Oh Please, Just Get Lost!

Optimizing for Serendipity

I used to be the queen of backup plans.

Actually, scratch that — I was the empress of an entire dynasty of contingencies, with Plan A through Z meticulously mapped out. Depending on how I look at things, my proudest achievement in life might be not making any catastrophic mistakes.

But when I look back, you know what really makes my life more fun? All those smaller "mistakes" that turned out to be anything but.

These weren't carefully choreographed moves on life's chessboard. They were more like those weird situations you couldn't script if you tried. They didn’t come from playing it safe. They came from dancing with the universe.

The Great Optimization Trap

We’ve stripped our lives of randomness and surprise. We filter our experiences through five-star reviews, algorithms, and itineraries. We’ve become maximizers, endlessly searching for the “best” option, only to run out of time and energy to actually enjoy it.

Every experience gets filtered through the lens of "but is it worth my precious time?" And the joy of discovery fades. We're all optimal foragers now, scanning endlessly for the perfect choice while operating in that strange state of Continuous Partial Attention — never fully here, never fully there. Always hunting for the next best thing.

Consider this: how often do you try something without knowing the outcome?

When was the last time you got lost, tried a new path, or said “yes” to something that scared you?

When we eradicate chance from our lives, we often function perfectly well—but we feel hollow. Not necessarily depressed, but languishing. Just existing.

I see it everywhere: we're optimizing for survival, for efficiency, for predictability.

We’ve become so careful, so calculated. We’ve moved from playing poker—a game of bets, luck, and guts—to playing chess, where every move is deliberate and optimized.

But life isn’t chess. It’s messy, chaotic, and full of chance. And that’s where the magic happens.

But I’m Scared.

We’re conditioned to fear uncertainty. Ambiguity triggers our anxiety, making us see it as a threat rather than an opportunity. We want to know what we’re dealing with, what’s at stake, and what we stand to gain or lose. But by cutting to the chase, we often miss the dance.

Research shows that the ability to navigate uncertainty is closely linked to creativity and resilience. Yet, we’ve become so risk-averse that we deem most things too dangerous, too messy. We’d rather stick to what we know, even if it leaves us unfulfilled.

The Aliveness of Not Knowing

The best moments of life often come when we’re off autopilot. Our senses sharpen, our attention heightens. Time slows down. We take in the details, the sounds, the textures of the world. It’s in these moments of serendipity that we feel truly alive.

We’re tingling.

Time perception shifts in these moments. It expands. We notice details we'd usually blur past — the way light catches dust particles, the specific timbre of a stranger's laugh, the unexpected sweetness of getting completely lost and finding something better than what we were looking for.

How More Becomes Less

We've reached this bizarre point where we have more of everything — information, choices, opportunities — but somehow feel like we have less.

Less time. Less energy. Less room for error.

Everything feels consequential now. There's more gravity to every move, higher stakes to every choice. We've become so careful about where we invest our precious resources that we've started treating most things as too risky by default.

And what happens then? We order the same dish at our favorite restaurant. We stay within our bubble, algorithmic feeds reinforcing our existing tastes like a digital echo chamber.

We stop exploring because exploration feels inefficient, and efficiency has become our god.

The Art of Planned Spontaneity

Dr. Chad Thatcher said something that stuck with me: "We are so plan-oriented we don't allow serendipity to happen. We are in such a rush, rush mentality... I know there's going to be chance encounters and I am setting my mind up for that. Through allowing time, I can allow space for that."

This isn't about throwing all plans out the window. It's about creating space for the unexpected. It's about developing what researchers call a "sagacious mindset" — being both prepared and open to possibility.

When I think about my best moments, they're brimming with serendipity. They're the stories that start with "I never thought I'd..." or end with "...and that's how I ended up dancing salsa at 3 AM with an elderly Cuban mathematics professor who changed how I think about infinity." OK, so maybe he was not Cuban, not elderly, and it wasn’t so much about infinity. But you get the point.

The Joy of Being Wrong

Don't succumb to the mental missionary position in life.

You know that voice in your head asking "But what if I don't like it?" Well, how about flipping the script: But what if you DO?

One of the greatest joys in life is the reward prediction error—when something surprises you in a good way. The best stories aren’t about how we were right; they’re about how we were wrong and loved the outcome. Think of movies like Yes Man or Billy Elliot where characters take risks and discover lives they never imagined.

Formulaic Existence

Look at entertainment today — it's an industry built on formulas. Take any screenwriting course and you'll never watch movies the same way again. You'll see the beat sheets, the act breaks, the carefully engineered emotional peaks.

But then someone comes along with nothing to lose and flips the table. They do something different, something we would never bet on. And suddenly, we remember what it feels like to be surprised, to be delighted, to experience something we didn't know we needed.

Rewilding Our Lives

We need more free-range humans in this captive-bred world.

We need to let ideas mate in dark corners, to say "yes, and" to whatever the universe throws our way. To silence the productivity porn and let our minds wander into unmarked territory.

Because when we optimize purely for survival, when we try to eradicate chance from our lives, we might keep breathing, but we stop living. We need those "I would have never thought of that" moments. Otherwise, our weeks shrink to three notable days — Monday, Friday, and Sunday — while everything else blurs into a forgettable haze of efficiency.

Optimize for Serendipity

So maybe it's time to get a little lost. To take the weird route home. To talk to strangers (within reason). To order the dish you can't pronounce. To let the universe lead the dance sometimes, even if it steps on your toes.

Because opportunities aren't floating around like clouds — they're attached to people, to moments, to the unexpected turns we usually try to avoid or simply don’t notice when scrolling our lives away.

The best stories in life aren't about how we were right, but how we were wrong. And how much we turned out to love our mistakes.

It's about choosing curiosity over fear, about using up all your potential instead of preserving it like some finite resource.

Life isn’t a rehearsed performance. It’s the ultimate improv class.

Don’t miss the Forrest for the trees.

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To invite more serendipity into your life, you need grit, tenacity, and a willingness to lean into the unknown. Here are some ways to ignite your inner explorer:

1. Say “Yes, and”: Embrace opportunities, even if they seem inconvenient or risky. Treat life like an improv class, where the goal is to build on what’s offered.

2. Be Present: Serendipity thrives in the here and now. Put down your phone, look around, and engage with the world. The next life-changing opportunity might be attached to a person sitting right next to you.

3. Get Lost: Wander without a destination. Explore those back alleys where the weird stuff happens. Let your curiosity lead you.

4. Challenge Assumptions: Stop filtering everything through the lens of efficiency. What if you didn’t choose the “best” option? What if you just chose?

5. Surrender Control: Life isn’t about perfect execution. It’s about creating space for the unexpected. Embrace the art of surrender and let the universe surprise you.