So I finally got my recruiter to let me take the ASVAB and OAR. I told him multiple times I’m 100% committed to joining if the opportunity’s there, but now that it’s actually happening I’m wondering how true that is.
Quick background: I used to be a web developer and was good at it. I had a stable job and had saved about $1.4M in investments, then I caught the digital-nomad bug during the pandemic and spent a lot of time in Colombia and the Philippines. I had a kid abroad—unmarried, partly a personal choice because I don’t like dating in the U.S.—and then things got messy when I returned to the States.
Shortly after coming back I had a bad bicycle accident and broke my femur. My dad, who owns the house I was staying in (a basement in Boston), decided to kick me out around the same time. I didn’t push it; arguing with him wasn’t worth it. Between the injury, a kid on the way, and losing that living situation, I panicked and quit my job to try to sort things out and take care of family.
I’ve recovered physically and I bought a house in the Philippines for my newborn. I’m 37 now, living a sort of mini-retirement there, but I’m worried long-term. I still have the $1.4M, but I need income that won’t drain that nest egg. I’ve tried re-entering tech, but there’s a 1.5-year gap on my résumé, I’m overseas, I don’t want to relocate my family to the U.S. (marriage and cost-of-living issues), and employers prefer local candidates who’ll grind for less.
Family won’t help much—siblings have their own lives and I don’t want to rely on them. Living with them hasn’t worked for me; it’s draining and sidelines my progress.
That’s why I’ve been talking to a recruiter in Guam. Military pay is a step down from what I used to make, but it offers structure, housing, benefits, and a clear path. With my degree I could aim for an officer track, and I might get into cyber or a related field that complements my background. The recruiter probably wants me to take whatever billet is available, but I’m not so intrigued by the potential career and training if it's different than my current background unless I stay military the full 20 which I really doubt I'd want since I am already likely early retired.
The downsides: I’d be away from my daughter and girlfriend in the Philippines for a while. I don’t fully trust the long-term reliability of that relationship if my gf is in USA, but longterm in Philippines is suprisingly good for us. I worry about legal and financial exposure if things go south in the U.S. (I’ve thought about prenups but still think keeping GF abroad is easiest and safest) but ultimately think the opportunity this country offers would actually steer her away from our relationship just like what I see it do to most. Base pay looks low on paper—roughly $37k after taxes for 11 months of the year—but BAS/BHA and other benefits help. There’s also the unknown of military life: will I like it, or will I regret giving up years to something that isn’t a great fit? If I get married will I lose half my investment earnings? How long will it last? Will my decisions be the best for my daughter's best long term.
Alternatives I’m considering:
- Use the $1.4M and keep the mini-retirement going, maybe take a part-time job. The only practical part-time option I can see is truck driving—flexible, portable, and reasonable pay (~$23k after tax for 3–6 months work). But it’s not a long-term career path I want, and the lifestyle/risks aren’t great.
- Try to bootstrap back into tech while overseas—build a portfolio, freelance—though re-entry looks hard right now.
Where I’m at: leaning toward the Navy because it’s structured, removes reliance on family for housing, could lead back into cyber/networks, and gives opportunities to learn and lead. But I’m not sure how committed I’ll feel once I’m actually in Guam and about to take the tests. Right now I’m even reluctant to study because my head’s been elsewhere.
If you’ve been through this, especially Navy folks, I’d appreciate candid perspectives on:
- How likely is it to transition from enlisted (or officer candidate) into cyber/IT roles? Is prior dev experience helpful?
- How disruptive is being away from a dependent overseas, realistically? Any tips on managing that?
- Practical pros/cons you saw after joining vs. what you expected coming in.
- Anything I should know about taking the ASVAB/OAR from Guam/recruiter logistics.
I’m looking for real-world advice—what actually worked, what didn’t—so I can decide whether to commit and start studying, or take a different path. Thanks.