June 2, 2020

Mistakes Made and Making The World Better

Our world is hurting. Your world is hurting.

There will always be the poor and the powerful.

There will always be people who do something about it. They make the world better.

There will always be people who make it worse.

I want to make the world around me better. I've been too timid. It wasn't timidity at the time. It's timidity moving forward if there is no change.

Moving forward even when in pain is not for everyone. We're all in a collective wilderness now.

Moving forward in the pain of your wilderness is the path to become your best self. We need leaders who lead from their best self more than ever now.

There's so much that I can't help with or heal in our hurting world. But there is one specific way I can help and heal.


I don't trust leaders who aim to build perfect communities. I learned this the hard way in my early 20's. Trying to build a perfect community is futile. You lead with an authoritarianism that harms more than heals. The focus is in the wrong place because it's more about the community developing than the individual. All sustainable change is built on individual transformation.

I don't trust leaders who believe that you engineer society at a massive scale. They believe by building systems they can transform communities that then transform people. No change in human history has ever been positive or sustained with that approach.

Change starts at the individual level. The transformed individual impacts their micro-community. That community shapes systems that move society forward. This is the way.


For the last decade I've built my life around this idea. What is the way? Micro-apprenticeships for leaders (short engagements of coaching) so they can transform their communities.

That was smart. It's the best allocation of my life. And I am most in flow and fulfillment when taking that approach.

But I've also made mistakes.


You'll learn more from your mistakes than your successes. It's difficult to know all the underlying reasons that contributed to the win. The mistakes are fertile ground for advancing awareness.

  1. Learn to analyze your failures without suffocating under regret.
  2. Then you can isolate the possible reasons something didn't work.
  3. After you isolate the reasons you can start attempting what works and what doesn't.

I've had to rebuild from failures. Plural! Each was a gift. Each gave me a lifetime of experience.

Feedback-rich environments are key to accelerated learning. You need to be in a place where you are at the edge of your abilities and learning what is or isn't working. I learned more from a book called What I Learned Losing A Million Dollars than in my entire Master's program.


I wrote a book on mistakes in 2015 (TheRiderBook.com).

That book is a conversation between a rider and a driver as he coached him through seven mistakes. I knew when I titled the book I could talk about seven winning habits. There's a time and place for that. I didn't want to. I wanted the purity and honesty of my own expression of the 7 most monumental mistakes I had made. Those were the 7 mistakes that caused me unnecessary pain and suffering.

Then I could view the mistakes as gifts. The suffering had meaning.

On Thursday I'm going to share 5 new mistakes I've been making.

Want to root out mistakes and impact your world?

Two of those apprenticeship systems are about to go live.

1) New webinar coming up next week (June 8th at 10am EST):


You'll learn:

  • The #1 reason 'working harder' isn't producing the results you want to see (the answer may surprise you)
  • How to use every challenge for growth (working with what you have rather than waiting for perfect)
  • How to get where you want to go AND enjoy getting there

Save your spot HERE.

2) Figure That Parenting Out:

It's coming! I'll be offering a free event soon and teaching you about building a healthy family culture (in the midst of all the crazy of 2020, this is how you can help your kids). I hurt for families and the pain our kids are processing right now. Click below for a quick video about this:

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Are you ready to work with one of our coaches to make this your best year yet?

apply to work 1-on-1 with us.

Our team will reach out to book a free discovery call.

If we both agree that it’s a good fit, we’ll start the signup process for the SightShift Coaching program and pairing you with one of our Certified Coaches.