How Can You Prepare for High-Impact Unknown Events?
Published 2/8/2025
This episode includes practical techniques to prepare for the unexpected by identifying vulnerabilities and building resilience, using the "curse question" and the "assumption audit" to help you turn potential problems into strategic advantages.
• Uncover how to use a "curse question" to expose vulnerabilities you didn't know you had, by imagining realistic negative scenarios and what could go wrong.
• Learn how to move beyond resilience to antifragility, turning unexpected events into opportunities for growth and strategic advantage, by making them benefitial rather than harmful.
• Discover why your medium-confidence assumptions might be the most dangerous and how an "assumption audit" can help you rate them and their potential impact if they are wrong, to help you better understand your weaknesses.
• Explore why preparing for a range of possibilities, including black swan events, is more effective than trying to predict specific outcomes, and how to spot opportunities in the unexpected.
• Learn why focusing on areas of fragility and identifying risks can be more useful than focusing on trying to avoid negative events altogether.
• Understand that counterfactuals can help you challenge your assumptions and create more robust plans.
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Transcript (Generated by OpenAI Whisper)
I was sitting in the emergency room last week with my family when a doctor told me that my father needed to be taken by ambulance from that emergency room to another hospital, that he had had some kind of cardiac event. Now, I'll ruin the rest of the story for you. My father is doing pretty well, but he did indeed have a cardiac event that ended up leading to a triple bypass surgery. Fortunately for him, there was no damage done to his heart. Of course, we are incredibly grateful for this outcome, and I look forward to his recovery. And I'm learning lessons through this process. Of course, not every personal story is worth talking about on a podcast, but having done this podcast for over a decade, I feel like these lessons are worthwhile to share. The truth is, everyone listening to this podcast will have some kind of surprising event in their lives. You might have a surprising event this week, whether good or bad. We can't really predict everything. That's the nature of life. I want to talk to you a little bit about preparing for the unknown. Now, to be clear, the rest of this episode is not going to be commentary on my father's situation, but rather using that as that backdrop and inspiration for this thinking. Unexpected events are unexpected. We can't predict that they're going to happen. We could predict some level of potential that they would happen, some kind of calculation, an expected rate, for example. But no matter what we do, those unpredictable or unlikely events, what Nassim Taleb calls black swans, they still happen. And the impact of these kinds of events can totally be predicted. We can't predict that they're going to happen. We can't predict that they're going to happen. We can't predict that they're going to happen. We can't predict that they're going to happen. We can't predict that they're going to happen. We can't predict that the course of everything else that's going on. So what do we do? How can we prepare for this kind of thing? Some things, frankly, you just can't prepare for. Some things are totally unpredictable. And when they occur, there's not really much that you could have done and not really much that you can do about them. This is more of an acceptance opportunity. In other words, we just kind of have to deal with it. Once again, Taleb says instead of predicting these events, instead of trying to spend our energy predicting them, we should prepare for them in some way. So being prepared for a catastrophic event might be a better use of our time and our energy. But how do you prepare for the unknown? We're going to talk about a couple of different ways. In today's episode, and the first way is an inverse to a positive psychology technique called the miracle question. Miracle question goes something like this. Tomorrow you wake up and overnight, while you were unconscious, while you were sleeping, a miracle has occurred. You don't know that the miracle has occurred yet. What are the first signs that you see that lets you know that the miracle has occurred? I should give credit where credit is due. I first heard about this concept, the miracle question concept, recently while listening to Dan Heath's book Reset. Dan was on Developer Tea a couple of years back to talk about his previous book, Upstream. But the miracle question is often used primarily in therapy contexts. For example, in family therapy or some other kind of interventional therapy. What I'd like to do is flip this question or invert this question such that instead of a miracle, you've experienced a curse. Overnight, while you were sleeping, a curse has befallen your situation. You could say that's you personally. You could say it's a project that you're working on. You could say that it's, you know, a company, whatever your kind of context is. You could imagine this applying. Now, you don't know the curse has been applied. And your job is to determine what signs you would see, what kinds of, you know, what is true. What are you experiencing that first tips you off that a curse has befallen you? It's important to note that the, these curses are, you know, you shouldn't think about these as magical effects or unrealistic or impossible effects. Otherwise, you know, those are not only are, would that simulate an unexpected event, it would simulate an impossible event. Okay. So imagine that, you know, the curse is kind of restricted to only possible things. So let's say you run a, you know, an engineering department. Perhaps the first signs of the curse could be that your engineers start resigning, or maybe all of your engineers start releasing code that brings down your production servers, or maybe all of the providers that you use start immediately increasing their prices. You know, you could list five or 10 of these things. And what you've just done unknowingly is you've listed threats. You've listed threats that you've not yet experienced. Now, these might seem outlandish if you look at this list, but they are directionally instructive. What does that mean? It means you've identified potential threats, things that if they were to happen, or if, if that was to come to pass your company, your endeavor, whatever it is that has received these, you know, curse events would be threatened. You'd be in trouble. So now you can take this list and decide what to do about it. This is kind of the, the initial starting point. And we're not going to get into necessarily, you know, how do you dissect this list and what do you do about it necessarily? You know, one, one thing, for example, that we mentioned was your engineers start, you know, resigning. What would you do about that? Right? What, what can you do? Maybe you should look into how you can protect retention. Is retention something that you're investing in? Is it something that you're investing in? Is it something that you're investing in? If not, then that unlikely event is a little more likely, right? A lot of these strategies, a lot of these kinds of approaches that we're going to talk about in this episode are about shifting your odds, right? Shifting your odds. That means you're taking action to make what is already an unexpected event even more unlikely. Right? You're moving away from a risk profile. You're trying to reduce and in some rare cases, totally eliminate the risk that something may happen. Leaning once again on language that Taleb uses, you are looking at areas where you may be fragile, right? This is what this curse question might expose is areas of fragility. Where are you vulnerable? To problems. Now there's multiple ways you could think about this. You could invest directly in retention, which would avoid the potential incidents of the event itself. Or you could think about planning for what happens if the event occurs. In other words, maybe having a strong recruiting pipeline of interested engineers who might be available in the future. This amounts to some kind of contingency plan to deal with the incidents if it does actually happen. Leaning on Taleb once again, an even better strategy in his kind of framework of thinking would be to invest in anti-fragility. So the contingency plan kind of gives you a robust or what Taleb might call a resilient structure. But an anti-fragile structure takes a lot of time and effort to build a structure that is resilient. And so you're going to have to think about what would otherwise be considered an incidence of an unexpected event or a black swan event and turns it into a potentially beneficial event. So for example, you may have an employee mobility program that encourages employees to develop skill sets that they can use elsewhere in the company. And what this does overall, a systemic effect that this might have, is that it allows employees to develop skill sets that they can use elsewhere in the company. And so you're going to have a system that allows employees to develop skill sets that is improved skill sets across your entire workforce. In the short run, you might see an engineer leave a given team and join another one. But in the process, that engineer has chosen not to leave the company, but instead to invest in the overall learning and kind of knowledge equity that the company holds. So resourcing this program or making this program possible would mean that you're creating that resilience structure first, so that any one engineer is not necessarily a bottleneck or holding all of the information. And losing one engineer doesn't cripple the rest of the team. So this kind of progression from fragility, where you're wanting to avoid the event altogether, to anti-fragility, can help you to create a resilient structure. And so this kind of progression from fragility to help give you a roadmap for what kinds of preparation you can do to be ready for an unexpected kind of black swan type event. We're going to take a quick sponsor break, and then we're going to come back and give you one more exercise for preparing and thinking through unknown events. One of the unknown events that has occurred in the past, let's say 10 years or so, is that website builders have gone from antiquated tool of the past that produces terrible code and limited control to Wix Studio. Wix Studio is a node-based builder that lets you add full stack JavaScript to any site. With Wix Studio, you can spend less time on UI coding, hosting, and security. And you can also use it to create a new website. So if you're a new user, you can more on custom logic and functionalities that truly matter. This is a good unknown that has occurred. Developing your preferred coding environment online in a VS Code-based IDE or locally through a GitHub integration. Either way, with Wix Studio, you're deploying in a click. Extend and replace hundreds of powerful business solutions and custom-built features with APIs and integrations. And when you need to speed things up, Wix Studio's AI assistant is on hand to generate tailored code snippets, troubleshoot your bugs, and reduce the amount of time you need to do so. You can also use Wix Studio to create a new website. So if you're a new user, you can retrieve product answers in just a few seconds. All of that is neatly wrapped up in an automatically maintained infrastructure for total peace of mind. You can work in a developer-first ecosystem at wixstudio.com. That's W-I-X-studio.com. Thanks again to Wix Studio for sponsoring today's episode of Developer Tea. The next exercise that I want you to go through, I'm going to call the assumption audit. What you're going to do is write down a list of your fundamental assumptions. Now, it's important to understand that you make tons of assumptions every single day. There are assumptions that are relevant to this exercise and assumptions that are not. Assumptions that are not relevant, for example, might be you assume that the sun is going to rise. This is not relevant because if the sun doesn't rise, then you have much bigger problems than whatever you're trying to evaluate your assumptions in order to achieve, right? So try to limit this list to things that are germane to the problem at hand. For example, if you are developing, uh, an iOS application, one of your assumptions might be that the Apple app store will remain stable and that the, uh, you know, the, the contract, maybe the sales contract or the in-app purchases contract that Apple has established will remain, uh, stable as well. Right. That those might be assumptions that you have. Other assumptions might be that, uh, you know, you, the, the app you're working on that, uh, you're not going to be able to do anything about it. You're not going to be able to do anything solution is novel, that there's not a competitor out there that's getting ready to release a similar solution. This is an assumption about the marketplace that you're entering. Another good example of this, let's say you're searching for a job. You may assume that all of the applications that you submit will actually get reviewed. This is kind of our default assumption, and it's probably almost certainly true that your application is not getting reviewed every single time. So you can probably see where this is headed. What I want you to do for each of these assumptions, I want you to rate your confidence that the assumption is solid, that the assumption holds true, that it is essentially a fact, right? Where 10 is, it would be extremely difficult to convince you that that assumption is threatened, that maybe it's not true, right? 10 would be you're extremely convinced. One would be, you know, a breeze out of the window, you know, a note passed to you by a stranger could convince you otherwise, right? It'd be very easy for you to change your mind about the assumption. And what I want you to focus on is the thing that you're going to be able to do is you're going to be able to do a lot of the things that you're going to do. Things that are in the, about the four to six, four to seven range, okay? Maybe the five to eight range. These are things that because we are, you know, our tendency as humans is to try to categorize things, to create binary categories in as many options as possible, where we say something either is or is not, right? We believe that we're going to be able to do that. And so that's something either is true or is not true. For example, the assumptions that are in the four to six, five to seven, five to eight range in terms of confidence, you're more likely to treat them as if they are tens. Think about this, right? These are assumptions that you are making decisions based on that even though, you know, you have a, a general belief that it's more likely that it's true than not, you are not preparing for if that assumption fails because your brain is, is kind of rounding up, right? Your brain is treating something that has only some certainty, right? Only some confidence. It's treating it as if it has full confidence. And especially for the things that you rated as 50 or 60% or five out of 10, six out of 10. These are things that now in your kind of slow thinking, right? If you're using the Danny Kahneman's language is slow thinking, you are able to evaluate that there might be a problem with that assumption. Something may be threatening that assumption, right? And you can also, if you want to create a third column, if you're doing this in a spreadsheet, for example, you may, want to rate the impact of if I'm wrong, if this assumption does not hold true, uh, and something else, some other counterfactual is actually the case is actually true. Then what impact does it have on what I care about? If, you know, let's say if Apple's in-app purchases, uh, you know, contract, if they change, you require that people pay them half of all in-app purchases. For example, I don't, I don't know anything about these contracts by the way. So I could be totally wrong about these numbers, but let's imagine that Apple demands that everybody pays them half of all in-app purchases. What level of impact does that have on your business model? Presumably if Apple was previously only giving or taking, let's say 10% of that, then a lot of your assumptions about what would, be required for market viability might change. Your pricing model might change. Your marketing model might change. Your product may change. Fundamentally, you might even abandon the project altogether. But if you had already kind of planned for, you know, potentially Apple could change this, then you may not necessarily have a vulnerability to that, right? You may have, like we said before, contingency plans in place. Uh, you know, trying to move towards anti-fragility, but at the very least having resiliency in these categories, having, uh, some way of responding to them so that you're not exposed and you're not in that fragile category. This, uh, this is how you can address these, these problems. So, uh, again, going back to that list, you're looking at your list of assumptions. Assumptions are kind of the, uh, the, the, kind of the, uh, the raw material, right? For finding where might something unexpected occur, because assumptions are really laying out what you expect to be true. You're laying out what you expect to either happen or not happen in the future. So by auditing your assumptions and especially focusing on the ones that you have, you know, some mid-level, medium-level confidence in when you do this audit, and especially the ones kind of, even, even more narrow, the ones that you have medium-level confidence and they would have a high, uh, impact. Let's say you're rating it low, medium, high, uh, look at the ones that have medium confidence and high impact. These are the ones that, uh, you should focus on preparing, creating resiliency, hopefully moving towards anti-fragility to, uh, to deal with if this assumption is wrong. Now, it's also important to understand that assumptions, might be a singular statement, but there may be multiple counterfactuals that challenge the assumption. What does that mean? It means that let's say, for example, that your assumption going back to the Apple contract example is that Apple will continue, you know, uh, taking only a certain percentage of your in-app purchases. Well, the counterfactual could be that Apple disallows, uh, you know, purchases altogether. Right. That, uh, they're not going to take, they're not going to allow you to do in-app purchases at all, that they're only going to allow, you know, certain companies or something like that. Right. That's one counterfactual. Another counterfactual might be that Apple actually decides to take none. They take 0% of your sales, right? That's, that actually challenges your assumptions, but perhaps the impact of that counterfactual, uh, is, is positive, right? Uh, and then of course there's probably a hundred other ways that could go. Maybe the Apple store shuts down altogether. Right. And so, uh, not only is your assumption wrong, uh, about Apple, but it's, uh, challenged at its core because Apple no longer exists. Now, again, think about the confidence of that, right? Your, your assumption that Apple will exist. You probably have a fairly high confidence that Apple will continue existing for the duration of, you know, the app that you're building, the, the life cycle of that application, that confidence, let's say is eight or nine, right? Fairly confident, but, uh, your confidence in Apple's, um, you know, maintenance of the current contract that you have, perhaps that's a little lower. And so your strategy may not be, uh, uh, wrapped around the potential for Apple to be wiped off the face of the planet, but instead you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, you're, Your strategy might be wrapped around de-risking your in-app purchases in some way. So all of this is about risk. We've already said this. It's about trying to identify these black swan events. These are things that we don't think are necessarily likely. Otherwise, they wouldn't be expected. Those two things basically go hand in hand. You know, there's some percentage of likelihood that would identify something as expected or unexpected. If you have a .00001% chance of winning the lottery, it would be unexpected. There's some percentage chance where you could reasonably say it was expected. It's not necessarily a binary chance. But, you know, if you had a 20% chance, then... You might say, well, it was kind of expected that I could win. And it's not surprising that I won. So with both of these exercises, what we're really trying to do is look for the opportunities. Okay, look for the opportunities, both in the curse exercise, which is kind of mining for problems. As well as the assumptions exercise, which is mining for areas. Where you might be surprised. Both of these can yield opportunities for preparing for risk. Thank you so much for listening to today's episode of Developer Tea. I hope this was an enlightening episode. Hopefully you can think about risk and the unexpected events a little bit differently. Thank you to the folks who listened to this, who have already talked to me about our family situation, our family health situation. With my father. Fortunately, I expect a positive outlook for him in the coming weeks. So thank you to those of you who have reached out. Thanks so much for listening. And a quick thank you to today's sponsor. Wix Studio. Wix Studio has a developer-first ecosystem. You spend less time on tedious tasks, more on functionality that matters to you and your customers. By working in a VS Code based IDE locally via GitHub. You can extend and replace a suite of powerful business solutions. And ship faster with Wix Studio. Thank you. Thank you. Wix Studio's AI Code Assistant. All inside of an automatically maintained infrared for total peace of mind. Head over to Wix Studio.com to get started. That's Wix Studio.com. Thanks so much for listening. And until next time, enjoy your tea.