Having a perfect bracket is basically impossible. Predicting what’s going to happen in the first round is relatively easy, since all the teams are set. Early upsets can be very costly, since they can hurt your chances of getting some of the later games right.
Playing it safe and going by who’s ranked better is fast and easy. But it’s easy for Jim and Bob, too. If you don’t bet on a few upsets, your score will be identical to theirs.
Picking the winner of the tournament is relatively easy. The underdogs may connect a few games, but it takes much more to win it all.
Here are the analogies for you:
If you are making a project or business plan, focus on what you know. Planning too far into the future is not planning. It’s guessing.
Taking risks may not feel comfortable, but it could be your best strategy.
Invest in yourself and your skills. In basketball or business, one does not become the champion overnight.