Moving On
Is it ever too soon to quit a bad job?
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You started working at a company a month ago, and after the honeymoon period, you have a sinking feeling that you made a huge mistake.
Maybe the person you thought you were going to work with is leaving. Maybe the decision-making process doesn’t actually include you. Or maybe you’re learning that the company culture just isn’t a great fit.
We hear flavors of these stories all the time... The question everyone asks is: Can I quit even though I’ve only been there for ____ (insert seemingly short timeframe)?
Yes.
Quitting is scary, especially for overachievers. It feels like giving up, admitting defeat, and letting the world know that you made a mistake. So you question what you know, in hopes that you’re wrong, and that it’ll get better.
But moving on quickly can be a great decision. Just take a look at former YC founder and Stripe engineer Laila Chima’s story:
We talked to Laila about her experience: The unnamed startup Laila joined was one she’d committed to nine months prior to graduating. By the time she came onboard “The person who hired me was on vacation, and when he returned, he quit. Everyone who hired me had quit. There was a lot of churn and in-fighting. As a new grad, I needed more guidance and mentorship to succeed.” Without it, she realized she wouldn’t be able to work on interesting things.
From the vantage point of a college senior, Laila had been through an exhausting recruiting process — including inevitable rejection — and jumped at the first offer she received. Then, when she realized things were going south, she wasn’t in a financial position to quit. After bombing an interview with an alternative prospect, she remembers having a panic attack on the floor of her roommate’s bedroom.
She decided to message some friends from Stanford to see if they were also unhappy at work — i.e. “maybe this is par for the course?” She was surprised to hear one of her friends respond “actually I’m pretty happy at work — we’re building some cool things.” Laila dug in, and that’s how she got connected to her next opportunity: a seat on the Stripe rocketship.
As we’ve always said: the best opportunities come through great networks.
If you’re considering quitting, we’ve put together a list of questions you should ask yourself as well as our best advice on how to say goodbye with grace.
Questions to ask yourself if you’re considering quitting:
Do you see a future for yourself at the company? Ideally, every role you take should set you up for better opportunities in the future — because you’re gaining skills, experience, and relationships with people who believe in and can vouch for you. In every work experience, you should be able to point to things you’ve owned and impacted. You should be able to tie your contributions to the success metrics of business. Reverse engineer your future resume: Will you be able to look back on this experience and share examples of how the impact you’ve made will contribute to your success in your next role? Is there a path to professional growth at this company? Write down the things you care about and want to work on, and see how the opportunities you have at this company line up.
In the moment, quitting a job can feel like your world’s imploding — especially if you’re not sure what’s next. But if you’re working somewhere that’s not a good fit, and you know it’s not salvageable, not quitting is ultimately worse for you. First, there are opportunity costs — your time is your scarcest resource. Second, if you feel so negatively about work, it’s likely that your colleagues see this; why stick it out until you eventually get fired? Careers are long and there are plenty of other opportunities. Don’t stay at a company that isn’t a great fit for you because you’re adopting a scarcity mindset.
Is work a constant emotional suck? All jobs have stressful moments. But if you’re waking up every day dreading work or constantly venting to your partner and friends about how you hate the people at work, or how frustrated you are at their incompetence, or how you’re not able to get anything done, there’s likely a bigger problem.
There’s a difference between being occasionally frustrated at work and feeling disempowered, unable to communicate openly about how you feel, and always being frustrated or angry — the latter feels like being in a bad relationship. Work should, for the most part, bring out the best in you. It should be challenging and engaging. You should feel like your strengths are high impact for the growth of the business, and you should feel valued by your coworkers and leadership — and conversely, respect them. If none of these are true, it’s time to consider quitting.
We suggest using the heuristic: “you can quit, but don’t quit on a bad day.” Wait until it’s a “good day” so you know you’re not just at the trough of an emotional roller coaster. If, even on the best day, you feel like quitting, then quit.
We’ve seen friends talk themselves out of quitting by reasoning that things will get better “if:” they get promoted, the company had more headcount, they hit the next OKR, or the company landed one big project/customer/client/etc. Banking your work happiness on X or Y happening is always risky. Remember that companies don’t owe you anything. You should feel pretty good even in the doldrums of work. If you don’t, diagnose that right now instead of waiting for “one day soon.”
Part of knowing whether you’re making an overly emotional decision is knowing yourself. Do you have a short attention span or lower grit than you’d like? Then stay a bit first. Do you typically love the long-haul and have an infinite ability to grind, but you’re just itching to leave? Then run.
Our best advice on how to actually quit:
Establish a decision-making process and commit to the outcome. What inputs do you need to decide to quit? Do you first want to talk to your manager or do you want to chat with colleagues on other teams to scope out potential opportunities? Give yourself a deadline to gather these inputs and make a decision. After this date, make a resolution that you’re not going to be swayed by new info and that you’re going to commit to a decision. Once you’ve made this decision, don’t re-evaluate for anything other than the most extreme reasons. Be decisive. Reorient your world to the new you, to the new job, to the next project.
Don’t burn bridges, but don’t go out of your way to please people. As Laila says, it’s ok to tell your manager, “this is not for me” or “this is not what I signed up for.” If your manager is a reasonable person, they’ll understand. Some founders however, won’t have a “reasonable” reaction to your quitting — but try to remind yourself that this reaction probably isn’t all about you. Founders will have their own insecurities and stressors that color their reaction to an employee leaving. But do quit gracefully: give at least two weeks notice and potentially even offer to be helpful in finding your replacement in that time (the latter is more important at a resource-strapped small company). Stress the positives of the experience you’ve had, and don’t make quitting an opportunity to point out to everyone all the things that went wrong. Don’t waste your time dreaming (or indulging your resentment by hoping) that your feedback (in exit interviews or what not) is going to fix anything. Too late for that. You’ve moved on, so move on — your time should be spent on what’s next.
Do double down on the good relationships you’ve built at the company. Tech is a small world. If there are colleagues you particularly enjoyed working with and respect, let them know. The best way is by pointing out specific things you appreciated about working with them: “I’m moving on, but I loved working with you on X and Y, and I hope we get the chance to work together again one day.” Share your personal contact details, and when you do leave, stay in touch. You never know how you’ll be helpful to each other in the future. Careers are long, the tech community is small. My former manager invested in the FYSK fund and brought in another one of our former colleagues to invest as well. This wouldn’t have happened if I hadn’t left on good terms and kept in touch with them over the years.
Learn from your mistakes. If you’re quitting not long after joining, it’s likely that you just had a lapse in judgment. Don’t make the same mistake again. Maybe you joined something pre product-market-fit and you felt like running the idea maze with the founders wasn’t the best use of your skills. In your next role, look for something more mature. Maybe you didn’t spend enough time doing diligence on the company — next time, try asking the founders these questions during the interview process.
Own your narrative. Write it down. You’re always going to be asked why you left, and you should have a great story for this that doesn’t diss your former company. Write down these three things: 1) What I expected before I joined; 2) What I got or what did not meet my expectations; 3) What I’m looking for that’s different in my next role. Writing this down will help clarify your thinking, make it easier to tell your boss why you’re leaving, and help you tell your story in future interviews. Ideally you also have a narrative that ties it all together with a somewhat upbeat take on the positives of the experience.
Not everything has to be on LinkedIn. If you were only at a company for a few weeks to a few months, why even put it on your LinkedIn? The narrative of “I don’t want to have gaps in my career” is a bit outdated nowadays. If you really need to explain a gap in your career, you can always make up a fun LinkedIn entry about taking a career sabbatical to double down on your pickleball skills. For comedic inspiration, my brilliant friend Stan, who has changed jobs 4 times in 4+ years, has the best LinkedIn I’ve read.
Run towards something you’re excited about versus running away. If you’re experiencing all the negative and stressful feelings associated with quitting, it’s probably hard to make a great decision about what to do next. It’s just hard to think clearly under duress. If, financially, you know you can’t quit before getting another offer, make sure you’re still focused on finding something you’re excited about, rather than jumping at the first opportunity just because you’re anxious to leave.
If you’re able to take time between quitting and starting something new, use this time to reflect on what you want next and approach the job search with fresh perspective and renewed energy. Writing can be a really productive way to reflect on your experiences — and be helpful to others. When I left a startup, I spent the summer afterwards writing about my experience being the first business hire (in case you’re curious, it’s A Generalist’s Guide to a Career in Tech). Medium
Finally, If you’re thinking about quitting, but don’t know what you want to run towards, join us at a Founders You Should Know showcase. We do a ton of curation and diligence on the companies we feature, and we believe they’re at a good risk-adjusted time to join (i.e. growing quickly, often lots of revenue, but still plenty of upside and growth ahead).
The best opportunities in tech come through the highest quality people networks, and the companies we feature are nominated by top-tier investors, other FYSK community members who are currently working at those companies, and founders who previously presented at the show. It’s good to get as much signal as you can on startups you’re considering.
In short, don’t be afraid to quit if your current job is just not a great fit. There are plenty of opportunities out there that can use your time and talents in a way that makes you feel valued and impactful. You just have to do the work to find them. And we’re here to support you.
PS. If you find an exceptional company as you’re interviewing — even if it’s not the perfect fit for you — send them our way! Many of the companies we feature have actually gone through the diligence process of other FYSK members who have attended our show previously. If you had a great experience interviewing there, and you were blown away by their growth, or you were impressed by the founder, please nominate them so others here can meet them as well.
Thank you to Laila Chima, Stan Chen, and Ivan Zhao for all their incredibly candid insights and valuable insights to this piece. And a huge thank you to JLai for his remarkable editing and contributions to bringing this piece to life!
Laila’s decision to quit a startup soon after joining ultimately led her to an engineering role at Stripe. She’s also a former YC-backed founder. If you’re looking for career coaching by someone who’s been through it, Laila’s offering 1:1 sessions — reach out to her here!
Stan is like a juggernaut at quitting and landing on his feet. Four jobs in a little over 4 years? Check. And he’s still eminently employable — a fact that we attribute to his brilliance, good humor, and great hair. Stan’s sharing his super candid advice with you because we asked him nicely, but he asks that you please refrain from sharing this piece with any of his former bosses. 🙂
Ivan is a designer and engineer with a love for interaction, graphics, and type. He’s also a risk-taker when it comes to joining things early — and quitting them. Ivan’s humble enough to admit to his mistakes, move on, and share them with you in hopes that you’ll benefit from them.
This is such apt advice, and helps to destigmatize the widespread dogma that "short hops on resumes are always bad." On the contrary, self-awareness is a feature (NOT a bug), and "calling it" quickly when the lid doesn't fit the pot can actually serve a more productive narrative vs. trying to tough it out and having the fit devolve further -- this can diminish one's confidence and yield poor references because you're likely not going to be your best in a job that you know is a bad fit. Thanks for sharing! (whatwoulddaledo.substack.com)