Thinking Toys

Pick a goal you have, ideally one with some already associated actions. Maybe it’s starting a side business, or having a tough conversation with your partner, or becoming President. Now imagine that the deadline passes (or a bunch of time, if there’s no deadline) and you’ve failed to achieve your goal. How surprised are you? If you’re not particularly surprised, consider what that says about your goal. (Not what it says about you!) But all is not lost! As vividly as possible, imagine the experience of your future self in this hypothetical failure state. Ask it, what is the most likely reason that we’ve failed? Perhaps you haven’t scheduled a time to act and will then forget. Perhaps you don’t have running shoes and then can’t go for a run. Perhaps you’re accidentally leaning on the Fail button. Once you have a predicted failure case, update your plan of action to account for it. Now rinse and repeat: 

  1. imagine yourself taking the action — executing the plan
  2. check how surprised you will be if you fail
  3. ask yourself what the most likely cause of failure will be (assuming you will fail)
  4. update your plan to avoid it 

This is pre-hindsight — using imagination to predict obvious failure modes.

I have a flight to Thailand coming up in a few days and hadn’t thought much about it until recently. I was planning on winging it upon arrival but decided to try pre-hindsight to see what might go wrong. Right away, I realized that if I have issues it may be due to visa requirements. A quick search revealed that visas wouldn’t be an issue as long as I had an exit flight already booked. I added this to my todo list. Another pre-hindsight check then painted a picture of me sitting in a Thai airport staring at “buy exit flight” entry on my todo list. So I immediately bought a ticket. This seems like a trivial instance but the core mental move was the one described above.

Pre-hindsight can help with revealing more painful failure modes, as well. I have a goal of getting the Thinking Toys Newsletter to 1000 subscribers by the end of the year. Running pre-hindsight on it doesn’t paint a pretty picture. Not only am I unlikely to succeed but it’s not even clear if I’m doing anything to make it possible. My current plan is to continue doing “more of the same” but extrapolating the current trend has me falling far short of the goal. Pre-hindsight helps highlight when I’m dealing with a wish rather than a goal. And this is valuable to know. I’d prefer not to be trying to fool myself any more than necessary. How much of your life revolves around goals without a corresponding plan of action? 

This power is a bit curious to me. By imagining a hypothetical, our mind can identify “obvious” new insights. But if they’re so obvious, why didn’t we already know them? Why must we consciously move our attention in this pattern of pre-hindsight to reveal the insight? We may be toeing the edge of the capabilities of our mind. Powers that are accessible but require a conscious nudge to access. Perhaps enough practice with a broad enough set of Thinking Toys makes such superpowers available to everyone.

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Also published on Medium.

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