Inside Out Leadership

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On practices

Welcome entrepreneurs, I’m so glad you’re here.

As people around me receive the vaccine, basketball leagues start back up and more people actually have food brought to their table in a physical building (crazy, I know), I’m starting to get antsy. The same feeling when you’re driving and you have to pee only a little, but then you get to the exit and all of a sudden you can hardly stand it. That’s where I’m at re COVID.

I have a ton of excess energy, and have leaned on my practices to stay sane and productive during this stretch, the same way I did when the lockdown had just started. Since I can’t control outcomes (a fact which has never been more clear than this past year), I focus instead on controlling the micro-practices tuned to take me where I want to go (so far so good; my coaching practice is full, I’m helping to launch what I think will be a world-changing community product, and I’ve never been healthier or felt more connected with my family).

I’ve built my habits intentionally, targeted toward the results I want to achieve and built on the neuroscience of how habits form. Laura will tell you I’m extremely reliable. And I’ll tell you that’s not an accident. Practices are the building blocks of our lives. So this week, I thought we’d take a dive into how mine work.

On Practices: How a dope beat can help you defeat the snooze button

I rode a Peloton today for 45 minutes, and I didn’t want to.  

When I got off the cushion after meditating, I heard the voice in my head saying not to.  The voice reminded me that I’d hurt my foot skiing the evening before, saying “maybe you could just take today off.”  

I heard the voice.  And my foot did hurt.  I was tired.  I only got a 75 sleep score on my Fitbit, so I was empirically tired.  It was reasonable to just skip and go read for a while.  But I got off the cushion after meditating, and because it’s what I do when I get off the cushion after meditating, I went to the closet and grabbed my shoes and headphones.  And because what I do after that, what I’ve done since we got the Peloton late last year, is grab a glass of water, place it on the table next to the bike, and then climb on the bike and clip in, I did that, too.  

The screen told me I had options.  I could choose 20, 30, or 45 minute rides of various intensities, coached by anyone I liked.  The most prominent choice had the words “your usual” written under it though, so instead of looking through all of them I just picked that.  It was easier.  That turned out to be a 45 minute Power Zone ride, which is Peloton language for “we’re going to kind of, but not totally, kick your ass for most of an hour.”  The voice in my head asked me if I was sure, but I’d already clicked the button so it was easier to just do it.  

And then, partway through the ride I got to thinking.  As the coach called out the song’s cadence at 102-rpm and I felt my legs speed up to match the beat, I got to thinking just how helpful it is to have a beat.  I wouldn’t be going this fast, I remember thinking, if the song was a little more chill.  Or if there was no song, if I was just riding a bike in my basement.  But how handy is it that the people at Peloton put a 102-rpm song here?  “You don’t have to push today, today is recovery” the voice said.  But it was easier to just peddle to the beat. 

So I rode for 45 minutes this morning, peddling to the beat.  I got my ass kicked, kind of, but not totally.  And I didn’t want to do any of it. When I got off the bike afterward I input my exercise output into my Fitbit app.  15.5 miles in 45 minutes, average output 204 and just over 800 calories burned.  “Hell yeah,” the voice said.  “You did that.”  And I did.  I didn’t want to, but it’s what I do when I get off the cushion after meditating.

And I meditated because it’s just what I do after I write.  Three-ish pages of stream-of-consciousness drivel which I’ve found both clear my mind and help me think.  Creativity coach Julia Cameron calls them Morning Pages, and says they’ll change your life.  I think they have mine.  I’ve been doing them every morning for the better part of a year, first thing when I wake up.  I wake up at 5am, which I know is obnoxious to some people but isn’t so bad really because I go to bed at about 9:30pm.  I miss the end of most basketball games on TV, but it’s a small price to pay.

I haven’t always gotten up that early.  Laura will tell you I was a literal vampire in college.  Sleep at 7am after watching the sunrise in the cafeteria, wake up by a 2pm class.  That was fine for college (although I almost didn’t graduate after failing weightlifting because it started at the crack of 11am).  But then one day long enough ago that I don’t remember it, I decided that doing things in the morning, things like journaling, meditation, exercise, reading and basketball, I decided that doing those kinds of things was worth sacrificing an hour of TV.  So every night I make the decision to go to bed at 9:30.  At that moment, reliably, the thought of having a great, productive morning feels better than an hour of TV.  

And then every morning I ride. And meditate, and journal.  Not because I want to do those things, but because it’s just easier to do that than to do something different.  The habits, chained together like they are, have created a kind of beat to my mornings.  And it’s easier to simply pedal to the beat. 

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“People don’t form productive practices because they’re disciplined,” people say.  “They do them because it feels better to do them than to not do them.”  

I think that’s true.  Or it is for me at least.  It feels better having done my morning practices than it does when I go to bed late.  When I stay up for the Super Bowl, for example, my morning looks different and my day feels... off, somehow.  Like it’s being built on a shaky foundation.

It’s true, but I also think it’s not complete.  I don’t do all those things just because it feels better, because the truth is it feels incredible to stay in bed in the morning. When I wake up before my alarm I do a little horizontal dance because I get to stay under the covers.  The truth is, while it feels good to have done all my practices, on many days it feels just as good to hit the snooze button. 

“People form productive practices because it feels better to do them than to not do them.” Sure, but my calculus is different every morning.  

The other part of the equation, the other key to producing habits we feel good about, is structure.  Routine.  A beat.  Following routines feels good (not just to me; turns out following routines adds meaning of our lives in the real “what is the meaning of life” sense), and research says that the more we follow our routines and structures, the more the decision to do them shifts from “being internally guided (e.g., beliefs, attitudes, and intention) to being triggered by situational or contextual cues.”  

Said a different way, the more often I bike after meditation, the less that biking has to feel good for me to do it.  

That’s why I rode a bike when I didn’t want to, kind of but not totally kicking my own ass.  Why I meditated, journaled and woke up at 5am.  I didn’t want to do any of these things, but I’m a creature of habit, just like we all are, and so when my brain learns to associate the ending of a meditation session with riding a bike, no matter what the voice tells me, it’s usually just easier to ride the stupid bike.  

Same with meditation, writing and waking up at 5am.  I want to do none of those things, and if I were deciding between any of them and sleeping in, I’d get much more sleep.  Which is why I don’t decide between any of those things and sleep.  All those things are part of a routine that starts the night before, when I go to bed at 9:30.  

Because at 9:30pm, when I’m watching TV or doing whatever, at that moment it reliably feels better to think of all the intentional stuff I’ll do the next morning (read: “someday in the future”) than it does to finish watching the basketball game or whatever.  That’s the moment at which I make the decision to do my practices the next morning — not the moment of the snooze button — because when I decide the night before I always choose to do them.  

I make the decision at the moment I always choose yes. The rest is just machinery, all the way to the showers.  

(HT: David Burt, Ergest Xheblati, and Compound for editing!)

FIVE THINGS I READ THIS WEEK

One: The Pandemic has Erased Entire Categories of Friendship (Atlantic)

“A few months ago, when millions of Americans were watching the Netflix series Emily in Paris because it was what we had been given that week, I cued up the first episode and was beset almost immediately by an intense longing.”

I have a thing for great opening lines, and this one sticks. The article itself examines how our sense of belonging is supported by more than just the people we cohabitate with — the loose connections we make getting coffee or lunch play an important role in helping us feel part of a community. And that’s all gone. And it’s normal to miss it.

LINK >>

Two: A simple template to better co-founder relationships (Tapestry)

Two coaches of whom I’m a big fan just dropped a pretty impactful single, as Steve Schlafman and Eric Friedman launched Tapestry last week. Tapestry is a simple template to help you and your co-founder better understand each other, and maximize your working relationship. You and your co-founder can complete Tapestry on your own, or you can hire a coach. Either way, if this is your first time working with your co-founder, this is for you.

LINK >>

Three: The Power Trip (WSJ)

Following up on the article from a few weeks ago (Vulnerability may make you a good leader, but it won’t get you promoted) is this related take from the Wall Street Journal, which basically says that even vulnerable leaders become assholes once they rise to the top. “The very traits that helped leaders accumulate control in the first place all but disappear once they rise to power. Instead of being polite, honest and outgoing, they become impulsive, reckless and rude.” Like everything else, leadership styles are complex and there isn’t one answer.

LINK >>

Four: Who’s got the monkey? (HBR)

One of the most challenging transitions a founder has to make is from the guy who does everything, to the guy who does very little (but empowers others do everything). Tons of fear wrapped up in this transition, which I’ve discussed here.

One of HBR’s top articles ever (as in forever-ever) approaches this from a different perspective, and it’s as relevant now as it was then. There’s monkeys in your office. Question is, who’s holding them?

LINK >>

Five: Don’t work in venture capital (99 Derisible)

I’ll admit, I’ve had moments operating a company when I thought, “man, wouldn’t it be nice to just be a VC?” I have a few friends who made just such a transition. But a VC friend of mine sent me this article which outlines why, for the majority, building a career in VC kinda sucks. Caveat: she is very happy in VC, as is the author of the article, but don’t hold that against them.

LINK >>


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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.