How I Became a Milwaukee Nomad

 I came to Milwaukee as a travel writer and cardiac monitor technician and became a nomad. Dread Pirate Roberts, here I come!



Lyft Glow in Windshield
Image by the Author

Confessions of a Lyft driver.

If you haven’t seen nor read The Princess Bride by William Goldman then stop here and do that.

One may miss Wesley’s super ambitious, though logical, quest to seek his fortune across the sea. It is no less ambitious than The Richest Man in Babylon’s.
Wesley says something to the effect of, “I shall work sixteen hours a day, beg for food, and sleep on the street, saving every penny until I’ve amassed a fortune.”

That journey is, of course, the very start of a much larger one that leads to even greater payoffs and rewards. But what a start!


There I was, a cardiac monitor technician on a travel assignment to Wisconsin, imagining myself as Wesley who was setting out to amass his fortune. But, my sea faring vessel was an old minivan sputtering its last remarks, stuffed with a few personal belongings.

I was skeptical of sleeping in a vehicle with the temperatures nearing negative fifteen. So, I played it safe and rented a room in a hostel while I considering the possibility of really moving into a car.
What? Was I in my early twenties, again? I mean, back then it was easy. I just rolled with the punches. But now, I’d rather avoid the pain as I near fifty.


Driving to and from work was bearable, though the van had no heat nor air, so the frostbite would get pretty threatening right near the end of my fifteen-minute ride; also near the ends of my fingers and toes.

While lying in my tiny bedroom between work hours, I started feeling guilty of my lack of productivity. So I grabbed my laptop and ordered a LYFT to Starbucks to do some writing.

On the short ride with LYFT, a young man informed me that I could drive with the ridesharing company by using a rental, which they provide. So, I looked into LYFT’s express drive program and found a car they would rent me for two-hundred and twenty dollars per week. It was a hybrid electric vehicle, so I would spend minimum dollars on fuel.

While sitting there with my coffee, I thought to myself, “This vehicle will run quite nicely on its electric motors and stay warm while parked throughout the night. And it’s probably as spacious, not to mention cleaner, as the Hostel I’m paying for monthly.

Sleeping in a car might not be impossible after all.”

I immediately opted for a gym membership with Planet Fitness. This way, no matter where I was in the city I could utilize their 24/7 facilities.
Besides, when you’re living in a car all day and night, one enjoys a potential daily escape to exercise, socialize, and shower.

I considered all I had learned, and weighed the pros and cons of not having a place to call home…


Milwaukee parking is a bitch. Many consider parking tickets a right of passage to newcomers. Most parking is done on the street but you must move your vehicle to the other side of the road everyday. Having two vehicles was going to be a nightmare. So, I decided to find out if I could find a place to park both of my cars for a monthly rate and weigh that against the price of rent.

I was surprised to find that there are monthly parking spaces available for as low as forty dollars a month. Also, I had many co-workers offer me a place to harbor my vehicle if needed.

Once, I saw that living this way may be possible, I started truly considering what it would mean, and began devising a plan to set it all in motion.

There were questions but I found answers:

  • Where would I get my mail?

UPS stores let you use them as a local address.

  • What would I use as my permanent address?

I signed up for a virtual mailbox with ipostal.

  • What if my rental broke down and my van wouldn’t start after sitting in the cold for so long?

I paid for AAA annual membership and kept a two-hundred dollar emergency fund for a night’s hotel.

  • What if someone broke into my van and stole all my stuff?

Neighbor.com, where I paid for my parking space offered insurance for my belongings. I opted in, just in case of such a disaster. Plus my car insurance let me drop my coverage to storage mode.

(Important documents like titles, birth certificates, and stuff, you keep in a safe deposit box after saving them in the cloud at dropbox.com)

While I was moving the things out of my rented room and back into my van for storage, I tried to imagine what I would do with my extra thousand dollars a month. But, once I got everything moved into the parking space and took up residence in the Prius one night, I started doing real calculations for my budget and realized it wasn’t going to all be profit.

Settled into the heated cloth seat, comfortably reclined at a travel center just outside of Milwaukee, I opened up my laptop, powered by the dc/ac converter I had purchased at Advanced Auto Parts for 25 bucks, and started punching expenses into excel.

Author in Car
Image of the Author

I’m saving a thousand a month foregoing rental.

Paying 13 bucks a month for my virtual address.

AAA was an annual membership for a hundred bucks.

The spot I rented for the van was 200 a month, but it was insured and in a nice place.

The safe deposit box and Dropbox membership was 20 bucks a month.

Then the big one. The car rental is 225 a week, so that’s a whole 1000 out the door unless I could drive to make that payment. If I couldn’t make the rental fee driving, I would be taking a loss!

But the sweet part was in having a 2022 model vehicle with heat. No more worrying about breaking down or freezing.

All things considered, something told me that this was the right move to make. 

I was going through a divorce, my father had just passed away, and I had found out I was allergic to my cat. No dad, no wife, no kids, no cat. I was a teenager, out on his own again.
Or, maybe this was my mid-life crisis.


What is a nomad anyway?

One without a home? Someone who moves around for a living? Nah, that’s a gypsy, right?

I don’t know. I kinda think back to when my Dad sat us around the dinner table and made us set goals. Everyone seemed to want to be something in particular, but me. I just said I’d like to be a doctor as a long term goal, seeing as that would make the most money enabling me to do as I pleased when the time came. Realistically, I had absolutely no interest in doctoring anything.

What did you want to be when you grew up?

Honestly, there was nothing I wanted to be. At least nothing that anyone else had ever been. I mean, do the elements of the periodic table come into existence and decide, “Hey, I’d really like to be copper for eternity?” I think even the elements radioactively decay over time. Kinda like we do, I suppose.

Just to think, the elements with the most electrons take the longest to decay.

Strange, that.

The most positively charged ion that has gathered the most negatively charged friends around it lives the longest…

Facts of life, peeps.

I dunno, I guess there is something to be said about those who pick a profession and go for it for life. They eventually become the best at what they do. When they die, they become stars in the sky. A lingering memory. A definite personality.
I have no personality. I was told this fifteen years ago buy an ex-girlfriend right before we split up. I in-turn, asked her who she’d prefer I act like. This only further infuriated her.

Truth is, I have always been a really old man in a young guy’s body. Old men are beyond personalities. They are in no hurry to beat anyone to the tactful punch unless it’s a total original. Old men are constantly drowning in dead metaphors and watch young men serve them up like they aren’t old news.

All these years, I’ve just been waiting on my body to catch up is all. Getting closer everyday. Being a little bit of everything is better than being a great big something anyhow.
Personal opinion.

I’m still a star. I’m just always on the move. The shooting ones are prettiest anyhow. What do they say? It’s better to burn out than to fade away? That’s Highlander not Def Leppard.

Anyhow, nothing in this world will ever be achieved if all the possible objectives must first be overcome. So, here goes nothing! Car living here we come.


Staying in the car is actually pretty nice. I have blackout curtains I can hang up between the windows like a makeshift fort for sleeping during the day. But in a pinch, I pull my beanie down over my eyes and curl up with my rainbow colored quilt.

Customers ask me all the time what that thing is hanging in my windshield. A dreamcatcher my daughter crafted at school. I’ve yet to be asked why I would have a dream catcher in the car.

Dreamcatcher in Car Window
Image by the Author

When people ask where I live, I give them my virtual address in Florida. If they persist, I tell them the town in which I have been spending the most nights. Then if it comes right down to it, and some one exclaims that I am living in my car. Well, then I tell them I prefer to say I work from home.


Join me me on the rest of my adventure soon when I release my new manuscript "Confessions of a Rideshare Driver" in the fall of 2022.

Leave me your email here to keep up-to-date on the book release.

Help pay my kids’ child support here!

Wanna collaborate? Connect with me over a cup of coffee…
but not here.
That would just be weird.

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