TDC 050: Give Up Good for Great: The Secret to Making Bold Life Decisions

#050: Courage for the Rest of Us: Giving Up Good to Go After Great

Most of us aren't afraid of failure—we're afraid of other people seeing us fail.

Episode Summary

In this episode of The Digital Contrarian, host Ryan Levesque dives into the true nature of courage and why giving up "good" to go after "great" is so difficult.

You'll learn why the opinions of others hold more power over us than our own fears, discover Brené Brown's "Square Squad" technique to silence the noise, and find a simple 30-day experiment to build courage.

Question of the Day 🗣️

What's one decision you know you need to make, but just need the courage to finally make it?

Key Take-aways

• We fear losing the image of our life more than losing the life itself
• If people call you "crazy" at a crossroads, you're probably doing something right
• Only people who fit on a one-inch square of paper get a vote in your decisions
• Courage is a deeply personal act, not a heroic one
• Living minimally teaches you how little you need to be truly happy

Timestamped Outline ⏱️

00:00 – Why this video is a "contrarian quickie"
01:33 – The real fear that stops most people (not what you think)
03:00 – Why being called "crazy" is often a good sign
03:25 – Brené Brown's "Square Squad" technique
04:30 – The science of courage (preview from upcoming book)
05:15 – China-to-Texas transition story
06:30 – Austin-to-Vermont farm transition
07:05 – The 30-day minimalist experiment to build courage
08:00 – The question you need to ask yourself today

Links & Resources 🔗

• The Digital Contrarian newsletter → https://thedigitalcontrarian.com/

Next Steps & Subscribe 🚀

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Credits

Host: Ryan Levesque
© 2025 RL & Associates LLC. All rights reserved.

Transcript

Most of us aren't actually afraid of failure, we're actually afraid of other people seeing us fail and where that will leave us. Courage for the rest of us, giving up good to go after great. Consider today's video a contrarian quickie. 

I just finished seven and a half hours of driving, taking our oldest son and a teammate to multiple soccer games on opposite sides of the state while Tyleen took our younger son to an all-day lacrosse tournament. And this was all through torrential rains and monsoon conditions. And it's now 11 19 at night. 

We just got home and if I can be real with you for a minute, I am completely wiped. But I didn't want today to go by without fulfilling my commitment both to you as a viewer and to myself to get this week's newsletter and this video out to you. So with that being said, today's brief is going to be, well, a bit briefer than normal. 

So without further delay, let's dive right in. Earlier this week, I delivered a presentation to Stu and Amy McLaren's Village Impact Club group. And during the Q&A, someone asked me a fantastic question about courage. 

I just finished sharing several personal stories about the time I left a six-figure job on Wall Street to move to China, the time I left a lucrative career in China to start a business selling e-books online, the time I left an eight-figure business in Austin to move across the country with my family and start our farm here in Vermont. And each of these decisions came with risk. Each of them required me to give up something good in order to go after something great. 

And in each case, the people closest to me said the same thing. You are crazy. But over the past few decades, I've observed something in both myself and the people closest to me when it comes to taking bold action in life, that most of us aren't actually afraid of failure. 

We're actually afraid of other people seeing us fail and where that will leave us. And that's something completely different. In other words, when we're faced with an opportunity to choose the road less traveled, it's often not fear of losing the life that we've built. 

It's fear of losing the image of the life that we've built. The status, the stability, the identity that we attach to it all. It's the golden handcuffs that keep us tethered to the trappings of a life we've come to know and maybe even enjoy.

But what I've also learned is this. If you're ever at a crossroads in life and the people around you say you're crazy, well, you're probably doing something right. Let me explain. 

In my seven and a half hours of driving today, I was listening to an interview with Brené Brown on the topic of courage and she shared something that reminded me of her book, Dare to Lead, wherein she talks about something she describes as her square squad, which if you're not familiar is the following. What she says is, find a one-inch square of paper, write down the names of the people whose opinions actually matter to you, and that's it. Nobody else who doesn't fit on that one-inch square piece of gets a vote. 

Now, the idea that courage isn't a heroic act, but it's a deeply personal one, is one of the reasons I've become so fascinated by the nature of courage itself. It's also why it's something that I'm exploring in my upcoming book, The Return to Real, with an entire chapter focused on learning how to follow the contrarian voice of your heart and having the courage to return to what's real for you, even if it isn't popular. Now, it's taken me down a series of twists and turns in my scientific research around topics like, where does courage come from? How much of it is genetic? Is it something that we learned? And more importantly, is it something that we can build, like a muscle? And the results, by the way, which I talk about in the book, are kind of surprising in a few places. 

But in my presentation earlier this week, when I was asked that question about courage, and I explained my personal observation that most people are afraid to give up good in order to go after great, I share the following story. When we moved back to the U.S. from China, and Tyleen and I donated everything that we owned at the time, except for one suitcase each and a cat that we had adopted in Hong Kong, we moved into a tiny one-bedroom apartment in Brownsville, Texas, less than a mile away from the Mexico border. Our apartment had bars on the windows. 

We just had a mattress on the floor, two lawn chairs in the living room, a $500 laptop, an internet connection, and a library card. And with nothing but a vision and a dream of starting a business together, that was it. But it was one of the happiest seasons of our life. 

And fast forward 15 years later, after building a seven-time Inc. 5000 company, eight-figure business, when we left Austin for Vermont to start our farm, we did it again. But this time we had two kids in tow. 

We road tripped our way across America, one suitcase each, hopping from Airbnb to Airbnb with nothing but a vision and a dream, once again, but this time of starting a farm together. And that was it. And once again, it was one of the happiest seasons of our life.

When I look back at our ramen noodle days, back in that apartment with bars on the windows, I'm incredibly grateful for the experience because it taught me that even if I lost everything tomorrow, and all I could afford was a tiny little apartment with a mattress on the floor and lawn chairs in the living room, everything would be okay. And by the way, if you haven't had the opportunity to live that season of life yourself, here's a simple hack for you. Try it on for size for the next 30 days. 

In fact, go online, look for the cheapest, smallest Airbnb you can find. Pack one suitcase worth of stuff. That's it. 

Bring your laptop and your library card and nothing else. It's incredibly liberating to realize how little you actually need to be happy, particularly when you're pursuing the work your heart is calling you to pursue. All to say, that contrarian voice of your heart, it may not be the loudest voice, but it is the most important.

So listen to what it whispers to you. In fact, I want to invite you to reflect on the following question. The question is this, what's one decision that you know you need to make, but just need the courage to finally make it? What is that voice inside of you telling you? Okay, I'll leave you with that for now. 

Remember to hug the ones you love. And if you enjoyed this video, or if it's helped make you think, be sure to like, follow, and subscribe to be notified when the next video drops in this series. Until next week, I'll see you again soon. 

Take care.