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.