Answer by Joe Blitzstein:
I've been playing chess for 25 years (my US Chess Federation Rating is about 2100, about midway through the Expert range) and living life for 35 years.
Before my main answer, let me mention the awesome chess scene from The Wire:
They do a nice job drawing analogies between chess and the drug trade.
This is an extremely open-ended question so let me just point out a few key similarities and differences.
Similarities: the following considerations are essential for success.
Planning for the future. Doing this well involves a mixture of strategy (long-term planning) and tactics (short-term calculations about how to achieve your goals).
Time management. Time is a precious resource (which reminds me, I shouldn't spend too long writing this answer…). In chess, time management is required both on the clock (when playing a timed game, as is always the case in tournaments) and on the board (the unit of time is called a tempo, and wasting tempi is a recipe for disaster).
Pattern recognition. Both in life and in chess, reasoning well about complicated problems requires recognizing patterns, structures, and analogies, so that the situation can be chunked into simpler pieces and to make it easier to effectively use past experience.
Differences: here are a few key differences between chess and life.
Randomness. Chess does not involve rolling dice, flipping coins, or other stochastic components. Chess players do sometimes say things like "he got lucky" after a loss, but it's debatable whether that is really luck. Life is suffused with randomness (which is a major reason that we need probability and statistics!).
Information. Chess is a game of complete information, unlike (for example) poker. You know exactly where your opponent's pieces are. You know exactly how your opponent's pieces are allowed to move. You know exactly what the rules of the game are. In life, it may be hard to know what the capabilities of your enemies are (and it may even be hard to know who your enemies are, or if you have any), and there isn't a standard definition of "success".
Zero-sum. Chess is a zero-sum game: if one player wins, then the other player loses. There are also draws (ties) in chess, but that is considered "splitting the point" (in most tournaments, a draw results in each player gaining 1/2 point, whereas a win results in 1 point and a loss results in 0 points). In life, it's often very possible — and very important — for people to work together collaboratively and do better than they would have if they approached everything as a cutthroat battle.