Life's Infinite Paths

Uncertainty, maximizing, and the paradox of trying to live the best possible life

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Just Enough to Get Me in Trouble is part of Wayfinder, a writer collective exploring questions that matter.

A couple of times each week, I meet with a small group of writer friends over video chat. We help each other grapple with our writing ideas and challenges. And we’ve become good friends, despite never meeting in person (yet).

I have family in town for the Memorial Day weekend and I thought it would be a great time to hand over the reins and introduce you to one of them, Mark Koslow. Below is one of my favorite pieces of his.

Before you go, be sure to subscribe to his newsletter, The Middle Path, for future issues:

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There is a tide in the affairs of men,

Which, taken at the flood, leads on to fortune;

Omitted, all the voyage of their life

Is bound in shallows and in miseries.

- William Shakespeare

A few days after getting laid off last May, I texted a friend, “I’m excited to float for a while.” I hadn't renewed my East Village lease during the pandemic, so I was untethered from a job and an apartment. I was free from obligations — free to decide how and where to spend my days. 

It turns out I’m not very good at floating. 

I’m more like a toddler in the pool, splashing around in search of something to grab onto. It could be a job, a community, an apartment. Anything to stabilize myself on. Anything to keep me afloat amid the waves of uncertainty.

These waves arrive in the form of questions. What should I do today? What should I work on? Am I spending my time off in the best way possible? 

In these moments, I romanticize the lives of friends in finance, law, and medicine. In their early 20s, they made one hard decision that eliminated one thousand others. Now, their career paths have crystallized in front of them. Wealth, status, and job security are virtually guaranteed. Their path, though difficult, is now set, and they simply have to continue along it.

These thoughts often trigger a more urgent series of questions. Should I move back to NYC? Or what about SF? Should I start interviewing? The idea of routine, friends nearby, and income is enticing. All would be “right” in the world. Or, at least, stable. I’d be back on a path, nevermind which one.

And then comes the rebuttal. No, don’t start interviewing until you have more direction. Enjoy this time off. Write. Meditate. Travel. This may be your last chance before you settle down, get married, and have kids.

As this internal debate builds, the weight of uncertainty grows heavier.

Life’s Infinite Paths

Life’s big decisions share a painful combination of ambiguity and impact. What profession should I choose? Who should I marry? Where should I live? How we choose to answer these questions will change the course of our lives, but it’s impossible to know exactly how. It reminds me of this tweet from Tim Urban: 

Most people find this image hopeful. I find it overwhelming. 

Life is a labyrinth of potential paths and each path will have a unique outcome. We may be happiest on one path, have the greatest sense of purpose on another, and be the most financially successful on a third. As the image suggests, one decision can dramatically change our eventual destination. With this frame of mind, decisions can become paralyzing.

But only for some people. I have a few friends that float through life, making decisions with seemingly little effort or mental turmoil. 

I admire them. I admire their decisiveness, which is usually rooted in a combination of faith, intuition, and conviction. But are they making the best choices? I’m skeptical. Life’s big decisions are too complex to navigate them optimally and effortlessly.

So what explains why certain people can float while others fall into analysis paralysis?

The Paradox of Choice

The Paradox of Choice: Why More is Less taught me that the answer runs deeper than decisiveness. In the book, psychologist Barry Schwartz offers a framework that breaks people into two groups: maximizers and satisficers. 

Maximizers, when faced with a decision, need to know they are choosing the best option. Satisficers don’t need to know they’re choosing the best option. Instead, they’re comfortable making a decision when they see an option that is good enough and meets their standards. 

Everyone is a combination of maximizer and satisficer, but most people gravitate toward one. People can also be maximizers in certain areas of their lives and satisficers in others. For example, you may care deeply about maximizing your professional success, but be indifferent about finding the best apartment. (You can find out whether you’re a maximizer or satisficer by answering these ten questions. I promise they’re not from BuzzFeed.)

For maximizers, uncertainty is their kryptonite. To know they’re making the best choice, they have to know the likely outcome of each option. But uncertainty obscures these outcomes. It’s like driving in a heavy fog, where they’re trying to choose the best possible route but can only see as far as their headlights. 

It turns out I’m a pretty severe maximizer. I’ve taken the quiz a few times and have scored 80-90% maximizer each time. 

The distinction between maximizer and satisficer is important because it affects not only how we make decisions, but also how we feel about our decisions. 

On the latter point, Schwartz paints a grim picture for maximizers. Compared to satisficers, maximizers savor positive events less, don’t cope as well with negative events, ruminate more over past decisions, and feel anticipatory regret over current decisions. They also tend to be “more pessimistic, anxious, stressed, worried, tired, depressed, regretful, and disappointed than satisficers. And they were less optimistic, content, excited, and happy.”

Yikes. I cringed as I recognized parts of myself in his description. I grew determined to free myself from maximizing.

But then Schwartz complicated things. It turns out there’s a silver lining for maximizers.  

The studies show maximizers tend to get better objective outcomes than satisficers, even though they subjectively feel worse about those same outcomes. Despite feeling worse about their jobs than satisficers, “Maximizers landed jobs that had 20% higher salaries compared to satisficers.”

Ah, fuck. 

My newfound resolve quickly abandoned me. My maximizer self was not okay with 80%.

What now? 

In typical maximizer fashion, I want the best of both worlds. How can I get the objective outcomes of a maximizer and the subjective well-being of a satisficer?

Schwartz, unfortunately, never answers this question directly. Instead, he dedicates the final pages of the book to outlining recommendations for maximizers:

• Embrace constraints on decision-making and limit time spent on unimportant decisions.

• When ruminating thoughts arise, practice gratitude for the positive outcomes of past decisions. 

• Don’t have excessively high expectations about the outcomes of decisions. 

• Avoid social comparison and focus on what makes your life meaningful and joyful. 

These are helpful reminders. But, for me, the most impactful takeaway was hidden in a paragraph about halfway through the book.

Just after Schwartz describes maximizers and satisficers, he introduces a paradox: the best strategy for maximizing is to abandon maximizing as a strategy. He quotes Nobel Prize-winning economist and psychologist Herbert Simon, who introduced the idea of “satisficing” in the 1950s, saying, “When all the costs (in time, money, and anguish) involved in getting information about all the options are factored in, satisficing is, in fact, the maximizing strategy.” 

This assurance “satisfies” my maximizing mind.

It showed me that the maximizing strategy is to follow Schwartz’s advice and be satisfied with the “merely excellent as opposed to the absolute best.” By freeing myself from the psychological demand to live the best possible life, I can give myself the best chance of living a great life.

Floating

Armed with this lesson, I’ve found that floating has become much easier during this period of uncertainty. The waves of uncertainty still come, but overall I feel more buoyant. More at peace with past decisions. More assured that my current decisions will lead to a great future. And more empowered that I alone am the arbiter over the quality of my life.

Schwartz’s book also offered a framework that changed the way I understand myself. I used to attribute my tendency toward regret and indecision to a baseline neuroticism, but now I realize that I’m just a maximizer. Having that explanatory power over these behaviors has transformed my subjective experience of them. Now, when I notice regret or indecision arising, I can label it, “Oh, I’m doing that maximizing thing again.” And the negative thoughts and emotions associated with regret or indecision start to soften. 

I’ll leave you with a question. 

What if you just decided to believe that you are on the best path — that you’re living the life you’re supposed to be living? 

If you did, how would you reinterpret your past? How would it change your experience of today? How would it affect your aspirations for the future?

Happy floating,

Mark

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