Successful people plan. People who don’t plan rarely become successful. You might hit the lottery, but if you want to succeed, you need a plan. Easy enough.
But one plan is probably not enough. Now, someone who makes a plan and then stops thinking about it is way better off than someone who doesn’t plan at all, but he’s still not in the best position he could be in. Why? Well, most plans go to shit. (Or, “life is what happens while you’re making plans”, if you want to be couth.)
Really successful people make contingency plans.
Really successful people don’t rely on every step of their plan falling neatly into place and being executed perfectly. Really successful people realize that their plans rely on other people who are at best uninterested or preoccupied with their own lives, and at worst lazy, incompetent, or evil.
This applies to every aspect of life. Let’s take traveling. When you’re traveling with a defined itinerary (even something as simple as: must be in London on Thursday, then Paris on Saturday, then Barcelona on Wednesday), if you just make one set of plans, everything might go perfectly. But, part of your plan is likely to encounter a problem. Whether your driver doesn’t show up, or the hotel loses your name, or you get sick, or the fucking baggage handlers go on strike and shut down the airport, or whatever. Shit happens. If you want to ensure everything goes smoothly, you make backup plans. I’ve arranged for Tony can pick us up if Al doesn’t show. We can definitely get a room at this hostel if something happens at our hotel. I can take a bus up to Girona and take a flight out of there if the Barcelona airport shuts down for 3 days because the fucking baggage handlers go on strike. Hell, Tim Ferriss makes sure he has the best nearby hospitals on speed dial wherever he goes.
Weekend plans, trips, educations, career paths, relationships. It’s extremely helpful to examine it all through the eyes of a pessimist on a regular basis. What can go wrong? How can this get screwed up? When is the worst time this guy I’m relying on could drop the ball? Who might intervene to make this unworkable?
Shit will hit the fan at some point. Guaranteed. Expect it. It’s easier to lay down some plastic tarp now than it is to scrape it off the carpet after the fact.