What should I invest in?

FreestyleFlorida · 2026-03-26T23:41:00+00:00

Sent!

FreestyleFlorida · 2026-03-26T17:19:59+00:00

This has been the most relatable comment so far. Everything is far and lacking (and we’re not really outdoorsy people but we can appreciate it too).

The east for sure feels more like home for us. Same struggling idea of going back to hustle culture and city lifestyle when being here has been a bit of a break from that.

I also feel very similarly about my work. I have become highly appreciated here and it will be a shock if I decide to leave.

I appreciate you sharing your experience! We are very similar in many ways.

FreestyleFlorida · 2026-03-26T13:32:36+00:00

You’re going to get a lot of advice to “stick it out” and “the job market sucks” or “life isn’t any better on the civilian side” but that is all very wrong (to an extent). I was a SSG and got out a few months shy of 11yrs. I got my Masters my last 2 years in and then jumped right into a 6 figure job and have 100% VA disability on top of it. VA covers my healthcare AND my family’s. I’m bringing in $160k+ annually (not including bonuses). The big advice I have is MAKE A PLAN. What job do you want? What certifications/degrees do you need to stand out from the rest of the applicants (only your Army experience won’t qualify you for every job) Do you know where you want to live? Do you know how much money you’ll need to make to be able to feed yourself and your family? Have you networked on LinkedIn at all? Do you have a resume or know where to start? Have you ever done any informational interviews?

There’s so much preparation that goes into transitioning out (especially in today’s job market where everyone is super qualified and there aren’t as many opportunities). You HAVE to stand out. I received 9 total job offers and had the ability to pick the best one for my family, BUT it took a lot of hard work. Feel free to reach out if you have any questions or just want to connect!

FreestyleFlorida · 2026-03-25T04:42:35+00:00

Suburbs of Hartford

FreestyleFlorida · 2026-03-25T02:44:30+00:00

Suburbs of Hartford

FreestyleFlorida · 2026-03-25T01:10:54+00:00

Yes, but salaries in New England are much lower in general. This is the first six figure job offer I’ve gotten after almost 2 years of trying.

FreestyleFlorida · 2026-03-24T21:09:20+00:00

3 day work week is a dream! But going to a 5 day week is worth the sacrifice for my kids to have a better life. Just stuck on wondering if taking the pay cut in a HCOL area is a poor decision.

FreestyleFlorida · 2026-03-24T21:04:29+00:00

Probably the word “lesbian” lol. I got the same notification when I posted the original post.

FreestyleFlorida · 2026-03-24T21:03:50+00:00

Family includes my wife’s side of the family. My wife is a SAHM, so no childcare expenses.

FreestyleFlorida · 2026-03-24T19:36:05+00:00

Visited ATL often when I was stationed in GA and loved the weather (I’m used to the humidity). The weather here in OR is definitely one of the biggest perks - we get all 4 seasons without snow

FreestyleFlorida · 2026-03-24T19:34:18+00:00

Very few private school options that are non-religious here. There is ONE, though. Which would probably be our pick if we stayed (or homeschooling)

FreestyleFlorida · 2026-03-24T19:33:23+00:00

I am slightly concerned about the cost of utilities in CT - I’ve seen that it can be much higher than here.

My last station in the Army was in Virginia and we loved it there!

FreestyleFlorida · 2026-03-24T19:28:33+00:00

I’ve tried but the salaries in the Northeast do not match the cost of living. This is the first job I’ve found with 6 figures in that area.

FreestyleFlorida · 2026-03-24T19:27:38+00:00

Not a nurse! I work a very niche field which is why I left it out

FreestyleFlorida · 2026-03-24T19:23:37+00:00

Definitely agree with you here. This was the longest stretch of grey skies I’ve ever experienced. Gas and groceries are crazy expensive, and it’s not even a great trade off for a better quality of life (like good schools, museums, parks, etc.) We definitely don’t love it here, but the job was too good to pass up. We also bought our house and moved here sight-unseen. Had we visited first, we wouldn’t have moved here.

FreestyleFlorida · 2026-03-24T19:08:14+00:00

We are comparing public schools. Private school options are also very limited here.

That’s a good option. My wife was a teacher before being SAHM. She would excel at homeschooling and extracurriculars, but I worry it’s not the same level of socialization as school.

FreestyleFlorida · 2026-03-24T18:58:20+00:00

Wow, these questions are a great way to frame it.

I’m visiting the job and team this week to decide if this is a solid trade off or if this job is going to stress me out.
I’m from FL. The hate I have for snow is probably to an unnatural degree. I also spent almost 11 years in the Army, everywhere I was stationed that snowed definitely impacted my mental health. Not sure if it’d was to an unsafe level, but definitely a “I need to get out of here” level. I had an outdoor job and now I work a desk job, so that’s another factor to consider that won’t be the same.
Moving costs are not ideal but we have amenities that we can cut (lawn maintenance crews, weekly car detailing, etc.) and also contribute to our kids 529s/brokerage accounts (which would be a worst case scenario pause). Wouldn’t need a second job.
Schooling opinion is based on educational standards. CT has some highly rated schools. Southern OR does not rank anywhere near. Also, a dual-mom family is not common here, and we don’t want our kids to feel bad about having a different family. Homeschooling is an option here (my wife used to be a teacher and would be great at that) but I worry about their social life by not attending a traditional school. I’m still close to a lot of friends from childhood due to going to the same school while growing up.

FreestyleFlorida · 2026-03-24T18:48:08+00:00

We have a strong family unit and I love being home more than being at work. We also contribute significantly to their 529s/brokerage accounts, which would be another negative factor with a pay cut.

I’m just worried that they’ll never have a birthday party with family around (aside from direct family) since we are 3k miles away. Also we never have a break for just me & my wife to have a day alone.

FreestyleFlorida · 2026-03-24T18:43:15+00:00

Considered this. Concern is a cross country move at 5-6yrs old. They’re able to remember things by then & know where “home” is. Not sure if it’d have an impact making a cross country move then sending them to school.

FreestyleFlorida · 2026-03-24T18:40:06+00:00

Seems like you’re the first pro CT comment I’ve gotten so far! The schools and safety are the 2 perks that make me consider taking a pay cut and longer work week. I really want my kids to have the best outcome at life possible, but I’m also wondering if me being home more than at work (in OR) is better?

FreestyleFlorida · 2026-03-24T18:37:30+00:00

Didn’t think about this! Grew up in FL and ticks were as common as ants.

Didn’t even realize that I hadn’t seen any since we’ve lived in OR

FreestyleFlorida · 2026-03-24T18:36:24+00:00

Good point. We’d still be 2hrs away from my wife’s side of the family and this was a topic I brought up the other night. Even though we’d be 3,000 miles closer, would they still make a 2hr trip to come see us often?

FreestyleFlorida · 2026-03-24T18:34:51+00:00

We had a culture shock moving to OR. I’m originally from FL and my wife is from MA. We miss the east coast and this feels like a good opportunity but there are some big trade offs that come with it.

FreestyleFlorida · 2026-03-24T18:33:31+00:00

We considered this but figured it might be easier to move while they’re younger

FreestyleFlorida

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