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I took a big risk these last couple of months and started working for a startup catering to nonprofits/schools/healthcare orgs and I am the only person with my role and responsibilities
Before I had only worked in really big companies that had a general purpose and I was one of many people doing the same thing. I find it so much more meaningful to build from scratch and do everything myself instead of working in a large team of others doing the same as me. It’s valuable if you prefer that but for me I really enjoy the chance to work independently and get specific on my purpose

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LMFAO this plot twist!!! I know you guys have been rooting for me along this journey so Iā€˜m more than happy to continue oversharing.
A few months ago, I asked to cross-train into my current company’s core revenue-generating business. They were receptive, but the process kind of stalled out, so I started to look for other opportunities because I really am ready to move into something new, and there’s no future in my current career track.
After I had already started the interview process, I finally got the green light to start! I ended up doing so well at my first assignment that the team I’m training with said I’m progressing unexpectedly quickly, and they were genuinely impressed. The work is pretty precise and strategic, and the assumption going in was that the learning curve would be steep and take some time to adjust to, so it came as a surprise that I took to it so quickly.
Now I’m wondering if chasing novelty and short-term gain would mean walking away from long-term growth, especially after building strong relationships and trust across the company, all the way up to executive leadership…
I have this pattern of fantasizing that the grass is greener on the other side, sometimes to the point that I disregard who I actually am. I thought I wanted to develop entirely new skills, but this work uses my existing strengths in a new and meaningful way, and it may be a better fit than I realized. This is a lucrative and highly gatekept profession, so being given the opportunity to learn from successful veterans in the field is incredibly rare, especially for someone without a formal education like me.
If I stay and commit to this role, the potential compensation increase would match or surpass the one I’d get from leaving—effectively doubling my income, while staying fully remote with a flexible schedule and great benefits. I was kind of into the idea of LARPing as a girlboss but honestly I love sitting around all day with Benny and Bunny without even having to wear pants.
I’m going to see how things unfold, but I might already be exactly where I need to be 🫢
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A senior-level colleague from a different department at work asked me this when we were collaborating on a project that's outside the scope of my regular job. I answered honestly that the work I do is not something I'm passionate about and I've done it out of necessity/because I lacked other opportunities, and that I would prefer to do something that's more intellectually stimulating and impactful.
Since that time he's been guiding me into opportunities to grow and develop lots of new skills and advocating for me along the way and it's been really nice! One of the best things to happen to me this year and it was really nice to have someone pick up on that and ask me.
Dec 11, 2024
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I’m in a similar boat where my career is something I enjoy, but I cannot deal with the people I’m working with. What I’ve found is that if you’ve got the time, doing little creative projects for friends/ people whose missions you support is a great way to build a portfolio and strengthen connections. You can do it for money or favors, either way you get the satisfaction from doing your work, the physical material to use if (or when) you start looking for employment elsewhere, and a better connection with the person you worked for so they’ll be more likely to bring you back for another project!
TL;DR - Freelance in your spare time, but don’t take a project you wouldn’t be proud to put your name on, don’t work for a person you wouldn’t want to be associated with, keep all that you can, and help bring othersā€˜ missions into reality without sacrificing your own values!
Jun 11, 2025

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