When to quit your job & how to do it gracefully
... so that your co-workers hate to see you go, but love to watch you succeed
Well, I’m hoping the title didn’t give it away but… I quit my job! And got another one. So, while it’s fresh in my memory, I want to share how I went about it.
To get ahead of the one spicy comment that I always get about not having groundbreaking advice—disclaimer: this is not groundbreaking advice. But it’s the advice I wish I’d personally gotten before going through the process and learning it the hard way, and I do believe in the value of having it be all in one place, easily digestible, and written by someone who’d been in your shoes recently. Hope this is helpful!
When to quit your job
Lots of people aren’t happy at their jobs. That doesn’t necessarily mean that they should all quit.
In fact, sometimes the difference between hating your job and enjoying it really is your own perspective. Put aside the self-pity and think deeply about the source of your misery. Do you have clear line-of-sight into the ‘why’ behind what you’re doing? How long have you been unhappy—is it a ‘this week’ or relatively new problem? Have you been in your role long enough to get over the ramp-up period? Have you got the structure and support to change course (whether it’s your team, manager, or scope) within a reasonable timeframe? Do you have realistic expectations for this role?
It’s easy to believe—especially when you’re unhappy—that there are perfect jobs out there, and it’s just up to you to go and get it. Nothing reinforces that false belief more than just scrolling LinkedIn for jobs and seeing shiny, sexy job descriptions at hotter, more interesting-looking companies. But I’ve learned the hard way that it’s much more productive to know what your personal priority stack is, and differentiate between your true dealbreakers (“My job must [be in a certain industry or have XYZ in the title]”) and your nice-to-have’s (“It’d be great if my job [paid me at least 20% more than my last role]”) so you land in a role that energizes you, warts and all. There is no perfect job. That said, life is short. There’s no need to be a martyr if you’ve done the critical self-reflection and know that there’s just not a path forward in your current role that excites you enough to endure in the interim.
So, consider leaving your job if:
Hating your job is affecting your personality. At my last role, I got asked to take on an additional area of focus: technical integration of our product with health plans. No offense to all the healthcare heads out there, but for me personally, this was about as far from my interests as it gets. I tried—I really tried—to attack this with zeal, but the days were starting to stack up with more and more meetings that were completely draining and frustrating, exacerbated by an ambiguous team structure. There are good days and bad days on any job, but I was starting to feel skeptical, annoyed, frustrated, and exasperated all the time. Nights and weekends included. It was bleeding into my life outside of work. One day, I realized that this job was beginning to make a permanent impression on my personality: I’m an excitable, happy, naturally optimistic person, but I was becoming cynical, suspicious, wary, and easily inflamed.
You’re no longer building skills that will help you get your next role. Read that again. Sometimes you’ll be in a role that you know isn’t forever (my entry-level cuties, I’m looking at you), but you’re developing a skillset that will get you to the next level or the next role. I always advise folks to imagine what they’d like to be doing two jobs from now. The exercise isn’t intended to force people to commit to a long-term plan, but rather to validate that you’re on a meaningful stepping stone to achieving your broader career goals.
So let’s say you’re my friend and I’m tired of hearing you go off about your job every time we hang out. Your goal is to be a Director of Growth two jobs from now. I’d pull up LinkedIn and search for ‘Director of Growth’ and look at the profiles of people who match that description. What did they do in their last position? And the position before? What skills did they demonstrate to qualify for Director of Growth? Then I’d look for open roles for Directors of Growth. What do they list under requirements? Are you in a role whose duties match any of those bullet points? My point here is that we have a lot of data, publicly available and at our fingertips, to help you form an informed vs. emotionally-biased perspective on whether your current role is advancing you towards your longer-term career goals.
Getting to a role you’re happy in would require a systemic change. In my exit interview, I was asked, “Is there anything we could’ve done to keep you?” For those of you who are contemplating quitting, consider what your response would be to that question. If you legitimately believe that you could be happy if just one thing changed about your particular role, it’s worth seeing whether that’s a possibility. Is it that you’re not getting paid at market-rate—can you get a raise or have them match another job offer? If you don’t vibe with your manager, can you switch to a different team? If you’re not loving your function (marketing, sales, etc.) can you get exposure to a different one?
But if what you require is a systemic change (e.g., you don’t trust or respect your executive leadership, you don’t believe in your product) or if you can’t seem to nail down an ETA (e.g., by the end of the year, or in 6 months, etc.) for change, it might be time to start thinking about your exit strategy.
Life is short and careers are long
That was my guiding principle for navigating the transition between jobs. You never know when your paths might cross with someone at a previous company, and how you navigate beginnings and ends has an outsize impact on your professional reputation. I had another co-worker who left the company before I did, and he straight up stopped showing up to meetings in his last few weeks. I guess his rationale was, “What are you going to do? Fire me and give me a sweet severance package?” but I don’t think that’s wise. And you’d look like an asshole. We don’t want that.
Create an offboarding plan. This may sound self-explanatory to my consulting friends who are quite used to hopping on and off projects and having to leave a detailed paper trail for the next person, but be structured about your transition. I created a detailed table with a line-item for everything I handled, whether it was an ongoing, recurring, or ad-hoc responsibility, who is the right new owner (discuss this with your manager in a 1:1, and make sure that person is not surprised by this new task on their plate!) and helpful links to all the documentation you’ve created about it. This plan is not just for your manager’s eyes only: be proactive and share it across your team and with cross-functional partners to make sure everyone’s on the same page and nothing glaringly obvious is missing.
Be transparent—but gracious. No one likes an unpleasant surprise. Align with your manager but err on the side of telling everyone as soon as possible so that they can collaborate with you on the aforementioned transition plan. There’s nothing more chaotic than a Friday announcement that it’s someone’s last day.
Schedule, and prepare, for feedback sessions. Depending on your company culture, feedback is either an afterthought or taken really seriously. Regardless, it’s up to you to show up to last 1:1s or conversations prepared to ask for and give helpful feedback. Most of the senior leaders I spoke to did ask for feedback, and I was glad that I’d taken some time before the conversation to share something that was both thoughtful and reflective of my genuine desire to see the company succeed.
Do goodbyes right. I’d noticed at my previous company that half of the time, employees would depart without any notice. You’d just one day notice that their Slack account has been de-activated or wonder why you haven’t heard from someone then discover on LinkedIn that they’ve moved on. I personally think that it’s smart for companies to play the long game—again, careers (and memories!) are long—and celebrate employees for their contributions and wish them well when they move on. That said, you can play by your own rules. I spent a long time investing in this: I scheduled quick 20-minute 1:1 chats or directly messaged folks that I either worked closely with or viewed as a mentor/advocate within the company. I sent a heartfelt goodbye email to a larger subset of folks (most of whom already knew at this point) a few days before I left, and another more personalized one to my engineering team. I mention this because companies tend to shut down employees’ accounts early so be prepared and do this a few days in advance.
Spend time reflecting on lessons learned. This is hands-down, the most important piece of advice I can give to folks who are leaving. When you’ve got a new job locked down, it’s easy to give into the temptation to mentally check out and go into professional senioritis. But I took a few hours between jobs to sit down and reflect on the following:
Lessons learned at the company-level (for me, this included the insight that I don’t want to be in healthcare, and that large enterprise B2B sales models don’t excite me right now)
Lessons learned at the personal-level (for me, this included things that didn’t go so well for me—specific instances of my rushing through ramp-up on a new team, agreeing to do a task without pressure-testing it first, etc.)
What are my strengths? Do an honest assessment here, not just the marketing answer you might give in an interview.
What are my areas of improvements? Again, honest assessment.
What worked really well at this company (for me, this included ‘the 'little things’ like sharing calendars publicly for transparency, regular virtual game nights with my engineering team, etc.)
The average person has 12 jobs in her lifetime. So, throughout your career, you’ll most likely switch roles and companies several times. But it’s important to make sure you’re leaving your role (cue The Bachelorette) for the right reasons, and to execute a transition with a great deal of care. Good luck!
I think you're an excellent writer and these recommendations will really help people as they navigate their career. I'm reading this and know I need to do better in at least a couple areas, myself. Thank you for sharing! :)