint your primary reason for leaving. Make sure you’re really taking that new job because you believe in the vision, and not because the sound of Trish’s voice makes you want to stab your eyes out with a Sharpie pen. (If you’re a fan of the show, you probably have your eyes on the prize — er, no pun intended — but, ya know, it never hurts to do the forensics here.)
But if you look at your bag o’ reasons for quitting and you think, “Man, I actually don’t know if my reasons are legit,” then here’s a principle that should help:
It’s always better to be running toward something than away from something.
If your reasons are primarily about fleeing an unpleasant situation, that’s usually a red flag.
If your reasons are more about chasing a desirable situation, that’s generally a good sign.
And that desirable situation might not be your dream job or absolute end game. It might just be a positive direction — for example, taking an internship at an ad agency because it’ll open doors into marketing, or moving to Austin because that’s where the tech companies you admire are based, or backpacking for six months to various monasteries to deepen your spiritual life.
In other words, the thing you’re running toward might not always be super specific. It can just be your North Star.
It’s also worth noting that this isn’t a hard-and-fast rule. For example, I’ve talked to tons of people who, dissatisfied with their jobs and sitting on some savings, decide to take some time off to recharge and reflect. Then they start reaching out to their network, interviewing with different people, and landing great jobs they didn’t even know about when they quit.
Those people aren’t necessarily being irresponsible by leaving an undesirable situation. They’re taking a risk, for sure — but it’s a calculated risk, and they’re not putting themselves in a dangerous position.
But even then, those folks are still running toward something: a better understanding of who they are and what they really want. And that’s because they used that time off wisely. If they were sitting on a beach in Barcelona binge-watching Naked and Afraid for six months, that’d be a different story. How you spend your time, what your intentions are, what mindsets you’re going into that break with — those make all the difference.
Questions to Ask Before Quitting Your Job
If you’ve articulated your reasons for leaving and you’re still unsure about what to do, then here are a few more questions that’ll help spark some new insights:
- Do I look forward to most days at my job?
- Am I inspired, stimulated, enlivened by most aspects of my role?
- Am I still growing and being challenged as a professional?
- Are those challenges still mostly enjoyable and productive? Or are they mostly unpleasant and unnecessary?
- Is the company doing well overall? Is my future in the company looking bright? Are there untapped opportunities for me within the organization?
- Do I mostly like and respect my colleagues, especially my peers and my direct boss?
- Do I still believe in the vision and mission of the company?
- Am I working toward something concrete — a major product launch, a meaningful milestone, a valuable target, or a great promotion?
- When I think about quitting, is it a fantasy of escape from a tough situation or a dream of something more fulfilling?
- Could the downsides of this job pop up again in another job? Or are they unique to this workplace?
- What would have to change for me to be happier, more engaged, more fulfilled? Are those changes available to me now, or are they fixed by my environment?
- Is the environment I’m in truly dysfunctional and toxic? Or can I control the negative aspects of this workplace to some degree?
Once again, I recommend carving out some time to really answer those questions. Just like the earlier exercise, this one will lead you to insights and next steps that will either change your current job or inform your job search.
I also encourage you to talk your answers out with a few trusted friends, colleagues, or mentors — ideally people who have been in your shoes at some point — and get some additional perspectives. These are fantastic questions to weave into your networking. They’re also a great excuse to reach back out to people you know (or even meet new ones) by asking for advice.
Should I Stay Or Should I Go Now?
Doing the above exercise will make the choice you’re facing a lot clearer.
If you realize that it’s not time to leave — that the change you’re looking for is possible, but that it can start with you — then it’s time to come up with an action plan.
Figure out which habits, approaches, and mindsets you’ll need to cultivate to change your experience — make it more efficient, make it more fun, make it more meaningful.
Talk to your peers and bosses about the changes you’d like to make — how you relate to one another, what you can achieve together, how you want to manage or be managed.
Find a new connection with your mission, product or stakeholders to bring more meaning into your job, and set new goals that’ll help you reengage with your role.
In my experience, some combination of these changes can completely transform your experience at work.
But if you realize that it is time for you to leave — that the change you’re looking for will only come with a new opportunity — then it’s time to…
Figure out your next move.
There are a few schools of thought about whether you should have your next job lined up before you leave your old one.
Some experts say that you should definitely have it locked down before you give your notice. Others say it’s totally cool to leave without having a new job in the bag — or even knowing what you’ll do next. Some experts even encourage taking that risk.
If you do have another job lined up, then I recommend waiting till you have the job offer in writing before you give notice, so you don’t jump the gun and then have the new job fall through. (I’ve seen that happen a bunch of times, and it is rough.)
As we discussed, if you don’t have another job lined up, that might be okay too — as long as you have some kind of direction when you quit.
If it’s not a new job, it could be an experience — like traveling, studying, reflecting, recuperating, or doing an unrelated job for fun (e.g., volunteering at an NGO, doing a short stint in an unrelated field, etc.). If you can afford to take the time off, this is often time well spent.
In fact, a friend of mine named Sylvie — a super Type A management consultant — once quit a firm with no job lined up to recover from a decade of nonstop work and travel. She finally had a long-delayed shoulder surgery, got her yoga certification, attended silent meditation retreats around the world, traveled, and read a bunch of books she never had time to finish.
When she interviewed for consulting jobs 18 months later, she told the partners her story, what she learned about the world, how she planned to bring that life experience into her conversations with clients. She felt healthy, balanced, and inspired again, and no one else had a story like hers. She got the job. Now she’s a top partner there herself, and she’s crushing it.
If you decide to take a Sylvie-style gap, though, just make sure you’re not faffing off and escaping real life, but using that unstructured time to get more in touch with your interests, passions, goals.
If you’re studying Portuguese and writing a business plan for a new company while you volunteer with Habitat for Humanity in Brazil, that could be an excellent investment. But if you’re “recuperating” by getting turnt at Dave & Buster’s three nights a week with your college buddies while you sleep on your LinkedIn messages, then I’d check in with yourself and make sure you’re really moving in the right direction.
Again, it’s all about that North Star.
The other good reason to jump ship without a plan is if a job is taking a major emotional toll on you, or otherwise putting you at serious risk.
For example, if you realize that you’re part of an objectively toxic workplace, and the office is creating real mental and physical stress — like panic attacks or recurring illness or feelings of unworthiness or a sense of dread — then it’s probably best to remove yourself from the situation.
(Although I would still encourage anyone in an intense environment to find ways to manage and cope with a tough environment before bailing. There are definitely high-pressure places out there — whether it’s working in M&A on Wall Street or fixing oil rigs as a deep-sea diver — and sometimes we need to improve our response to them in order to thrive.)
Another good reason to quit without having another job lined up is if you discover that something illegal or unethical is going on at your company. Not only do you not want to contribute to a shady enterprise, you could get caught up in or even implicated in criminal activity if you don’t leave soon enough.
Sadly, this happens all the time. Lars, another one of our listeners, was once indicted for insider trading at 27. The other guys at his firm pinned the whole thing on him, and they wriggled out of it unscathed. His parents had to hire a lawyer and fight the charges to prevent him from going to prison while the a-holes who actually profited from the insider trading walked away.
These are truly dangerous situations, even if you’re just tangentially involved. If Lars had caught wind of the crime in advance, I would have told him to resign immediately.
(And by the way, if you ever do find yourself in that situation, document everything you see and report it to the proper channels — management, HR, law enforcement, etc. — and book a consultation with an attorney. It’s the right thing to do, but it’s also a CYA move. That’s just Jordan “I’m a lawyer but I’m not your lawyer” Harbinger talking here.)
Set Your Course, Even If You Don’t Have a Destination
Whatever you decide, I encourage you to figure out the direction your ship is heading, even if you don’t know which continent you’re going to hit. As the famous Tolkein quote goes, “Not all who wander are lost.” To that I would add: “IF they have a good inner compass.”
That means getting clear on your goals, intentions, habits, and mindsets. It means coming up with a basic plan for how you’re going to spend your time off — whom you want to meet, whom you want to get closer with, which skills you want to hone, which ideas you want to explore, which space you want to focus on, and which attitudes you want to embrace.
In other words — what kind of person do you want to be on the other side of the job you have now? Figure that out, then work backward to the behaviors you’ll need to adopt to become that person.
Of course, if you have a job offer in hand, or you know exactly what you want to do next, or a great opportunity just falls in your lap, then don’t overthink it. Lock that down before you quit. There’s no need to take extended time off unless you want to.
But once you decide to jump ship, it’s time to consider some practical concerns. Starting with how and when you let everyone know you’re heading out.
Give your notice.
Once you decide to leave, you’ll have to notify the people you work with. This can be a tricky dance, so here are some principles to consider when crafting your goodbye message.
Consider your audience.
If you work at a massive multinational corporation with loose bonds, a workplace where people come and go a lot, or an organization run by people you don’t really care about, then shooting off an email to your boss saying, “Them’s my two weeks dawg, PAYCE!” might be totally fine.
(Or, you know, some version of that. Just make sure you spell “dog” as “d-a-W-g” in the email, for street-cred purposes, yo.)
But if you work at a small business or startup where you’ve formed deep connections with your colleagues, or you’ll be leaving relationships that you want to protect for the future, then you’ll want to have that conversation in person, and it should be very thoughtful.
The content and format of your notice should reflect the person receiving it.
The stronger your relationships in the workplace, the more care you should put into your notice. You owe it to your colleagues. That usually means breaking the news to your boss in a one-on-one meeting, and then following up with a larger email to your other coworkers.
The more distant and transactional your relationships, the less you have to worry about protecting them. But even in those workplaces, I still recommend being respectful. No matter the organization, it’s always tough when a boss loses an employee, and most bosses (except truly toxic or shady ones) deserve a thoughtful goodbye.
So if you’re breaking the news to a distant senior VP who oversees 50 people in a call center that experiences a ton of turnover, you can probably give them your two weeks by email and feel secure in that choice.
But if you’re breaking the news to the founder of a family-owned business who personally hired you, you probably want to schedule a face-to-face chat and share your reasons for leaving.
This is basic etiquette, but I’m always amazed by how tone-deaf some people can be when they’re leaving a company. Maybe because that decision is, by definition, self-interested. But that’s why you have to step outside of yourself and consider the context.
Break the news in the right order.
Years ago I worked with a young lawyer who told all his peers over drinks one night that he was weighing a job offer from another firm. The next day, one of the partners called him into his office, clearly hurt, and confronted him about it.
My friend was caught out. He then had to tell the partner — who was the one who advocated for him being hired in the first place — why he was leaving after the partner had already gotten wind of it. Obviously not an ideal situation.
If you’ve decided to leave, your best policy is to keep that information to yourself until you’ve told your direct bosses.
They deserve to know first. Then you can notify other executives through formal channels. And then you can break the news to your coworkers when you’re ready.
Learning that an employee is leaving is critical information in any organization. I would keep that information close until you can thoughtfully share it with the people who deserve to know first. If you tell anyone else in advance, make sure it’s someone you absolutely trust. And know that you’re still taking a risk. The water cooler is real. Word travels. And it could seriously compromise the tenor of your exit.
Share your reasons for leaving.
When you quit, you’ll have to tell your bosses why you’re deciding to leave. If you’re leaving to take a new job, that’ll be pretty straightforward. If you’re leaving because you’re unhappy, that’s a trickier conversation, and you’ll have to be delicate.
How honest should you be about your reasons for quitting? Again, that depends on the nature of your relationships. If you’ve worked closely with a boss you admire, you probably owe them more of an explanation for why you’re leaving. If you’re not as concerned about honoring or protecting those relationships, you can afford to be vaguer.
In general, I think it’s smart to share your reason for leaving — even if it’s a little difficult to hear — up until the point it starts being hurtful or stops being useful.
For example, telling a boss at a difficult workplace that you’re taking a new job with a more supportive culture and better work-life balance is a diplomatic way to say, “This place is too toxic for me.” But unloading on them for 45 minutes about everything you hate about their office probably isn’t doing anyone any good. Unless they ask for very pointed feedback, you’re not obligated to tell them every single reason you have for bailing.
Your best bet is to share the headline: “I’m leaving to do X, it’s calling to me because Y, and I decided to pursue it because Z.” If your boss asks for more insight, then you can share a little more, and see how it goes.
Read their cues, respond to their interest, and whatever you do, make sure what you share is in a spirit of helpfulness rather than spite, regardless of how tempting it might be.
Years ago, after a summer associateship at a hoity-toity law firm, the partners asked me for candid feedback about my experience. I held my tongue, sensing they didn’t really want to know the truth. I was shocked when they ended up giving me a job offer, given how awful the whole experience was, but it was helpful to have that offer in hand when I went into the job market.
So you also have to balance the value of candor with the need to protect your own interests. For me, the defining factor is whether the people you’re leaving want and deserve to hear the truth — and how they’ll use it.
Figure out a fair time frame for leaving.
How much notice should you give before you leave a company?
As it happens, the standard two weeks’ notice actually isn’t sanctioned by state or federal law, although two weeks is generally a fair amount of time to wrap things up and give your employer a chance to find a replacement. Ultimately, though, you get to decide how much advance notice to give.
Once again, the nature of your job is a huge factor here.
If leaving within two weeks would throw your team into chaos, then it’s probably a good idea to stick around a little longer. If you’re leaving a super complex role with tons of dependencies and milestones, you might even give two or three months’ notice. I have one friend who landed a new job and negotiated a start date four months out, because he told his new employer that he absolutely owed it to his old company to make sure they were set up for success without him.
Your relationships with the product and your colleagues also matter here, too.
If you believe in the mission of the company and you have strong bonds with your teammates, you probably won’t want to leave them in the lurch. If you still have positive regard for your old employer, I think it’s usually worth sticking around for at least a few weeks.
In my experience, your exit timeline is a great thing to bring up at the end of your conversation with your boss.
After breaking the news and telling them why you’re quitting, one of the best things you can say is, “I know this hasn’t been the most fun conversation, but I’m going to do everything I can to make the transition as seamless as possible. I want to make sure you guys are set up well without me, and I’m here to help in any way I can.”
Which actually brings me to a bigger principle — probably the most important.
Make a helpful exit.
I get emails every week from people asking how to preserve their relationships with their boss and peers when they leave a job.
Be as helpful as you can be on your way out, I always say. Find ways to make the transition as smooth as possible. And do everything in your power to set your team up for success after you’re gone.
Tying up loose ends before you quit isn’t just a considerate thing to do. It’s also how you protect and even deepen your relationships on your way out the door.
Depending on your role and workplace, that might mean:
- Wrapping up open projects or action items and handing them off to the right people
- Automating/systematizing your responsibilities, so that they can continue without you or be easily picked up by another person
- Finding and training your replacement, maybe with the help of a handbook you create to capture your responsibilities, key processes, principles, etc.
- Transitioning client/vendor/stakeholder relationships to new people so there’s no interruption to the business
- Anticipating problems and questions that will arise after you’re gone and making yourself available for questions and ideas on your way out
- Taking out a few of your favorite colleagues to coffee or lunch to thank them for their contributions, discuss the transition and cement your relationship
But even more important than the practical stuff is adopting the right attitude during your transition.
For some folks with a new job lined up, the last few weeks are just a chance to run out the clock while they collect a paycheck. In the process, they miss opportunities to leave a legacy and grow closer with their colleagues. Some of them even compromise their colleagues by not setting them up for success once they’re gone, which is a great way to burn bridges on your way out.
But employees who focus on being helpful on their way out the door are employees you can’t help but love, even when they’re disappointing you by leaving. Adopting that mindset is hands-down the best investment you can make. It’ll pay dividends with your old managers for years. You can then build on that goodwill and invest in those relationships long after you leave.
The Power of the Goodbye Message
One last practical tip here: Take the time to craft a great goodbye email to your colleagues.
In that message, take a few moments to really consider what you appreciated about this workplace, how you’ve grown, the accomplishments that meant the most to you, and your well wishes for the team after you’re gone. The more specific, meaningful, and even funny you make this email, the more impact it will have.
You can also share where you’re going next, if you feel comfortable. Most people will be wondering, and sharing your next step is a great way to build your brand and reputation.
I also recommend ending this email by saying that you’re always available if anyone wants to get in touch. Include your personal contact information and invite people to reach out. Be open and friendly, even if there are colleagues you’d rather not hear from. You usually can’t go wrong leaving the door open on your way out.
A killer goodbye email is one of the best arrows in your quiver to make a positive exit. Put in the time to make it sing.
Share some thoughts on your way out.
Darren, a friend of mine who worked at one of the early electric-vehicle competitors to Tesla, has one of the greatest quitting stories I’ve ever heard.
After half a decade of working with the CEO — who hired him out of college and became a good friend — he decided to start his own company.
Before he officially wrapped up, he sent the CEO a brief memo sharing some insights and advice for the company as a whole. In that memo, he laid out his predictions for the industry, the challenges he believed the company would face in the next three years, and what operational changes it would have to make in order to survive.
The way Darren told it to me, he was actually quite blunt about the mistakes the company had made — mistakes that actually contributed to his decision to leave. But he felt that being honest was actually one of the greatest gifts he could give his boss on his way out the door.
He was right. The CEO read his memo and called him a few hours later to talk about it.
“This wasn’t the easiest thing to read,” he said. “But it was one of the most important things I’ve read in a long time.”
The CEO then incorporated Darren’s ideas into his new strategic plan after Darren left. That memo is still being circulated at the company today.
So I wasn’t surprised when Darren told me that he and the CEO are still close, and that they talk shop on a regular basis. Then, a few months ago, the CEO invited Darren to consult for the business — years after he quit.
I think about Darren a lot when I think about how to leave a company. He embodies all the principles we’ve been talking about: being helpful, being collaborative, being generous up until the very end. He’s a great case study in how far candor, hard work, and generosity will get you.
But you don’t need to work at a fancy start-up to have that mindset. The same attitude will get you far if you’re working at a restaurant, a mechanic shop, a drop-ship business, or a university. All organizations run on the same principles. You’ll never go wrong giving as much of yourself as you can until the end.
So as you head out, consider sharing a few insights and recommendations with your bosses. It could be a casual conversation in the break room or a formal memo by email to top executives. It could even be pulling a teammate aside and encouraging them to pursue an opportunity that you couldn’t while you were there. As long as you’re respectful and open when you do it, you’ll hit the right note.
That’s how you leave a mark. And give a gift that’ll keep on giving long after you head out.
The greatest job-quitters I know, like Darren, are still in touch with most of their old colleagues. They don’t view the end of their time at the company as the end of their journey together. They know that their relationships will last much longer than the job, and they invest in them deliberately.
For many people, quitting is the end of the story. “Done with that place!” they think. “No more tedious emails, no more pointless meetings, no more lame bagel breakfasts listening to Trish!”
(Which, to be fair, might be an appropriate response if you hate the place you’re leaving. But even the worst workplaces have one or two gems.)
But there’s another way to look at this transition — that quitting is just the beginning of a new phase of your relationship with an organization.
So open up your aperture a little bit. Once you leave, pick the handful of people you like and admire, and stay close with them. Keep investing in those relationships. Find ways to help them out. You’ll be amazed by how those relationships pay dividends down the road.
Abel, a listener of the show, recently told me that he quit his job in sales to pursue a more lucrative position as a corporate recruiter. In his last two weeks, he not only found his replacement, but brought in three other great candidates to the business.
His HR managers, amazed by his ability to recruit talent, asked him how he found good people so quickly.
He told them it was his favorite thing to do, and invited them to hit him up if they ever needed help finding more candidates.
Sure enough, a couple of months later, his old HR managers asked him for help filling a few open roles. This time, he formalized the relationship by bringing his old employer on as a client in his new recruiting firm, and earned a killer commission in the process.
In one fell swoop, he had built his book of business at his new company by adding value to his old one.
Of course, you don’t have to benefit in such a literal way in order to help your old company. The benefits could come in many other forms: introductions to good people, access to valuable information, insight into new opportunities, greater negotiating leverage and job security, and stronger connections in general.
Plus, the colleagues you continue helping are on their own journeys. Who knows where the guy who worked down the hall from you will end up in a few years? Who knows which job openings, ideas, and experiences you might learn about if you stay close?
The more you invest in your old colleagues, the more you help them grow, the more opportunities will organically flow back to you.
So my final piece of advice is to stay close and stay connected.
Keep adding value to your old colleagues long after you quit. If you know they need talent, refer candidates to them. If you learn that they’re struggling with sales, send new clients their way. If you hear that one of your old peers is looking for some guidance, reach out and offer to lend an ear. In my experience, you’ll never regret putting in that time.
A New Lens on Quitting
Let’s be honest: Quitting is stressful, even if your next step is exciting. You have to worry about whom you tell, how you tell them, and how that news will be received. It’s never fun telling a company that you’re moving on. It’s basically a breakup, except with multiple people at once. (And you don’t get to keep their hoodie or record collection, so it’s even harder.)
But if you reframe the situation by a few degrees, quitting can become an incredible opportunity. It’s actually a chance to explore your reasons for making a major change, to alter the trajectory of your life, to create new forms of value for your colleagues, and to deepen your relationships.
It’s strange that all of these upsides could come from such an unpleasant conversation, but that’s the power of approaching this situation with a new mindset.
So as you navigate this big decision, I encourage you to think of it less as an awkward obligation and more like a transitional state that can serve up new opportunities. The end of your time at a company doesn’t have to be the end of your connection to it. It can just be a new phase of a relationship that will evolve in exciting and surprising ways.
Focus on nurturing that relationship, and you’ll find that quitting is far less daunting than it seems — and far more rewarding than it looks.
[Photo by Marten Bjork]