One of the core characteristics of agile is that it’s very failure tolerant. The premise is that instead of fearing and avoiding failure, you set up systems that support innovation and allow people to fail very fast. The faster you fail, the faster you get to something that is successful… and the more things you try, the better.

This is overall a great idea. It’s wonderful for companies (where fear of failure can keep your best employees from feeling allowed to innovate) but it also works for magic and personal planning. When you are trying to manifest a future vision of your life in a high chaos environment, you’re going to need to do some experimentation and try out different paths. It’s the same with the magical work we do to get there.

But — and this is a big but — this wild and free-wheeling attitude to failure only works when the cost of failure is low.

Take sigils for example. With nothing more than a piece of paper and a pen, you can work magic… it’s fast, easy, and basically free. It doesn’t have to be at any specific time (though timing can be useful) and it doesn’t take all night (unless you want it to). It’s also highly within your control. I don’t know how you think about sigils, but I think of them as imps — little servitors that I create to go out into the world and do things for me. These imps are wholly my creation, tied to their card, which I keep in my position, and with limited lifespans. There’s no Goetic demons to propitiate, no major offerings to make. The risk of failure is just that the imp can’t do its work. It doesn’t even matter why. Maybe the statement was wrong or not strong enough. Maybe the timing was suboptimal. Maybe the sigil moved the odds, but not enough. The cost of failure is extremely low and it’s mitigated by volume. Wrong statement? Do 20 more variations until you hit the mark. Wrong timing? Launch over and over and eventually you’ve be in synch with the universe. Not enough juice for one little sigil? Do 15, 50, 100… eventually the needle gets moved. The risk of failure is very low, so why not fuck around and find out, right?

But what if the risk of failure isn’t low? What if it means your livelihood or that of your family? What if it means risking everything on a chance roll of the dice? What if you have to give up everything to get what you think you really want?

That ‘fuck around’ attitude doesn’t sound nearly as good now.

When I was in high school, one of my teachers said something I’ll never forget. She said that people naturally become more conservative as they age because they have more to conserve. I don’t think this is always true of course, but it does resonate with me now. When you have nothing, you have nothing to lose. When your responsibilities are few, your risk tolerance is higher. Hiking across the country might sound like a grand adventure or devastating homelessness — just depending on there you are in your life (with a baby? 50 and with a bad back? running from the law?). The same activity can have wildly different costs of failure.

I’ve talked about Taleb’s extremistan before (go see this quick summary) but one thing that I’d never really thought about is that all outcomes are outsized in extremistan. In a high chaos environment, failure might have huge costs, which makes the mantra to try lots of stuff and fail fast really problematic.

One of Taleb’s bits of advice (and for all his epic douchebaggery there’s a lot of good advice to extract from his work) is that you keep your options open. When you have lots of options, you are more agile and better at dealing with chaotic environments. That not only means keeping your investments low, but also keeping the cost of failure low.

Let’s say I want to start some kind of business. The wrong way to do it is to invest everything I have and stake it all on the business success. That’s wrong because it closes off my options AND the cost of failure will be very high. Starting something online with a domain and a crappy blogger site… well, that’s how I started Circle Thrice. So even if it went down in flames (there’s still time!) I wouldn’t have lost much. The investment was low and the cost of failure was low — I close up shop, digitally speaking, and slink off into greater obscurity. That gives me a lot of license to try things out here and see what works and doesn’t.

But let’s say that I have a low investment business where the cost of failure is very high. Maybe failure means going to prison (I suppose this would be like being a drug mule?) or destroys your reputation so you can’t get a new job (I’m picturing some kind of wild influencer scandal here). This means that even though your investment is low, the costs to fail are very high.

Frankly, I’m convinced that many a politician is in the exact situation. They have people giving them money to run for office, but those people demand things from them. And if they don’t deliver those people may have information that can destroy them and their families. So they don’t have a lot of room to try things out because they can’t afford to fail.

This changes the agile game a bit doesn’t it?

At the same time, if you can’t experiment wildly and fail fast, then you risk never really succeeding either. You can’t count on staying stable in an unstable environment and we, my friends, are in an unstable environment!

OK, so here’s what I figure the mitigations for this issue are:

  1. Avoid being in high failure cost situations. Of course some high failure choices are normal and may be a tradeoff you want to make (having kids is in this category). But don’t take on more of this kind of risk than you need to. If you need a day job (as many of us, myself included, do) then you have a little risk. But if loosing your job means finding a new one and maybe taking on some consulting in the mean time, that’s very different from losing your pension and having an undesirable skillset. So even within the day job category, there are very different risk profiles.
  2. Focus your experimentation on low-failure-cost areas of your life. Can’t fuck around with your day job? Fine. Find places where you can and do that. This doesn’t have to be just financial either (though having a side hustle is a great thing). For example, maybe you can’t get out of your boring hometown. So you experiment wildly with your hobbies to keep things interesting. Or maybe a physical limitation keeps you from doing some things, but what CAN you do? Go crazy where it doesn’t count (and make it count).
  3. Do all the divination. If you’re going to experiment in high failure cost situations (and in this environment, where daring to have a birthday party for your 8 year old can be a high risk activity, you may not be able to help it) then do all the forecasting you can! Don’t ask “what will happen if I do x” ask “what thing will get me to x with the lowest risk.” This is honestly the most common sort of divination I do for my clients. You want x (where x = home in the country, success in business, moving to a less oppressive country) and you have some ideas to get to x. Which ones will work and which ones will crash and burn? Or where’s the black swan coming from? Where do I need to be careful and where can I go crazy?
  4. Go heart first and follow your values. If you do that, then even if you fail and the cost is high, you’ll be able to live with yourself. Things can feel really fraught right now, but it’s important to remember that we’re stardust in mud suits and this crazy world isn’t all there it. How and who you love and your integrity as you move forward are the most important things.

Wild experimentation doesn’t happen in a vacuum and I think that is one of the critical ways we need to adjust our thinking moving forward. Agile still means trying things out, but you need to do it with an eye to the costs when things go wrong.

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