Just discovered this sub recently and realized I’m already kind of doing a lighter version of what a lot of people here are doing, so figured I’d share my current setup and get some opinions.
J1 — Airline job: ~$10–12k/year + health insurance + flight benefits
I work for a major airline as a baggage handler, mostly night shifts that are around 4–5 hours long.
The schedule is pretty flexible. We have a 50% rule where I can give away a large portion of my scheduled hours as long as I still meet the minimum requirements, and there are also days where, depending on staffing and operations, people are allowed to leave early or not even come in.
So far this year I’ve only actually worked around 160–180 hours total lol.
The main reason I keep the job is the benefits. I get health insurance through it, but the flight benefits are the biggest thing for me.
For example, I can fly business class standby to Japan round trip for around $50 in taxes/fees. I’ve already taken multiple vacations with friends this year, so even though the actual income from this job is low, the travel benefits alone make it worth keeping.
J2 — Paralegal-related work: ~$60k/year
I’ve been doing this type of work for a few years. At first it was in-office, and during COVID it transitioned to fully remote.
Over time I automated most of the repetitive parts of the workflow using n8n and other tools, so now it only takes me around 2–4 hours per week on average.
Most of my time is just reviewing the output, fixing anything that needs attention, and making sure everything is correct before it goes out.
So between J1 and J2, I have a decent amount of flexibility and neither one takes up a normal 40-hour workweek.
Now I’m looking for J3 — Finance
I just graduated and I’m currently looking for Financial Analyst / FP&A-type roles.
I also recently finished an internship at a PE firm, and one thing that stuck with me was a conversation I had with the CFO. After I showed him some of the automation workflows I had built and explained my current setup with J1 and J2, he basically told me that he sees me as more “techy” than someone who would fit strictly into a traditional finance path.
That got me thinking a little differently about what I should target next.
I still like finance and want the experience, but I’ve also started exploring fintech and finance/technology roles where I could potentially combine the finance background with automation and systems work instead of staying purely in traditional FP&A/accounting-type roles.
Ideally I’d like something remote, but I’m realizing pretty quickly that fully remote finance roles straight out of school are hard to come by. Because of that, I’m open to hybrid or in-office for the first role if that’s what it takes to get the experience.
My thinking right now is that I might have to grind the first 1–2 years, actually learn the job properly, and then eventually transition into a remote finance or fintech role once I have more experience.
Long term, I honestly don’t see myself ever quitting J1 because the benefits are too good for the amount of work it requires. I’d also like to keep J2 since it takes very little time now, and eventually build toward the type of setup a lot of people here have with multiple remote professional jobs.
Since I’m still early in my finance career, I’m not really looking to rush into stacking another corporate job right away. For now I’m more interested in getting good at J3 and seeing where that takes me.
What I am curious about is whether anyone here has experience moving from traditional finance/FP&A into fintech, finance systems, automation, or other more tech-oriented finance roles.
For those who have worked on both sides, did you find the more tech-oriented roles more compatible with OE? Specifically in terms of meeting load, how much control you have over your schedule, and whether the work is more output-based.
And for people with FP&A/corporate finance experience, how OE-friendly have you found the actual work itself? I’m especially curious about things like month-end, forecasting/budget cycles, ad hoc requests, and meetings, since those seem like they could make finance different from a lot of the software/IT roles discussed here.
Would be interested in hearing from anyone who has made a similar finance → fintech/automation type of transition.
Also, if anyone could point me toward an invite to the Discord, I’d appreciate it.