The day of reckoning came sooner than expected. I ran out of money. My checking account was practically empty, and my credit cards maxed out. It was a day I knew was coming, but it happened a little sooner than I’d anticipated due to some sudden and unexpected expenditures. So, I activated my backup plan, which was to jail-break some funds I’d locked away in a CD, but things got complicated when the banker gave me misleading information, then flat-out wrong information, then explained that to get my money, I’d have to run around in a circle eleven times, bark thrice, do a 350 degree back flip, and cough up $6000 first.

Anyway, with the help of some friends, it looks like I’m going to be able to get my money out, but only enough to last me a couple of months. Which is to say, I got a two month extension on my day of reckoning. But it’ll come back, and hopefully I’ll have a better plan the next time I come to this juncture.

It’s not that I haven’t been thinking about this problem. In fact, I’ve put a lot of thought into my next steps, but I simply haven’t been able to make a decision. This is a new phenomenon for me. My life has always been guided one way or another, and whenever I came to a fork in the road, I somehow always knew what the next step should be. Sure, I’ve had some tough decisions to make, like in 2005 when I had those two enticing job offers, one from this big company called Yahoo, and another from this pimple-faced Harvard dropout named Mark Zuckerburg who wanted me to come work on this little website called TheFacebook.com. But, as difficult as that was, I knew in my heart which option I wanted to take.

Now, I’ve got options, and I’m not entirely sure where my heart is. So, let’s turn my life into a little Choose-Your-Adventure game, shall we? What, dear readers, do you think should happen next in my life, and by extension, to this blog?

Here are the options (in no particular order):

• Adventure A: Go back to work full time. Part of the problem right now is that my expenses are way too high. I’m still making monthly payments on my land, as well as my car, then there’s health insurance, car insurance, phone bills, credit card bills, etc, etc. All told, I need over $1200 per month just to keep up with my bills, and that’s not including food and gas. Yes, it’s a sad state of affairs, especially for someone living a fairly frugal lifestyle in the woods, but that is the truth. However, I could make enough as a software engineer, so that if I went back to work full-time, I’d be able to pay off all my debt and save up some, in just a year or two. Once my recurring expenditures have come down to something more reasonable, I can come back to the woods, and spend a year or two without worrying about money. Of course, that would still only be a temporary option. Though not impossible in Silicon Valley, it’s highly unlikely that I’d be able to make enough money to last me a life time, which means I’d eventually need to find some way to make money again. I also left Silicon Valley cube farms for a reason, and I don’t know if I can stand going back for a year or two of office life without losing my soul.
• Adventure B: Stay on my property for the winter. When I first started thinking about my land-ventures, my plan was to buy land, spend a year on it, then write a book about my experiences. I’ve been up here now for the better part of this year since late-Spring. If I could stay the winter, that would constitute more or less a year, and I might have enough material for a book. At the very least, I’ll have more material for this blog, which I won’t have if I left again for the winter.

  As far as adventures go, staying here for the winter seems like a pretty good one. It’ll be quite a challenge, and it seems like the odds are pretty good that I’ll be miserable for the better part of the colder months, but it’ll be an interesting experience nonetheless. Besides, it’s the only way to get a realistic view of conditions during the winter, and unquestionably, there is much to be learned. There’s also the satisfaction of being able to say “I live on my property for a year.” As it stands, I can only claim to have spent the nice warmer months here, and that’s pretty lame.

  The problem, of course, is that I’m out of money. Or will be out of money again probably around December. Additionally, I’d need to buy more gear to survive the winter reasonably comfortably, so I’d need even more money. One option is to try and find some contract work that I can do while on my property, but that’s a little iffy. While I can get decent internet up here through Verizon’s wireless network, I’m not sure how much power I’ll have over the winter. The days will be short and sunny days will be far and few between, so I won’t be able to generate as much solar power. I’d probably also get a wind generator, but those obviously only work if there’s good wind. Most contract jobs also require some face-time with the clients, but I could conceivably get snowed in for weeks at a time. The paved road will be kept plowed, but I have no idea what kind of condition the dirt road that leads from my camp to the paved road will be in.

  One possibility is to do some contract work full-time for a month or two. With the rates I get, I can probably earn enough to last me several months that way, and if the timing works out, I can still spend most of the colder months here. Naturally, this option depends on finding the right gig, and has the same problem as Adventure A, in that I’ll come back to where I am now in a matter of months. While I may be able to write a book, it would be foolish of me to assume that I’d find a publisher, much less that I’d make any money off of it.

• Adventure C: Enlist in the Air National Guard, followed by career change. Now for something completely different, as Monty Python would say. I started looking into the Air Guard a year ago, when I was in a somewhat similar situation as I find myself in now, and saw a recruitment billboard for the 129th Rescue Wing while driving up Highway 101. I must’ve driven past that billboard hundreds of times when I lived and worked in Silicon Valley. In fact, I’d noticed the sign before, too, though I’d always been happily and gainfully employed, and so never gave it much attention. This time, it was different.

  Having never outgrown my boyish fascination with things military, I’ve always been interested in the armed forces. But being something of a pacifist, I’d never considered a career in uniform, especially not with an organization embroiled in two conflicts I don’t agree with. Besides, I was massively obese for most of my adolescent years, then I became a computer nerd and spent a decade sitting on my ass in front of the computer screen, and it just didn’t seem like I’d have the brawn to get through military training. But as I passed that sign, one late Autumn day last year, something felt different.

  For starters, the billboard depicts an HH-60G PaveHawk helicopter plucking someone out of the water. Rescue. Rescue is good, even for pacifists. Then another part of my brain piped up saying “You always did love helicopters.” I drove on in silence. “Wasn’t doing aircraft maintenance one of your childhood dreams?” Quipped my brain, suggestively. “You just spent months in the woods. You’re pretty fit. Probably about as fit as you’d ever be.” My brain had a point. I was intrigued.

  I did a little research online, and learned that the Air Guard works very differently to the regular Air Force. For starters, National Guard units belong to individual states, unless loaned to the federal government. With the Air Guard, you get to choose your unit and occupation when enlisting, so I’d be reasonably sure that I wouldn’t end up a door gunner in Alabama, for instance. Guardsmen (and -women) serve one weekend a month, plus two weeks a year, and can lead mostly normal civilian lives the rest of the time. The 129th had an opening in helicopter maintenance. The job came with a $20k bonus.

  So one warm day in December last year, I walked into their nondescript recruitment office located just a couple of blocks from the restaurants and cafes in downtown Mountain View bustling with Silicon Valley tech workers on lunch break. The recruiters were happy to see me. For starters, I wasn’t obese (“it’s rare these days” they explained), I had a college degree (two pay-ranks’ promotion off the bat), and no known medical conditions (they suggested I keep quiet about the braces behind my lower teeth). But, ultimately, I didn’t continue with the process then because the helicopter maintenance job I’d wanted had just been filled. They had an opening in engine maintenance, and though I find aircraft engines to be fascinating and can explain the difference between turbojet, turbofan and turboshaft engines, I ultimately didn’t want to be an engine geek; I like helicopters, and I want to learn all about them, not just the engines.

  Over the past year, I’ve continued to think about this option. It’s compelling in a lot of ways. If nothing else, it’s something completely different, and I think it could be a challenging but interesting experience. If I time things right, I could let Uncle Sam feed, shelter and clothe me during the colder months while I’m in training. If they’re still giving $20k bonuses, that’d go a long ways towards paying off my debt, and once I’m out of training I’d also secure 4 days pay a month (they pay double-time) thereafter. I could also use the education benefits to go back to school, and retrain for a career change in my civilian life. Military training might also teach me skills that could help me get a job as a seasonal firefighter near my property, since that’s basically the only well paying job around here (besides, who wouldn’t want to be a firefighter?).

  So, why haven’t I enlisted yet? The short answer is, fear. And it’s not the fear of being deployed, which is what my friends seem to worry about. Rather, it’s fear of the unknown. The fear of being thrust into a foreign culture. The fear of commitment. There’s also the fear of losing my individual freedom, especially during the 5-6 months of training. Then there’s the fear of failure and ridicule — that I’d show up and they’d laugh at me and say I’m too short, old and weak… and worse, that they’d be right. But then, I hate the feeling of succumbing to my fears, of letting my unfounded worries prevent me from living. And while less of a consideration, the thought that enlisting would be looked upon unfavorably by those around me also weighs on me. I don’t generally let my friends and family tell me how to live, but it still takes an extra ounce of conviction to do something without the support of the people who are important to me. And on this one, I’m not sure I have that extra ounce.

When I quit my job at Google a year and a half ago, I thought, or wanted to think, that I’d return after a break. But as the months ticked by, it’s become clear to me that, as a software engineer, I’m like a racehorse with a broken leg; I may never race again. Sure, I can run in short stints, but a full-blown comeback with any chance of success is starting to seem less and less likely. Ironically, that makes any plan that involves making money as a software engineer unsustainable in the long run. Of the three options above, the one that may seem the most brash –enlisting– seems like the best option in the long run because, in addition to providing short term employment, it also has the potential to fund, or otherwise prepare me for, what I probably need: a career change. But, no doubt, it’s also the scariest and most controversial option, hence the indecision.

Any thoughts?