It gets a little repetitive and boring at times but I'm able to save so much time and energy this way to focus on what's important to me.
When you're young, you have all these things to worry about - should you go there, what about your mother. And you worry, and try to decide, but then something else comes up. It's much easier to just plain decide. Never mind - nothing is going to change your mind. I did that once when I was a student at MIT. I got sick and tired of having to decide what kind of dessert I was going to have at the restaurant, so I decided it would always be chocolate ice cream, and never worried about it again - I had the solution to that problem.
Whenever I'm at a restaurant, or ordering food for whatever reason, I will check the menu for an item that prominently contains mushrooms. If such an item exists (and it doesn't sound awful or ridiculously expensive), then that's what I'm getting. Decision made.
I started doing this mainly because I like mushrooms, enough that it felt like a really easy way to hand off decision making. It's also good in that, unlike the above, I don't get just the exact same thing every time (although mushroom burgers are starting to seem pretty same-y).
Also reduces the odds that you'll be looking at someone else's plate thinking "I wish I'd have ordered that instead" :)
When you don't have to spend mental energy on it, it's automated. I think that's the real benefit of Steve Jobs's standard outfit: don't have to choose, don't have to shop, just wear clothes and get on with the interesting stuff.
For work clothes, I have 5 decent combos which I repeat M-F. Doesn't bother me to repeat. Helps that I'm a dev so I'm always Feynman-ing myself away from unnecessary meetings and face time with business side clients.
For commute routes, I watched my phone's gps for a few weeks, tried different routes, seeded new ideas for routes and detours by brute forcing options into the backend and now I can consistently get home within 50 mins of leaving work which includes driving down a few floors of parking at 10-15 mph. I used to take anywhere between 45-90 minutes before. Plus my mpg is usually at a respectable 26-28 mpg for a midsize sedan.
Hope this helps.
Here's a <a href="http://i.imgur.com/VNJ08Ra.png">screenshot</a> of the thing I made in Flask to keep track. Orange needs to be washed next time I wear it, red needs to be washed now.
Having five sets of the same clothes certainly makes life easier. And when I finally do change my attire the office gets a laugh out of the fact I actually went into a clothes shop.
One caveat, though - if you do this, commit to it. Don't do what I did and keep one or two pairs of non-conforming socks just because I liked them. Because now they just recirculate through my sock drawer, gumming up my otherwise perfect system. :P