My name is Jedidiah Jenkins and I am a travel writer. This is a new profession, really a risky new chapter that I dove into to at 30. I went to Law School right after undergrad and then worked for five years at a charity called Invisible Children. That was an incredible experience but as I approached my thirties, I knew it was now or never to chase my dream of being a writer. I decided to quit my job and ride my bicycle from Oregon to the tip of South America, Patagonia.

Why did you decide to go on your bike trip?

It stemmed from my dream to be a professional writer. But I didn’t want to write without doing something interesting first. It was a risk and scary, so I thought if I did something objectively interesting, it might make a good book. So here I am, at 33, after the trip, writing a book about it. It’s scary. I’m still testing it all out. But I’ve never felt more alive.

How does someone prepare to go on a long bike trip?

To be honest, I walked into REI and asked the bike guys. They gave me tons of tips. But the best help came from a friend who had done a similar trip. If you can talk to someone who’s done it, or read the blogs of those who have really documented it, you can learn a ton. But the best advice I got was ‘just start going. You'll figure it out as you go. You’ll need more or less than other people, but you won’t know til you’re on the road. Don’t let prep slow you down. Just start.’ I think that’s amazing advice for anyone doing almost anything.

What are the costs involved with a trip like this?

Bike equipment and gear probably totaled out at $2000. Then hostels and food and housing for 14 months, if you did it cheap and mostly camped, would be around $10,000. You could do it for less if you only camped or stayed with host families (which you can do with CouchSurfer and an app called Warm Showers). Or you can easily do more if you want to treat yourself to hotels and nice meals in the bigger cities. I mean, surviving for 14 months without a job requires saving up some money, so it takes a bit of planning or the good fortune of having money saved.

What are the best parts of going on a bike trip?

The pace of travel. The new people you meet. The way you feel the road and every turn and the wind at your back (once in a while). You feel like you are connecting with the place, not just visiting. The feeling of total freedom. Sometimes no one knows where you are, and you realize you can make any choice, stop anywhere, sleep in the wild. Total self sufficiency. That’s not always the case, but there are moments of that, and it’s incredible.

What are the biggest challenges of traveling by bike?

Homesickness. Bike maintenance. Just getting used to life on the bike. Transporting the damn thing when you need to take a bus or a boat or a plane for whatever reason. But you get used to most all of those things, and it becomes totally normal.

What advice would you give someone who's thinking about taking a bike trip?

Try to do a week long one first. Bike the coast of California. Or Maine to New York. Sleep in the woods. Give yourself a taste. You might find it’s your favorite thing. I didn’t do any tests and just committed. That’s the thing, if you want to take a very long trip, you need to publicly commit. Tell everyone. You’ll get scared sometimes and want to back out. If all your friends and family expect you to do it, it’ll help make you stand by your word. Use peer pressure to your advantage.

Any other helpful resources or links on this topic?

Just search bike-touring online. There are a million blogs to help you get started. Lots of people are doing it and there’s a whole community behind it. Here’s a place to start: