Heads I Win
Decision Making Hacks
Decision making is hard. There’s no way around that. There are useful mental models and tricks to help out though. One heuristic I like is based on the old “heads I win, tails you lose” game. This mental model works best when you have a question of the form “should we do X”. You are presented with a decision to make — do you continue on the path you are on, or make a proposed change?
The trick works like this:
First try to identify the best case and worst case scenarios of making the change. Make sure to consider as many of the benefits of the best case scenario as possible, and try to stay realistic on evaluating the worst case. No, that email you’re about to send probably isn’t going to get you fired or your company to go out of business, but it might get forwarded to the wrong person and require some explaining.
Next, think through what the likely outcome of staying on the current path is. If you don’t take this action, if you do nothing, what is likely to happen? This should be easy — you should usually have a good idea of what you’re working towards. The future is always uncertain, but that doesn’t mean you don’t need to have a plan or a prediction. Plans are worthless, but planning is everything.
Finally, compare the two options. If the best case outcome of making the change is not at least as good as just staying the course, it’s probably not a good idea. You’re setting yourself up for failure by guaranteeing a worse outcome. Even if the idea works perfectly, you end up worse off than you would have been not having tried it.
Why This Works
The reason I think this works so well is because humans tend to be terrible at predicting outcomes, especially for unfamiliar opportunities. Most people have a pretty good guess of where the current path they were on will take them, but have terrible intuition when they step outside of this comfort zone. We are good at putting on optimist/pessimist hats and imagining best-case/worst-case scenarios.
The other valuable part of this exercise is that it forces you to imagine these best-case and worst-case scenarios of an opportunity. What if you can’t even think of a good outcome? You’ve just found your own version of the Kobayashi-Maru, where the only way to win is to not play. And even if you do decide to take the opportunity after evaluating the worst-case scenarios, you’re doing so fully aware of the risks.
Switch Things Up
You might see this advice as pessimistic. Why try anything new if it’s only going to hurt my situation? That’s not the goal here! To start playing the game more optimistically, simply play it in reverse and start looking for opportunities that pose the opposite risk profile. These are choices to make, things to try or decisions to make that have a very low, or no, risk but pose large upside. If you try enough of these, they can start to compound.
The old saying “It’s easier to ask for forgiveness than permission” is a perfect example of this. The premise here is that asking for permission poses a large downside — the risk of being denied and little upside. Just doing something and seeing if anyone gets mad, poses significantly less downside with potential upside. The upside is that you get to do what you wanted without having to slow down and ask, and potentially get told no. The downside is a potential apology, which should be cheap. Of course, this only applies to situations where the cost of an apology is cheap.
Great, you’ve now hopefully applied the first half of this rule and have eliminated a whole bunch of bad decisions — ones where the best potential outcome is worse than doing nothing. You might even be playing in reverse and looking for good decisions. You should be way ahead of the pack because you only make decisions that at least have the potential to improve your situation. Why stop here though? You already did the hard work of identifying opportunities with great potential outcomes.
Instead of rushing right into that opportunity you just evaluated, try to think of some better ways to achieve that same outcome. These could look like ways to get to this end state faster, or cheaper, or with less risk. You also figured out what the worst case outcome of this decision would be. Can you think of a way to mitigate that? Improving both the best and worst case outcomes puts you on an even better track.