Decisions and Regrets

I do not regret the decision I made to retire my law practice, sell my house, and go off on my epic road trip.

I regret pretty much every decision I’ve made since I returned to Green Bay.

Remaining in Green Bay

For two years straight, I contemplated leaving Wisconsin once and for all, and for two years straight, I chose to remain in Green Bay. I don’t think I fully understood why I remained here last year. But when I decided to stay here this year, my reasons were very clear. To go anywhere else in the country (or world, for that matter) would have meant abandoning everything and starting life over from scratch. Don’t get me wrong – that idea has always had its appeal. But my friends are here, and remaining close to them was (and still is) important to me. To leave would have meant going somewhere where I had no family, no friends, and no job. At least by staying in Green Bay, I was only without family and a job.

I figured that when winter rolled around, I would regret my decision to stay here. I am regretting my decision, but for once it has nothing to do with the cold winter. This time, my regret is founded in the fact that I’m not travelling. I’ve got cabin fever, dialed up to eleventy-billion. My job has more to do with that than anything else. What I’m really regretting is that I chickened out and resorted to a traditional home and a traditional means of employment.

Waiting for the Shoe to Drop


My job is making me feel a bit bipolar. I can be complimented by a superior one day and screamed at the next. I quickly learned that a lot of the screaming and complaining is work politics and folks projecting onto others their own inadequacies. Basically, if they can make someone else look bad, it draws attention away from the shit they do wrong. Of course, this is nothing new.

I did go off last week – in a moment of peak frustration – on my supervisor. And then she went off on me. I thought for sure my days were numbered (hoped for it, really). But the very next day, she acted like the incident had never happened.

The other day, one of my superiors was telling me that our pay raise structure is 10 cents every six months. I wouldn’t mind that if my starting wage wasn’t so pathetic. As it is, I’m making less money now than I did fresh out of high school 20 years ago. Now I find out that IF I stick around for 18 months, I can be making a nickel more than I was out of high school? And what the hell is the point of a flat raise every six months. What incentive do I – does anyone – have to work hard? Why did I bother taking inventory training?

Oh, and that’s another thing. Apparently, everyone is being stripped of their inventory credentials at the end of the year. From then on, a team of five will be the only ones in the store who can alter inventory. I honestly don’t give a shit about the change in policy, other than it eliminates a huge portion of a lot of people’s jobs. And with store business going down after the holidays, I’m concerned about reduced hours and/or layoffs.

So with all the shit that goes on around there, plus my growing frustration and short temper – I’m betting I get laid off or fired pretty soon. While I might not be physically preparing for such an eventuality, I have definitely been mentally preparing for it. The slightest bit of bad news might just be enough to set me off. I’d abandon everything, take to the road, and not look back.

Joyless Ride

Last night, I went for my annual winter storm joy ride. It sucked, frankly. I’ve done this route for about 4 or 5 years now, and it’s become quite boring. Plus, there was no storm. We had just gotten 3″ of snow from the 24 hours before. Figured with my limited nights off, I couldn’t be too picky.

But the reason I mention the joy ride is because about halfway through it, I got a warning light on my dashboard. Something was wrong with my rear left tire. I checked the pressure and there was no reading. Fearing the worst – that yet another tire had blown out… AGAIN – I checked the tire with my mirror. It seemed okay. A few moments later, the tire pressure registered on my dashboard and was normal. A little later on, I pulled over, shut the engine off and turned it back on, and the warning indicator went away. It hasn’t come back yet. I also inspected the wheel for signs of misalignment, since I couldn’t be absolutely certain what the warning indicator was telling me.

Best as I can guess, the sensor that measures tire pressure must have failed temporarily. The tire seems fine.

For the time last night when I was driving and trying to diagnose the problem, I wondered what I would do if another tire had blown out. It’s an expensive repair. One I can’t afford to make right now. A lot of ideas ran through my head, preparing for the worst-case scenario. Once the crisis was over, I began to ponder whether life on the road should include my truck. It’s invaluable for lugging around cargo and providing shelter from the elements. But it is expensive to fuel and maintain, and eventually replace. More and more, I am convinced that to be truly free on the road, I might have to resort to leather tramping or bicycle tramping.

This is certainly not the first time I’ve thought about giving up the truck. There are pros and cons to all of these various types of tramping, and I’ve previously decided that being a rubber tramp was ideal for me. But with the repairs I had to make in September and the increasing likelihood that I might give up on a formal business or job hunt, I’m thinking it’s time for me to reconsider formerly rejected options.

The Letter to Myself

Last week, I decided to re-read all of my blog posts from the North American Road Trip. It was fun re-reading all of the predictions I made while I was on the trip, to see which ones came true and which ones did not. The really funny one was the blog I wrote right after I met Zombie for the first time. I mentioned that there was a possibility that our paths would cross again later on in my trip. Little did I know at the time that our paths would indeed cross again – about 24 hours later!

Re-reading the blogs reminded me that I intended to write a book about my experiences. So now that’s on my to-do list, as well. Y’know… cuz I’ve got so much time to kill!

The most interesting thing I remembered when I read the blogs was the letter I wrote to myself. At the advice of my counselor at the time, I wrote myself a sort of “pep talk” letter. We predicted that the full weight and realization of being homeless and unemployed might hit me like a ton of bricks while I was on the road, that I’d be depressed, and that I would need to remind myself why I was doing what I was doing.

Funny thing is – I never read that letter while I was on the road. Not once. I saw it when I returned to Green Bay and unpacked. And I kept the letter as a memento. But I never needed that pep talk. On the contrary, my time on the road was the happiest time of my life. It wasn’t until I returned and started living in traditional housing that I was overcome with depression. A depression that has only worsened since I began working a traditional job.

And I think that tells me everything I need to know about myself.


Theoretically, the reason I’m living in this house and working this job I hate is to buy myself some time to save money and start a new career or business so that I can sustain myself on the road. This… “plan” as it were has been countered by a “Plan B” of just quitting my job, taking to the road with no plan, and figuring things out as I go along.

Part of my reluctance to go with Plan B is because – after a 13 month sabbatical – my cash reserves are considerably less than what they were in July 2017. But the reason I could afford a 13 month sabbatical was because of the sale of my house, and the fact that I sold it for a lot more money than I expected to sell it for.

And so it occurred to me today that right now, I have the exact same amount of money leftover in my savings account that I had saved up for my 2017 road trip before I sold my house. I’m in the exact same financial position now that I was in June 2017. And in June 2017, I intended to go on my trip, regardless of whether I made a dime off of the sale of my house.

So why am I so reluctant to quit my job now, if I’m in the same financial boat as June 2017?

Well, for one thing, I’ve had the experience (and frustration and humiliation) of trying to find a job after quitting my law practice. It was even harder than I imagined.

Still, knowing that I am as well off now as I was 18 months ago makes me question why I’m staying here. With my high rent and vehicle expenses, the longer I stay here, the greater the risk that I’m going to lose the money I have saved before I ever get back out on the road.

Motel 6 Nostalgia

There’s a Motel 6 just a couple blocks away from my house. Every time I drive past it, I get a little nostalgic. Even though it would be an entirely unnecessary expense, I’ve been thinking about staying there for a night – perhaps during my vacation later this month.

At first, I thought I just wanted the atmosphere and a soft bed. But I realized that what I really want is 24 hours (20 hours, really) to do some quiet thinking. It occurs to me just how distracting all of the stuff in my house is. I like the peace and quiet of just having my duffel bag, a notebook, and a pen.

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