The Path of Least Pain: The Shortest Route to an Unsatisfying Life

Why the easy way doesn't necessarily lead to the best outcomes.

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Which way would you go?

Summary in Three Sentences

Ever wonder why you avoid the hard stuff and take the easy road? Your brain is programmed to prefer comfort over challenge, which might hold you back. Opting for the bumpier path could be your shortcut to a more fulfilling life.

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Dear Friends,

Imagine you're at an intersection, waiting for the light to change. You have two possible routes home. One is the road you’re familiar with—smooth, pothole-free, scenic. The other is unfamiliar and riddled with bumps, turns, and overgrown bushes. Still, it will get you home five minutes faster.

Which way would you go?

If you're like most, you would choose the easiest road, or what I call the path of least pain. In other words, most of us opt for what is most familiar and comfortable.

But let's flip the script for a moment and explore the counterintuitive world where discomfort becomes an ally rather than an enemy. This story is about what happens when you opt for the bumpier road. This tale weaves in everything from behavioral economics to the perils of procrastination.

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Now, procrastination isn't simply laziness. It's an emotional seesaw, a dance between immediate pleasure and future satisfaction.

I like the way Webflow, a no-code website builder, describes procrastination in one of their videos: “Procrastination: The often delusional idea that whatever you are doing instead of doing the thing you are supposed to be doing is somehow less painful than the consequences of putting it off until later. Procrastination usually involves focusing on lower priority things.”

Vast research in delay discounting and intertemporal choice suggests that impulsive decision-making often leaves us worse off. Scholars like Ainslie & Haslam and Berns, Laibson, & Loewenstein have demonstrated that our impatience has tangible negative consequences.

We all know we should save for retirement. Yet, the pleasure of an immediate purchase often supersedes our long-term interests. Research shows we opt for what is easiest, not necessarily what is best.

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Here's where things get interesting.

Daniel Kahneman and Amos Tversky, pioneers in behavioral economics, introduced the idea of loss aversion. Their studies revealed that the pain of loss is psychologically about 2.5 times more potent than the pleasure of gain. In other words, our present behavior is more motivated by our perception of future pain than pleasure. This is important because every action is intended to bring us either joy or help us avoid pain.

Not surprisingly, the greater the time between our action and the consequence of our behavior, the less the influence on our current choices. One reason the death penalty is ineffective at deterring crime is that the time between the crime and the execution is too long—nearly twenty years.

All of this is to say we’re more driven by our fears than our ambitions. It's as if every decision is underscored by a hidden emotional calculus that amplifies potential losses and dampens possible rewards. Unfortunately, humans are not very good at predicting future emotions.

On this point, my mind is more likely to notice so-called “bad” drivers while ignoring “good” drivers. Why? Because it sees the few drivers who, at any moment, are driving too close to my bumper, weaving in and out of traffic, or driving 90 MPH while disregarding the majority driving normally. So, I’m inclined to drive more cautiously than I would otherwise. My relationship with technology is similar—I don’t notice when it’s working, but I’m painfully aware when it isn’t.

Consider the role of resolutions in our lives, particularly those set at the start of a new year. Last year, my local library posted a message: “It’s the New Year, so it’s time to try to become your best self once again!” The keywords were “try,” “best self,” and “once again” as if to imply you’ve failed every other year, but this year will be different.

Pursuing a "best self" becomes an annual theater, staged with great fanfare but often leading to anticlimactic outcomes. You see, resolutions suffer from an existential flaw: they are outcome-oriented, requiring extreme willpower. Instead of liberating us, they tether us to the fears, pains, and anxieties we're trying to escape. What is my library touting this year? Apps to help us stick with our resolutions.

So, what is the way out of this paradox?

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What if I told you the key is embracing discomfort and deliberately choosing the bumpier road? What if we abandon the rigidity of resolutions for something more gentle and supple, more attuned to the path rather than the destination?

One way to navigate this emotional landscape is to alter our approach. What if we start with the most challenging and fear-inducing tasks? By doing so, we get them out of the way and experience an emotional high. This psychological boost propels us forward.

And remember to consider the allure of emotion itself. It's like a magnifying glass that can either fan the flames of anxiety or amplify the warmth of pleasure. We could change the equation if we consciously channel this emotional energy to see more clearly.

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So the next time you're at that intersection, think twice before you choose the easy road. Opt for the path less traveled, where bumps and turns are not obstacles but opportunities for growth, joy, and a future you've always wanted but never thought possible.

And who knows? You might find that the bumpier road is the shortcut to a better life.

Choose the path of discomfort,

Ryan

Lupin

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