Winning vs Losing

A client of mine is a trader. When he makes money in a trade, he says it’s a “good” trade. When he loses money, it’s a “bad” trade.

This good vs bad system causes him to have emotional reactions to the trades. When they’re “good” he feels happy, relieved, and comfortable. When they’re “bad” he feels stressed, guilty, and sometimes even entirely lost and worthless.

But is he viewing things accurately? Is “losing” the same as “bad”; and “winning” the same as “good”?

This is a thought-experiment I want you to consider if you’re also someone who reacts emotionally to wins and losses.

Consider a Chess Grandmaster

To achieve this title, you need to be one of the top 1,000 or so players in the entire world (you’re better at chess than literally hundreds of millions of people).

And yet when you review any Grandmaster’s chess game history, including world champions like Magnus Carlson and Gary Kasparov, you might be surprised to discover that they lose chess games… often! And they’ve lost recently!

In fact, most chess masters and Grandmasters lose games almost as often as they win. Such is the nature of competitive chess – the better you get, the higher your rating, which means you must play higher rated players. Your win/loss ratio stays about the same as you improve because you’re always taking on tougher competitors!

For a chess player to feel “bad” about losing is absurd. Losing is built into chess; it’s a fact of life for players. In fact, they get their best wisdom and development from analyzing the games they lost, as chess is really a game of making less mistakes than your opponent, given that you’re often equally rated.

It is in fact necessary to lose almost as often as you win to get great at chess! If you have an undefeated record in chess, it only means you refuse to play against better players, and are instead choosing to deliberately only play against people who are much lower rated than you.

Think for a minute: is there any pursuit of greatness that doesn’t follow these same win/loss principles?

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All masters lose

All great fighters have been knocked out and injured. They’ve lost fights. Does this mean their development pathway was flawed? No. These were not mistakes. They were the inevitable consequences of pushing your comfort zone. Only someone willing to get knocked out can become a masterful fighter – this is why martial arts that feel safe to practice don’t work in real life fights.

Perfectionism is the idea that someone can make progress without any failures; a line on the graph that just goes up without any fluctuations. This might be possible in a few pursuits, but you’d have to go so slowly and carefully to avoid any potential losses that you’d need to live 1,000 years to master something with this perfectionist approach.

The right amount of failure

Obviously, there is the other extreme. You can fail too often, and lose too severely.

In my client’s example, he knows traders who gamble like madmen with their trades, and even if they win big, they inevitably crash in a major way because their approach is unsustainable. It’s too wild to learn from, so they don’t make good progress in the long-term.

So clearly the most effective way forward is somewhere in-between; an ideal ratio of wins to losses. The right amount of successful attempts, which are honed and developed further with the right amount of failures and losses.

But most of us have been conditioned towards perfectionism. We think any failure or loss is the same as total disaster, as if we’re on the other end of the spectrum. We panic, and often overcorrect, either with knee-jerk triage reactions that usually make things worse, or with total withdrawal and reluctance to keep playing.

Rationally, it’s clear that we should instead be seeking the right kinds of losses, and balance those with wins so that we make progress and develop wisdom without either hurting too badly or getting too complacent and comfortable.

Knowing the limit

Think of lifting weights. During any given set, the first few reps are within the comfort zone – obviously, because you can easily keep lifting more. At a certain point, you’ll hit your current limit, and your form starts to deteriorate until eventually you cannot complete a rep. That’s probably about the right amount of win/loss ratio for building strength.

If you stop lifting while it still feels easy, your muscles aren’t actually being worked out. There’s no inflamation, no growth. But if you were to keep lifting well after failing – burning your already-damaged muscles – you’ll simply injure yourself and provoke so much inflamation that you’ll delay your growth and risk causing permanent problems.

This is why having a set number of reps decided before you start lifting doesn’t make much sense. You should be paying attention to your muscles’ reaction to the lifting rather than counting an arbitrary number of reps.

With trading, there are the trades that you know are relatively safe and you have a high success rate with. Then there are those at the edge of your comfort, risk and knowledge. You bet a smaller amount of money on these, because you’ve already accepted a higher loss rate, and you’re more interested in learning from them than actually making a profit.

Balancing easy wins with developmental losses

When I was learning to meet strangers, I’d go out with a group of friends (my safe zone). We’d get a table at a bar. Then periodically I’d go approach a stranger and talk to them until I “failed”. Then I’d return to our table to recover and chat with comfortable connections. Once I’d regained my courage, I’d go “lose” again. Over the years, I learned to master socializing, while my friends who never left the table (always “winning”) ended up atrophying socially.

If I got too many “rejections” and did not learn from them, I felt reluctant to socialise. I became scared of talking to people. This is not ideal. But if no-one had rejected me in a while, I knew I was playing it too safe. I keep up this win/loss ratio to this day, though it’s more business related now that I’m married.

Loss does not equal “bad”

To fail or lose is not a bad thing. It’s neutral. It all depends on the ratio and – more importantly – how much you learn from the experience.

This gives us an insight into how failure and loss can be reframed as something that is always “good”. If we can always react to these upsets in a way that increases our long term likelihood of success, then there’s no failure or loss that actually makes our life worse.

It’s really simple: like chess masters, we must analyze any “loss” and gain some kind of wisdom from it, with at least some intent to apply this learning in a near-future attempt to cement the understanding in our brain.

If a girl rejects you, first you assess if this was inevitable (i.e. she’s just not into you). If instead you realise it’s because you were mumbling to your shoes the whole time, then you should immediately go talk to another woman and focus on speaking loudly with eye contact.

If you lose money on a trade, you should first determine whether this was a normal luck-based loss that’s built into any investment strategy, or did you do something stupid? If you made a dumb move that has nothing to do with luck or unpredictable market conditions, then make another trade tomorrow with a more sensible approach.

Always add more weight when you go to the gym, but stop lifting somewhere in-between the reps that are comfortable and those that are painful and clumsy. And if you feel sore the next day, identify where you overdid it and adjust your workout plan to prevent making the same mistake next time.

You’re winning overall

Never lose sight of the fact that you were born with NOTHING. Anything you have now – skills, knowledge, possessions, muscles, relationships, money – you’ve ADDED since being born.

This means that any time you feel like you’ve “lost” something, your timeline is too narrow. If you have more now than when you were born, you have a NET PROFIT. No matter how many times the line on the graph has wobbled up and down, you’re “up” in the long term. What you’re doing is working more than it’s not.

Just because you demanded or expected a certain result, it doesn’t mean that falling short of that is a loss. If you “only” did 7 push ups when you planned to do 10, you haven’t “lost” 3 pushups. You’ve done +7 pushups. If you “lost” $10K on a “bad” trade, but you have money in your bank account and don’t need to declare bankruptcy, then overall you’re winning financially.

And if it’s the case that you objectively haven’t made any progress since you were born, (e.g. you have no friends right now), then at worse you’re the same, not less. You can only go up from here.

“Loss” is a fiction; a dishonest narrative your mind uses to explain the sadness and stress you feel when you don’t get your imagined perfectionist results.

Until you die, you’ve only gained or maintained.

You don’t need to lie to yourself with false-positives. If you’re not taking care of your finances, health, relationships or psyche, you can acknowledge that what you’re doing is having a negative effect. Just don’t confuse this with “losing badly”. If you learn from it, correct your behaviour going forward, and keep the average trajectory of the graph in an upward direction, then you’ve gotten wiser.

That’s a win.

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