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Stinking Overthinking

By: Michael Blankenship |

“I am always doing that which I cannot do, in order that I may learn how to do it.” 

– Pablo Picasso

Learning a new language is hard

(As I’ve recently discovered)

I moved to Portugal last year in November and so I’ve been trying to learn Portuguese. 

Originally, I spent a ton of time… 

🤔Trying to find the perfect app. 

🤔Trying to find the right course. 

🤔Making a weekly plan to master the language as quickly as possible. 

🤔Or creating a calendar to practice my vocabulary. 

I was doing everything…

Except practicing Portuguese. 😂

Ultimately, this led nowhere. 

So I chose a more experimental route. 

Now I buy my morning coffee and strike up conversations with café owners. I watch Portuguese soaps, movies & I pick up so much slang. I try to practice my pronunciation with the new friends I’ve made here. 

It’s fascinating how ditching the plan has led to REAL progress! 

Many times we spend so much time strategizing, worrying about getting everything “just right”, that we forget the valuable insights that come from simply trying. 

This journey reminds me of Nassim Taleb’s (author and mathematical statistician) insightful concept of “convex payoff”. 

It means that the potential gains from a successful experiment outweigh the losses from an unsuccessful one. And as long as the downside doesn’t lead to ruin, you’re always setting yourself up for long-term benefits.

With me learning Portuguese, the upside has been immersive learning, forming genuine connections, and truly living the Portuguese way.

But if it doesn’t work — if I fail at learning Portuguese — it’s no problem. I can always use Google Translate or go back to speaking in English. 

If you’re overthinking or over-planning something in your life, maybe consider the ‘just try’ approach. It could be any adventure—a new job, picking up a new skill, diving into a different culture, or tackling a challenge at work. 

Ask yourself:

  • What are the potential rewards?
  • What’s the worst-case scenario, and is it manageable?
  • What experiences and stories might I gather along the way?

By focusing on opportunities with a convex payoff, we can challenge norms and set ourselves up for moments of learning, growth, and delightful surprises. 

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