And so I stop. These aren't real goals; I recognize them as daydreaming. I'm already defeated before I've even begun. And thats where you're going wrong. There's nothing stopping you from doing a single thing on your list besides you. Sometimes being naive about what it will take to accomplish something is actually whats needed to do it. Not to mention most of the things on your list, while amazing experiences, take…
> You could be biking across Canada by Tuesday and $1500 later if you wanted to. No. He needs to practice riding and get in better shape for a month or three first. But he can start doing that tomorrow. Don't go riding cross country without some practice first, some fitness, and some knowledge of things like patching a flat tire.
I disagree. He can bike as far as he wants each day, at whatever pace he chooses. You don't forget how to ride a bike, he may be wobbly for the first few minutes but he'll be cruising soon after.
Practice and fitness aren't needed. All you need to do is be able to ride. He could start off biking 5..10...20KM per day if he wanted to and slowly build up as he gets in better shape as long as you plan your route accordingly to make sure you have a place to stay.
> and some knowledge of things like patching a flat tire.
This is true, but nothing you can't learn at a bike shop and a few patch repair kits can't help with.