How Our Masks Create Our Lives
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Before getting into today's issue I want to be clear that, while this issue is about masks and mentions COVID, it's actually about something much older. It's about the masks we wear in business, and in life, in an subconscious effort to belong.
More specifically, it's about the surprising impact removing your mask has on those around you.
Hope you enjoy.
My son Leo is three. Three and a half, if you ask him. And up until a few weeks ago, when his school changed their policies, he’d worn a mask in public for as long as he could remember.
I’ve heard a lot of opinions about the impact of masks on kids, most of them in the vein of “I don’t know what it’s doing to our kids to have to wear masks all day during such a formative time in their lives, but I’m sure it’s not good.” I’ve had my own questions, with two boys between three and five, both of whom have been mask wearers most of their conscious lives. That said, without a control sample it has been difficult to get a sense of the actual impact.
And then, for the first time in his life, a few weeks ago Leo took his mask off.
We heard it first from his teachers. “For most of this year we were worried about Leo,” they said during parent/teacher conferences. “We thought something was wrong. He didn’t talk to many people, and we thought he might not like it here at school. But now we see that he’s just been walking around smirking all the time, like he’s thinking of an inside joke. I always thought he was sad, but he’s laughing inside all day!”
A week later, the family barber brought up his experience with Leo when he was cutting my hair. “I’m playing the long game with Leo,” he said. “I think I’ve finally gotten through to him. I used to think he wasn’t listening when I’d joke with him, but finally he’s starting to smile and crack up. I feel like I’m finally bonding with your little dude.”
A few days after my haircut, for the first time a classmate asked Leo over for a playdate. While she and Leo played with her toys, Laura asked the little girl if she played with Leo in class, too. “Leo doesn’t talk that much, but I like him,” she said. Then, a few days after that, Leo reported on another new friend with whom he played Pokemon on the playground. And then another. I realized I had to spend some effort learning all these new names.
Up until a few weeks ago, everyone had seen Leo as a quiet boy. Vaguely unhappy. And in seeing him in this way, they left him to himself. But then he took his mask off, and the world saw him for the bright, silly, loving, quiet kid Laura and I have always known him to be. And in truly seeing him, the world around Leo transformed overnight.
While it’s not as simple for us, taking off the masks we wear as leaders is no less impactful.
I spent fifteen years with my mask on. A decade and a half striving to be the most competent, certain CEO I could be, because that’s what I thought the world expected of me. I tried and tried to play that game, to be one of the calculating visionaries I saw raising millions of dollars all around me. And for fifteen years, business felt ruthless. Like a mortal game played between finance dude-bros and humble-bragging hustlers, all of whom neglected family and hobbies to pour their souls into changing the world. Into becoming somebody.
But the day my board of directors asked me to hire my replacement as CEO, I knew I could no longer be the somebody I thought I was. So, kicking and screaming, I took my mask off.
I wrote about my pain, my struggle. I wrote about my excitement and joy. My boundless wonder at the sheer fact that we’re alive, and my thirst to feel it all. My skepticism as to whether all this hustling and sacrifice will really make us happy, and my belief that there is a better way to build.
And when I showed the parts of myself I’d kept hidden behind a mask of competence for so long, the funniest thing happened: the same people who had for so long felt like adversaries started talking to me differently. They spoke about their sadness, their loneliness. Their love and passion for their craft. All these powerful founders and investors, they talked to me for the first time about their humanness. And business started to feel different.
We all wear masks some of the time. I know I still play the occasional role. Teacher, coach, leader. I know that my life changed when I took my mask off, but I didn’t see how influential this could be for anyone, at any stage of life, until Leo took off his mask. It took a situation that literal to help me fully appreciate just how powerfully the masks we wear conduct those around us. How thoroughly these masks teach others how to treat us, and in doing so, create our lives.
When we don’t have many friends on the playground, or when business feels like a life or death struggle, it’s easy to think the problem is out there. But life isn’t inherently hard, and I’ve learned neither is business. Life and business only develop shape and meaning in response to the way people engage with them.
It might be the scariest thing you ever do (it was for me; I can’t speak for Leo), but taking your mask off doesn’t just change you for the better. It changes everyone else, too.
What I'm reading
Book: Four Thousand Weeks: Time Management for Mortals
I just finished this gem last week, and have gifted it twice already. In the startup world we are inundated by productivity porn, and under the guise of yet more of it, this book delivers a deep, multifaceted, and well researched perspective on what it means to live a good life. Written by a reformed productivity nerd, FTW analyzes the foundational flaw in mainstream productivity advice (that it is possible to ever, in fact, get everything done), and then paints a picture of a way of orienting to life (the titular countdown to its end) that might actually help you get the most out of yours.
I loved this book and now find myself itching to talk to others who've read it.
LINK >>
Article one: We are multiple (Schlaf.co)
My friend and fellow coach Steve Schlafman wrote a magnum opus on Internal Family Systems (IFS). If you've ever had the sense that different parts of you wanted different things, this framework can be immensely useful.
LINK >>
Article two: Meet the A.I. that draws anything at your command (NYT)
AI is getting to be pretty freaking good at art, after it already got pretty freaking good at prose. The implications are vast, but one big one I can't avoid is that the metaverse will not be created by humans.
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