The Tentative Quest

John playing guitar

February 2011. Apartment in Logan Square. Photo by DCH.

There are two moments in life in which I recall feeling most like anything was possible and both occurred at age 15. The first was during a family vacation in which we drove from Illinois to Colorado. I was listening to my portable cassette player through my headphones and the song playing sent a shiver up my spine. As the guitar swelled to full volume I couldn’t believe the power it had over me and I thought, “I wish I could do that…” immediately followed by “Why can’t I do that?” My parents nurtured my dream with a guitar and lessons and I’ve been playing ever since.

The second was during Driver’s Ed class when one day a pair of women from the local insurance office came to give a presentation, except it wasn’t a presentation on insurance; it was a presentation on motorcycles. Some of it covered how as new young motorists we should be especially careful to be on the look out for motorcycles on the road, and that’s important, but the part that really interested me was the fact that at age 16 with the proper safety class and parental permission I could get a motorcycle license. Now I was very smart and nerdy then (and now), and when I acquired my motorcycle license people told me I couldn’t do that, that it wasn’t who I was. In the same instance I learned anything was possible I learned I didn’t have to be the person people expected me to be. I only wish I’d understood that as fully then as I do now.

John on Triumph Motorcycle

August 15, 2013. First motorcycle in 12 years. 1996 Triumph Thunderbird 900.

I know that it’s possible to make a living as an artist because I know many people that do it, I was just discouraged enough to not pursue it myself. Recently I finished reading Chris Guillebeau’s The Happiness of Pursuit (read my review here), and I’ve been thinking about what kind of quest I could take on in life (the book is about purposeful quests). Actually, it didn’t take long to come up with the prevailing idea, but I’ve spoken of it to very few people. Part of this is because I know people will say I’m crazy and it isn’t possible. Another part is because as exciting as it sounds, it scares the hell out of me and I’m not sure how to pull it off successfully. I feel like once I write it down and click that “Publish” button, it becomes the thing I have to do.

The Tentative Quest: Travel by motorcycle with guitar in tow and play a paying gig in all 50 states.

It marries those two pastimes that I took on when I first realized anything was possible. It’s a proper challenge of skill, endurance, and the elements.

The Challenges

  • Nearly two years ago I purchased my first home. It’s a nice enough place and the idea was that I had enough for a down payment that my mortgage payment would be less than I was paying in rent. This would have been true if not for the expense of keeping up the place and the purchase of appliances and supplies. So in addition to taking on a mortgage and existing student loans I have taken on a not small (but not insurmountable) amount of credit card debt. Can I sell my house and all my stuff and come out on top enough to travel the US for some amount of time by motorcycle? How much money can I really earn while one the road?
  • Where does one stay when traveling the country by motorcycle? Take a tent and sleep in campgrounds? Couchsurfing in exchange for playing house parties?
  • How long should one plan for such an undertaking? How much rest is required between shows? If I spent a whole week in each state it could be done in a year, but no one wants to drive a motorcycle through Wyoming in December.
  • Alaska is technically drivable, but what about Hawaii?
  • My motorcycle probably isn’t quite up to the task…Also, I’ve crashed and spilled on bikes more often than I care to admit.
  • Who do I think I am and who wants to hear someone they’ve never heard of play acoustic covers and originals?

The Possibilities

  • If I recorded an EP and printed up some more original screen printed designs I would have some merch to sell along the way and maybe gain some new fans of my art and music.
  • If I’m going to drive to Alaska, may as well play a few gigs in Canada on the way. Boom! Internationally performing artist!
  • Traveling to so many places and meeting so many new people would force me to be more social and shake off my usual hermit ways.
  • If the performance schedule isn’t too tight I could continue to make art and write while on the road.
  • Take a photography class beforehand and document the country through photos along the way.


  • Ditch the motorcycle and do the whole thing by car. Pro: Gives some shelter to sleep. Con: Feels like wussing out.
  • Write a song collaborating with one person from each state. Could even do this from home with Skype or something. Pro: More flexible. Con: Really have to be more social and cooperative plus it still feels like wussing out.

There are of course other challenges, possibilities, and alternatives. I don’t know much about booking shows, but I know where I can get that information. I’ve done some preliminary research on trailers for motorcycles and bigger models that are better suited for cross country travel. I’m writing this early in the afternoon before going to Anderson’s Bookshop in Naperville this evening for a presentation/book signing by Chris Guillebeau. Maybe I’ll find just enough further motivation to start selling all the stuff I really don’t need and make this possibility a reality.

8 thoughts on “The Tentative Quest

  1. John A. Morton

    I vote for the bike route. Yes a trailer would make it easier. You are young enough to do whatever you want and then do something else you want. A caveat, whatever road you take in life, it is almost impossible not to wonder about the road not taken.

  2. John Post author

    True, you cannot take all roads and you can always ask what would have been different, but I doubt I will ever ask “what if I’d remained a third shift machine operator?”

  3. Heather

    So, any updates after the book signing? Did you hear about the guy that set out on a quest to work in all 50 states? When I heard about it I thought, that’s ridiculus; who’s going to hire this guy that they know isn’t going to stick around? But I think making his “quest” public helped him get those jobs. People will want to pay you to play because, “aren’t you that guy traveling the U.S. by motorcycle to play his guitar in all 50 states?!” Maybe you don’t have an exact plan of how it will work out. Maybe you have a plan of how it will start out, and hope the rest works itself out. The best laid plans don’t often work out, and my best adventures have been when I didn’t plan as much as I probably “should have.” Was it sometimes a really bad idea and I could have really gotten hurt or in trouble? Yes. But I didn’t and it was great. And I don’t think you would have to sell the house to do it. If you ran out of merchandise, you have people ship more stuff. I say do it.

    1. John Post author

      No real updates. His talk seemed more geared towards people who hadn’t yet read the book and might consider reading it, so I didn’t walk away with any new information. I had one question I wanted to ask, but was tangental to his exploits, and didn’t get time to ask it and forgot when I was in line to get my book signed. I feel like I should have been more social and tried to meet some other people, but if nothing else it was a boost of inspiration.

      I’m not sure publishing a book on photography is my style, though I certainly enjoy looking at photography. I guess I should have been more specific saying I’d like to publish a book with a substantial amount of words. I have had some thought that if I buckle down and start writing now I could have the thing I’m writing done by spring in which case it could be a book/EP/art tour while also playing music.

      You’re right, I may not have to sell the house, but if I’m not in it I’d have to at least rent it out. Then the other concern is making enough money on a regular basis to continue to pay whatever other outstanding/regular bills I have, student loans mostly, but also health insurance, fuel, etc. That’s where it will be helpful to have some sort of financial cushion before setting out.

  4. Heather

    Also, especially if you document with photography, you could get a book published about it after your trip and cross another one of those things off our list.

  5. David

    There is a motorcycle trailer that you can get that is essentially a mini pop up it is only really big enough after popping up to lay down in i will send the link if i can find it again but if you pass through colorado I want to see you and i will go to your show and even buy a Robot shirt (really want to see you and really want the shirt)!

    1. John Post author

      I think I have seen something like that. It might be a consideration. I might set it up so that I play primarily house parties in exchange for food and a place to crash. The trailers I’m looking at now are narrow which makes it a little more possible to avoid road hazards as one really hopes to avoid potholes and roadkill on a motorcycle.


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