🍪 Forget, Regret 🍪

But Treat Yourself to a Chocolate Chip Cookie

"Make the most of your regrets; never smother your sorrow, but tend and cherish it till it comes to have a separate and integral interest. To regret deeply is to live afresh."
-Henry David Thoreau

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“I’m just being rational.”

“I’m just stating facts.”

What do these two statements have in common?

These are two of my least favorite phrases in hot-take-infused arguments.

If I could, I’d ban them.

At best, these statements are conversation stoppers, attempting to halt a discussion dead in its tracks to avoid further debate (spoiler: it never works.) At worst, this is verbal jiujitsu employed to avoid answering challenges to a relatively weak argument.

This may surprise you if you are new to Moneyball Judaism. Discussions about data, heuristics, and evidence can lead one to quickly conclude that, if you use these tools, then you will be the person who can say that you’re “just being rational” the next time you are arguing about politics, religion, money, etc. People will stare in awe of your brilliance!

But it doesn’t work like that.

Reasoning is a messy process, and the more complicated the decision, the messier the process. Facts only take you so far.

At any given time, a healthy leadership practice requires an intentional approach to making decisions. While the world outside remains messy and painful, in the end, people in positions of authority will still need to process critical decisions about which they will be held accountable, either by themselves or others.

And while rationality can be powerful, regret is far more.

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Regret Aversion

As you look ahead to the short-term, medium-term, and long-term, perhaps you see a significant decision looming on the horizon:

1. Will my contract be renewed?

2. Should we renew the contract of our top professional?

3. Can my organization afford expansion?

4. Would now be a good time for a career transition?

5. Will major donors stick with us through a transition?

6. Could now be the time to stop running a long-beloved program?

In some cases, you and others will express unanimity on what the decision should be. But those cases are the exceptions, not the rule. In most cases, once you decide, you will ponder the road not taken, perhaps even regretting your choice for years if the results are not what you hope.¹

In theory, none of this should matter.

As we learned from Richard Thaler, if we functioned like “Econs,”² regrets should not enter our decisions because emotions do not enter our economic choices. But by now, you know these decisions are always more complicated because emotions always play a role. And regret is a sneakily powerful force that can play an outsized role in making these decisions and others.

Building upon the work of Kahneman and Tversky, Graham Loomes and Robert Sugden (L&S) wrote an article in 1982 that takes the early work on heuristics and asks how to incorporate regret into human decision-making, what they call (shocker) “regret theory.”

L&S argues that although there is ample evidence that most people do not optimize their decision-making under all circumstances, most people can imagine what an optimal decision might be or should be, even if they did not make it. For example, today, my daughter made chocolate chip cookies and asked me if I wanted to have some:

• Optimally, I should have, at most, one cookie

  • If I were a muscular cyborg like Rich Roll, I’d have no cookies³

• Instead, I have three (in my defense, they were delicious)

• While I understand that I did not optimize my eating habits by having three cookies, in hindsight, I am aware of what my optimal choice should have been

L&S asserts that the space between what we actually do and what we optimally should have done is a space called “regret.”⁴ The formula might look like this:

(🍪🍪🍪)-(🍪) = Regret (🍪🍪)

(Actual Decision) - (Optimal Decision) = Regret

L&S concludes that because people experience “regret and rejoicing” and try to “anticipate…those sensations” when making the decision, it is inaccurate to say someone is acting “irrationally” when taking those feelings into account.⁵ In a vacuum, a specific decision may be the optimal one, but factoring in the role of regret describes how people actually make decisions versus how classic economic models claim they do.

Naturally, this appears to give you more bad news. 

If you hope there is a way to make one of these decisions devoid of feelings, you’ll be waiting forever. But as we learn every week, there is a silver lining to any bias…

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The Good Enough Job

I guess the previous section had the most significant emotional effect on anyone making an employment decision, whether that is a decision about you or someone else. And to help you move forward, I would encourage you to read Simone Stolzoff’s The Good Enough Job.

Job changes are the most common instance of regret entering our work. Should I switch jobs? Should I terminate an employee? Should I stay in a toxic workplace? Reaching a perfect conclusion to any of these questions is impossible. At the same time, Stolzoff argues that we must question the mental and emotional toll jobs can take on people who take them too seriously.

Rest easy: This is not a book that encourages you to make peace with the mantra that “it’s just a job.” I hate when people say that.

While family, friends, and personal passions may be more emotionally important to me, at this stage in my life, work, by necessity, takes up the most significant portion of my daily time budget. And if I am going to need to spend most of it on work for reasons financial or otherwise, I’d like for that time to be valuable.

Instead, Stolzoff argues that there is an alternative to what Derek Thompson calls “workism,”⁶ the tendency of white-collar workers to see their careers as akin to a religious identity, a part of their lives that should be their primary source of meaning, community, and transcendence. The Good Enough Job is Stolzoff’s attempt to share cautionary tales of people who fell into the workism trap and found more professional satisfaction by tying their self-worth less to their professional success. 

Using me as our example (or punching bag), work is one of my identities. But I also am a father, husband, son, friend, writer, reader, mediocre triathlete, defensive-minded Little League coach…you get the idea. Stolzoff argues that

“When we give all of our energy to our professional lives, we deprive the other identities that exist within each of us—spouse, parent, sibling, neighbor, friend, citizen, artist, traveler—of the nutrients to grow.”⁷

My children are getting older every second I am working. And while I want and need to give it my all as a rabbi, if I am not constantly providing my identity as a father with nutrients, one day, I may wake up and realize those identities stagnated or, worse, wilted away.

This book is challenging for most of the professionals who read this newsletter, as Jewish professional life is one of a variety of professions notorious for being labeled a “calling.” As such, there is an inherent barrier to separating life from work, one of the reasons why helping professions and nonprofit organizations have such high burnout and turnover.⁸ That said, Stolzoff includes a teaching from a poet named Anis Mojgani, who said:

“Work will always be work. Some people work doing what they love. Other people work so that they can do what they love when they’re not working. Neither is more noble.”⁹

Deep.

Challenging.

And Important.

Read the entire book to learn more.

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Cal Newport and Simone Stolzoff

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500 billion¹⁰

The number of words Chat GPT was trained to identify. 

By comparison, a human child by the age of 10 has absorbed approximately 100 million words. In other words, a Large Language Model (LLM) knows 5000 times more words than a ten-year-old.

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What I Read This Week

1. 500 Cables That Run the Internet: This article surprised me, but it was incredible. Meet the underwater wires that run our lives.

2. The Art of Making Good Mistakes: Have you made a mistake this past month? I have. Here’s a beautiful piece on mistakes in a new book by our friend Amy Edmondson. I just read her newest book and am debating whether or not to review it.

3. Women Who Tried to Warn Us About AI: I’m a little late to the party on this article, but Rolling Stone had a great profile on women who foretold the harmful effects of AI before the rest of us.

4. Why the Internet Isn’t Fun Anymore: My first thought upon seeing this title was, “You just realized that the Internet is not fun?” Read anyway.

5. Adventures in Nonprofit Math: Ridiculous examples, but hilarious and true. My favorites are 5, 7, and 13.

1. You missed my bumming you out, didn’t you?

2. The more issues I publish, the more technical terms I will assume that people know. However, if you are newer to Moneyball Judaism, know there is a cheat sheet to look up the big ideas in a glossary and a bibliography of sources I cite.

3. I suppose Cookie Monster is the only creature where you could argue that he should optimally eat as many cookies as possible…

4. Graham Loomes and Robert Sugden, “Regret Theory: An Alternative Theory of Rational Choice Under Uncertainty,” The Economic Journal, Volume 92, Issue 368 (December 1982), 820.

5. Ibid.

6. Derek Thompson, “Workism is Making Americans Miserable,” The Atlantic, 24 February 2019.

7. Simone Stolzoff, The Good Enough Job: Reclaiming Life from Work (New York: Portfolio, 2023), xxiii.

8. I am far from the best person to encourage people to make this break, as I do this newsletter for free because I love my work.

9. Simone Stolzoff, xxii.

10. New section: One number you need to know.