Punishing yourself

Ever punish yourself? Many people are constantly punishing themselves. We typically start with some kind of policy for idealized action. “I won’t check Facebook on my phone.” Then we watch themselves violate that policy. “Here I go again, checking Facebook on my phone.” Then they proceed to punish themselves. “I’m such a bad person, I can’t even control this simple thing.” Or maybe even something like “Argh! Well, according to my punishment policy, now I need to delete the app from my phone for a week.”

Does this even work? For a self-applied punishment policy to succeed, it needs to be reliable. Punishing yourself requires an ability to be aware of when you are breaking the rules. When your mind gets punished for doing something, it tends to stop. In this case, it is more directly getting punished for being aware, not for doing the “bad” thing. So it will be pretty good at learning to stop noticing your “bad” action. 

Where do we get the idea to punish ourselves, after all? Seems painful. The Guru Papers presents an interesting hypothesis. Society is built on dynamics of control — people controlling each other with promises of rewards and the threat of punishment. For whatever reason, our minds may have a tendency of importing this dynamic into how it relates intrapersonally — how our mind relates to itself. When living in a world where punishment for transgression of policy is a common threat that seems to work for controlling our behavior (not without side effects, as detailed in the book and Chapman’s notes), it’s perhaps not surprising that we try to use it on ourselves.

Competing commitments

You have some “bad” habit you want to get rid of, or some new “good” habit or goal you want to undertake. However, there are only 24 hours in the day — and you are already using them all! I keep getting stuck on how powerful this idea is, at least for me. You are always and already using all of your time. To do something new, you have to give something up. Also, our capacity for reason is incredibly limited. Our habitual actions form over years of conditioning (classical and operant). Most of the behaviors that have stuck around are doing something for you. They are rewarding you, somehow. Sometimes it’s for eating high-density energy stores (junk food counts). Sometimes you create a plausible social excuse for failing at something, thereby allowing you to maintain your identity (changing that is hard).

We rarely have any idea why we do what we do. When you consciously try to replace an action that you’ve reasoned to be “bad” without a strong sense of what it’s doing for you, it’s quite likely to laugh at you.

Yummy actions

Do you know that yummy feeling you get when fantasizing about a favorite food or activity? An itchy excitement, a wellspring of energy. You go to great lengths to get yummy stuff. Not surprisingly, the yumminess is a big factor for whether a goal or plan succeeds. Does it feel yummy, does it excite you? Not just the “win” scenario — where you achieve the outcome — but the actions you expect to need to take. If it doesn’t feel yummy, you will likely have a hard slog ahead of you. You may be trying to force something onto yourself — using reason to try to convince yourself of a decision that your gut disagrees with. You can try to will your way through it, but success rates for this are not so inspiring. Instead, can you find a variation that is yummier?

Yumminess is a spectrum. Writing code may not be as thrilling as watching Netflix, but for many, it is more enjoyable than doing the dishes. Some actions that feel relatively yummy to you may be painful to others. It may not be obvious how but you can usually find a way to get paid doing pretty much anything. Consider the possibility that you don’t need to change who you are and what feels good in order to succeed.


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.

Thinking Toys Archives

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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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Thinking Toys #15 — Presencing

We often find ourselves in heated situations. Sometimes in the middle of arguments I “snap to” and wonder how I got there. It seems like this often occurs through a kind of Flow state. We “lose ourselves” — our sense of embodied agency — andbecome the interaction, for better or worse. On the plus side, this can bring a lot of passion and energy into our actions. It can also backfire, as we’ve all experienced. There is one powerful mental move for interrupting these flow states: presencing. You can presence yourself in many ways — one is by placing your attention over your entire body. You may immediately notice your energy levels, temperature, heart rate, and random discomforts. Then you can expand your attention to also encompass your surroundings. This may trigger noticing of objects in your environment that were being ignored. It may bring you to see other people in a new light. A pause can often be enough to turn an unpleasant interaction completely around. Or to identify possibilities hidden from view.

Depending on whom you ask, this is a variation of “mindfulness”. Luckily, you don’t need an app or a trip to the monastery for it. You already do it all the time. Yet, being aware that you can control it is empowering. By widening your scope of attention, automatic patterns get interrupted. Thoughts and actions can come to a screeching halt. It often feels quite pleasant. I deliberately try to trigger presencing moves when I become aware of a variety of warning signs. For example, when I am feeling excitement combined with contractive emotions — frustration, stress, righteousness. In general, if I notice myself trying to Feel Right about something, I try to enact a presencing. Also, I’ve built a few deliberate habits around the move. Lately, I’ve been doing it every time before unlocking my phone. 

By flow states, I mean something a little bit different from Csikszentmihalyi’s version. I’m in flow whenever my attention is moving in patterned, predictable, automatic ways. This is always happening within some specific, narrow field of attention. In an argument, we will be laser-focused on the way people communicate their reasons. While writing, we concentrate on sensing the resonance between written words and feelings. When brushing our teeth, some attention is in tune with a sense of how much time we spend in each part of the mouth. When cued by a reward, we have a hard time avoiding thinking about it. There are peaks and valleys of reward and punishment, predictable stimulus and response. These are spirals of affect generated as we bounce off the world in familiar ways. Some of these flow states are more fun than others, of course. But they all inhabit modes of habitual patterns of attention. There is nothing good or bad here, but being in habitual pattern makes it difficult to take new action. By rearranging the field of attention, presencing breaks us out of these flow states and allows for new, unpredictable action.

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Thinking Toys #14 — Implementation Intentions

Coming up with goals that feel worth achieving can be a struggle in an of itself. Unfortunately, merely formulating a desirable goal is rarely enough to succeed. The next critical step is planning the implementation. Forming implementation intentions helps with this. In my experience, it is one of the most powerful mental moves. They start where goals leave off: some outcome that you want to achieve. From there, you choose an action that will move you towards that outcome. Given that action, you form an implementation intention by choosing a specific when, where, and how. You envision and commit to the details of what your action will be in response to which precise cues. This planning process helps form a new stimulus-response pattern. With practice, it will automatically — subconsciously — occur under the envisioned conditions.


I use a simple implementation intention to help with my goal of learning more from other people. The cue is whenever someone excitedly mentions going to an event. The action I take in response is to ask them “What was your biggest takeaway?”. To install this pattern, I mentally practiced different variations of people presenting the cue — specific, recent examples — and then taking my response action. After a few weeks of practicing a few minutes a day in my head, and a few real-world triggers, the pattern of response became automatic.


A few conditions can increase the odds of success for an implementation intention. First, the triggering cue should be clear and precise. Something concrete that you can visualize. Rather than “When I wake up” try “When I press the off button on my alarm”. Second, the intended action needs to happen with consistency. You want to desire to, and be able to, always take the action when you encounter the cue. If there are situations where you don’t think that will happen, try to carve them out of your cue. For example, “When I press the off button on my alarm, except on weekends or when it’s raining out or when someone is sleeping over”. Finally, ensure that the action you want to take is one that furthers a goal you care about. If you don’t see the connection between your action and your goal, you won’t care enough to execute on it. Be able to answer why you want to take the particular action. If (cue), then (action), because (reason).


It’s hard to overstate the power of implementation intentions. I want to keep this introductory post short to communicate the basic idea. I intend to write a follow-up post to highlight the wide variety of possibilities made available with this tool. To hint at the potential, here are a few ideas for implementation intentions:

  1. Every day after brushing your teeth in the bathroom, do 20 push-ups
  2. Whenever someone is presenting a contorted facial expression, ask them what they are feeling
  3. When someone tells you their name, repeat it back to them and do it again at the end of the conversation
  4. When you finish a block of work and want to take a break, make a short note on what you think the next steps are
  5. Every morning right after turning your alarm off, sit up and smile
  6. While taking out your phone and unlocking it, close your eyes and take 3 deep breaths while paying attention to how your body feels


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Thinking Toys #13 — Miracle Question

Is there something in your life or work that you’ve been trying to solve but can’t seem to make progress on? Perhaps it even seems impossible. Try posing the miracle question… Imagine you wake up tomorrow morning and a miracle has occurred. What’s a small change that would make you exclaim: “wow the problem is gone and here’s how I know!” Answering this can be difficult. Your first response will often be “I don’t know”, or something along those lines. This is frustrating but normal. Sit with it for 5-10 minutes. Start generating a list of responses that are not quite right or even obviously bad. Eventually, you may hit on something interesting and surprise yourself. Once you have an answer, you can often generate a way to move towards it. Ask yourself, what can you do that would help you move towards this new world, even if only in a small way? This may generate a specific goal or action. Ideally, frame it as a positive rather than a negative: something you do rather than something you avoid doing.


I’m experiencing a growing frustration with a lack of progress on a big project I’m interested in. I’ve been nibbling along the edges but have a sense that a lot more is possible. Posing the miracle question helped. After about 5 minutes of “I don’t know”, I was able to start generating some bad answers. After another 5 minutes of those, I wrote down something that seemed quite good. In hindsight, it seems silly that I didn’t think of it right away, but that’s often how these things go. I found that I’d feel like my sense of a lack of progress would resolve by seeing the results of an experiment. Specifically, a hypothetical experiment on a few friendly participants that tests some implicit assumptions. My next action follows pretty smoothly from that realization!


Sometimes finding a positive action or goal is the difficult part. You know what the world would look like when your problem is gone but you have no idea how to take a step in that direction. Fortunately, having a list of bad ideas is better than no list at all. If you can carve out enough examples of things that won’t work, you can try inverting them. Also, you can compare new ideas to the bad ones to try to help understand what is missing. A bad model is better than no model at all.


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Reason as Attentional Prosthesis

What are we doing when thinking, or reasoning?
Often, thinking is goal-directed. There is some outcome we are trying to achieve or problem we are trying to solve. In hindsight, answers often seem obvious. “Why didn’t I think of that?” For the most interesting problems, there is no formula or system that will lead to an optimal solution. The hard part becomes framing the problem. How do we do that? I have some thoughts on the role of attention.
But first, pigeons! In an experiment, pigeons are rewarded for pecking a toy banana hanging from the ceiling of their enclosure, but only while standing on a box placed below it. They’re also rewarded, in a separate setup with no toy banana present, for moving a box to randomly marked spots on the wall of their enclosure.
And then they’re faced with a novel puzzle:
“When these pigeons were confronted with the banana out of reach, the box present but displaced from under it, and no spot was on the wall, they looked back and forth between banana and box at first, appearing “confused” to human observers. Then, within less than two minutes, they abruptly began to push the box in the direction of the banana, stopped when it was underneath, climbed and pecked.” (Epstein, Kirshnit, Lanza, & Rubin, 1984).
A conundrum that stresses the bird brain. Its attention is drawn to the banana, motivated by reward previously reinforced, and yet something is wrong. The pattern is not quite the same as before. Our feathered friend has yet to encounter a banana and a box at the same time where the box was not under the banana. Also, he has not been previously rewarded for moving a box except to a marked target location on the wall. To solve this problem, the pigeon seems to need to somehow suppress its default, habituated behavior. We can see it struggling to do so. Perhaps this is the pigeon-equivalent of “dropping preconceptions”, or our habitual way of seeing a situation. Once a primary reaction is suppressed, it can hold attention on other options which don’t immediately seem like answers to its problem.
Even more is demanded of the pigeon. He must figure out how to combine familiar behaviors in a new way. The pigeon experiences pleasure — anticipated reward — when he sees a box and a marked spot on the wall. Now, there is no marked spot. He also experiences pleasure when he sees a box under a banana. Now, the box is elsewhere. How to fit these pieces together to cause new behavior? Presumably, he is doing something like reasoning. He is aware of the box, an ability (affordance) to move boxes, and the good feelings associated with a box under a banana. He must be able to ignore other aspects of the scene which are not relevant. By first simplifying his experience to relevant aspects, he can attempt novel combinations. Once perceiving a candidate solution, new action is a foregone conclusion — the pigeon is quick to push the box across the cage.
Reason seems to serve as a kind of attentional prosthesis. By default, humans, and pigeons, are responding reflexively — according to habit. When reflexes aren’t good enough, we need some way to explore pieces of past experiences and recombine them in new ways. In the process, we need help navigating our attention away from what is often the most attractive stimulus. Reason functions as such a mechanism. We recall memories of situations where only certain aspects (“abstractions” or “concepts”) are attended to. For each aspect, we trigger a re-cognition — a re-experiencing — of previous experiences that are somehow related. The relation can be a similarity of stimulus, but also, crucially, similarity of outcome or response. This is also known as functional or mediated generalization. By compressing into relevant aspects, the mind seems to be more capable of chaining together previously unrelated “sub-experiences”. If a chain is conceivable to an emotionally-appealing outcome, action can follow.