Should I just give up on #1? Or is it possible to maintain a Mustachian lifestyle there?
If you can afford SB then you'd prefer to find out now rather than later. You'll either figure it out within a year or two, or you'll decide that you're spending outside your range and need to go somewhere else. You might even decide that you can afford SB but you'd rather live somewhere else, and you certainly want to test out that hypothesis as soon as you can.
It'll probably start at "way too expensive", and then you'll figure out how to bring down the costs. Maybe it's renting just a room, or maybe you'll end up in a bigger place with roommates. If you find a crappy structure in a nice location then you'd be able to barter sweat equity labor along with cheap rent. You might move two or three times over several years until you find the perfect compromise of price, location, and amenities. Your key to success will be living in the middle of the real estate market so that you're ready to jump on a property before someone else snaps it up. That can take several months of researching online and driving through neighborhoods to re-familiarize yourself with the area so that your preparation is ready to snap up the next opportunity.
If SB has a sizable college population then you'll find plenty of places where you could live like a poor college student. If you're expecting to stay for the long term (not just for four years) then you'd be able to negotiate a better rent in exchange for handyman or manager services.
If you don't want to live in SB then most people choose their location by family or climate. Or maybe you'll choose to roam around (RV or short-term rentals) until you find a place you like. This is also a good chance to see the world your way instead of the Army way-- if you've ever enjoyed one of your overseas locations then you could try it again for a few months to see if you want to live there like a local.
I don't want to ever work for a hierarchical organization again. I'm not sure I even want to work again but the first sentence puts me out of the running for 95% of the jobs I'm qualified for.
What is a recommendation for using my education benefits for getting a non hierarchical job?
If you don't want to work for a hierarchy then you might as well BE the hierarchy.
Hopefully you've already been through the transition seminar and you've had a retirement physical. If you haven't done a VA disability screening then do so as soon as you can. One reason is so that (if you indeed are considered disabled) you can reduce your taxable income by receiving VA compensation (in exchange for giving up part of your military pension). Another reason is to see if you'll qualify as a "disabled veteran" (even if your rating is just "0% disabled") for the purpose of owning a California business (and getting veteran's preference for contracts or other funding). A final reason is that it might take literally a couple of years for your claim to work its way through the process.
I'm under the impression that CA has an extensive menu of state veteran's benefits, even at a 0% rating, and even if most people in SB don't care for veterans. You can work through Military.com's list at:
http://www.military.com/benefits/veteran-state-benefits/california-state-veterans-benefits.htmland see what applies to you. You may even be eligible for CA state benefits leading to a whole new degree or certification, not just your year of the federal GI Bill.
The local college campus will have some sort of veteran's benefits coordinator. You could start there to figure out how to maximize your federal/state educational benefits, and then to figure out what you want to study. Maybe you're interested in an executive MBA program (short duration but more intense) or maybe you'll prefer to build on the VA's entrepreneurship program. Again, since you don't need a steady paycheck, you'd be perfect for a startup-- whether you're employee #6 or a co-founder. Most entrepreneurs are in their 40s and just have to figure out how to navigate the legal/administrative wickets.
Ideally the college VB coordinator is a military veteran who can help you find both cheap lodging and a study path to an independent career. If there's no VB coordinator then you may be a one-eyed man in the valley of the blind-- again if you're a long-term resident then the college might be willing to hire you in that capacity to create the program for them.
Another couple of independent career ideas could be:
- Housesitter. Someone's going on vacation (or a protracted assignment) and they want you to be the caretaker, security guard, maintenance/repair guy, and possibly pet feeder. I suspect that your military experience is an asset.
- Realtor. I know it has vicious competition and you're not interested in working in the field, but when you have a license then you have an easier time tapping the databases and scooping up a housing bargain before the general public finds out about it. If it seems like something you want to do then you don't need a steady paycheck from a real estate company, so you could be totally independent or you could work for commission with a local realtor. Military spouses do this all the time.
- Instructor. One of our local realtors is always seeking a veteran who can give VA home loan seminars. You'd have to stand up in front of a crowd and click through a PowerPoint presentation... only this time in a different uniform. Another military retiree with an instructor background was making a great supplemental income by teaching Economics 101 online to people who couldn't make the class schedule in person. Your local college would be a good place to look for that opportunity, either through them or through another accredited educational institution anywhere in the nation.
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Blogger. Online freelancer & entrepreneur. Take a look at Pat Flynn's SmartPassiveIncome.com. If you can watch a video to figure out how to set up a WordPress blog then you can start selling goods or services online. I know a dozen veterans doing that right now, and they'd all be happy to share their advice.
- Surf instructor, especially stand-up paddleboarding. You'll want a surfboard rack for your bicycle anyway...
Instead of thinking of yourself as unemployed, you could consider yourself to be on half-pay and needing only half of a job-- especially if housing is part of the compensation package. That opens up all sorts of opportunities.
As part of this process, you'd want to network the heck out of SB. It starts with your Linkedin profile, and you may find a number of Linkedin groups oriented on SB. As a military veteran, you're eligible for a free year of Linkedin's Premium services:
http://the-military-guide.com/2013/08/22/military-veterans-rate-a-free-one-year-linkedin-premium-upgrade/Other conventional networking methods include Rotary, Lions, or Toastmasters. You might find a local veteran's group like MOAA or IAVA. I'm constantly being pestered around here to join one of these organizations so that they can put my skills (and volunteer labor) to good use. Figure out how to join, show up at one of their meetings, try to look clueless, and let them show you the ropes. They'll understand if you're allergic to hierarchy and they'll help you figure out ways to work around it.
None of this is easy, but it's all relatively straightforward. The Army may have given you a "military inferiority complex", but you have a huge inventory of "soft skills" like working with people, public speaking, writing, crisis response, calm under pressure, stamina, sleep deprivation, persistence, and motivation. You probably also know how to show up on time, sober, and ready to work the mission.
It seems hard to believe after a military career, but the civilian bar is not so high. After a year or two in business you'll see opportunity everywhere you look.