Contemporary Mentors

Jul 05, 2020

The phrase “contemporary mentors” popped into my head on loop number six of eight on my morning run. I’m training for a Covid marathon, which is 27 loops around my property.

My pace is tentative as I’m still gearing up after a long break due to a back injury, but I’m letting the miles and the time on my feet build on the weekends.

Running in circles for hours is different than running in the mountains in Aspen during the summer. But, I’m afraid of going to Aspen right now because of Covid, and I’m afraid of leaving my property and running on the roads or the trails near Boulder.

So, I’m embracing the circles. Amy likes it because she can keep an eye on me and let Cooper come out for the last couple of loops. While I think he could run with me forever, she worries about him when he goes for more than three loops, which is about six miles for him given all the back and forth he does.

I’ve decided that I’m going to approach the second half of 2020 differently than I approached the first half. This weekend, I turned off a bunch of inputs. I had several long conversations with Amy, right after I meditated, but before I did anything else, including one today where I acknowledged that the organizing principle I’ve been operating with for the last year isn’t working for me. I spent a lot of time outside, but without feeling tethered to anything. I allowed myself to feel what I was feeling, instead of trying to catch up or get on top of the stuff. I laughed at the few absurd things that crossed my path, rather than letting them aggravate me. I thought some more about what I wanted to spend my time on and what I was going to delete.

None of this is new for me – it’s a regular repeating cycle. Sometimes it’s part of my burnout loop or a boom-bust work cycle. Other times it’s a function of not knowing my limits and getting depressed. Once it was a function of a self-induced depressive episode because I stupidly took Ambien for two weeks on an international trip. And sometimes it’s just random.

A little more than a year ago, I came up with a new organizing principle for how I was going to address my work. I thought it was clever, was proud of myself for coming up with it, and tried it for a while. About a month ago I realized that it was a failure and that I wasn’t happy with it. While several aspect were working, several weren’t, but most importantly I realized that my frustration with it and my determination to try to make it work, even when it wasn’t, was making me unhappy.

So, about a month ago, I threw it away. I didn’t stop any of the activities I was doing, but I threw away the organizing principle.

This morning, I told Amy that I had thrown it away. It was the first time I was able to articulate this clearly. I don’t have a new organizing principle yet, but I knew the one I was using wasn’t working.

When my running loops increased, I realized I needed to listen to something while I’m running. Usually, I run “naked” (without headphones), especially when I’m in the mountains or on trails. But, after a few 0.95-mile loops, I want some stimuli other than “another loop.”

I decided to go through some Tim Ferriss podcasts and listen to some of my friends that he interviewed. I think the world of Tim and have learned a lot from him, even though we haven’t spent a lot of time together. And, whenever I listen to any of his podcasts, I learn at least one thing, and they often cause me to think about a few things.

In order, over the past few longer runs, I’ve listened to:

It was in the middle of Seth’s interview that the phrase “contemporary mentors” popped into my head.

I was searching in the background for a phrase different than “entrepreneurial heroes.” I started my first business in the 1980s and my entrepreneurs heroes include Bill Gates, Mitch Kapor, Steve Case, and Dan Bricklin.

But Seth, Jerry, Ryan, Tim, Madeleine, and Jim are in a different category. They are mentors of mine, in a long list of mentors. Some – like Jerry – are soulmates. Others, like Madeline and Jim, are people I know a little bit but respect enormously. And Ryan and Tim are contemporaries on a different vector entirely.

Aha – “contemporary mentors.” The ideal mentor-mentee relationship is when the mentor and mentee become peers and learn from each other. But peer mentorship has never become an easy category for me to explain as it implies an evolution from a mentor-mentee relationship. What if that’s not what happened.

Tim and Seth – thank you. As I listened to you today on my run, I learned from each of you, while having a close emotional connection from my own relationship with each of you. And from it came a new phrase for me: “contemporary mentors.”