When You Feel Like Quitting Your Startup

Don’t leave a startup because of politics or a bad manager. Quickly-growing organizations are also quickly-changing organizations; and these things have a way of working themselves out.

If you’re at your wits’ end and can’t take one more day, here’s my advice: pretend like you just resigned. You just met with your direct manager and announced that you’re leaving. You’ve been thinking and talking about it for months, and you just pulled the trigger. You’re giving two weeks’ notice so you can wrap up and transition your work, then you’re free.

Now that you’ve already put in your notice, you don’t have anything to lose by speaking your mind and giving immediate direct feedback on the things that are causing you to leave. Have a 1:1 coming up? Well this is your last one, so don’t just give status updates—tell your manager what’s broken and what’s going wrong for you. Haven’t had a 1:1 in three months? This is your last chance, so schedule one right now so you can tell your manager how you really think things are going and what could be different if you hadn’t been holding back your thoughts for so long. Ask your manager everything you’ve ever wanted to know about cultural problems and bad company decisions so you can get some closure before you leave forever.

Your coworkers and friends at the company? You haven’t told them you’re leaving yet and you only have a little bit of time left, so get to know them better, learn everything you can from the good ones, and make sure the ones you like and admire know it and know why. When they find out you’re leaving, they may not be surprised, but they’ll be sad. Make sure you give them a great last impression so they’ll genuinely wish you well in whatever you do next. Make sure the best ones and the ones destined for success will want to hire or work with you in the future under much better circumstances.

If you get an e-mail that would’ve really bothered you before you quit, now you get to politely explain why what someone just proposed doesn’t make sense, why their idea would be bad for the product or the culture, or why someone can’t treat their colleagues or reports that way. Call them out. Call every single thing out you see that’s wrong. You have friends at the company that will be staying, and by sticking up for them, you can make their lives easier. Don’t let anything slide, this is what got everyone here in the first place. So write what everyone’s thinking when they see that email. Write what important things someone didn’t think of before they sent it. Of course, even though you resigned, you don’t want to burn any bridges so you won’t be belligerent or rude, but even if you rock the boat, there’s nothing they can to do you because you’re already leaving.

At the end of two weeks, so how you feel. You know what I think? After doing this just a few times the first day or two, you’ll feel completely different. You’ve released your resentment and frustration by giving automatic, candid and completely honest feedback as soon as something happens. Doing this just a few times after holding it in can be so liberating it’ll change your entire perspective. You have no idea how much say you have in a company until you start actually saying things. You may have thought you have already stated your case and aired your grievances, but until you don’t let any messed up thing happen without someone recognizing it as such, your manager and everyone else may not have understood what you were trying to tell them or just how bad it is.

If, instead, after two weeks of treating every interaction and day at the company as one of your last you feel as negative as you did at the outset, or you felt better about some things but you still have the fundamental concerns, you’ve tested and proven your hypothesis and the conclusion is to leave. You’re exactly where you need to be, and now with certainty. That’s how to make a big decision. Congratulations!