I’m 27 and unhappy.

A post. because it’s been a while, and I miss writing.

I’ve been at my current job since the end of March. That’s what my last post was about. I took the job mostly because I wanted the chance to work for my now-boss again, partly because I knew there would be opportunities to transfer internally within this company after about a year, and a very small amount because I wanted a bit of a life challenge (more structure, more using my brain).

The other things I said in that post, unfortunately, are also still true. It isn’t my dream job (I still don’t know what that is). It’s still in software development, but I’m now further removed from actual developers, teams, and interesting technology (I didn’t know I would miss those things, but I do–on good days). I originally said that I would wait a year and then look for something else if I still hated it. That timeline has been dramatically reduced. I knew within the first few weeks that I didn’t like the job, and after a month or so, I knew that it was very different than what was actually pitched to me during the interview process. Pretty soon, I came to realize that my boss had also been somewhat hoodwinked into taking her role, and that she had also grown increasingly unhappy during her time in her job. Fast forward to early August, when she left for a 2-week European vacation and came back with a clear head and reset life goals: she told her boss that she was quitting, even with nothing else lined up, because that’s how unhappy she was. Since then, she’s been able to re-claim her previous role (also internal at the same company), but with more responsibility, higher pay, and several new direct reports. Her last day as my boss is next Friday. I’m very happy for her.

However, this leaves me in a difficult position. I’m 6 months into a job that I hate, newly responsible not only for my own duties but hers as well, and teetering on the verge of handing in my resignation on a daily basis.

My 27th birthday was on Sunday, and in keeping with my sort-of-tradition, I booked a trip. I went to Minneapolis for a few days to explore and (mostly) to get the hell away from Charlottesville. The week off work was the most relaxed I’ve been in a long time. I’ve had trouble sleeping for about a year now (maybe longer?), but every night of my vacation I slept like a rock. I even slept on airplanes, surrounded by total strangers. This is completely unlike me, but in the recent past I’ve come to be a person I don’t always recognize. I like it a lot.

I’m rambling a bit, but I’m trying my best to create an accurate record of my thought process over the past few months, since I don’t post updates here often enough to have it captured.

For the first few months I was at my new job, I daydreamed a lot about quitting and setting off on a cross-country road trip with the intention of choosing a few ‘spotlight’ cities to spend longer periods of time in, in order to gauge whether I could see myself settling there permanently. I’ve lived in Charlottesville for my entire life aside from the 8 semesters I spent at Virginia Tech, and I’m so far beyond burned out on this town that it’s ridiculous. I’ve known for a long time that I’m done here, but I haven’t had the guts to change that fact. I made a list of places I’d want to go, including the cities I thought I wanted to move to, and started looking for remote work opportunities as well as jobs located in each place. That sort of fizzled out, and I don’t remember right now exactly why.

Next up, I thought I’d apply to grad school (again). My life dream for so long was to be an architect, and I was actually accepted to a Master’s program in Architecture in 2010. I thought I’d give it another shot. What’s 3.5 more years of school? I’ve been in the working world and hating every minute of it for 4 years. It seemed like a good possibility. Then I borrowed some GRE prep materials from a friend, never opened a single one, convinced myself that I’m not good enough at math to pursue this, got stressed out by the thought of trying to cobble together application essays and terrified by the thought of asking former professors for recommendation letters, and promptly gave up on that path. Again.

So now, after my week away from the office and a small taste of freedom, I’m back to the road trip dream. I was 100% ready to give my 2 weeks’ notice upon returning to work today. I’ve been trying to find someone to rent out my house, and I’ve started telling people (mostly family) that I’m going to quit my job and finally take this trip. I talked about it with my sister this weekend, and she told me “Katie, you’ve been talking about this for so long that if you don’t do it, I’ll be mad at you. You absolutely deserve this.” It was really nice to hear validation from someone else that I am in fact deeply unhappy with my career path, the lack of any real purpose in my life, and the fact that I am still in my hometown. Another item of note is that my dad, who is the staunchest of believers that you NEVER quit a job without another one lined up first, has been fully in support of my harebrained idea for a few months now. I’ve been confiding in him about my plans for an extended trip + eventual relocation for a long time now, and he has finally come out in full support. “Just do whatever you need to do, and I’ll support you,” he says. The last person I really need to convince is myself.

So now, as soon as I can get my house rented out, I’m going.

I went back to work today and told my boss that I’ll be tendering my resignation soon. I didn’t do it today (although I so wanted to), because I know it would be foolish to run off into the sunset with a mortgage payment, no income, and no itinerary. She gave me a lot of great suggestions about how to set myself up to leave this job on the best terms possible, a list of people I should get in touch with before leaving for remote working opportunities, and a still-growing list of cities I should visit. She’s been nothing but supportive of this travel dream for a while now, but I don’t think she realized until today how serious I am about needing to leave everything behind, and what I’m willing to sacrifice in order to do it.

So as of today (and this could very well change by tomorrow), my dream is to work until the end of November or a bit into December, try my very best to line up some sort of remote work opportunity, get my house rented out, and then hit the road in January after spending the holidays with family. I envision heading south for the winter, slowly making my way across the US, with home being literally wherever I find myself that day. I realize that it sounds insane, and that I might quickly come to hate such a nomadic lifestyle, but after 4 years of hating my various desk jobs, it’s time to try something new.

I hope to be back here more often with updates. I miss using my voice.

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One thought on “I’m 27 and unhappy.

  1. WorthyStyle says:

    Thinking of you! I’ve so been in your position and it’s the most mentally/emotionally/psychologically draining thing to do – be in a job where you aren’t appreciated or it isn’t what you signed up for. Find yourself again and become your best self in a new place – you deserve it.

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