Hashing Out My Weekly Schedule

Lately I've been in a quandary.

There's only so many hours outside of my current 9-to-5 job to pursue both daygame and location independence. While I'm currently on track make it to location independence by June 2015, I'd like to be able to supplement the investment income I'll be living off with location-independent income if need be. In other words, I'd like to have a developed skill set to deal with contingencies such as slow stock markets, higher than expected expenses ... or even boredom.

My initial research suggests that freelancing on sites such as Elance may do the trick, given my skill set - but not overnight. As I understand, it takes time and effort to not only learn how to freelance, but to also build a reputation to the point where you're earning decent hourly rates. Last thing I want to do is to give my goodbye to corporate America, only to have to come crawling back because I wasn't prepared to generate a sufficient location-independent income on top of my investment income.

Am I being too conservative though? Even now, I'm in good enough financial shape to lead the life I want. So even if the stock market ends up being flat to today in June 2015, I'd still be fine. And it's not like even one bad year would put me in the poor house. It's just that I'd be dipping into my principle, which I could probably replenish by freelancing at that point. And before that even happens, I'd probably be regularly trying to make some money off my hobbies, with the hobby being the primary focus, and the money being just icing on the cake.

With all that being said, here's what I think my typical weekly schedule should be:

Monday - Friday, 9 to 5: Work
Monday, Wednesday, and Friday nights: Lift
Saturday and Sunday mornings: Errands
Saturday and Sunday afternoons: Daygame
Saturday and Sunday evenings: Hang Out w/Friends or Freelance
Tuesday night: Date, or if no Date, Freelance
Thursday night: Date, or if no Date, Daygame, then Hang Out w/Friends

Of course, the schedule will be adjusted for post-June 2015 location scouting visits. Those visits are the primary reason I'm still in corporate America.