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Dear Sam: How do I quit when I’m friends with my boss.

Intelligent sentiments and fun conversations don’t need to be mutually exclusive. So here are your career questions answered using a dating analogy.

Dear Sam, I have worked at the same company for 3 years, but I am ready to move on.


She’s taught me so much, really nurtured my skills and has given me key client accounts to grow my responsibility. My problem is that I want to move onto another company where there is room to grow, but I know she thinks I am here for the long term. What do you think I do?

From Henrietta

Dear Henrietta,

As a person who’d rather change my phone number and move to another state than tell a guy that I’d prefer not to share a plate of tacos while he tells me about his day, I’m going to give you some advice on how to deliver break up news.

With dates, it all depends how he asked you out. If he asked you out by text, type out the following: “I’ve had a lot of fun getting to know you, but I do not see this going anywhere.” He’ll quickly respond, “That’s totally fine, thanks for being honest. No problem.” And then you continue to enjoy your life guilt-free. If he tries to suss out why you aren’t interested in moving things forward, don’t take the bait! Just keep re-iterating that you two are better off as friends.

If he asked you out face-to-face you’re going to need a little bit more of a composed response, which is probably best on the phone. Keep it as short as possible.

Don't go into reasons, don't tell him that the thought of seeing him naked makes you want to puke.


In the work world, you can’t be quitting via text. So you need to pull your boss into a meeting room (put a time in her diary), and like with the date; keep it short, upbeat and firm. Always stay professional. Flip the situation on it’s head, if you were calling a meeting to ask for a raise, you aren’t going to leverage your personal connection and tell her that you need to money to move out of your boyfriend’s apartment.

So you don’t need to let your friendship blend into your decision to quit either. Sincerely thank her for everything and list some of things you recognise that she’s taught you, explain it’s being a hard decision, and express that you can’t wait to hang out outside of work.

You don’t need to bring your personal life into negotiations;


However, and this is important, for both the guy you broke up with via text and for your ex-boss. You can’t be weird when you see him next. You are now a robot and it’s your mission to be cool as shit. If you’re weird, it’ll make him feel 100x weirder, trust me. The ball is in your court since you did the dumping. Never bring up the text or email you sent him.


You have to act like he's your best friend's


Love Sam.

If you have a question to ask, email me at

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