Details

So maybe things will go something like this:

I will finish law school over the next 3 years, then quit my job.

Before quitting I’ll be sure to have purchased all the equipment I will need for long-distance hiking and bicycle touring as well as tucked away enough cash to purchase a small sailboat when the time comes.

After quitting I will begin a cross-country bike tour taking me from Boston to San Francisco. I won’t have any kind of schedule or hotel reservations to keep up with but I would like to plan the trip a bit more than my previous attempt. When I tried doing this when I was 18 I fell shy of reaching the Pacific Coast and only ever made it to the Great Lakes. What I learned from that is that not having a schedule is just as freeing as one would expect it to be. However, not having a route was a problem. It prevented the trip from being as good as it could have been. I have a feeling I missed a lot of great sites and put up with a lot more hassles than I had to. The next time around I intend to have a list of sites to visit as well as a well-researched route on how to reach each one of them so as to maximize the pleasantness of the riding.

After that, however many months it takes, I’ll return home to recuperate for a few weeks before setting out on some long-distance hikes. I’d like to do the Maine portion of the Appalachian trail at least. If I like the experience then continuing on would be in order. But I hold no great goals of doing the entire trail, certainly, it just seems like it might get boring.

After the hiking I think more home-time recuperation would be in order. Then, if I liked the hiking, I think I’d like to keep going back to the trail and hiking for a week or two at a stretch and then returning home to recuperate, repeating the cycle until I am completely bored of the activity.

Once the hiking is out of my system I’d like to finally get on the water. Doing some canoe camping would be fun. Some week-long trips around New England rivers would be a nice start.

Eventually, once I’ve had my fill of rivers though, I’d like to splurge on a sailboat. Something in the 25′ range. Just big enough to accommodate me and occasionally someone else for short stretches. I think I’d like to treat the sailing just like the hiking; sail north for a couple of weeks to do some exploring, come home. Then south around cape cod and Rhode Island, then home again.

Before I could give up sailing I do think I would need to make at least one excursion lasting at least two months that takes me to a secluded beach somewhere off the south eastern coast or in the Caribbean. Doing that I think will result in two possible courses of action: Either 1. I fall in love with cruising and never want to return to land again, or at least not for a few years anyway; Or 2. I feel like I have accomplished what I set out to do, enjoyed it, and now want to move on to something else.

I think 2 is more likely.

At which point hopefully the traveling bug will be out of my system. I’d like to return home and get a job in the legal field that is utterly fascinating yet only occupies 1-2 days of my time per week. Perhaps working for some kind of non-profit or as some small town/county prosecutor or just my own side practice.

At this point I think I would like to take the time to organize my life just how I want it. That would include having a house and a lifestyle that is not dependent on me handing my money over on a regular basis to religious nut-jobs who will charge me whatever they wish for their fuel. This would include having a food supply that is independent as well. This does not necessarily mean I need a cabin in the woods or even a single-family home. The right apartment in the middle of the city with a southern facing deck would suffice. Perhaps owning some rural land would make me feel better as well. A timber investment in northern New England would be perfect. It provides that peace of mind that I have a place to run to if I have to while also being a sound investment and a smart way to diversify my portfolio.

After those things are just how I want them I might try adding something else to the pile in addition to my 1-day per week job.

The rest of my time I’d like to spend being entrepreneurial outside of the legal field. I’d like to start some kind of low-overhead, fun, one-man business. Most likely it would be software or software-service based, like my businesses in the past. But again, something that wouldn’t require more than a few hours per week of my time yet something I could pick up and work on when I feel inspired. I have a few ideas that would fit the bill.

From then on life might start to look a little more mainstream. Hiking/Camping on the occasional weekend, work during the week, a vacation now and then. It would be nice if I could find a way to affordably keep a sailboat around. The biggest cost of ownership is the storage of it when not in use. Moorings can be pricey, slips always are, and trailering it requires two things: Owning a vehicle hefty enough to tow a large boat and having a place to park it when not in use. Hopefully a friend or family member with a big back yard could step up. But if I have to go without that’s fine. I could just make a friend who has one.

So there’s a basic idea of some things I might try to do.

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