Do Hard Things. Move to the Caribbean!

My best friends are crazy.

I just returned home from a month living with some of my best friends on Vieques, a tiny island off of Puerto Rico.

They don’t live on “mainland” Puerto Rico. Instead, they’re on a tiny island, only accessible by an irregular ferry or an eight-seater airplane.

They are building a bed and breakfast overlooking a stunning 270-degree view of the Caribbean Ocean and the world’s most luminous bioluminescent bay. They are building out of concrete because anything not made of concrete gets destroyed by hurricanes. But getting concrete, or simply groceries, is a full-day journey that requires careful preparation and timing.

All the difficulties are exactly why my friends moved to Vieques. For the love of a challenge.

Do More Scary Things

I appreciate the irony. Do hard things, move to the Caribbean!

And while most of us probably aren’t going to move to a tiny island in order to make our lives more difficult, there are a lot of simple habits that can help.

Identify One Thing Every Day That Scares You

Identify something that scares you.

  • Notice someone you are intimidated by.
  • Recognize a moment when you avoided speaking up.
  • Identify one moment in your day when you feel physically nervous or afraid.

You don’t need to take action – not yet! Just bring attention to one uncomfortable moment.

Start with awareness.

A Daily Movement Practice

There is a lot to be said for daily exercise.

Exercise is hard. When you push your physical limits, you get better at pushing the boundaries of what’s possible everywhere else in your life, too.

Unfortunately, more than two thirds of Americans are overweight or obese, so clearly pressuring people to exercise doesn’t work.

My approach to movement is different. Having broken my neck on a trampoline, I also know the negative consequences of pressure. Instead, I make a habit of moving every day to build the confidence that I can learn new things.

If you’re interested, here’s a short video about my movement practice.

Coffee Shop Challenge (h/t Tim Ferriss)

Try this challenge: go to your local coffee shop and ask for a 20% discount.

The rules are that you are not allowed to give any explanation for why you are requesting a discount or any additional details alongside your request. If asked why, just say that you would like a discount and that is why you are asking.

The point of this exercise is that you are going to be uncomfortable. It will take you outside of your comfort zone.

Notice how it feels to make this request. Notice the tension in your body and your voice. It doesn’t ultimately matter if you get a discount or not, so long as you try.

(As a former coffee shop owner, please give that 20% back to your barista as a tip!)

Do Something Difficult Every Day

Do one thing today that is out of your comfort zone. It could be as small as a short exchange with a stranger, a much-needed conversation, or advocating for your opinion.

  • Thank someone in their native language – If you first have to learn to say “thank you” in a language you don’t speak, all the better.
  • Have a conversation with your spouse or a friend – You probably have something that you’ve been meaning to share, but haven’t gotten around to saying yet. Say it!
  • Try to persuade someone of something – We are all selling to and inviting each other constantly. Advocate for your preferred restaurant or movie.

When my friends first moved to Vieques, I was skeptical. I’m all for beautiful ocean views, but it was so remote and isolated. (And the hurricanes!)

Now that I’ve spent a month living in that remote paradise, I understand their motivation a little better. Living there is difficult. Every day is a stretch. And that’s the point.

In a world where I – and probably you – enjoy every other modern convenience, it is easy to get complacent.

Perhaps we could all use a bit more discomfort in our lives.

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