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Reader Question #18: I want to shake the dust of this godforsaken place from my feet, but I also want to keep my job. How do I tell my boss?

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Hello Captain,

For the past seven years I have worked in a fantastic office for a great company. I love my job, my coworkers are like family, and I have an excellent relationship with my boss and all of the management above me. The only bad thing, however, is that this company is located in a big city in a flat part of the country and I am done with city living. DONE. My partner and I share a vision of rural living, in the mountains, in the woods, far from urban or suburban sprawl.

It’s no secret around my office that I long for a country life, but these plans are starting to get a bit more tangible, like things might happen as early as this summer. So, how and when do I talk to my boss? Here are the things to consider: 1) this job is my only professional experience in my field, and really my only “grown-up” job, so I will need to list my supervisors as references for any new employment possibilities. 2) There is a possibility of continuing to work for my current employer after relocating on a seasonal part-time. I don’t know details, though, because it’s always been thrown around as a “oh yeah that could happen talk to me when it comes up” sort of thing. 3) While relocating could happen as early as this summer, there’s an equal chance that plans might not move that quickly. I need to either find a job (see problem one) or have a solid sense of how much I could earn from seasonal work (see problem two). I don’t want to disrupt my current professional life for a whole lotta maybes, but I can’t really get plans rolling without resolving numbers one and two.

Thanks Captain Awkward,
Fleeing the City

Dear Fleeing,

Thanks for your question.  I think the actual conversation with your boss and working things out will be the easy part of this, given the relationship you describe and given that (s)he has said “Okay, that could work, talk to me when it comes up” about the possibility of seasonal work.

What you have here is a research project, followed by a plan, followed by a decision, followed by a conversation.  Because when you sit your boss down for a conversation (this advice is for everyone), you need to have a response to the question “So, okay, what do you want?”

"Don't lose out on the chance to better yourself because you feel afraid."

A.  The Research Project: How will you and your partner live in your chosen place?  What kinds of jobs are available and how will you support yourselves?  How much do you need to save to accomplish the move and give yourself a cushion of savings for the first year?  What will you do about health insurance?  Most importantly, if your current company won’t give you part-time work, or if they say pilot that for a year and then decide it’s not worth it, what is your backup plan?

Sorry to turn into Captain Obvious for a second, I’m sure you and your partner are working all this stuff out.  Still, when you are on the verge of a major decision, it’s helpful to ask yourself two questions:

  1. What is the worst thing that can happen?
  2. What will we do if that happens?

Usually you find that you can handle whatever that is, which helps you actually make the decision and then take what comes as it comes.

B.  The Plan:  How do you see your part-time/seasonal relationship with the company continuing?  What kinds of projects, hours, and pay are you expecting?  What are your accomplishments and contributions as an employee?  Why would they be crazy to lose you and lucky to keep you?   Then complete two short writing assignments:

  1. Write your own job description for how you’d like this to work in a perfect world, with an emphasis on how this position you are creating serves the company.
  2. Write a cover letter applying for that job and highlighting all the reasons you’d be perfect for it.

You might not ever show these to your boss, and I definitely wouldn’t lead with them, but you can’t depend on your boss to plan out your life for you.  So when you do end up talking this over, you can ask “You’ve mentioned before that seasonal or part-time work is possible, how do you see something like that working?”  Your boss may in fact have a plan, so it makes sense to ask before you launch into yours, but (s)he may not, at which point (s)he’ll turn to you and say “I haven’t thought about it all that much, what do you suggest?” and then you say “I did some thinking about how I’d like things to work, let me run it by you.”  

"Announcing your plans is a good way to hear god laugh."

Now yo u have a starting basis for negotiation and you’ve done your homework and can advocate for why it’s a great idea.

If I’m your boss, I’m going to ask you “So, what do you want?” and it sounds like what you want is:

  1. You want a good reference when you seek new employment.  Easy.  If you’re a good employee and the relationship is as good as you say, your boss will speak well of you to others and want to see you succeed.
  2. A continued part-time/seasonal job with the company and 3.  The knowledge that if things don’t work out this year that there will be no hard feelings and you can continue on as before.   This may not happen.  The second you open your mouth to say you are thinking about leaving, really leaving, you may become “the person with one foot out the door, who will be the first to be laid off in times of crisis and who won’t be assigned any new projects.”  It’s human nature – bosses invest a lot of time in their employees, why would your boss continue to invest in someone who is planning to leave?  Accept that part-time employment for you might not be a good business decision for your boss.

C.  The Decision: I know it’s risky, but if you’ve done your homework, you’ve come up with a viable plan B, you’ve come up with something to present to your boss, you’ve crunched the numbers and saved as much as possible, and it’s really what you want, just move to the country already.

If you don’t have enough saved and can’t make it work right now, make the decision to hold off for another year while you save, and do not bring anything up at work until 3 months before you’d actually go.   So make the decision that in one year you are going no matter what and work toward that end.

Here’s a secret:  Sometimes you make a giant mistake and you fail.  And sometimes failure comes despite all your planning and saving.

Al Swearengen

"Pain or damage don't end the world. Or despair or fucking beatings. The world ends when you're dead. Until then, you got more punishment in store. Stand it like a man... and give some back. "

Here’s another secret:  You will survive failure.  You just will.  It’s not death, it’s just a temporary sucky time that you’ll look back on later as a learning experience.

Eleven years ago I left an okay-paying, benefits-having job in what I thought was my chosen field to move to a completely new city where I knew no one.  I brought with me a suitcase and a cat, and I shipped 10 boxes of books to a sublet with roommates that I’d never met.

That first year was very hard – there was a recession on, and I had to depend on temp work and some very odd jobs to get through – but I made friends, found work I loved, and went back to school.

Because here’s another secret:  When you make a decision and set a goal, the world lines up a little behind you in a way that it didn’t before.  I said “I’m going to leave D.C. and move to Chicago.”  Forty calendar days later, with only about $4500 in the bank, I lived in Chicago.  I packed some stuff, sold the rest, unloaded my apartment, found a new one, bought a ticket, and left.

I might have done a lot of things differently about that move if I’d thought it through more, but honestly, if I’d thought it through more I might still be thinking about it now.

D. The Conversation:

Hey, boss, remember when we talked about the possibility of staying on part-time if I moved to the country?  Well that time might come a bit sooner than I originally thought.  Can we talk?”

If you’ve done your research, made your plan, made your decision, the conversation part should be easy, because you’ll be okay no matter how it works out.  Good luck and let us know how it went?

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3 comments
  1. Stephanie said:

    Good lord does this entry speak to me. Swearingen’s presence doesn’t hurt either.

    • JenniferP said:

      I don’t know if I did the best job explaining why I went for Deadwood references with this question, but if you’re going to light out for the territories you could have a worse advisor than Al Swearengen.

  2. Lucy Looseleaf said:

    Thank you, Captain. I think I’ve been tricking myself into believing that I’m immersed in the research part of the project because I spend my spare time reading seed catalogs to plan my future garden. I can tell you all the places to buy a frosty mug of locally brewed beer in my future home, but I need to not just research the fun parts.

    I love the suggestion to write a job description & cover letter for my ideal working situation–my boss is great but he can be a little scatterbrained, and he’s the sort of person that would probably take that job description and go to bat for me with the higher ups to help me make that happen.

    I went through all of this once before, but I was 21, I had just finished college, and I was leaving the woods for the big-bad-city with nothing but an empty checking account, a pickup truck full of books, and the promise of a couch to sleep on when I got here. It worked then. I know I can do it again!

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