I've read some of Bob Kastigar trip write ups and I'm seeing other people planning trips and it makes me wonder how people do it.

I'm itching to do some short tours this spring and summer, however I can't imagine that I'll be able to do much more weekend camp trips since I can't take all that much time off of work.

For people who have done longer tours, how do you support yourself? Are you self-employed? Do you have seasons off of work? Do you just not worry about finances and live like a bum? What about health insurance?

In my head I have a fantasy of traveling the country and living simply, but how do others deal with financial obligations?

Thanks in advance.

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Let me explain how I do it:

I've got a decent (union) job and I've been there long enough that I get four weeks vacation a year, plus 3 personal days and a day-off when I have to work any of the five holidays a year.

Another benefit to the union contract is the ability to take off two-weeks without pay each year after working twenty years. Several years ago while one a bike trip I called in to get my schedule for my return to work. I found out a good friend and co-worker - many years younger than me - died from an illness. That shook me up. I'd never taken the unpaid leave until then, but I've taken it every year since his death.

Life is too short. Ride your bike.
jamimaria,
I have done a few longer tours now and have been pretty lucky. First, I was waiting tables and didn't give a shit about the job, had a lot of roommates so rent was low, and made a point to keep all expenses super low in my life (i.e. no car, credit cards, etc). My tour down the coast was done during grad school. Saved up enough to cover the trip, talked to my land lord about paying less during summer for my apartment (he was flexible), and again, had no outstanding bills. For my super trip I saved up money working as a special education aide at a local high school, and now I'm just waiting for the weather to warm up. Oh, I took the super fun step of moving in with my folks for a while to save cash to tour. It is a little degrading as an adult, but I have been planning to go on a long tour for a while, and it was a vital step. Also, when on tour, I live like a bum. So, I have taken a different approach to touring than Bob, but it is very deliberate and takes some sacrifice to achieve. I know for those with steady jobs/careers, it is tough to just up and quit or take a lot of time off (both financially and psychologically). But as a friend of mine likes to say, "It doesn't have to be epic to be a great experience." I agree. But epic is fun too.

So, I would suggest working in education where you get breaks and summers off.
Or, use the modern depression as an excuse to drop out and travel west, like all them travelers in the 20's and 30's:)
Or, more feasibly, utilize your vacation days for three day weekends during the summer for weekend trips. Use Metra to get out of the city, then ride a day, camp (free or state park), then loop around to a different Metra to get back. There are plenty of folks around here looking for fun long weekend trips that a touring posse is super doable.

I hope this at least answers your question about how someone might go on a long tour. I also wish you could come with me on my trip out west then north.
Scott
Thank you very much. Working in education definitely seems to be an idea. I like kids. I'll have to look for some part time education programs. I have a dream of supporting myself with balloon art, however the whole self-employment thing seems unbelievably scary to me.

I'm planning some shorter three day weekend trips this summer. On the list this summer is the Indiana Dune and the Illinois Beach State Park for short camping trips. Using the Metra as a slingshot is something I need to keep in mind more.

Good luck on your epic tour. It sounds like an amazing time. I'm originally from Washington State, and I hope that the Washingtonians are good to you!

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