Obvious example: paying off your credit card debt and starting an automated savings plan is playing the long game. In contrast, carrying credit card debt because you cannot manage your month-to-month spending is playing the short game.
Having clear and specific financial goals--and taking clear and specific steps to achieve them--is excellent long game. Not having financial goals (or worse, allowing your ego to convince you that you "don't want to be preoccupied with money like that") is short game. And delusional.
Playing the long game means not only understanding how compounding works, but taking action based on that knowledge. Pontificating all-knowingly about how compounding works without having any meaningful savings or investments is pure short game.
Impulse purchases are short game. Not having an emergency fund is short game. Using debt to make impulse purchases when you don’t yet have an emergency fund is laughable short game.
On the other hand, having a year's worth of expenses saved up in an emergency fund is good long game. Having two years' worth of expenses is really good long game, and it will entirely change how you think about work.
Have you read any of these highly regarded personal investing books? Not even one of them? You're playing a short game. Why tolerate this in yourself?
Basing your retirement strategy on hope (as in "I hope it works out" or "I hope I earn 25% annual returns in the stock market") is pure short game. A retirement strategy based on clearly established savings and investment habits is long game.
You can apply the long game/short game framework to individual stock investments too.
Owning stocks, but not really knowing what they do or why you own them, is short game. Claiming you don't have time to fully understand what you've invested in is short game. Prepare to be rudely separated from your money.
Getting mad or sad because a stock went down after you bought it is short game.
Long game, on the other hand, is thinking of yourself as a part owner of a business. Long game also means understanding that stock prices fluctuate, and it means having the courage to reassess an investment when its price declines. Perhaps you should buy more.
Knowing your stocks is long game. In general, this means being able to articulate what the company does, what its competitive advantage is, what the industry dynamics surrounding the company are and what your investment thesis is for owning the stock. If you can do this, you’ll be better prepared than 90% of investors out there--including the professionals. If you can't do this, or don't want to do this, keep reading: there's a solution for you in about four paragraphs.
Humility
Being humble about the outcome of any investment is playing the long game. Buying AAPL at $700 a share (after it's already gone up more than tenfold) and confidently presuming it will go higher is doofus short game. Investing in something because you saw some blurb on CNBC is incompetent short game.
Playing the long game means grasping an important meta-idea: every investment you make involves someone on the other side of your trade. If you're buying, they're selling. If you're selling, they're buying. Asking yourself why a person would take the other side of your trade is one of those questions which, when asked, answers itself. Long-gamers think humbly and carefully about this.
By the way, most of your fellow shareholders will usually be playing the short game as they invest in stocks alongside you. Many will panic out of a stock at the worst possible time. Knowing this--and knowing what this might imply for each the stocks you own--is extremely sophisticated long game.
Then again, it’s also excellent long game to realize that "knowing your investments" may very well require more time than you wish to allocate to investing. An intelligent long-gamer can solve this by using a diversified collection of low-fee index funds as an investment strategy.
Going Beyond Finances
The long game/short game metaphor extends beyond mere financial issues. We can go much further. A few examples: Willingly eating a poor diet is short game. Eating whatever you want because it’s yummy and you want it is short game. Making reasonable, conscious decisions about what you eat with an eye to your health and well-being is long game.
Confusing buying a lot of expensive athletic gear with getting in better shape is short game. Starting (and more importantly, maintaining) a habit of regular exercise is long game.
Do you talk about a hypothetical novel you're going to write someday, musing about how great it's going to be? Or do you build a daily writing habit and stick to it?
Do you think long-gamers are a bunch of know-it-all killjoys who don't know how to have fun? Your ego is playing short game with you. It wants you to rationalize your poor choices rather than seek solutions.
What is the last bad habit you've eliminated from your life, or the last good habit you've added to your life? Long gamers can list at least a few right off the bat. Can you? Why not start playing long game, and pick a habit to eliminate (or add) right now?
Readers, I believe each and every one of you is a natural at playing the long game. In fact, the very fact that you're still reading this post is a strong signal that you have more--much more--long game in you than you may think.
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