Should I Quit My Job?

I’m jazzed to share some big news with you guys today: I’m taking a sabbatical.

A day or two after our wedding on June 6th, Joel and I (and Jacko of course) are packing up the new pickup truck, hitching the Airstream to the back and hitting the open road. We plan to travel for just over three months all across the country. I couldn’t be more excited … or terrified.

Photo Sep 13, 11 00 15 AM

The rough sketch of our route has us going from Rochester (where we’re getting hitched), straight out to the Grand Canyon, over to the West coast, meandering up the Pacific Coast Highway, all the way to Victoria Island and Vancouver, up into the Canadian Rockies, hitting Whistler and Jasper and Banf and Lake Louise, and then back down through Montana, Colorado and Mt. Rushmore, and then finally making our way back East to Vermont for our friend’s wedding in September.

Photo Apr 14, 1 25 55 PM

Holy shit, right?! Joel is going to make me stand in front of so many points of interest in order to take awkward pictures.

I think it’s going to be magical (… and a challenging few months of intensive exposure therapy for my fear of the dark and aversion to being cold).

This trip is not on a whim. We’ve planned and worked and saved for it. We moved from a beautiful loft in Brooklyn with a deck to a small apartment in New Jersey with a commute in order to save money. We’ve attempted to stick to an incredibly tight budget for over a year. We negotiated out of our lease early. We’ve forgone dinners out, new clothes, other trips and Christmas presents in order to save. But we were happy (most of the time) to do it.

This is a shared dream of ours.

We want to take a step back and out of the daily grind and the lifestyle we find ourselves in currently, to catch our breath and reestablish how we want to live our lives going forward. We want to be a bit more deliberate about it. We want to remind ourselves that we have choices. Not everyone lives this way, and we can design any life that we want.

Joel is part owner of his company and his awesome partners are being supportive in granting him a few months of unpaid leave. We don’t have kids or a mortgage or any real debt to speak of so, I think were looking at as many green traffic lights as we will ever see.

And so, I have a decision to make.

You see I have a full time job, too. Not necessarily one that I love, I’m grateful for it, of course, or at least I try to remind myself to be. But, what I really want is to do is be a full-time blogger. I know, super easy, right? About as easy as my best friend being a stand-up comic.

The decision I need to make this week is whether or not to ask my boss for an unpaid leave. He could say yes. He could say no. I really have no idea. I’m prepaid for either of those situations but, the question I face remains: Do I want to ask?

Argument for asking: (the argument of logic) There is no harm in asking. We’re hitting the road either way, and I might as well give myself as many options for the future as possible. He could possibly say yes and then I’d have the peace of mind of having an income again in September. With Joel at his job and me coming back to this one, we’d be in a good financial situation to do whatever we want going foward. If I could just be happy in this goddamn job, we’d have all the money we need for as long as I stayed.

And again, if my boss says no, we’re going anyway.

Argument against asking: (not to be dramatic but, the argument of my soul) I don’t want to. There, I said it. I don’t want to come back to this job. I don’t want to give myself the option to come back to this job. I don’t want to even think about this job while I’m on the trip. I want to be contemplating what I’m going to do going forward not whether or not I’m going back. I want to be free. Rip off the bandaid. Not. look. back. Asking feels like not fully committing to what  I really want and sending mixed signals to the universe … or something. Feel free to roll your eyes at me.

I don’t know what to do or why I am making such a big deal of it in the first place. I am just trying to listen to my body. As I make the decision to ask, how do I feel? As I make the decision not to ask, how do I feel? I’ve been practicing listening to my gut for years now and it’s never steered me wrong, but I just can’t really hear it at the moment.

The wedding/trip is just under eight weeks out and I feel I should talk to him about it in the very near future, if I’m going to talk to talk to him about it at all.

And so I continue to contemplate…

Any thoughts? I sure would love to hear ’em.



  1. You are empowered either way, whether you ask for leave or whether you quit, you KNOW that you are GOING. You can always quit when you return from your trip if you like, so my feeling is that I would want to extend my options to allow for time to think further about it and see what my future brings. Then, if God forbid, you do need to return to your job, then so be it. Best of luck to you! And congratulations to you and Joel! 🙂

  2. Thanks so much, Janice! I really appreciate the response. I didn’t mention that option, you’re right. I could always quit upon returning as well!

  3. Team Joelumbo! I believe you should go for it! When you get back you can decide what you want to do and how you want to do it. You have great people supporting you no matter what!!!!

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