Boosting your confidence is useless, this isn't soccer, I'm here to help you stay real.
I've never hopped a train in my life, I hitchhike. However, I do have a few tips that cover any traveler.
Keep in touch with loved ones, you don't want them to worry (they'll worry no matter what, especially if you don't stay in touch). And when I say worry, I mean like a heart attack, people can worry themselves into a panic attack which can lead to a heart attack, especially if a loved one goes missing.
A tarp can make a tent with a stick, tent stakes, and a string. You can even forget the stick if you can tie the up side of the tent to a tree. To learn how to do this, look up tarp tent on google images. If you think you're gonna get stuck in the rain, best get a tarp.
A can opener is crucial, if you're hungry and the only food you can get your hands on is in a can, you'll want a can opener or a big knife. However, if you have a big knife when you're asking for food, people will run. can openers can be small, light and easy to pack.
Don't bring more than one set of clothes, you're going to get dirty no matter what. Plus, free clothes is almost as easy to find as free food while traveling.
Bring 3 pairs of socks. Don't wear waterproof footwear unless you like bootrot. The better your shoes can breathe, the better. Also, good arch support is important for lots of walking, test your shoes by walking around all day (best bring your pack too) to see if they're comfortable.
Bring an atlas. People give good or bad directions during day, people give worse directions at night. GPS units can break, require batteries, are slow, and confusing for tech illiterate people.
Bring a good book and learn a hobby that you can take with you (you'll have a lot more free time than you know what to do with).
A sharpy marker plus a card board sign is referred to as a credit card. If you need a bit of money for tobacco or whatever keeps you happy, don't be afraid to use it. Nobody wants an upset hobo, so take care of your needs as you please.
Never let your pack leave your sight.
When you pack your pack, don't bring anything you want to keep, and be prepared to wear your pack for a long, hot, day of walking, for several days. Make sure it's comfortable and light, and test it with a day trip.
Train hoppers use a bandana to breath through in tunnels where the air gets dirty for a few miles and call it a "skank", some prefer theirs to be as dirty as possible to add filtration (lol, dirty s****). Contractors, laborers, bikers, skaters, hikers use a bandana to absorb sweat and stay cool and don't call it anything particular (bandana, rag, sweat band, whatever). Since it's summer, you might as well bring two. I would imagine you would want one to absorb sweat and stay cool and another for a "skank". (apology to the mods for my language)
Don't trust a home bum (hobos and home bums are two totally different breeds), and don't expect a home bum to look like a home bum (they can look well dressed and clean). If they're hustling, they're a hustler, that's what they do.
Don't argue with cops, but do ask them for directions (unless you're wanting to be directed to something illegal, then don't).
You'll meet travelers along the way, come up with a way to see if they respect you and have a sense of empathy. To test respect, I tell a joke in a prolonged, hesitant, yet still funny manner, if they have the patience to listen to the entire joke, I'll know they respect me enough to listen to my drawn out joke. To test empathy, see if they can relate emotionally to experiences you've had before that reflect a certain emotion. If they pass both of these tests, you know they have morals and you know they respect you, I would consider that worthy of trust. Do this as soon as you meet a person, I do this and it tells me a lot about them.
Don't expect anybody to have all of the answers, people can help you, show you how to do things, but they can't show you how to live your life, that's something you have to do on your own.
Churches can (can, not always will, but they should and they can) help you a lot with food and clothes.
A mission for homeless people will feed you plenty, give you pajamas and a bed, give a good sermon/nap time. However, they do not allow you to get intoxicated, stay out late, carry weapons. If you're weary and want to have a few days to rest at night, this will do just that. However, it almost feels like attending church, eating like in jail, showering after high school PE, and sleeping in bunk beds like in summer camp, but with a bunch of homeless people. I really enjoyed the LA mission except for the fact that I was the small white guy and we all showered in front of each other (for a country boy who didn't shower in the lockers in high school, HA! Awkward!). Hell it's an experience though. I felt a lot more comfortable skinny dipping in front of a bunch of people after that, and shutting my brain off for other things too now that I think of it (extreme sports and stunts).
When people claim to be Jesus Christ on the street (I've met a few), don't believe them. That's one thing He warns us about.
When you run into an emotional problem, find a sober person to talk to about your problem, if you ignore it, it will keep kicking you, if you face it, you will understand it and eventually learn how to deal with it.
If you get yourself into a pinch. You could ask us, but we're on the internet and you'd have to either borrow a laptop at starbucks (or whatever place with wifi and laptops), or use a library computer (sometimes easy, sometimes not, but timely response can be an issue). However, you're best off to come up with a plan on your own.
Be honest. Stay smart. Play safe. Trust lightly and love deeply. Keep in touch. Have fun.
That's all I can think up right now.
