Hey Andy & Emma,

I want to move to California. And soon! Ideally, I would work remotely at my current job until I get established in my new city, then quit for a more fulfilling gig. Right now, everyone at my current job is working remotely for COVID, with the assumption that the office will return to 30% capacity in September — but no one really knows for sure what’s going to happen. It feels like a good time to broach the subject of permanent remote-work, but I feel a little guilty since I’m not planning on being a permanent employee.

When do I ask (tell?) my boss about this? How honest should I be about my plans? If they say yes to my move, do I owe it to them to stick with the job for any amount of time? What happens if the answer is no? All advice is appreciated.

Andy: Congrats on the big move! I’ve taken a risk like that: quitting a job and moving across the country. I’m so glad I did it.

Emma: I wouldn’t know you if you hadn’t! It makes me so excited for your move, Letter Writer. Just imagine who you’ll be co-writing newsletters with some day.

Andy: I also remember how complicated it felt to commit to such a big change. I too had a lot of “strategy” questions around timing, how much to tell, to whom. My situation was different — I was planning on quitting from the get-go — but I for sure wanted to do it all The Right Way.

Emma: Fortunately, you don’t have to worry too much about screwing this up. The Right Way is whatever is right for you.

Andy: Got it? Okay, next question!

Emma: Lol let’s take these one by one. First things first: you do not owe your job, your boss, or the company you work for anything more than the job you are being paid to do. And you will continue to not owe them anything if they say yes to your request to do that work remotely from California. Asking for a change does not automatically indebt you. It is important that we myth bust this out of our brains.

Andy: Extremely important. You know that Mary Oliver quote, “What is it you plan to do with your one wild and precious life?” The answer cannot be, “Whatever my company tells me I should do.” Your company does not orient its decisions around you. It makes the best decision for the business. You are the CEO of your life. If the best thing for your life’s business is to propose working remotely from California, do it for four days, and then quit, that is fine. Good people quit jobs all the time.

Emma: Next up: how and when. You have lots of options. I know that might not be very comforting — who doesn’t prefer some boundaries? — but that’s just what happens when you’re making big, empowered decisions about your life.

Andy: In your case, there’s a continuum between asking and telling, and a timeline that starts now and continues until the day you move. What you choose will depend in large part on your own sense of safety and security, and how collaborative you want to be with your boss in this process.

Emma: Don’t worry. We have examples.

Four Ways to Ask (or Tell) Your Boss About Your Exit Plan

You have a lot of freedom when it comes to talking to your boss about your exit plan. You can broach the discussion whenever it best serves you, with the level of intensity and honesty you’re comfortable with. We do advise holding some cards close to the vest — it’s in no one’s best interest to say, “And FYI I’m going to quit as soon as I find something better.” They know that already. It’s the unspoken truth we all carry with us every day when we show up for work. If you have never said those words to your boss before, no need to start now.

Here are some ways we might approach the conversation.

Get buy-in without revealing the whole picture

“I love remote work, and I think I’m going to want to continue even when the office reopens. Would it be possible to keep doing this job remotely into the future?”

Collaborate with your boss on a plan starting now

“I’d really like to move to California. And, I’d really like to keep my job. How do you think we can make both work?”

Give your boss an early heads-up and ask for accommodation

“I’m going to be moving to California on August 15. I’d love to work remotely from San Diego — is that possible?”

Inform your boss at the last minute

“Starting Monday, I’ll be sheltering in place in Monterey. I’d like to work remotely from there even once the office reopens. Are there any blockers to making this happen?”

Andy: It might feel easier to finalize your exit plan by working your way back from the things you’re scared of — like the possibility your boss will say no. What happens then? Seriously, I want to know. Will you still move? Why or why not?

Emma: You also mentioned you are interested in finding more fulfilling work. How long are you willing to keep this current job if it’s not from your dream city?

Andy: Brain dump all these questions and your fears on paper and get concrete about them. Knowing in your bones the answers to every worst-case scenario you can think up is the first step to planning your next move.

Emma: If your move is absolutely contingent on keeping this current job, then you might as well ask right now and find out the answer. Or, you might decide to wait until you have a few months of living expenses saved so you can quit in a flame of glory the second your boss dares to utter no.

Andy: One very real fear that has kept me from asking for what I want is that after they say no, they’ll also somehow punish me for daring to ask.

Emma: So draconian!

Andy: And not outside of the realm of possibility. I’ve worked for plenty of draconian bosses. But that fear means I’m trapping myself. If my company is going to punish me, I need to be free of them — which in turn emboldens me to ask for the change I want.

Emma: Good luck getting where you want to go! I believe in your quest.

Andy: Send us a postcard from California.

Good Boss Achievement Stickers: Hitting the Road Edition

Five illustrations: 1. a moving truck with "CEO of my Life" on the back 2. a guy jumping out of an airplane with the caption "Finalized my exit plan" 3. a pink car stacked high with moving boxes captioned "didn't ask my job what was right for me" 4. a stick figure at a food truck saying "knew what i wanted" 5. a stick figure giving food from a food truck labeled "got what I needed