Inside Out Leadership

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The Juggling Act of a Creative Life

Welcome Entrepreneurs. I’m so glad you’re here.

Before we dive in, a quick announcement: I’ve begun a second series with Mindful Magazine on Conscious Leadership. Here are the first two pieces:

Grateful to Mindful for the platform to reach thousands of leaders across the globe.

Now then.

I work with people every day who have an almost limitless capacity for creation, like nuclear reactors driving the success of their companies. They show up fully in our conversations — sometimes lit up by the thrill and opportunity in front of them, sometimes scared to death. But every single time, they show up irrefutably alive. I’m fortunate in this way. I’m lucky that the relationships I get to have with these amazing founders are within the context into which they instinctively pour so much of their life force. 

But I’m also keenly aware that they often show up differently in other areas of their lives. That brightness, creativity and vibrance with which they engage in our discussions can be entirely absent in other contexts.

Such is the topic of this week’s essay.

The Juggling Act of a Creative Life

A few years ago, Laura and I were coming home from my in-laws’ house in Detroit, me driving our minivan during the two-hour trek down I-96 and listening to an audiobook with my AirPods in while the kids slept in back. I was immersed in my novel when Laura placed her hand on my arm. I took out my right AirPod, and she told me she felt like something was missing from our relationship. 

My mind immediately went to the worst case scenario, in the way that only kids of divorced parents will understand: I wonder if this is it, I thought. I wonder if after all this time we’ll end during a drive back in the sunshine. A part of me had always been worried that I was destined for divorce, that from the moment I met a partner it was always a matter of when, not if. Because people didn’t stay married forever. Forever could be 20 years, but no matter how much you wanted it to be, it wasn’t forever forever. Nothing was. That mostly-unconscious sense of inevitable dread derailed me and us for a long time, causing every disagreement to expand. But having identified the pattern in a previous conversation with Laura (as well as her very different learned expectation that whatever fights we had, we’d always leave holding hands), this time I took a breath and asked her to tell me more about what she was feeling.

Laura told me that she saw the way I was at work: driven, electric, a force of nature. She saw how much creative energy I put into strategy, into fundraising, recruiting, and into creating a culture that people loved. She saw that in me, and she told me that that was part of what she loved about me. That boundless creative capacity. 

And she said it also made her sad, because I wasn’t that way with her. Not anymore. 

Our relationship flashed before my eyes. The way I’d been the “social director” for our friend group in college. The care and nuance I’d put into not only her gifts but even their presentation. The elaborate dates and experiences I’d designed for us as we’d gotten close. And with it, the unavoidable realization that I didn’t do any of those things, anymore. Laura was our “social director,” and I built my company. 

I read a wonderful book once, called “Iron John.” Through a deep analysis of the Grimms’ Fairy Tale of the same name, poet Robert Bly paints a picture of the unique challenges faced by fathers and sons in the contemporary West. It’s the one book I recommend to every new father, and according to Amazon I’ve bought it 14 times. 

In its pages Bly explains how, throughout most of human history, young boys looked outside every day and saw their fathers toiling in the fields. They understood that at the end of each day, their fathers came in when the sun went down and engaged with their families, tired, but having earned the opportunity to rest. They saw the wholeness of their fathers’ lives, and in their watching they developed a sense of what awaited them in adulthood. Who their father really was, and through him, everything that it was to be a man, for better or for worse. 

Then in the 1950’s, dads started going to the office for work, and for the first time, observant sons didn’t get to see the vitality their fathers poured out during the day. The only father that most young boys knew was the tired guy who came home at night and didn’t have energy to play games. And that tired guy with a beer on the couch, for most young boys that was just Dad. 

After reading that book, I committed to treating my time with my kids after work as sacred, and with some exceptions I have (I’m still working on it). I know they’re watching, so I’m intentional about showing my two boys the best, most alive part of me, and not just treating family time as time to rest. It takes something, doing this. Many days I feel like all I need is to rest. But it’s an investment I won’t sacrifice.

And yet there I was, listening to an audiobook on my headphones while the most important person in my life told me that I’d become the tired guy coming home at the end of the day. 

There’s an adage, that life is a process of juggling three balls -- one representing work, one relationships, and one self -- only the latter two balls are made of glass, and the work ball is made of rubber. 

It’s so easy for entrepreneurs (I can attest) to laser focus on their work to such an extent that the other two parts of life become an afterthought, and their respective glass balls risk hitting the floor. Our society rewards this lopsided orientation, so these days I always ask founders to look deeply at all three areas that make up a full life, taking stock of each area in turn.

When we come to relationships, by far the most common response is “they’re fine. Everybody’s good.” It’s what I would have said, five minutes before Laura tapped me on the arm. 

Sometimes I’ll press. One time a founder told me that his wife and family were fine, and I asked him what it was about his relationship that made him so confident. I had no reason to suspect it wasn’t (other than the fact that he’d brought it up in session, which can be an indication), but was curious what data he’d used to make the assessment.

He thought about it. “Well, I think I checked to see if there are any problems, and there weren’t, so I feel like it’s fine.” 

I felt a pull on my heart. A recognition. For years, I had done the same. I poured my creative energy into imagining a future for my business that didn’t yet exist, and then using all the resourcefulness at my disposal to make it a reality. And for years, when it came to my marriage I simply scanned to see if there were any problems, and if I didn’t find any, I figured everything was good and went back to figuring out how to grow my company.

If this resonates with you, you’re not alone. In my experience, it’s quite normal for founders to treat the people around them as support structures to enable them to build their companies. Support structures that need maintenance, sure, but structures that ultimately serve as means to an end rather than as ends in and of themselves. The spouse of a founder has a uniquely challenging job in this way, understanding and supporting the need of their loved one to focus outward. But there are limits to this, which at first reveal themselves slowly, and then all at once. 

“What do you think would happen if you had the same approach to your company?” I asked. “What kind of company would you build, if you simply checked to see if there were any problems to fix and called it a day?”

“I’m not sure I would even have built one,” he said after a moment. 

It takes creative energy to build a company. As it does to build a marriage, a child, or a life. I was fortunate on the drive home that day, in that Laura helped me see how I’d fallen into merely maintaining our marriage, while I created elsewhere. She started a conversation that led to our consciously creating a life we want to live, together. The type of house, the location, the travel, the role in our community. All things that were easy for me to not think about, once. But in co-creating them with Laura, these are the things that now regularly bring light, love and energy to our relationship.

I don’t have any answers. I’m not an expert at how to live a life, and if I was being coached I certainly wouldn’t listen to someone else’s answers on such an important topic. I ask the question simply to direct founders’ attention, intentionally, to all three important facets of life. The rubber ball, sure, but also the two glass ones. 

Because I work with amazing people who have an almost limitless capacity for creation. And whether the people in their lives see some of that energy, or whether it’s all focused on creating a company that will change the world, either way the people in our lives notice.


THINGS I READ THIS WEEK

One: Working Multiple Jobs - AVC

It would have been unheard of a decade ago, but these days it’s not uncommon for leaders of the fastest growing companies in tech to be building two projects simultaneously. Or more, as Fred Wilson outlines here. I’m guilty myself. One might connect this dynamic to Reid Hoffman’s “Tours of Duty”, only for leadership (link to that article as well in-line).

LINK >>

Two: Why the ‘Big Short’ Guys Think Bitcoin Is a Bubble

So I’m Uber-long crypto and Web3, and long (but not quite as) Bitcoin. But then again, I didn’t predict the housing crisis of 2008. These guys did, and they’re all (at least intellectually) predicting that Bitcoin is a bubble. Noteworthy that they’re not actually shorting it.

LINK >>

Three: Tetris

This is wild. Turns out that after being traumatized, the best treatment (like empirically, via double blind studies) is to play Tetris. Play it as soon as you can, after removing yourself from the bad situation, to lower the rate of intrusive memories by over 60%. Please someone explain this to me

LINK >>

Four: Why write 1K angel checks instead of waiting until you have enough cash to write 5K-10K angel checks?

A friend of mine outlined her logic for not investing $1k angel checks into startups, and then Twitter did the magical thing it does and helped convince her to change her mind. Now she’s committing to doing ten $1k checks in 2022. Check out her logic for the change here (it’s pretty compelling).

LINK >>

Five: Sunshine

Presented without comment

LINK >>


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Executive Coaching for Entrepreneurs

There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.

I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency supporting founders to rapidly scale themselves as leaders, so they can thrive professionally and personally as their company changes the world. Leveraging 15-years as a founder/CEO and a decade of meditation & mindfulness training, I have helped leaders from companies across the world, funded by some of the world’s top venture funds, to design a more conscious life and make key changes to improve their performance and satisfaction. I coach entrepreneurs how I want to be coached:

  • Focused on the person, not the role.

  • Focused on results, without the fluff.