PROGRESSION: How to Play the Right Game, the Power of Boredom, and the Hard Thing About Hard Things
July 2022
I have an exciting personal update but it’s not yet time to announce so we’ll stick to our regularly scheduled programming for this email.
But I can tell you that I’m doing an Ironman triathlon on September 17. I’ve done a few half Ironmans (Ironmen?), but this is the first time doing the full. I actually signed up a month ago but was too scared to tell anyone. I thought I might back out. So now I’m telling the several thousand of you who read this email so you can hold me accountable. No backing out now.
Books, articles, etc.
The Hard Thing About Hard Things by Ben Horowitz (Book)
It’s funny how books impact you differently based on when you read them. I first read this book in 2014, shortly after it was published and right as I was moving into the tech world. The Neighbor leadership team recently decided to read it so I dusted off my copy and, wow, it hit a lot harder than the first time.
In this book, Ben Horowitz—successful entrepreneur and cofounder of Andreessen Horowitz—offers practical advice on building and running a startup. His advice is directed to entrepreneurs, but the lessons are applicable to all in the business world. His book tackles topics such as how to lay people off, why workplace training is flawed at most companies, and how to balance accountability and creativity.
A lot of management books are theoretical, boring, and overly simplistic. The advice is sound, but only in a perfect, clean world. This book is real, messy and anything but boring.
Long Distance Parts 1 and 2 by Reply All (Podcast)
At the beginning of the month I posted on LinkedIn that I’d be spending a lot of time in the car and wanted friends to share their favorite podcast episode. This one was recommended over and over again.
In these episodes, a telephone scammer makes a terrible mistake. He calls Alex Goldman. Rather than simply ending the call like most humans would, Goldman stays on, builds a relationship with the scammer, then ultimately travels to India to meet him in person. I laughed out loud on several occasions. Well worth your time if you’re looking for a change of pace.
Observations
Don’t Focus on How to Play the Game, Focus on Which Game You’re Going to Play
A few years back I learned a lesson that hit me like a ton of bricks. And changed how I think about life.
I started my career in investment banking. It paid well and I enjoyed working on high profile stuff. It was fun being surrounded by talented people. But I really didn’t like the work. I was competent, but I wasn’t awesome. I wasn’t playing to my inherent strengths. I worked hard but wasn’t motivated to go above and beyond. I was in the wrong game.
Years later I stumbled on this quote from Kwame Anthony Appiah that hit me hard:
“In life, the challenge is not so much to figure out how best to play the game; the challenge is to figure out what game you’re playing.”
For more on how to find the right game, read the full article here.
How Politics Is Killing Your Organization (And What to Do About It)
One of my favorite things about working at Neighbor is our No Politics rule. No, it’s not a rule against discussing politics at work, it’s a rule against BEING political. What do I mean by that?
In the words of James Courier: “The fundamental particle of politics is the simple act of saying different things to different people.” Companies can’t thrive in a political environment. Full stop.
Organizations where politics run rampant are draining. They’re exhausting. They suck the life and fun out of work. Employees are too busy playing political games or strategizing what to say to which person that they’re distracted from doing actual work that will move the business forward.
One way we avoid politics at Neighbor is by “exposing to daylight” any comment or idea that seems like it’s political. For example, if a VP of Engineering is saying something to me that he won’t tell directly to our Recruiting Lead, then we have a moment of politics. The antidote is to have the VP say it directly to the Recruiter. These direct conversations can be tough, but they're powerful and necessary.
Neighbor isn’t perfect, but consciously deciding to avoid politics has led to less friction and drama than is typical at a startup. New employees regularly tell me that the environment at Neighbor is refreshing and they love just focusing on doing good work.”
"No Politics" starts from the top but everyone plays a role here. For more on how to build strong companies where politics don’t exist, check out this James Courier article.
Gratitudes
I’ve found power in regularly expressing gratitude so I’ll continue the habit. I’m grateful for the creativity that comes on the other side of boredom. Last Sunday my kids got really bored. It was well over 100° F and we were all at home. We consciously decided we weren’t going to entertain them or watch anything on TV.
All of the ideas my wife and I came up with were “stupid”. The kids whined and complained about being bored. They argued. They bugged each other. But eventually they came together and headed down to the basement to write and create a short, silly play. It was awesome.
Some of our most creative moments come when we reach peak boredom. I’m grateful for moments like that.
If you've read anything worth sharing I'd love to hear about it. And do let me know if there's anything I can do to help you.