Take some plan or goal you have and imagine a brilliant success. Everything went great, and now you’re in the future celebrating. Maybe your team is there, or your family and friends. You may even be giving a speech regaling everyone with the story of what happened. So then try asking yourself: What must have happened in order for this success story to come about? Try to be as concrete as possible, point out things that an impartial observer can identify. This is pro-hindsight, essentially an inversion of pre-hindsight. Rather than imagining failure, we imagine success.

For the past year or so, I’ve been focusing on getting better at connecting with people. Both those familiar to me as well as strangers. To look back and have succeeded at this, I would need to become someone who can make others feel instantly comfortable. To be able to walk up and put someone at ease. I’d be at ease opening up and having deep conversations — sharing things about myself that most people rarely do. By painting this picture of success, I immediately notice outcomes that I can target. These tie to specific skills I can develop. To get better at this, I’ve started experimenting with ways to practice these individual skills (for many, by granularizing).

Like with pre-hindsight, there are “obvious” things that pop out once we imagine concrete scenarios and reason about their prerequisites. We often daydream of success scenarios — “fantasies” — but fail to go one step further and ask what must happen to get there. Maybe because this often deflates the fantasy, and if we’re having fun then let’s not do that. But if it’s something we really want to achieve, this move is helpful.

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With many Thinking Toys, it’s helpful to start with a specific problem. Yet, some are especially useful when you don’t know what you want. Rather than starting with an issue, begin by examining your resources. Who are your friends, what are your hobbies, and what skills have you mastered? What kinds of levers can you pull? Combined in different ways, these represent the set of affordances available to you. The actions you perceive yourself capable of taking in any moment. Effectuation is the process of exploring these affordances without knowing what they’ll lead to.


Rather than trying to create a causal, step-by-step plan to get from point A to B, we begin by experimenting. By trying new things, we uncover interesting destinations (goals). So interesting that we may decide to reorient towards them. Or we may fall on our ass and look silly. That’s a good sign, though — if you’re succeeding too often, you’re not learning. What are some low-risk, cheap actions you have available to you? Especially focus on ones that don’t seem useful, or may look weird. These are types of actions you wouldn’t normally try. They tend to lead to the most learning and surprise.


For the past few years, I have avoided having a permanent home. I’ve been staying in short-term rentals as I move from place to place. I’m not quite on vacation as I end up doing similar “productive” things wherever I am. It also may not be obvious why moving around would be helpful rather than annoying. But it’s not especially costly for me, so it seemed worth exploring. I’ve learned that changing how and where I live and work has a tremendous impact on my ideation process. By changing contexts, both physical and social, I’m growing quicker than before. Unexpected benefits include being less attached to physical objects and experiencing less neuroticism over living conditions. This has been tremendously valuable to me but was not a specific goal that I set out with.


Effectuation is useful even when you do have a particular goal in mind. It can be vague and open-ended, like “live a good life” or “make money”. It can also be specific, like “increase sales in Q3”. All that’s necessary is having an open mind about how you will achieve your aim. Perhaps you have the semblance of a plan but want to explore other options. Or, you may not even know what your first milestones are and can’t granularize. When you’re not super confident in your goals or your plan, you want to be in exploration mode. Follow paths of least resistance (be like water) and try cheap experiments (control your downside, the upside is harder to predict). In this exploration, you will be shaping your goals. Your desires will be shifting as you learn more about the world and yourself!


This makes effectuation especially useful when feeling stuck or overwhelmed by a problem. You can adopt the mindset that any new action will lead to more learning and information. This gives you more insight into the situation and makes taking future action easier.


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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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