My Best Relationships Are Antifragile

I have a relatively new friend who I couldn’t reach for a while. It was frustrating because I had a business question I needed to ask him. When I thought about how he hadn’t responded to my emails it made me angry.

I finally caught up with him recently on a zoom. He had a good reason for his silence. He was apologetic, sincere, gracious, and transparent. I left the zoom call feeling more affection for him and a closer friendship than I had before this sequence of events started.

It’s because our young friendship had been tested and had not only survived but had become stronger. Our relationship had become more antifragile.

Antifragile is a term coined and popularized by the author Nassim Taleb.¹ His concept is that certain systems and people become stronger when tested by volatility and danger, errors and lapses. Fragile systems are more likely to break under duress. Robust systems are inferior to antifragile systems because they don’t improve when their strength is tested.

Natural evolution is antifragile. Survival of the fittest happens through a series of successful adaptations to the constant strain of natural upheavals. That any of us are here today is due to a long line of antifragile (and lucky) ancestors stretching back into primordial time.

Taleb compares a bank employee and an Uber driver who earn the same amount of money per month on average. The banker’s salary is constant while the Uber driver’s fluctuates. The banker appears to have more security but in reality his position is fragile; in a financial crisis, his bank could go under and he could be fired and lose all his income. In contrast, the antifragile Uber driver is used to his income fluctuating and reacting by saving, cutting his monthly expenses, or working longer hours. ²

Taleb focuses his fragile-antifragile dichotomy on the worlds of money, investing, statistics, and some social sciences rather than focusing on personal relationships. He does make a few passing references to “helicopter parents” and “soccer moms.” You can guess from these derogatory labels that he believes children today are overly cosseted by their parents, making them more fragile and less prepared when they eventually face the real world of adulthood.

After my daughter graduated from college she revealed her supreme irritation when people said, “welcome to the real world.” So for a while I contributed to her antifragility by using that phrase whenever I could.

Antifragility and parental mistakes

I’ve come to think that my mistakes as a parent, at least those that can be laughed about in hindsight, are one key to my antifragile relationships with my children. They create the survivable lapses, errors, and volatility that underlie Taleb’s antifragility theory.

My mistakes have established that it is okay for my children to get upset at me for my imperfect behavior, and then we move past it. ³ Each miscue and subsequent solution makes us know that there is very little that parent or child could do or say that would cancel out a lifetime of bonding.

Here is one of my most infamous mistakes.

When my daughter Lauren was eleven we went skiing as a family. We had adjoining hotel rooms with the inter-room doors unlocked. Debbie and I ate downstairs in the hotel’s restaurant and left Lauren in charge of her younger brothers. Some evil spirit (perhaps named McCallan) inspired me to do the following.

I went upstairs to our hotel room. I could hear the television from the kids’ room. I crept into our bathroom and called (flip phone, circa 1999) the kids’ room through the hotel switchboard, implying that I was downstairs. When Lauren answered, I told her I feared that someone was in our bathroom. Could she investigate? She did. I popped out and made her scream. And then she laughed.

To be clear this is not recommended parental behavior. But Lauren has dined out on this story with her friends many times. Plus she has gotten a measure of revenge. Halloween, 2023, she devilishly placed a life-like figure of an evil witch in my bathroom, successfully scaring me. Around the same time, she put pictures of the Exorcist’s demonically possessed Linda Blair for me to discover when I opened various closet and medicine cabinet doors.

Practical jokes aside, Lauren and I are similar in that we cannot tolerate one of us being upset with the other. So when we do upset each other––and it can just be the use of an unwise word such as saying your very pregnant daughter looks “sturdy” ⁴ ––we are quick to call the other and apologize.

Another antifragility parenting tactic I recall is being home and available to the kids, which is a very different vibe than taking them to activities. We could never predict when one of our kids would walk in, ready to have a conversation that was vital to them. How could we, especially with teenagers?

These stretches of unstructured availability led to increased transparency––the lines of communication were open. Transparency deepens or accelerates time, which is a key to antifragility.

Time

The passage of time is antifragile. If something has lasted a long time, there’s a good chance it will continue to last. I’m friends with someone I met at school n 1968. At a young age we engaged in some unsavory gambling activities as partners in crime so we’ll always have that over one another.

There is something special about friendships that started in youth. I broke up with Steve, my best friend through high school and college, when I married my wife Debbie in 1985. Once I met her, I cared only about Debbie and dropped everything and everybody else, including Steve. He and I were twenty-three. We handled our conflict as people of our age usually do. Badly.

Two summers ago, at a dinner party at our house, my younger brother mentioned Steve’s name. By chance, Steve happened to be a house guest of our friend and dinner guest Natasha. We asked her to use her diplomatic charms to tell Steve we’d love to see him. Natasha succeeded in her mission, Steve and I were happily reunited. All was forgiven and we remembered why we had been best friends.

I think my friendship with Steve is a special case where we had deep history but we also had that long disruption that we could laugh about after the passage of enough time. If after that breach, our friendship could become very close very quickly again, then it is antifragile.

My female friendships

I’m going to make a gender generalization, dangerous yes, but based on recent personal anecdotal experience so it may only apply to my specific circumstances. In the last few years, I have developed some close friendships with women. I never had female friends before and I’m delighted to have them now.

These friendships have mostly arisen from shared participation in activities––tennis and writing––– which is a natural way for any friendship to flourish.

The generalization is that I find my female friends to be on average much more transparent with me than male friends about personal and vulnerable matters. And that leads me to be more personal and vulnerable with them. This exchange of confidences acts as an accelerant to friendships. It speeds up the antifragile effects of time. The more we know about one another the longer it seems we’ve known each other.

Perhaps because I’m a happily married man of forty years and my female friends, married and single, know my wife, the natural tension that might otherwise be an impediment to the blossoming of these male/female friendships is absent.

My Fragile Relationships

Most of my relationships have in fact been fragile. Most acquaintances are lost and never become true friends. Business “friendships” are generally transactional. There was the CEO who I was so close to in pursuing a deal and talked to every day. He turned out to be the wrong choice for the job so I had to fire my “friend.” There was my colleague who I worked arm in arm with for years. He left to go to another firm and we never talked again.

More haunting is that my relationship with my mother was mostly fragile. She had a bad temper and would get angry and say hurtful things. I’d then want to avoid her. I’d be afraid to confront her.

At one point she was irrationally afraid that she was losing all her money because her income took a dip. She decided to sell all her jewelry at a fraction of her cost to a dealer. I offered to match the dealer’s price because I wanted to keep the pieces in the family.

After I bought the jewelry, my mother and I had a fight about something else and she demanded that we reverse the jewelry transaction. I refused. She cursed at me. I cut off all contact with her for a week, which made her frantic.

We reconciled and never had another big fight. But only because I had scared her that she might lose me if she lost her temper again. That’s a fragile relationship.

Marriage

Unsurprisingly, my long and happy marriage is the most antifragile of my relationships. My marriage is the only serious adult romantic relationship I’ve ever had. So I have the opposite of a statistically significant set of comparable examples to reach any conclusions about what makes a marriage or any romantic relationship last.

I can only tell you the circumstances that I think have benefitted the staying power of our marriage, which the passage of forty years has made antifragile.

• Although we came from similar surface backgrounds––Manhattanites, private school, Jewish––we were raised in different circumstances with Debbie’s parents having made their own way in the world and my parents having grown up with wealth.

  The similarities and differences were very helpful, especially in raising our children amidst affluence. We “knew” each other culturally but we were different enough to combine strengths and battle weaknesses. For example, Debbie insisted on negotiated allowances. Left to my own devices, I might have been lazy and unintentional enough to have given our kids a credit card as many of their peers had.

• We recognized that we have made a good team as parents, which is an ongoing thirty-seven year “game.” This strengthened our bonds more than anything else.

• We’ve always been faithful to one another. I’m sure there are marriages that have emerged stronger after an affair. If the marriage survived, that could introduce a strong antifragile element into it.

• We’ve always been very much attracted, physically and otherwise, to one another. That may have made it easier to be faithful throughout the decades. That’s luck, genes, and individual taste.

• Romantic love finds its most passionate expression in private where only one particular person can “unperplex” the other.⁵ And it’s not just the physical.

As Wallace Stevens wrote:

“If sex were all, then every

trembling hand could make us

squeak, like dolls,

the wished-for-words” ⁶.

• We’ve always been able to make each other laugh.

• We’ve never felt like competitors. When we’ve had to arbitrate inevitable differences and fights, we’ve tried to resort to the principle of who cares the most. Sometimes, however, our behavior to each other is less than mature––see my post A Fight Reveals The Fault Line In Our Marriage.

• We do not keep score. The quote below from the poet and author Wendell Berry extols compromise in a compelling way.

  “As soon as the parties to a marriage or a friendship begin to require strict justice of each other, then that marriage or friendship begins to be destroyed, for there is no way to adjudicate the competing claims of a personal quarrel.” ⁷

• Finally, we’ve never had serious disagreements about money. With certain things, I’m the spendthrift; with most things, Debbie’s the frugal one. Our good fortune has generally allowed us both to pursue what we wanted to pursue.

A useful heuristic

The fragility-robustness-antifragility continuum is a useful heuristic⁸ to apply to all sorts of subjects. Works of art, books, and buildings that are still admired after hundreds of years are likely going to continue to last. It’s very hard, however, to predict the same long tenure for anything that’s been recently created.

But most useful of all is building antifragile relationships that are meaningful and last long. Writing this essay has made me realize that up until recently, outside of my family, I’ve been overly reticent.

Think of the risks taken by being vulnerable about yourself versus small talk. Vulnerability might frighten someone––fragile relationship––or it might lead to a leap ahead in closeness––antifragile.

So I aim for less small talk and more talk about what matters personally.

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Question for the comments: How might you apply the antifragility-fragility heuristic to something in your own life? Feel free to link to a post that

Notes

1. The book is Antifragile; 2012; Nassim Nicholas Taleb.

2. Taleb made his name and his money from the failure of the banks in 2008. He has contempt for many professions, including bankers, bureaucrats, statisticians, professors, CEOs, and most public intellectuals.

3. Recently, I behaved poorly with my son when he made an innocent comment touching on politics. I turned on him pretty viciously. He was upset not only at my behavior but said he “didn’t recognize me.” I soon called to apologize.

4. My daughter Lauren wants to set the record straight: “I wasn’t very, very pregnant, I had gained more weight than the average woman in my first trimester, I blame ritz (crackers), and so I simply looked chubby. You told me, as you sat like a silly king behind your desk, that I have been looking very sturdy.”

5. Unperplex meaning to solve, as in a puzzle. The word is from a poem by John Donne.

6. Quoted in Wendell Berry; Sex, Economy, Freedom, and Community from the title essay. Eight essays published in book form 1992.

7. Ibid.

8. Apologies for relegating my two younger brothers to a footnote. They are among my most treasured and antifragile relationships. My use of the word “heuristic” is for the benefit of my youngest brother. After I used that word in an earlier post, he bought me a tee-short emblazoned with “Heuristic”.