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Leading Through Chaos part 2: Don’t Die! (aka Barbells and Risk of Ruin)

Leading Through Chaos part 2: Don’t Die! (aka Barbells and Risk of Ruin)

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.

A picture of a fantastical Burning Man structure in a dry desert, juxtaposed with a picture of a soggy hippy trudging through the mud after a rainstorm.

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:

  1. How to reduce chances of that happening
  2. How to recover if it does happen, and
  3. 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.

Leading Through Chaos part 2: Don’t Die! (aka Barbells and Risk of Ruin)

Leading Through Chaos, part 1: What’s the Root Problem?

The world is pretty crazy right now, and it’s hard to know what to do. About anything. But even wait-and-see is doing something.

Or maybe, we can step up as leaders. Business leaders. And since everything is in flux, not just business, we can also be family leaders. Friend and community leaders.

Leading or not, we need a way to deal with the chaos.

The first step is understanding why chaos is even a problem.

America has decided to step down as a world power. Given our central role in the world’s economy, America shifts, and so does everyone else. Stock markets are dropping. Currencies are fluctuating. We’re talking decades of ripple effects. And that’s just the economy.

We don’t know what the world order will look like five years from now. We don’t know what our lives will look like. But different. Almost certainly, different.

Personally, I’m plenty scared. My whole life has been based on stories about the future:

  • There’s always opportunity available if you decide to grab it.
  • I have control over my future.
  • My later years will be spent with family and friends.
  • Physical health and fitness is possible, if you just put in the work.
  • The world will generally get better over time, leading to more opportunity, health, prosperity, and safety.

In short, I’ve assumed that everything needed for a vital, fulfilling life is available.

Do Lunch or Be Lunch

But there’s the rub. When those assumptions are up-ended, everything else seems in doubt.

  • Will there be opportunity, two years from now? As I write this, GDP forecasts have dropped from +3% to 0% in the last six weeks.

  • Will there be health care, sanitation, food standards, and public health that can help support me in my old age? It’s looking unlikely.

  • Will my country even be conducive to community, mutual support, happiness and love?

We want to know these things so we can plan for them.

My Harvard Business School professor Howard Stevenson changed my thinking more than anyone else. He has a knack for reframing life situations in powerful ways.

In his book Do Lunch or Be Lunch, he suggests that the fundamental human drive isn’t survival, it’s predictability. Predictability is what helps us survive.

We don’t want to Be Lunch; we don’t want to be the hapless victim of the Saber Tooth Tiger.

We want to Do Lunch. We want to be the ones in control. We want to build, plan, and do so we can be the diners, not the meal.

Building and planning means knowing the future. Or at least knowing what the future is likely to be. That’s why science is great. Science tells us how the world works.

When we combine “how the world works” with “what we see, feel, and hear” (also known as data), we can predict future:

There’s a huge tree outside my window. The branches are near the house (observation). Close branches + wind = broken windows (how the world works). Knowing that, I can ask an arborist to trim the tree.

Note to self: Call the arborist. That tree’s getting a little too close.

It’s far from perfect, but it works better than anything else humans have tried.

Risk? Defuse it!

When you “Do Lunch,” that’s risk management. We do it everywhere.

Financial professionals are always looking for ways to get high returns with downside protection—that’s risk management.

Ever hear of a “hedge fund?” They started as funds designed to help investors “hedge their bets” against downturns in other investments.

Households save for a rainy day. Or for college, just in case our kids don’t get a full scholarship (does anywhere even give full scholarships).

We buy life insurance policies for our families, in case we get eaten by a Saber Tooth tiger.

We audition for Broadway, and also learn a marketable skill, just in case we don’t get selected as Elder Price in Book of Mormon. (h/t to my friend Pete, who despite being a “triple threat” singer, dancer, actor, also learned to code.)

We don’t like chaos because it screws up our ability to predict—and thus control—the future.

Change, even good change, can be bad

The ultimate in predictability would be if we could freeze everything the way it is. I watched the 2023 movie Barbie last night.

In it, the character Gloria (delightfully portrayed by America Ferrera) tells Barbie, “That’s life. It’s all change.” (Barbie’s response? “That’s terrifying—I don’t want that!”)

Nevertheless, the world changes. We can adapt to slow change. It gives us time to learn the new rules. Then we make new predictions and new plans.

Fast change is another matter. Too fast and our systems start breaking down without giving us time to learn the new rules.

The fundamental human drive is predictability. — Howard Stevenson (paraphrased)

When change is too fast, we stop investing for the future. Consider college: Who wants to spend four years and thousands to learn advanced skills that might be obsolete in ten years? When college is a path to success, it’s a no-brainer. When the job market changes so fast that college is a six-figure gamble? Not so much.

We can’t plan long-term during unpredictability, so we have to settle for short-term tactics. But that’s dangerous. Because short-term gains often come at the expense of long-term health.

The way to deal with chaos is to find predictability wherever you can.

Start from your bedrock

Find what you can predict and plan for it. Then find other ways to deal with the unpredictable.

If your supply chain is breaking down, or your retirement savings drops by 30%, use risk management for some short-term options. Then learn some new ways to think about strategy under uncertainty. We’ll cover my favorite later in this series.

In the book Anti-Fragile, Nassim Nicholas Taleb lays out a proposal for how we manage risk. It’s a barbell strategy. We deal with the extreme downsides and the extreme upsides.

First and foremost, we arrange our lives to protect against the worst-case scenarios. The risk of ruin. Things there’s no coming back from.

My own retirement strategy started with an investment account that I couldn’t touch until age 59 1/2. It invested in low-risk, long-term, dependably predictable investments. If nothing else worked, it’s protction against ruin.

The second part of Taleb’s strategy is the other end of the barbell: the extreme upsides. Always make sure you have some exposure to the best possible cases.

We’ll cover everything in the next few newsletters — protection from ruin, managing to find upsides through turmoil, and where to lean in as a leader.

But let’s start at the beginning. In the next segment, we’ll look at how to protect yourself against risk of ruin.

Want to tank your profit margin? Just do a successful merger!

A fable of Maximus Grandeur, CEO of Gaping Maw Co[1].

Think you understand “synergies”? Think again. Most people don’t. Synergies can happen. The boost revenues and profits, but tank profit margin. In fact, math often guarantees it. Here’s an example.

In the Beginning

Consider two standalone companies. Milk Co and Ice Cream Co.

  • Milk Co makes $9 million profit on revenues of $300 million. That’s 3% profit.
  • Ice Cream Co makes $2.5 million on $50 million. That’s 5% profit.
  • Gaping Maw Co is a large food company that makes $80 million on $1 billion in revenues. That’s 8% profit margin.

Enter Maximus Grandeur, Gaping Maw Co’s new CEO. He’s been feeling inadequate in the bedroom, so in a misplaced attempt to shore up his self-esteem and fool himself into believing that he has agency in life, he buys the two companies to feel big and powerful. Publicly, he talks about “synergy.”

Just the Math, Ma’am

The acquisitions happen. He makes no other changes.

Maximus just screwed Gaping Maw’s profit margin. The new profit margin is (all numbers in millions):

($9 milk + $2.5 ice cream + $80 legacy)/($300 milk + $50 ice cream + $1000 legacy) = 6.78%, down from 8%

Let that sink in: for purely mathematical reasons, having nothing to do with actual business operations or performance, consolidating two businesses under an umbrella business mathematically decreased the umbrella company’s profit margins.

BUT WAIT! What about synergy? That was Maximus’s publicly-stated reason for suggesting the acquisition.

The Synergy is Real

The Maximus synergy is for Ice Cream Co to buy all their milk from Milk Co instead of other suppliers. He proclaims this brilliant strategy in the annual report, to rescue the profit margin. He implements.

The new, synergy picture is this: $10 million of purchases that Ice Cream Co would have spent with other milk companies now goes to Milk Co, which will make its normal 3% profit on all those tasty new purchases. Everything else remains the same:

  • Milk Co makes $9.3 million profit on revenues of $310 million. That’s 3% profit.
  • Ice Cream Co still makes $2.5 million profit on $50 million. That’s still 5% profit.
  • Gaping Maw Co’s legacy businesses still make $80mm on $1Bn, for 8% profit.

Considered individually, each division is doing as well or better than before the merger.

Each division is doing just peachy. In fact, Milk Co is doing better in terms of absolute sales and absolute profit. That means that Gaping Maw has $10 million more in revenues, and $300K more in profit. Each division is as healthy as ever!! Healthier, even!!

Sounds like a win, right? Wrong.

But Synergy Makes Everything Worse

Because now Gaping Maw Co’s profit margin is (all numbers in millions):

($9.3 + $2.5 + $80) / ($310 + $50 + $1000) = 6.75%

Synergies were realized, and it made the profit margin even worse.

Yes, you read that correctly. The synergies were realized, and it pushed the profit margin lower[2]! From 6.78% to 6.75%.

As a conglomerate, the profit margin has gone down, even as the absolute dollar amount of profits has gone up.

Here’s How to Think About It

Here’s why: intuitively, business units with lower profitability than the overall company drag down the overall profitability margin. The more revenues come from low-profitability businesses, the more overall profitability sinks, even though the business is doing better.

It’s also possible to acquire a high-profitability business that boosts overall profitability while absolute revenue/profit numbers may decline. It’s the math; it’s not about how efficient or well-run the business is.

But all the market cares about is profit margin of the overall company. So your stock price will tank, the CEO will get fired, and Maximus will take his golden parachute (equivalent to the last ten years’ profits of all three companies combined) and retire.

BUSINESS MORAL: Know the math before you acquire or “synergize.” Know the absolute numbers and the margin numbers. Assume investors will only pay attention to overall profit margin, which means they might push you to do dumb things to maximize that number. Don’t listen. If you’re going to do dumb things, at least do your own dumb things.

PERSONAL MORAL for Maximus: If your sex life is unsatisfying, maybe you’re spending too much time at the office. Regardless, don’t take out your frustrations on innocent companies that are doing just fine.


  1. This article is emphatically not about CVS, even though it was inspired by reading that CVS is going to axe 2,900 jobs and possibly split up their insurance and pharmacy businesses to "improve financial performance. ↩︎

  2. The real problem here is that we demand steady or growing profits when viewed as a percentage return. It is beyond the scope of a simple essay to give this topic the treatment it deserves. ↩︎

No, I’m Not Crazy but I Hike Barefoot! with Greg Stern

Many jobs are new spent at screens. We’re sitting all day, and frankly, it’s not good for our bodies. Greg Stern, founder of Ground-Up Physio, will be joining me to explain why barefoot is better, slouching is super, and what we’ve been taught about how to use our bodies needs more than a little updating.

Reefer Madness: Saving the World with Christian Campbell

In the 1930s, the movie Reefer Madness was the centerpiece of a campaign to discredit marijuana. Almost a century later, actor/entrepreneur Christian Campbell turned it into a musical satire and commentary on manipulation and propaganda. In fact, the industrial uses of Hemp might be a significant piece of climate-friendly business. But how to spread that message when you can’t advertise the product?

Join us for a lively discussion about reefer, propaganda,  madness, musicals and saving the world.

Supercommunicators with Charles Duhigg

We all know people who seem to effortlessly connect with anyone they talk to. 

What’s their secret?


Pulitzer-Prize-winning journalist Charles Duhigg spent years researching this question and finding the answer. In his new book “Supercommunicators,” he explains that great communicators are always working on three levels: the practical (what this is really about), the emotional (how we feel), and the social (who we are).

Great communication begins by recognizing which conversation you’re in. In this livestream, Charles will share the simple yet profound lesson: with the right tools, you can connect with anyone, anywhere. Don’t miss this chance to gain the communication superpower!

Business Culture for Life Success with Alex Draper

Do organizations really prioritize the well-being of their employees and families? Of course not. At least, many don’t. But some do. And today we’re going to explore how they successfully live both their business and their cultural values. Our guest, Alex Draper from DX Learning, brings an insightful perspective from his work helping leaders live out company values. The lives of employees, and their entire families, are in the hands of business leaders. Alex will explore small habit shifts that profoundly impact an organization’s entire ecosystem.Alex will share his innovative CARE model, and together we’ll learn how leaders can walk their talk on a daily basis.

Top-Tier Culture: What it Is, Why It’s Good, and How to Create It with Michael Weening

What does the President & CEO of a billion-dollar company think of “grind culture”? Work-from-home? Productivity?

Michael Weening can tell us. The President and CEO of Calix, Inc. (NYSE: CALX), which just broke $1 billion in annualized revenue, Mr. Weening’s experience spans multiple geographies and cultures, including North America, Europe, and Asia. He has worked for companies who dominate their industries—Microsoft, Salesforce, and Bell Canada—and managed people in every business function from sales to marketing to operations. He knows what it takes to succeed in radically different cultures, with radically different personality types.

Calix was named “Most Inspiring Workplace in North America” and has been heralded as a top-tier “Best Place to Work” by GlassDoor, Fortune, and BestPlacesToWork.com. It has earned awards for Happiest Employees, Best Compensation, Best Work-Life Balance, and Best Perks & Benefits.

Misbelief with Dan Ariely


Join me for a chat with social scientist Dan Ariely to discuss his new book, Misbelief. He’ll help us understand why even smart people find misinformation so seductive. He’ll help us understand how even otherwise rational people can adopt deeply irrational beliefs. Given the problems facing the world today, and the prevalence of accidental and deliberate misinformation, we’re sure to have a lot to talk about.

Dan is a leading behavioral economist and author. He is the James B. Duke Professor at Duke University. His research focuses on how even smart humans behave irrationally. He has written best-selling books including “Predictably Irrational” and “The Honest Truth About Dishonesty.” Ariely has co-founded several initiatives such as BEworks, Timeful, Genie, and Shapa that apply behavioral economics to real-world situations.

The Enneagram in Business with Karl Hebenstreit

Do you know what drives your team? Your co-workers? Yourself? I thought I knew myself, too. Until Karl Hebenstreit helped me see otherwise.Author of “The How and Why: Taking Care of Business with the Enneagram,” Karl will explain how you can use a psychological profile called the “Enneagram” to understand yourself, your team, and your blindspots.We’ll use me as a case study. I took the validated Enneagram inventory and the results were unexpected. I wanted to see myself one way, and the inventory said something different. Through our livestream discussion, we’ll explore how to resolve that gap, and how to understand the strengths and weaknesses of learning your (and your co-workers/partner’s) actual approach to life.