💡 The Letter I Was Afraid to Write

Fear doesn’t mean a choice isn’t meant for us, it’s usually the opposite. This letter is about how I learned to tell the difference.

As you read this, I’m here in Bogotá, Colombia where Michelle and I will be getting married on May 21. We’ll celebrate with close friends and family, then head to Europe to work remotely for a few months.

Ok, pause for a second.

To the Jim of 5 years ago, those two sentences would sound absolutely ludicrous.

But the truth is, we often overestimate what we can do in a year, and underestimate what we can do in 3 or 5 years.

If you are ever feeling unsure about a decision 👉 write a letter.

If I could write a letter to myself 5 years ago, here’s what I would say:

Jim, I’m really proud of how far you’ve come from being that shy kid in school that was afraid of rollercoasters and speaking in front of people. I know this might sound crazy, but you’re going to get married in another country in a few years!

You’d never believe me, but let me prove to you why this incredible future you have is actually possible. Every big step in your life has been when you took a risk and made it an adventure.

1️⃣ (2003) Going to the big college prep school in downtown Chicago, commuting with all the businesspeople on the trains and buses. You graduated from a class of 8 and went to a school with 1,500 other kids! You wanted to take the “safe” choice and go to the neighborhood school with your best buddy, but something in you knew you needed a bigger challenge.

2️⃣ (2007) Going to the University of Illinois after graduating from a class of 375, now you are at a school with over 40,000 students! I know you’re not a math whiz, but that’s exponential growth.

You wanted to go to a smaller school that felt more comfortable, but something told you the challenge of a massive school was the right choice.

3️⃣ (2010) Moving to Barcelona for a semester to study Spanish junior year. Most of your friends stayed on campus and you were worried you’d miss out on things and potentially grow apart from them.

But your gut told you to go towards your fear, and move from the college town of 85,000 to a foreign city of 5 million.

4️⃣ (2016) Moving to Miami to take a huge job consulting Fortune 500 companies. You had built an amazing friend group in Chicago and were living in the neighborhood you always wanted to.

You knew nobody in Miami and were intimidated by this huge career jump that doubled your salary and responsibilities. That was scary, but you followed your gut towards the fear, again.

5️⃣ (2020) Leaving your consulting job in April 2020, amidst the uncertainty of the pandemic, to go all in on your dream of entrepreneurship. People thought you were crazy for giving up your health insurance in the middle of a health crisis (they weren’t wrong).

Once again, you knew the scary choice was the right one, and you haven’t looked back since.

Every one of these choices led to a bigger version of you, one that attracted the greatest joys in your life:

1. Independence, confidence

2. Met your best friends

3. Fluency in Spanish, curiosity of other cultures

4. Confidence in leading/coaching, plus salsa dancing

5. Launched your business, met Michelle!

It’s now 2023 and you find yourself once again at the precipice of a major life choice: to pick what feels safe and comfortable or to lean into your fear to discover what’s on the other side.

More accurately, to discover what version of you will be awoken on the other side.

The Bottom Line

Don’t compare your past fears to your current level of courage.

When you were afraid to cross the street and you did it, that was a big deal!

When you asked that person out, rejection meant that you were totally done for.

There are scary choices you have now that demand your courage.

Appreciate how far you’ve come, and take that next big step.

My assignment for you is to write down 3-5 courageous things you’ve done in your life.

How old were you? Why was it so scary? How did you finally make the decision to go for it? Who did you become from it?

Hint: It can be anything like getting married, having kids, moving, or giving a speech, learning a skill, or forgiving someone. What matters is how much it grew you as a person.

Leave your thoughts on Twitter 

Complementary Call

If you’re craving more adventure in your own life, be it related to health, career, or relationships, there’s no better time than now to embark. Grab a time to chat —> here.

❗️IMPORTANT UPDATE

Since I will be getting married in less than two weeks, we have changed the frequency of the Adventure Chronicles from weekly to bi-weekly.

The extra good news though, is that I will be sharing adventure lessons with you from South America and Europe for the next 3 months!

My goal is to always provide you quality over quantity, and that’s what you can continue to expect my fellow adventurer.

That’s a wrap for now!

👉 If you know someone who would love perspective and stories like these, please forward this email or share this link with them to check out past issues: https://jimwall.beehiiv.com/

You’ll also be helping to grow this community of people who believe that life is the greatest adventure.

📢 Next week’s issue will be the lessons learned from living in Colombia for a month, and how to plan a successful remote working adventure.

Keeping living your Great Adventure.

Jim Wall