The Rational Flâneur: Embracing Optionality

I once flew to Ireland for a weekend. My wife and I showed up at the airport in Toronto expecting to fly standby to Paris, but the flight was full (merde!). So we hopped on the only other flight with open seats - the flight to Dublin.

We had no plan. Barely any luggage. And just six Guinnesses each on the plane. We then went on to spend two incredible days exploring the city at random, taking recommendations from the locals we met by chance, and making decisions based on the information we had at that moment. The trip was crazy, exhausting, and one of the highlights of my life.

I didn’t know it then, but I had become a Rational Flâneur. Unlike the tourist who’s stuck in a schedule, the flâneur embraces uncertainty. They alter their course easily based on new information. They keep their options open.

That’s the power of the Rational Flâneur. And you can use this idea to embrace optionality and capture upside in your life and work.

What’s A Rational Flâneur?

Flâneur is a French noun that means “stroller.” Nassim Nicholas Taleb defines the rational flâneur in his book, Antifragile: Things That Gain from Disorder:

“Rational flâneur (or just flâneur): Someone who, unlike a tourist, makes a decision opportunistically at every step to revise his schedule (or his destination) so he can imbibe things based on new information obtained. In research and entrepreneurship, being a flâneur is called ‘looking for optionality.’ A non-narrative approach to life.”

With this approach, you are a “wanderer.” You have a set destination, but you are always asking if there’s a better way to get there, or indeed, somewhere else you’d rather go.

The Rational Flâneur Embraces Optionality.

The flâneur loves optionality. You don’t try to control the future with rigid plans because you know the world is constantly changing. Instead, you stay flexible and nimble. You keep your eyes open for asymmetric opportunities - ones with far more upside than downside - and act quickly when they appear.

Here’s Taleb again:

“This ability to switch from a course of action is an option to change… Optionality will take us many places, but at the core, an option is what makes you antifragile and allows you to benefit from the positive side of uncertainty, without a corresponding serious harm from the negative side.”

To be antifragile is to be in a position to gain from disorder and randomness. My wife and I were in this position on our trip. We didn’t book any hotels in Paris because we knew there was a small chance the flight would be full. We planned to book once we landed. It was a good call because we never landed!

Because we hadn’t spent any money on plans, Dublin had a ton of upside. First, we had money for hotel rooms and excursions. Ireland is also an English-speaking country, so it was much easier to communicate with the locals and get recommendations than it would have been in Paris. And, because we hadn’t done any research, we learned the customs and culture in real time. This all made it a better trip than the one we’d been seeking!

My wife and I exploring the lush, rolling hills of Ireland.

Examples Of The Rational Flâneur Mindset.

My trip to Dublin is a good example of the flâneur approach. Here are some ways you can incorporate it into your life and work.

Don’t Be A Prisoner To A Plan.

Embrace randomness instead. Avoid planning your trip in mind-numbing detail. Just pick a destination, book your flights / accommodation, and then leave the rest to chance. Try to integrate with the locals as much as possible to get dining recommendations, find hidden gems, and get an authentic cultural experience, not the curated one.

When we were in Dublin, we chose restaurants that were full of locals. At one point, we were smashed into a pub shoulder to shoulder, singing at the top of our lungs to live music we couldn’t understand (sometimes those accents are thick!) and spilling our pints of beer all over ourselves. It was awesome.

You can also apply this idea to the content you consume. Pick out a book at random at a bookstore. Go to the theater and then choose a movie. Or just let YouTube take you down rabbit holes you never knew existed (but beware, there’s a lot of garbage out there).

Make Decisions based On Real-World Feedback.

It’s good to have a plan. But it’s better to change that plan if you get information that makes a different bet more appealing.

Tara and I apply this to our work regularly. We are very selective about what writing projects we take on. Before we commit to one (which will take up anywhere from six months to two years of our lives), we soft pitch a handful to the market to see what resonates. We use that real-world feedback to choose the right project for the right time. Only then do we get to work.

So pay attention to the feedback you get. It may point to a path, product, or project you never considered.

Iterate In Areas Of Competence.

Iteration allows for small course corrections as you work. Instead of committing to perfecting a single product or service, refine what you already have based on feedback, market changes, and personal taste.

I do this with writing all the time. I quickly learned that writing is rewriting. It’s making better today what I wrote yesterday. And iterating to improve as I go. This is how I take advantage of the most powerful force on earth: slow, incremental, constant progress in the same direction. You can too.

Diversify Your Bets.

Creatively, this means having multiple projects in different stages of development. Tara and I have finished scripts, scripts that need rewriting, project decks, loglines, and rough ideas scribbled on the back of cocktail napkins (usually unreadable due to said cocktails).

From an investing perspective, it means spreading your bets across assets and asset classes. Taleb has a recommendation for this too: follow the barbell strategy to maximize upside and limit downside.

Never Stop Learning.

Read widely. A flâneur never knows what could be useful in the future, so immerse yourself in different books. This could include blogs (like this one - thanks for reading <3), news articles, research papers, and books across a range of genres.

I read everything. Fiction, non-fiction, the back of cereal boxes and hair conditioners. The more I read, the more I start to connect ideas across industries. This helps me spot opportunities that others may miss.

So, become a Rational Flâneur. Not only will it help you gain from uncertainty, but your life will be a lot more fun.

Start now!

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Article Sources

Taleb, Nassim Nicholas. Antifragile: Things That Gain From Disorder. Random House Publishing Group. Kindle Edition.