Tao Te Cha-Ching: A Taoist Approach to Handicapping, Part 1

Encountering New Information

How do you react when you encounter an opinion you disagree with, data that surprises you, or an unexpected outcome? I believe that answering this question correctly, not in theory but in practice, is crucial to handicapping successfully.

As a bettor, it’s easy to become overconfident and entrenched in an opinion. The psychological impact of putting money on the line magnifies the impact of various forms of bias that can block our ability to think critically and objectively. We have to actively counter that. In a complex sport like football, we are constantly presented with opportunities to re-think our assumptions in the form of new data or opinions that conflict with our own. I think these opportunities are valuable.

Taoist philosophy often looks to nature for inspiration. Nature has operated in harmony with its laws longer than we have been on this planet, and the principles will outlast us. I like to reflect on the way flowing water encounters obstacles.

When water flows, it does not avoid or ignore what lies in its path. It embraces it and determines its true nature. When water encounters something solid, like a rock, it accommodates the rock, incorporates the shape of the rock into its path, and continues on its journey. But when it encounters something weak and without foundation, like a stick, it flows into and moves the stick, eventually depositing the stick somewhere off its path entirely. Sometimes an obstacle is so big and strong that the water permanently alters its path, rather than trying to fight through the obstacle.

We are so frequently wrong. But that’s part of being human and not something to feel ashamed about. Attaching ego to our opinions works to our detriment in both directions. Most obviously, ego can lead to continued operation under a false pretense even when faced with conflicting evidence. But it also can undermine our process and self-confidence when we have to adjust an opinion that is wrong, if we are too attached to that opinion.

Any good handicapper has formed their opinions through a robust process. It can be through film study, data analysis, macro trends, or whatever else. There are multiple paths to success here. But whatever method works will only continue to work if the bettor adapts to new information correctly, separating the ego from the belief. This applies most directly to player and team evaluations and in-season adjustments, but pervades every aspect of good handicapping.

This means that I am not ashamed of incorrect opinions I held in the past. I recall a lengthy debate with a good friend several years ago in which I ultimately insisted that Baker Mayfield would have a better career than Lamar Jackson. I had good reasons for this belief but I was ultimately quite wrong (almost certainly). Instead of hiding from this I try to learn. What, if any, mistaken assumptions was I operating under? What blind spots kept me from seeing how it would play out? This is why I never delete a Tweet with a bad take and why it doesn’t bother me when someone pulls an old opinion of mine and tries to use it against me. I welcome it.

More recently I predicted Daniel Jones would struggle this year with the Giants under Brian Daboll. Another bad take. But it’s also important not to abandon a good process just because the results didn’t go as predicted. By the time the Giants traveled to Philadelphia in the playoffs, Jones had proven me wrong. But I didn’t abandon my approach. Much of the Giants’ success came in situations I predicted they would not encounter against the Eagles, so I placed a large bet on Philadelphia. It wasn’t a victory lap moment for me, proving that I was right all along about Jones. I wasn’t right all along, but that’s irrelevant. I incorporated the new information accurately, and that’s all that matters.

There are several pitfalls to avoid if I want to be more like water. I never want to limit my exposure to people who think the way I do or agree with me. I crave challenges to my thought process. I also want to avoid the bias that comes with staking an opinion, especially when reacting to results. But I also will not abandon the results of a robust process because of the appearance of being wrong. I want to flow where my process takes me, withstanding invalid criticism and adjusting in response to valid criticism.

Of course, this is a challenge for me sometimes. I have an ego like anyone else. But reflecting on my philosophy helps reinforce my commitment to this approach. I’m writing this to myself as much as anyone else.

I have found that this approach leads to a better mental state and better results. I end up feeling more grounded and at peace when I focus on the process and not whether I am right or wrong in the short term. It gives my mind the necessary flexibility to adapt at the right pace and try to see things clearly.

But it also leads to strong results. In evaluating my betting history, one of my strongest performance-based trends involves betting on a team I had recently been below-market on or betting against a team I had recently been above-market on. These inflection points only occur when I have valid reasons for changing my opinion and the market is reacting late or overreacting.

Flowing water is an extremely strong force. Anyone who has been whitewater canoeing can attest to that. It moves with purpose and power. But it is not unyielding or stubborn. This is how I aim to move through life, but also through each NFL season.

If you made it this far, thanks for reading. I expect I’ll have more Taoist reflections in the future if you’re interested.

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