🔥 Shaking up this Newsletter, 📈 Finding Asymmetric Risk, and 🧪 the Power of Experiments

PROGRESSION: The Road to Ironman Championships, Vol. 1

During a recent podcast interview, I shared the importance of experiments. Too often we fall into the status quo trap, where we go through the motions, doing the same thing on repeat, not questioning why. We aren’t getting the results we want, but the energy required to shake things up isn’t high enough to overcome the status quo inertia. 

When the pod interview concluded, I thought about this newsletter. I love this forum for communicating with you and the many others who subscribe, but for months I’ve wanted to shake things up. Change was needed, but I didn’t exactly know to change. I was feeling stuck.  

In The Unconquerable Leader, I dedicate an entire chapter (ch 17) to the power of experiments. Here’s a passage from the book:

“Anytime I see leaders paralyzed by inaction, I push them to lower the stakes. I invite them to run an experiment. I encourage them to tell their team they are running an experiment. I challenge them to use the phrase, “I’m trying something new.” This creates space for them. If the experiment works, great. If it doesn’t, they get feedback that will help them improve. It’s a win-win.” 

In an effort to practice what I preach, it’s time to run an experiment. I’m going to make two changes to this newsletter:

1. The format 

2. The frequency 

I’ll start with the first change—the format. The first section, and the bulk of the email, will now read like a long-form post. Social media continues to incentivize short, catchy posts. But I like having space to go deeper on important topics. So going forward I’ll just dive right into what I want to share. The second section, which I used to call Books, Articles, etc., will be shorter and punchier. It will be called What I’m Learning and I’ll stick to bullet points. The third section, Gratitudes, will remain the same. 

The second change is frequency. I’ll shift from publishing once a month to publishing every two weeks. I have several reasons for making this change, but will spare you the details for now.  

Every good experiment needs a timeline, so I’m committing to this through the end of the year. I’ll then evaluate the results and make necessary changes. This newsletter has existed in one form or another since 2016. Whether you’re a long-term reader or just subscribed, I appreciate you reading and welcome your feedback. 🙏🙏

In December I’ll be heading to New Zealand to compete in the Ironman 70.3 World Championships. In future emails I’ll share the lessons I’ve already learned and will learn in the process. These are not triathlon-only lessons. These will be lessons applicable to all of us. 

You may think, I don’t care about endurance sports. To that I say, life is an endurance sport. You don’t win with a singular, intense effort. You win through hard work and painstaking attention to living life in line with your values. You win by showing up every day. 

The road to qualifying for the Ironman Championships has taught me several lessons which we’ll cover over the next few months. These include:

• How to set big goals and create plans to achieve them

• Why consistency is key to meaningful progress and how you can be more consistent

• How to overcome expected (and unexpected) obstacles

• How to build a team that will help you reach your goals

I’m excited to share my journey to New Zealand with you and I look forward to learning together. 

What I’m Learning

• I just finished reading the book, Die With Zero: Getting All You Can from Your Money and Your Life. This book challenged my thinking in several ways, but particularly on spending money. It goes against my default “be frugal, save as much as you can” mindset. The best argument the author (Bill Perkins) makes, is that money is more valuable to you when you’re younger because you can do more things.  

  • My favorite quote from the book: “People are more afraid of running out of money than wasting their life, and that’s got to switch. Your biggest fear ought to be wasting your life and time, not Am I going to have x number of dollars when I’m 80?”

  • This book isn’t for everyone, but I do love books that force me to challenge my thinking.

• I recently read how Mark Cuban kept risking it all early in career because he was broke and had nothing to lose. He talked about the power of asymmetric risks.  

  • “Asymmetric risk is when the upside of possible success is much greater than the downside of possible failure. When you face asymmetric risk, it makes total sense to be bold, to grab the opportunity at hand. 

  • At the extreme, when the downside is very low (or nonexistent) and the upside is really high, it’s actually riskier not to make the bold move. 

  • The downside of not even taking a chance is emotional: potentially a lifetime of regret and wondering What if?”

    • We likely have more to lose than a 20-year-old Mark Cuban, but it’s worth asking the question: Where can I find more asymmetric risks in my life?

Gratitudes

I’ve found power in regularly expressing gratitude so I’ll continue the habit. I’m grateful for dirt roads. Not far from my house, there’s a dirt road that stretches for miles. I love running here. It’s quiet and makes me feel like I’m hours from civilization. The monotony of putting one foot in front of the other is meditative. There’s a stillness I find on these roads. Having lived for years in busy cities, I value the quiet these runs provide. I’m grateful for dirt roads.  

If you've read anything worth sharing I'd love to hear about it. As always, thank you for reading.  

All the best, 

Nathan

Read my book, The Unconquerable Leader | Learn about coaching 

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