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S2 E11: "I tripped and fell into a career I don't like. How do I reinvent myself?"

Season 2, Episode 11: “I Tripped and Fell into a Career I Don’t like. How Do I Reinvent Myself?”

If you’re new here, let me get you up to speed: personal finance is personal. And as a result, it’s also often complicated—a Choose Your Own Adventure with multiple right answers and mitigating circumstances.

Which is why it is so easy to feel stuck in your career or financial journey. What do you do when you’re just fine… but you want more? How do you overcome crippling stagnation? How do you justify leaving the safety of your established, safe career… and risk everything to leap headlong toward your dreams?

Alternatively: when is the safe and not-super-fulfilling job sometimes exactly what you need? What could you do with the excess creative mental energy that a boring day job affords?

All these questions (and much talk of Spiderman!) on this week’s episode.

This week’s question

Today’s letter comes to us from Patreon donor Marta. And it’s a long one, but full of the kind of ambiguities and complexities we think y’all are gonna find resonant af. Marta asks:

I’m writing in hope of some advice, or probably just to get out of my own head and get an outsider’s perspective, because I’ve thought about this WAY too much.

I’m in my thirties, and I moved to a Richer Country from a Poorer Country (all within Europe) a few years ago. I had some truly shit jobs for a while, but got incredibly lucky eventually, and landed in my current job in December of 2018. I work for a charity that aligns with my values very well. I have a good boss. I’m paid reasonably well—my salary circles around average for my job title in my city, though I could probably make 20% more in a bigger charity, with the experience I now have.

Trouble is… I don’t really like my job? I’m an office manager/jack of all trades assistant, and I’m damn good at it, but I didn’t choose to do it out of a passion for filing invoices and fixing trivial IT problems. I chose it because I had a wide variety of skills that you don’t need a degree for (I have a degree, but it’s purely academic), and people like me are very appealing to small organizations that want one person to fill all the gaps. It was never going to be a long-term plan; I just wanted something that would pay rent while I found my feet in a new country. I don’t want to be solving other people’s petty problems ten years from now.

Now that my two-year mark on the job is slowly approaching, I don’t know what to do. Moving to a different role in the same organization is not an option; we’re too small for that. Do I try to pursue a career in corporate/charity internal training (very appealing, no idea how to even start)? Do I try moving to a different job despite being comfortable, so my CV doesn’t look like I’m too stagnant? Do I stay and buckle down and write after hours to fulfill my dream of writing a novel? (How do I deal with the emotional fallout of never being able to publish that novel, which is very likely?)

Do I just keep this job and wait until some kind of an opportunity presents itself? I appreciate that no one can solve this problem apart from me, and it’s seven kinds of immature to expect you’ll magically give me the golden answer based on a few paragraphs of summary. But it was kind of therapeutic to just write it out and know someone sympathetic will read it. Your blog has been consistently excellent at filling long social-distancing weekends, so thanks for that! Stay safe, and please don’t let The Evil Chicken bring you down.

– Patron Marta

Many thanks to Marta for acknowledging my horrendous struggles with Tammy Two, the Chicken from Hell.

Want to read more on the topic of career advancement? We gotchu:

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