This is just my opinion, and I've never had a real job. But here's what I've observed and been told.
My concerns mostly revolve around entering the job market upon return...cold. I'll have a great tan, but won't be 'current' in work 'skills.'
Yeah, you will, you'll be current enough. Believe it or not, you'll be more skilled than some of the people working in the jobs you're trying to get hired for.
When you're hanging out with the sailing crowd, keep alert for opportunities. You never know who you're talking to, and who's hiring. (The billionaires are probably scummier & scruffier than the rest of the crowd.) Sailors might be your kind of co-workers, even if you hadn't considered that field.
The bar is not that high. The time you've spent in the military has developed your leadership, management, and personal discipline skills. You've seen & done things that others can only have fantasies (or nightmares) about, and you've had far more responsibility for much longer than most people your age. Sailing will develop skills in self-reliance and planning (and risk management!) that most employers never see.
A few months ago, the network news fear-du-jour was about laid-off folks becoming chronically unemployed and I do admit that gives me pause. I've always felt my mil career would sway a future employer despite their views on my being unemployed for a year. I wonder...
Any HR folks in the room care to talk about 'returning to work'? Anyone have experiences in this area?
The places where you want to work will understand your reasons for your break. "Needed some time off to take care of family, didn't want to leap into work and have to take unpaid leave" will more than suffice. Or, "Had a once-in-a-lifetime opportunity to check off a bucket list item, which taught me a lot about how I can help your company..." or even "I tried self-employment but I learned that I prefer working with a team. However I also learned how to work independently on..."
If a company doesn't like your "lapse" of employment history, then you won't like working there.
When I was getting ready to retire I never even wrote a resume. I was getting calls & e-mails before & after my retirement date. I got another round of calls & e-mails at the six-month point after retiring (Navy ethics restrictions on employment). I've continued to get a call or e-mail every year since I ER'd, along with intermittent self-inflicted episodes of "I could SO do this job".
Maybe you could give yourself 4-6 months for the job search. I definitely think you should talk now with a headhunter or a coach about your plans, and how best to time your bridge career. (You could start with my spouse's shipmate Lynn Oschmann at
Oschmann Coaching - Life - Leadership - Transition Coach .) I think the key is to figure out what you want to do, and then figure out which company can benefit the most from your presence. Research the heck out of them and show them how you're a solution to one of their problems. Offer to intern or work on probation for a month or two.
You may also connect with Lions or Rotary or a veteran's organization or a volunteer group. Once you get to know the people in the organization or on the board of directors, then let them know you're considering a bridge career. At the very least you'll get part-time or contractor work that would let you stretch out your job search until you find the opportunity that's right for you.
At the very least you could join a LinkedIn group for your military branch/specialty. (I'm in "Submarine qualified" and "Naval officers".) Post your questions there and let the headhunters & career coaches thrash it out.
Our focus here is more on financial independence, but you might also take a look at "The Military Advantage" (
http://militaryadvantage.military.com/ ) or Carl Savino's books (
http://www.corporategray.com/static/transition_guide/about_the_authors ). I've hung out with Terry Howell, he's retired USCG, and I like him a lot. Ron Krannich is Impact Publications, and he's treated me right. Carl's a good guy who understands how to find the career you want, not just any ol' employer to hire you.