My best plan failed me in Portugal

The Daily Habit For Doers

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

~ Pablo Picasso

This year, learning Portuguese (as I've moved to Portugal) has taught me how experimentation more than planning, leads to greater progress.

When I (Mike) decided I'll learn this new language, I got caught up in trying to find the perfect app. 

Spent a ton of time looking for the right course. 

Made a weekly plan to master the language as quickly as possible. 

I even thought about how to set up reminders on my calendar to practice my vocabulary. 

All this didn't lead anywhere. 

The plan was just that… a plan. 

And then I chose a more experimental route. 

Now I buy my morning 'bica' (that's espresso) 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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