If you love planning, then that's great.
Personally, I'm not that keen on planning. I'm more of a ... OK let's pack up and go wherever the wind blows us ... sort of person.
And I have no regrets doing that. In fact, I'm very glad I did. For one thing, I ended up meeting, getting to know, and marrying my husband that way.

But on a less happy note ... because of medical difficulties that started June 2009, my energy and therefore my cycling, have diminished dramatically. In 2004 I decided to tour Australia for 3 months, which I did that year. If I had decided to wait 5 years, I may not have been able to do that.
I know planning can be fun, but sometimes you've got to seize the day ... even in a small way ... or it might never happen.