Large groups of people show you’re not alone; small groups show you have allies

I get a bit depressed during the winter holidays without family around, so last December I invited my clients to my home right before Christmas. I cooked dinner and they brought booze, and desserts. Later, we sat on my porch, drank bourbon and played a game called “If you really knew me, you would know that…”

People got very real.

It quickly became obvious that every single client was dealing with a significant personal struggle — family health issues, anxiety, depression, self esteem… on and on. It’s as if they each decided to run a marathon and strapped on a fifty-pound weight vest at the starting line. And they are hardly unique.

But something wonderful happened during that conversation. 

Back in the 80s and 90s we were promised that the geeks would inherit the earth and that has largely come to pass. We have been given permission by society to get our nerdly freak on, write code, design software interfaces and spend all day looking at screens.

We go to conferences and meetups; we’re a part of industry associations and spend more and more time online with a vast network of peers across the globe. In doing so, we realize we are part of an ever-growing tribe of people bound by a love of technology and entrepreneurship.

But the conversations that result are often surface-level. Whether it’s due to embarrassment, a lack of trust, a desire to appear like one is kicking ass or a dozen other reasons, we keep people at arms’ length. And that’s totally fair; you’re probably not well-served baring your soul to 100 people at a SXSW party. But knowing there are thousands of people out there like you is fundamentally different than knowing there are a few people out there Just. Like. You.

Back to dinner last December…

By the end of the night, the six founders and I were ready to bury bodies for one another. There’s something incredibly affirming that comes from sharing one’s deepest challenges and being seen. There’s a sense of safety that comes from stating clearly, “I’ve got some serious shit in my closet” and hearing in response, “Me too. Let’s figure it out together.”

Last Saturday was the 12th consecutive month I’ve hosted a CEO dinner. It is, without a doubt, my favorite night each month. I still cook for my clients, we shoot the shit over dinner and then we move to the porch and talk. We share the stuff weighing us down and all the wins we’ve had too, because one person’s success is another person’s hope. People cycle in and out and I’m constantly amazed by how accepting the original group is with new members, and how willing first-timers are to get equally real with a bunch of strangers. Startups are fucking hard. We all want to know that we have backup.

So, as the holidays look once again, I offer this advice:

Find your tribe. Find the people with whom you’re comfortable removing your mask. Find others like you who feel a bit broken inside but still have the guts to change the world while dealing with all that baggage. Creating a better future is tough work, so bring friends.

(Photo by Artem Bryzgalov on Unsplash)

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