Winning Long-Term Games | Alessandro Desantis

Highlights

The key to winning long-term games is to stop playing them as a succession of separate short-term games.
When considering how to play a given short-term game, examine the impact of all options on your longer-term goals and choose the option with the most positive influence.
You can win long-term games without addressing common causes of failure, but the chances are that you won’t.
To have a good chance of winning long-term games, you must be aware of common sources of failure and do something about them before it’s too late.
You don’t play iterated games. You enter each meeting (with partners, customers, etc.) as if it were a one-off transaction. This is fine if it is indeed a one-off transaction, but most interactions are iterated games (or should be). Approach them as such.
You kill your Goose. To get the proverbial Golden Eggs, you need to grow a Goose first: a reputation, a network, a team, a body of work, etc. However, when we see others producing Golden Eggs faster than us, we are tempted to squeeze our Goose to keep up, killing it in the process.
You have a non-reproducible definition of success. For example, aiming to become #1 in a field with a lot of competition is non-reproducible by definition because all it takes for you to fail is a single person more determined or luckier than you. You can succeed under these conditions, but you cannot guarantee success.
Your objectives are misaligned with your talents and dispositions. While you might win an uphill race, it will be much more difficult than winning a downhill one. Moreover, it will require so much time and energy that it will negatively impact the rest of your life. The alternative is to embrace your talents and predispositions.
You have mixed feelings about achieving your objectives. For example, you want to become wealthy but also have mixed feelings about wealthy people. This might become a major limiting factor.
In addition to these, take a few minutes to consider whether there are other common reasons for failure specific to your long-term goal(s). For example, if your long-term goal is to become a successful lawyer, think carefully about why people who studied law might eventually fail to achieve this objective.
Be careful about thinking, “This problem won’t apply to me because I’m smarter than they are.” Smartness is often judged post-hoc, so you do not yet know how smart or wise you really are.
Yet, the feeling of falling behind is strong.⁠iii And it is precisely this feeling of falling behind that makes many of us switch from good long-term strategies to poor short-term ones.
In fact, among those growing fast, we will find many skilled people, but among those growing very fast, we will find plenty of skilled people who are making short-term choices. As a result, if we emulate those growing faster than us, we are more likely to imitate short-term optimization than competence.
The tricky part is that people succeeding with non-reproducible strategies are often extremely intelligent and hard-working, which misleads us into believing that intelligence and hard work are sufficient to imitate their success. But that’s often not the case. Instead, luck or other difficult-to-reproduce conditions are frequently required, too.⁠iv
However, we should differentiate between bets that might not work and strategies that might not work-you can afford the former, but not the latter.
The same faulty reasoning applies to our evaluations of strategies. Of course, everyone who succeeded had a great strategy – if we use hindsight to determine how great a strategy is. That might lead us to overestimate how likely we are to succeed with a great strategy. It’s not that great strategies aren’t powerful. They obviously are! But it’s hard to know what a great strategy looks like without relying on hindsight.
The key is that good strategies do take gambles, but only when they make sense in the long term. They never take gambles whose failure might endanger future chances of success.
Good long-term strategies have three properties. 1) They are sustainable. They do not require risks or sacrifices that you cannot take for long without severe consequences, or that would clash with your other long-term goals. 2) They are constructive. They play iterated games and build, instead of consuming, the long-term assets that bring long-term success (such as trust, know-how, relationships, capital, etc). 3) They move towards inevitability. They proactively surface and address problems; they learn and adapt. They do not merely provide a chance of success but do what’s required to almost guarantee it.
If you have a long-term horizon to achieve a goal, it doesn’t make sense to use tactics that are optimal for holes-in-one. You want to use strategies optimal for a hole-in-three. Strategies that progressively get you closer to your goal. Ask yourself: what assets (skills, habits, relationships, resources, etc.) would make your future projects more likely to succeed?
Some believe that long-term strategies are lazy or excessively conservative. Usually, that’s because they look at driven people and notice that most of them use aggressive short-term strategies. However, driven people who consistently use long-term strategies achieve better results than those who use short-term ones, especially after taking into account survivorship bias. Hence, employing long-term strategies is not lazy or conservative, but rational and ambitious.
Playing the long game has nothing to do with delaying gratification-only with delaying comparison. You must resist the temptation to compare yourself with others based on your short-term growth rate or temporary success.
Ideally, avoid all comparisons, but if you must, compare yourself only against those who are also playing the long game. Those who are also unwilling to compromise their values, take excessive risks, or over-focus on a single area of their life to the detriment of others.
if you achieve average returns for an above-average amount of time, you receive well-above-average returns.
What matters is not the expected value of a bet but its distribution of outcomes.
Winning long-term games requires managing long-term risks, even if they seem small in the short term, and building long-term assets, even if they seem unprofitable in the short term.
This is a common paradox. Building long-term assets (such as skills, habits, relationships, etc.) never makes sense in the short term (there is always a faster way to meet short-term objectives), yet it is necessary for long-term success.
“Because the very important does not have a deadline, we have the impression that we can delay it for a few days. It is a huge mistake. Delaying something once opens the door to delaying it forever. If you think about it, the very important never feels urgent.”
Plenty of games are zero-sum over the short term and positive-sum over the long term. Therefore, playing long-term games as if they were zero-sum often hinders your long-term growth.
Never envy someone with a strategy that produces a worse distribution of outcomes than yours, even if, for them, it did produce a better outcome.
The lesson is that relying only on talent and hard work might not be enough. You must also increase your luck – or, more precisely, its surface area.
In large competitions, the sheer number of competitors means there will be more than one competitor talented and hard-working enough to have a decent shot at winning. Therefore, there is no reproducible strategy for winning large competitions. So, you shouldn’t enter any non-trivial competition that wouldn’t be good for you even if you didn’t win it.
Never compare yourself with someone who has different priorities or is optimizing for different objectives or for a shorter time horizon. Doing so leads to unhappiness and/or making counterproductive decisions.
Only goals that allow enough winners and can be played many times are reproducible. Choose reproducible goals. Or, at least, acknowledge that you chose non-reproducible ones and that, therefore, no matter your talent and determination, you have at most a chance at achieving them, but no guarantee.
Use your bets to build skills, relationships, trust, and other assets that last in time. They will make your future bets more likely to succeed.
Never risk your long-term assets. No bet of yours should, in case of failure, destroy your health, capital, relationships, and trustworthiness.
To maximize a project’s chances of success, dedicate as much effort as possible to it. However, to maximize your chances of success, work on as many projects as possible, dedicating enough effort to each to achieve a sufficient level of quality to give them a proper chance to succeed.
A common bottleneck to learning is what I call the effort trap: the belief that through sheer effort, we can overcome that thing we know we need to learn but don’t want to.
I always say that problems grow to the size they need to be acknowledged. If you want an easy life with only small problems, strive to acknowledge them as early as possible.