Learnings from an aimless bike ride

Finally let myself do something completely different on a Tuesday.

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

I’ve always related to myself as one who only needs 5-6 hours of sleep. I’ve compiled reams of supporting data over the last 15-years running high growth companies, but in the last couple months I’ve been forced to rethink.

On a whim (as if anything actually happens just on a whim, but let’s go with that), I decided to experiment with getting 7-8 hours of sleep every night, thinking that I would validate the hypothesis that I need less sleep than the average person and that would be that. Instead, I learned that while I can check boxes and feel “functional” at 5-6 hours of sleep, my mind is actually much more reactive—borderline chaotic—than I realized.

After only a week getting an extra two hours of sleep, my mind felt like someone had turned the volume down on everything. I realized that the background chatter in my head that had been constant for the last decade+ wasn’t “normal,” but was rather simply a symptom of my being tired. And when it disappeared, not only was life more pleasant, I was more focused and productive. I’ve experimented since, vacillating between 5-8 hours of sleep, and the results have held. When I get “enough” sleep, my mind works. But when I get more sleep, my mind works better.

Imagine that. Presence, peace and efficacy, all by sleeping in a bit.

Onto this week’s essay.

Bike ride

I round the corner, blinded by trees to what lies ahead. Wind rushes by my ears competing with the clicking of the bike wheels as I idle alongside the back of the high school. A gaggle of kids, dressed in matching shorts and t-shirts block the path 100 yards up, and I debate whether or not to turn around.

“Bike!” The voice reminds me of the possessive pelicans who nearly ate Nemo. “Bike! Bike! Bike!” The cross country team makes a chorus of the word as I approach. I smile as they part to let me through, the volume increasing until I pass the last of them, at which point they begin to cheer. For me or for themselves—doesn’t matter. The sun is shining, it is 10:30am on a workday, and it’s my first bike ride in years.

As I pedal away, I think of the conversations the kids had, or didn’t have, with their parents that morning. About masks, social distancing. About hand sanitizer. The kids were packed together, maskless and laughing. 

Later, the path becomes a straightaway that stretches to the horizon before fading into a haze of summer heat. On either side are flora of endless variety. A pond, punctured by reeds. Fir trees. Cat tails. Elm, birch, oak and maple trees, each 30 feet tall and dense enough to block out the world beyond. The crickets trill, a muted referee’s whistle without end. Between a sudden break in the trees, I spy a giant metal tower, outstretched arms holding power lines, standing tall with many others all in a row. Holding American society on their shoulders like so many contemporary Atlases. Most days, I know that feeling. Today, I hold only a backpack, a notepad, and a borrowed pen. 

Mile 5. I stop just in time to avoid crushing a garter snake underwheel, watching it swerve urgently to get to the other side of the path. I look up to a giant pyramid. The largest of its kind in North America, a building they say is unsellable because of a high-five-figure monthly heating bill. I take a picture, but I don’t send it to anyone or post it online. 

A half mile later, I turn around and head back. 

On the return trip, I am less present to the infinity around me. My thighs burn as I churn out the miles. No matter. As I coast into the driveway, I know the trip has served its purpose. I am full. 

I almost didn’t go; riding a bike seemed an indulgence when compared to my life’s work. Like many founders, I spend my days emptying myself in pursuit of a greater purpose. That’s what it takes to lead a company. It takes a pervading dissatisfaction and unfaltering perseverance. It takes a commitment to excellence, especially when you don’t feel like it. We glorify this part of leadership, the emptying of ourselves in pursuit of a greater purpose, our Puritan forebears looking down upon us, smiling. 

But leading a company also demands creativity. And creativity requires something different. Accessing our creativity asks that we refill that which we so readily empty in pursuit of our goals. That we nurture ourselves, following our passions and odd notions. 

So few of us do this. We keep ourselves on task, prevent ourselves from slacking, and then we look upon those blessed few “creative geniuses” with obtuse wonder, as we distance ourselves further from our own creativity with every box we check. Instead of filling our creative bucket with painting or literature or a wooded path, we double down on our disciplines and become one of the lopsided leaders hustling to wring one more dollar out of this process or that. There are so many of us, squeezing. 

And maybe we get there. Maybe the single-minded squeezing works, and we optimize the process to its utmost. We feel justified then; until we’re lapped by some stupid little toy a college kid cooked up. Some “creative genius” who decided to give himself the space to tinker and follow a hunch. 

Somebody who, maybe, took a bike ride. 

(HT: Julie Mosow, Jessica Kasmer-Jacobs, Adam Thomas, Charlene Wang, Darryn McCauley and Foster for editing)

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Who is Ryan Vaughn? 

I’m an executive coach for startup founders, a role in which I get to help high-performing founders design a more conscious life and expand into extraordinary leaders. I’m a 3x Founder/CEO who’s raised $20m+ in VC and built a market-changing company, as well as two other companies that taught me things. I’m an avid writer, meditator (decade+ practice), reader, athlete, father, husband, amateur physicist, student of leadership, and adventurer. I’m also none of those things. But I am glad that you’re here.  If that’s not enough, here’s a more detailed bio.


One: Organizing the World’s Ambition (On Deck)

For those of you wondering why I've spent so much time collaborating with OnDeck, CEO David Booth does a good job laying it out here.


Two: Hammering Eggs—Leadership and Problem-Solving (Ed Batista)

Longtime readers will recognize the author of this gem of a post, Ed Batista. I appreciate Ed because he's both a coach and a prolific writer and I think that combo makes sense (although I appreciate directly the sacrifices involved in both), and because he's excellent at walking someone who sees the world as a CEO through some of the challenges of leading a hyper growth company. Example: "a leader who continues to lead by doing more often becomes less effective and may even undermine the organization as it grows larger and more complex." CEOs take note, there's so much good stuff here.


Three: Free Will (Dr. Robert Sapolsky on the @hubermanlab Podcast)

I've spent a lot of time thinking about free will. I've long held that between nature (genetics) and nurture (circumstance) there's no room for it, but if you're on the fence here's a neurobiologist going on record with a much more thoughtful argument against humans having even a shred of free will.

I know folks who are pretty threatened by this, but to me it's so centering; whatever you're stressing about, don't. You'll do what you're meant to do, and it'll be just as it always must have been. 


Four: The Value Chain of the Open Metaverse (Packy McCormick)

It’s been said that the latest breakthrough innovation will look like a toy at first. Enter NFTs, the Metaverse, and Web3. Most folks I talk to poo poo these things if they know about them at all, but some of the smartest folks I know are preparing for them to change the world. I dismissed them at first as well, but then sat in on a few investor presentations on NFTs and had my aha moment. I’m bullish, and wonder if I should be more so. If you’re scratching your head on one or more of these things, Packy McCormick’s essay is a great place to start.


Five: Why the point of recycling is mostly just to make you feel good

Do you recycle?

Were you triggered by the implicit judgement within that question? You shouldn't be.

I was today years old when I learned that we've been programmed by the big oil companies to believe we're saving the Earth by recycling, when in fact the practice originated as a way to placate the masses into buying more plastic. This isn't me saying you shouldn't recycle. It's better than the alternative. But after calling a sample of our local recycling plants I've also discovered that pretty much the only substance that can be recycled economically is cardboard. So my hopes are no longer so high when I rinse that plastic container.

If you're up for rethinking some things you thought you knew about climate, click on. 

LINK 1 >>

LINK 2 >>

LINK 3 >>


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