The Winona Trip and Personal Struggles

In recent weeks, I’ve made two major payments on my final student loan. I’m poised to make the last big payment to get the balance down to zero in just a few days. I’ve made steady progress on all of the logistical work I have to do to sell my home and prepare for this trip.

Despite this progress, the last six weeks has been very difficult for me. Every week seemed to offer a new body blow. The common theme that arose from these hits was that of isolation.

Although I consider this to be “personal stuff”, I think it’s important to share these things. If you’re reading this blog and considering exchanging a shit job for a life of travel and adventure, it’s important to realize that it’s a difficult and challenging process.

The Winona Trip

Remy and me, at Garvin Heights Lookout, Winona, MN.

A month ago, we had a stretch of record-breaking warm temperatures. As anyone who lives in Wisconsin in February knows – cabin fever is a very real problem and one that we all tend to be anxious to cure. On a whim late Friday night, I packed a bag and the dog and hit the road with no particular destination in mind. We wound up sleeping overnight in Black River Falls State Forest. In the morning, we went to Winona, Minnesota. We wandered around for a few hours and then came back home to rest the rest of the weekend.

I didn’t choose Winona for any particular reason, other than it’s an old favorite haunt. In college, my Ultimate Frisbee team played an annual Halloween tournament there called HalloWinona.

We didn’t stay long. In fact, the whole trip – including drive time and our overnight stay – lasted about 17 hours.  Once again, it seemed like I was rushing through a trip in order to retreat to the comforts of home. But this time, I finally realized why I kept cutting my trips short.

No Loitering

The simple fact is – I don’t like lingering in any particular destination. I’m not especially motivated by the creature comforts of home. I just want to be on the road. I want to be moving. And it’s because I never feel welcome at my destinations.

It’s not the the locals are mean or rude. Rather, it’s a perception issue for me. For one thing, I’m almost always traveling with my dog. And as a single dad, I don’t have anyone to pawn her off on when I go somewhere where dogs aren’t allowed (which is EVERYWHERE).  Either I go places where she’s allowed, or I leave her behind – in which case my venture into no-dog land has to be limited and brief. This includes stores, museums, libraries, movie theaters, and more. Hell, most parks don’t even allow dogs! “Man’s best friend” indeed!

The other reason I never feel welcome is because I feel like I’m trespassing. In fact, oftentimes, I literally am trespassing. As a budget traveler, I prefer to do dispersed camping on public lands – be it a state or national forest or a highway rest stop. Navigating private and public property boundaries is tough, and the laws are not particularly friendly to itinerants. Even on public land – the slew of permits and licenses and fees and tags needed to camp legal and proper are enough to make you dizzy. And while I appreciate public lands and don’t mind paying taxes to support them, I’m not quite inclined to pay additional fees for the “privilege” of freezing my ass off in my truck in a forest with no paved roads, no lights, no security, no water, no electricity, no heat, or any other amenity or comfort.

So I don’t. And for the most part, I can get away with it because I know how to keep a low profile and be inconspicuous. But part of that strategy means never pushing my luck, never overstaying my welcome, and getting back on the road quickly before I can attract attention and get into trouble.

Companionship and Self-Reliance

Intellectually-speaking, I know that I could alleviate a lot of my problems if I found travel companions. Having a travel companion would ease the burden of taking care of Remy, because one of us could stay behind with her while the other took care of groceries or any other chore. An extra pair of eyes and another brain would make it easier to plan the trip, cope with obstacles, and solve problems. And after the North American Tour, having someone else around for emotional (and perhaps even logistical) support would make it less stressful when it comes time for me to find a new home and source of income.

The problem is, I’m extremely misanthropic. I don’t like people. I don’t like being around people. Even when I get lonely and seek out other human beings, I always want to retreat into solitude shortly thereafter.

Most of my life – both as a child and as an adult – has been one of disappointment in other people. Most people in my life have been untrustworthy or unreliable. I’ve always found it easier to be self-reliant. If something goes wrong – it doesn’t take me as long to find the cause. As a self-employed attorney, I’ve enjoyed a career that is self-reliant. (About the only positive thing I have to say about this job.) But now that I’m quitting my job in favor of a more simplistic life, I’m going to need to be able to rely on other people more than I ever have in the past.

Ironically, my NEED to become more social and outgoing is in line with my WANT to become more social and outgoing. It has been one of my hopes and goals in my travels that I would meet new people, make new friends, and be less introverted.  But I’m skeptical that my wants – or my needs – will change anything. They say that necessity is the father of invention, but in this case, I have my doubts. I can see myself being just as much of a loner in my travels as I am now.

Burning Bridges

Throughout the past six weeks, there have been several instances where I’ve done things to damage potential relationships.

I decided to bow out of a haunt project because the group still hadn’t obtained funding and I was running out of time to accomplish what I promised before my departure date (and other concerns, which I won’t get into). Objectively, I know I made the right decision, and I stand by it. But it meant abandoning the same group of friends for the second time in just a few short months. It also meant walking away from the biggest opportunity I’ve received to date to do serious haunt work.

Secondly, there was a date with a guy that I had managed to pull off thanks to some liquid courage. Things were going quite well, too. For the first time (ever?), I wasn’t mentally noting all of his flaws so that I wouldn’t feel so bad if he rejected me (in other words – the guy was perfect). Yet, he ultimately did reject me, on account of foolishness on my part.

Add these to the feeling I have that I’m giving a giant middle-finger to my local friends because I don’t intend to return to Wisconsin. You can understand how I might feel like I’m standing alone on a butte, burning every bridge to the mainland. I’ve never felt so isolated.

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