Hey Jacob, I'm with you most of the way here, but let me share a few of my life experiences.

1. Planning
   Whenever I plan on something, a trip, an action.. whatever, if it is more than a few days ahead of time, it was all a waste, because something ALWAYS happens to change those plans, so much so that they were unrecognizable from the original plan
2. Depending on others
   It is really pretty obvious that we cannot live our lives without depending on others in myriads of ways, but I see your point.
   In my declining days, I'd had so many DUI's that I'd lost my drivers license TWICE for 5 yrs. It was either walk (we lived 5 mi outside of town) ride a bike (very hot, very humid in the South and part of my journey was dirt road) so I ended up depending on others for rides. If they said "I'll be there by 2" I was ready by 1:30 at the latest. I was often disappointed because they (every they I tried) were more often than not, late or a no show.
3. Murphy's Law and its first corollary

"Anything that can go wrong, will go wrong"

1st corollary: anything that can go wrong, will go wrong "at the worst possible time"

So I don't plan, I set goals looking for flexible means for attaining those goals.
I hope you can get your plans achieved. Let me know if I can help.