This is the Second Roadtrip I took in 2011. Briefly what happened was I got a call from an Artist who I previously worked for and he needed someone to deliver his paintings down to Miami for the Art Basel Festival 2011. I had my truck available. I decided to take the job on the terms that I could bring my piano and dog with me. This gave me the opportunity to set up multiple incomes. In attempting to make money while traveling, the idea is to make your work, your play: Which is not an easy thing. This opportunity sort of fell in my lap out of the blue, but its important to have skills that allow you to Freelance with multiple jobs at once.

Here are the Stats for Roadtrip #2:

After every major task in life, its important to do an evaluation so that the next time you do it, you will do it 10 times better. 

We did it! The purpose of this trip was to do what I love (Play piano, Travel the world, and Meet people) while trying to make a decent living off it. This is the dream life.

  • Total Miles: 4,400 Miles
  • Total Days: 21 Days

  • Total Spent on Gas: $0.00
  • Total Spent on Hotel: $50.00
  • Total Spent on Food: About $300.00

  • Hours spent moving and packing: 20 hours
  • Hours spent playing piano on the streets: 15 hours

  • Total $$ from Delivery Jobs: +$1350.00
  • Total $$ from Playing Piano: +$675.00
  • Came home with $1700.00 in my pocket!

  • Major Cities Visited: Charlotte, Miami, Key West, Tampa, Gainesville, Atlanta, Athens, NYC.


Pro’s and Cons


-When speaking to the delivery clients I always made sure to tell each of them that I work for myself. This way, they don’t feel like they can skimp on fees. I was able to negotiate my own payment and get a great deal.


-I made my own hours and have flexibility for when I can make the deliveries.

-I spent very little hours actually working. Most of the work was driving anyway.

-I met some great people through and saved more money on hotels.


-The only downside to doing the deliveries was that coming back home I did get pressured for time by one of the clients which forced me to move quicker through the Carolinas and northwards.

-I didnt get to play piano as much as usual.


If I were to do this differently:

-I would organize dates and plan better so that each person I work with understands the dates I will arrive and deliver. Make sure to flush out all the specific information before taking on a job.

-I would play more piano in more locations as possible. I missed great opportunities in Key West, Everglades, Homestead, Miami, Tampa, Gainesville, Atlanta, and Asheville.

-Network and meet more people in general. I could have met many more artists and maybe even played piano at a few galleries or parties.

-Use more.

-Always do a little bit of research before going to a major city. Its good to wing it, but when you arrive in a city that is empty, its not fun. Its important to do some planning.