
I have long planned to buy a new computer in 2026. My current desktop is nearing its end of life, but it still limps along. I’d rather not invest right now; cash is tight, tariffs are high, and my portfolio is down. But supply chain disruptions might mean that prices jump later this year.
What do I do?
Do I stick to my original plan? Do I change my priorities and buy now? Do I sit tight and not spend money until I know what’s coming?
In part 1 of this series, I suggested that Nassim Nicholas Taleb’s “barbell” approach to risk makes sense here.
As Anti-Fragile made clear, our top priority is protecting against risks that could wipe us out.
Find What’s Likely to go Wrong (80/20 rule)
We can’t predict business-as-usual, but we can probably predict business as unusual.
We humans focus on best-case and worst-case scenarios. Right now, the best case is unclear, but the worst case probably isn’t. We often know where things are unstable.
We just need to know which major disasters could reasonably come our way. An asteroid strike? Probably not worth our attention. But a drop in order volume, or a rise in tariffs probably is.
The full risk assessments and risk management efforts I’ve done with clients have often taken one or more days, to be thorough. But things are changing too fast to reconsider everything each time there’s a shift.
Instead, focus your attention and your risk management efforts first and foremost on the things that are easy to identify: the things that could tank you and tank you fast.
Burning Man’s Risk Management Pays Off
Burning Man is a city that exists for one week each year. It’s built out of experiential art in the Black Rock Desert in Nevada. Most years, it’s hot and dry. But in 2023, it rained. As it happens, the playa dust turns a clay tarpit when wet. It became impossible for people to get it or out. Mud would collect on car wheels and mire the wheels in the ground.
The organizers did their risk management. They had considered this possibility and the Burning Man Organization handled ‘mudpocalypse’ just fine.

Plan for many possible downsides. Identify the government policies, external signals, and actions others could take that could lead to disaster for you.
For Burning Man, it was rain. For your business, it could be clients leaving you for political reasons..
For each scenario, brainstorm:
- How to reduce chances of that happening
- How to recover if it does happen, and
- How you’ll know that scenario is becoming more likely.
Don’t Panic!
I once considered buying a house as an investment. It needed a lot of repairs. About a hundred thousand dollars’ worth. YIKES!
Here was my thinking:
Pros 15 years of slightly better-than-breakeven expenses and rent. Then it becomes a steady income stream. If rents rise with inflation, it could fund part of my retirement.
Cons Guaranteed need to cover mortgage and taxes even if it’s not rented. It puts me in debt for a six figure amount. I’ve never managed contractors. Cost overruns could bankrupt me.
RUN AWAY!
The Cons scared the pants off me. I declined.
After looking up the property’s last assessed value, letting this deal go definitely ranks as one of the five worst decisions of my life.
What I should have done: tease apart different scenarios and consider them individually.
Avoid Risk of Ruin … But Be Smart!
The problem is that I was treating the Cons as if they were guaranteed. And I was treating the upside as if it was highly uncertain.
In reality, the opposite was more realistic. The upside was near certain, and the downside was only somewhat likely.
Furthermore, there were many ways to limit the downside losses:
- Property Damage. Take out insurance.
- Shoddy repairs. Pay more for a highly reliable contractor. (“More” yes, but in the grand scheme of things, not that much more.)
- Slow contractors. Structure the renovation to make payments contingent on completion.
- Too-large an amount to risk. Bring in an experienced real estate investor as a minority (or even majority) partner on the deal.
- Costs spiral out of control. (The “nuclear option”) Resell the building at below market, a modest loss, if expenses were too great.
When it comes to my new computer, the major downside scenarios are (1) wait and have my current computer fail or become obsolete completely, forcing me to buy at a much higher price if costs rise substantially (2) buy now and having a better model come out later and (3) buy now when the money could be used for other things.
When I listed the downsides individually, it’s pretty clear that the downside of waiting is an interruption to my business and a possible bigger purchase price. The downside of buying now is entirely opportunity cost.
Since I don’t have any opportunities on the table that would be hurt by the purchase, I placed the order while I was writing this essay.
(Yup. I really use risk analysis, myself!)
But this is only one part of the equation, limiting the existential risk. You still need to increase your chances of finding the upside in the chaos. We’ll tackle that in the next newsletter.
P.S. What are you afraid might happen? Where are your most likely risks? Let me know and I’ll choose a reader scenario to use as an example going forward.