The Enneagram’s true purpose

I’ve taken the Myers Briggs, the DISC, the Kolbe, a proprietary test that my executive coach administered, and probably a couple other assessments along the way that I’m forgetting. Usually they come up in the context of business, with utility like constructing a complementary team, or understanding your coworkers, but in all of them I always end up in the same spot: “Interesting. Now I guess I’ll go back to living my life.”

The Enneagram has been much more useful.

The original thoughts behind the Enneagram are either from ancient Egypt, or 4th century Alexandria, predating all the other assessments by quite a bit. Nothing lasts that long without having something of import to it (if the DISC is around in the year 4,500, we can revisit this).

Nevertheless, when I originally heard about it I lumped it into the same category as the other assessments, another way to categorize people that is neither more or less accurate than any other. And in a sense, honestly, it is exactly that. But where it differs, and becomes much more than a simple bucketing exercise, is in how it’s intended to be used.

From the Enneagam Institute:

One of the most profound ways of understanding the Levels is as a measure of our capacity to be present. The more we move down the Levels, the more identified we are with our ego and its increasingly negative and restrictive patterns. Our personality becomes more defensive, reactive, and automatic.

The movement up the levels is simultaneous with being more present and awake in our minds, hearts and bodies. As we become more present we see our personality objectively in action rather than “falling asleep” to our automatic personality patterns. There is therefore the possibility of “not doing” our personality.

I’ve found that the best leaders, and myself when I’m at my best, are those people who are fully invested in the person they’re leading. The more present the person, the better the leader. For that, but not only that, reason, I’ve spent considerable time and effort rewiring my brain to focus on being ever more conscious in and to the moment.

Beyond leadership, this is also my understanding of the Path that is in some way referred to by nearly all the wisdom traditions (Buddhism, Hinduism, Advaita Vedanta, Christian Mysticism, Kabbalah, Taoism etc), as well as plenty of secular thinkers (Sam Harris, Brene Brown, etc). Even Lululemon bags note that “living in the moment may be the meaning of life,” although that probably only proves I’m subject to marketing.

Either way, as a longtime “intellectually superior atheist” this wasn’t the path I’d expected to go down. If the me of today were to meet the me of any age between 17-33, I’m sure I would have laughed at myself. Or

But then again, viewing that conversation through the handy lens of the Enneagram, that would have been a level-6 laughing up at a level-2, from deep in the clutches of his automatic and defensive personality patterns.

I’m good with that. The 17-33 year old me wasn’t near as effective a leader.

Focus on the road, not the wall

Running a venture-backed startup before profitability is like flying a plane you can’t steer toward a thick, steel wall. The only option is to throttle up faster and faster, accelerating to take off with enough distance to clear the wall (reach profitability), or somehow find a way to move the wall backward before you hit it (raise follow-on financing).

There is precedent to this wacky situation, out of which has come best practice.

Professional NASCAR drivers are trained to focus solely on the road, because history has shown that if they allow themselves to look at the wall, they’re likely to hit it.

It’s so difficult when running a startup from a balance sheet to not fixate on that wall, but Jeff Gordon might tell you your life depends on it.

When to stop “crushing it”

I’ve been “crushing it” for almost as long as I’ve been running a startup.

That’s not to say that things have always been up-and-to-the-right. We’ve had more than our share of WFIO moments along the way. But to most anyone I spoke with, we have always been crushing. I made sure of it.

I have always kept the key metrics by which we actually were crushing it at the ready at all times, because you never know who you’ll talk to and you need to be on your game when opportunity knocks.

There’s tremendous value to this. I have literally been in an elevator with an investor of limitless resources, and needed to position my company in the best possible light in less than 30 seconds to pique his interest enough to take an actual meeting with me. If I didn’t have that highly packaged version of our story at the ready, I legitimately would not have closed that round of financing. I certainly don’t mean to diminish the importance of presentation, as it’s critical to startup success.

That said, it’s worth knowing when to turn it off, too. And doing so can counterintuitively be a path to success.

If you’re always “crushing it,” you risk sugarcoating real problems that need attention, and prevent the outside perspectives that may actually help solve those problems from having a clear way to engage. In “crushing it” you present the image of success, but you may unwittingly do so at the cost of real, actual success.

Startups are hard. Over time we’ve cycled through periods of legitimately crushing it, and periods where I didn’t think we would make it. That up and down ride is the nature of the game, and the secret is that EVERY startup hits highs and lows, even though most don’t talk about the lows.

That’s for good reason. Talking about the lows will never get you funded. But on the other hand, “crushing it” communicates that you don’t need any help.

And sometimes we all do.

Czeslaw Milosz, on Love

For this Valentine’s day, I’m reminded that the prerequisite to loving someone is loving yourself. Like an airplane mask, you can’t care for someone else if you haven’t cared for yourself first.

Love means to learn to look at yourself
The way one looks at distant things
For you are only one thing among many.
And whoever sees that way heals his heart,
Without knowing it, from various ills.
A bird and a tree say to him: Friend.

Then he wants to use himself and things
So that they stand in the glow of ripeness.
It doesn’t matter whether he knows what he serves:
Who serves best doesn’t always understand.

~ Czeslaw Milosz, New & Collected Poems 1931-2001

In college I often found myself looking for hidden meanings in poetry, but these days I find myself surprised at how literally things like this seem to be meant.

My favorite hot spot I thought I’d never go to: The Hermitage

I’ve gone on retreat a number of times now, so far all domestic although I hope to visit Tibet or Nepal soon (and a hike of Machu Picchu coming up may almost count, depending on how meditative my hiking becomes), but for the longest time I’d thought that retreats were much less accessible than they actually are.

I thought that in order to go on a contemplative retreat you’d have to travel to Colorado for a week with a guide, and the whole thing seemed like such a big to-do that it was never the right time. Fitting a week of “doing nothing” into a busy startup founder schedule is unrealistic, I thought. And because of that, I didn’t experience the true depth of reflection and force of insight that are possible through retreat until early 2019, when a friend of mine introduced me to The Hermitage.

The Hermitage is a Christian-flavored retreat space in Three Rivers, Michigan. I am not a Christian, so when I first checked out the website I was a bit nervous that I would not be welcome, but my friend reassured me that it was a space that was welcoming to all, as long as you were looking to go inward. Besides, I am also not a vampire, so a couple crucifixes aren’t going to hurt me. The part of the experience that initially appealed to me, in addition to the inaccessible mystique that a “retreat” had developed in my head, was that The Hermitage was purpose built for short retreats, as short as a single day. I’m sure they do longer ones as well, but the opportunity to retreat for a whole day with only a single hour drive each way got me over the hump. I was finally able to justify the investment, and in hindsight it was ignorant to wait as long as I did. The opportunity cost of not doing the introspection was larger than I had thought.

It’s way out in the country, sufficiently away from everything such that even the travel there starts to put your mind in a different, more relaxed, posture. Theres a multi-purpose sign at the driveway that says “slow down.” The campus itself consists of two large buildings, one a sort of multi-functional gathering area complete with a chapel (which I couldn’t bring myself to spend time in initially) and a sitting room/library (which of course I loved), and the other a lodging with a kitchen in which they serve regular meals (although I’ve endeavored to fast each time I’ve gone) and a bunch of rooms for retreaters. You can rent the rooms out for the day, as I’ve done, or I’ve seen people staying there for the weekend or the week.

In addition to the two larger buildings, the real beauty of the Hermitage is the campus. A few acres of wooded trails extend from the main residences, interspersed with natural and cultivated landmarks like a lean-to at the top of a steep cliff overlooking a river, and an ankle-high spiral maze within which you can practice walking meditation. It’s beautiful everywhere you look, but in totally distinct ways. It’s breathtaking both in its scale and its complexity.

My favorite part of the campus is the cabins. Four, single-room buildings dot the deep woods, with names like “Thoreau,” “The Hut,” and similar. Each of these is slightly larger than the bed contained within, and also includes some sort of desk area, for reading/writing. The bathrooms are outhouses, which may be a turnoff for some but since I try to fast while there have only served as scenery adding to the comprehensive different-ness of the place. My habit now is to rent out one of these cabins for the day, and then split my time between sitting meditation within the cabin, walking meditation around the grounds, and a bit of journaling inside the lean-to (because of the view).

Since I was introduced to this space, I’ve brought a few friends with me as well; I’ve found that running a business tends to demand so much of a person that retreats can be quite appealing, although like me most think of them as something monk’s or artists do. Going deep internally with friends–we always end the day in the sitting room to discuss our experience–has added to the depth of some of my closest friendships.

There are no “rules” for retreat, per se, but people there generally try to observe silence. This is amazing, and not as difficult as people think it will be (the hardest part for someone as social as me is not saying hi if you happen to pass someone on a trail). But that’s not a rule, and you won’t be kicked out if you do talk. In an effort to get the most out of my time, I also make it a point to, and I can’t stress this enough, leave my cell phone in the car. To make this work I always let people know I’ll be inaccessible for 8 hours, and surprise surprise, the world doesn’t end while I’m away.

If you have interest in contemplative retreat, and you have not yet gone on one, I highly recommend finding a local spot like The Hermitage. A day is plenty of time, and can be a great introduction into the benefits of taking time to dig internally. It’ll take more than that one time to go beyond all the roles you play and find out who you truly are underneath all those mental constructs, but that process is a lot like the old adage about eating an elephant (as are so many things worth doing). And if you are in Michigan and would like to try out the Hermitage with me, I’d be happy to “host.”

The (not so) new leadership: Context > Control

Many leaders still see their job as directing the activity of the people working for them, setting up detailed systems designed to remove the variability from human behavior and achieve predictable outcomes.

This approach to management stems all the way back to 1911, when Frederick Winslow Taylor released his opus, Principles of Scientific Management. His techniques were responsible for dramatically increasing the output of industrial era factories by limiting the freedom of employees to make decisions, instead creating detailed scripts to drive very specific, management-prescribed, behaviors. By creating a system that forced every employee to conform to standards in every situation, Taylor ensured maximum compliance, which at that time equaled productivity.

But that was a different time, and those employees were doing repetitive tasks in a factory. Today’s workers are asked to navigate rapidly changing markets and produce results in all kinds of situations, so compliance, at best, comes with many caveats. But many managers still use those techniques today. You see the issue.

Today, the most successful companies adopt a context > control philosophy to management. At VNN, it looks something like this:

  • Leadership’s job is to create context
    • Establish long-term vision, short term milestones needed to move toward that vision, and set any hard guidelines outside of which employees may not go (the goal is to make these as broad as possible)
    • From there, avoid making decisions wherever possible
    • Instead, ensure that everyone within the organization has the appropriate context to make their own decisions. Ensure everyone is aligned to where the organization is going, and understands their role in achieving the vision.
    • Then align some more (HT Patrick Lencioni).
  • Individual employees’ job is to use good judgement
    • Each employee is empowered to make the best decision for every situation in which they find themselves, based on the context provided by leadership

This way, the people closest to the situation, the ones best equipped with the most information about the situation–namely the employees–are the ones making most of the decisions. Meanwhile, leadership spends most of their time answering questions, providing feedback, coaching, training and generally ensuring that the decision makers (employees) have the context needed to make decisions in the moment that are aligned with overall company priorities.

Doing this admittedly requires humility on behalf of the leadership, as they need to embrace the fact that they cannot keep up with the pace of business on their own, and empower their team to help them make critical decisions (and then support them when they decide things different than you would). But I’ve found that if you empower your team, and expect them to step up, they do.

When they do, the rewards are many. In addition to better serving customers (by ensuring the person they’re talking to is empowered to help them without checking with their boss), this approach has proven to lead to a more engaged and productive employee base, and a greater level of innovation throughout the organization.

I remember the moment when I realized we had implemented this effectively at VNN: I had given feedback to an employee that I didn’t think a project he was passionate about would work, but I also let him know that, as always, my opinion was context and it was his decision, within the parameters we had constructed. He decided to go forward with it, busted his ass on the project around his core responsibilities, and it’s now one of our most successful business lines. I had to eat some humble pie on that one, but there’s no question that VNN would be less successful if I had dictated that particular decision.

What was a radical philosophy as recently as a few years ago, what I’ll call “context > control,” is quickly becoming mainstream. It’s not there yet, but organizations like The Ready, Whole Foods and Google are all leading the way, and VNN is working every day to do the same.

Many leaders still want to control every aspect of their organization. But the companies that let go of that control, democratizing decision making and embracing the full capabilities of their employees, will outpace those who centralize decision making and look to control results.

They already are.

In a future post I’ll detail exactly how we went about implementing this approach at VNN, and the structures we use today to ensure everyone has the appropriate context to UGJ (Use Good Judgement, which we stole from Netflix like any good artist).

It’s also worth noting that the above is nowhere near the leading edge of management. Recognizing the futility of pretending to control the future, some companies have gone so far as to eliminate the annual budget entirely. We still have a budget, but I must say this is very intriguing.

The mistranslation of Dukkha

The Buddha’s first Noble Truth is that “life is suffering.”

This concept is recited all over the wisdom traditions, as well as, retrofitted, in many contemporary thinkers like Sam Harris and Jordan Peterson.

When I first heard this, I thought it was unnecessarily gloomy.

Life’s not ALL suffering. I’m generally happy. Everyone says I’m an optimist. Maybe I’m not ecstatic right now, but I’m definitely pretty good. And I was great last month, when I closed that financing. I might suffer sometimes, sure, but life is much more than just that.

I learned much later that the Buddha used the sanskrit word Dukkha, which actually translates to “unsatisfactoriness.” So, in effect, the teaching is that life, by its very nature, is unsatisfactory.

Life is not enough. Ah, now we’re getting somewhere.

Life is not enough, and cannot ever be enough, because we always want more. When we’re sad, we want to be happy. When we’re happy, we want to be over the moon. And when we’re over the moon, we quickly become afraid of the inevitable come-down. Closing a financing, hitting revenue numbers or even selling your company, there is no situation in which human beings–never mind founders–can ever get enough, or experience enough, or accomplish enough. We’re not wired for that.

The “be all that you can be” mantra we’re taught in America feeds us right into this misery, amplifying our innate desire to want more, strive more, achieve more. Many of us are good at playing this game and trick ourselves into thinking we can win, amassing lots of things and experiences in the process. But no amount of getting, achieving or having will ever change life’s fundamental not-enough-ness. The game is rigged.

Instead of killing ourselves trying to get enough (things or experiences, money or status), what if we worked on really seeing what’s right in front of us? What if we got past ourselves, and really saw the people suffering around us, and in seeing that, simply endeavored to help?

For that matter, what would a company that did that look like?

We live in echo chambers

I’m so right. All the time, I’m always right.

When I log onto Facebook I see it. Everyone is posting about politics, and every post berates the bad guys and glorifies us. My party. Everyone is saying the same thing: that I’m right. Those guys are bad, but we’re good. “What’s wrong with the world,” I’ll say before logging off.

Sometimes I enter into a business meeting with an agenda. Not the kind that helps to run an efficient meeting, but the kind where I intend to convince my teammates to do what I want. In these cases, I don’t bother listening, because I already know the answer coming in. And I make sure to ask the head of R&D his opinion, because I know he understands. If someone disagrees it’s because they’re wrong, so I just need to explain myself better. Eventually we go the right way. Or sometimes we don’t, but everyone makes mistakes.

In traffic, I’ve been told I’m the worst, but secretly I don’t believe it because I drive well. Some people, on the other hand, they zoom past you, then swerve into the front of the line of cars in which you’re waiting. That’s the worst. Immediately I get hot with fury, because I have somewhere to be. The selfish jerk.

I’m right at every level of my life, and every area of my life is all about me.

This morning I was late to a meeting so I had to cut into a line of traffic. Luckily there was a space between the cars so the guy behind me couldn’t have been too put out. It was unfortunate, but necessary. I waved at him..

I settled into the front of the line, and for just a moment, it seemed like something might change.

But then I quick pulled up my phone and checked Facebook, and the world looked Right again.

How to cure the grumps

Laura called me out the other day, asking me if I was grumpy.

It was second or third thing in the morning, on a weekend, and I was making breakfast per her request. I vividly remember my completely normal reaction.

The defensiveness bubbled up, immediate, visceral, hot.

I wasn’t grumpy. What the hell was she talking about? And even if I was, it was justified. I’d had to change my morning routine to deal with a sick kid, I hadn’t gotten anything done that I was supposed to, and…

This whole inner monologue took less than a second to get me worked up, but at about that point I noticed what my brain was doing. In stepping back I saw the machinery, and realized I had a choice.

“Yeah, I think I am grumpy,” I admitted. It was the hardest thing to do.

“Okay,” Laura said, giving me a side-eye and going back to what she was doing, which I noticed was juggling both of our boys so that I could cook in peace.

When I put eggs and bacon on the table, I realized that I wasn’t grumpy anymore. I couldn’t tell when the feeling had passed.

We went to the zoo that day with friends. I still remember Laura and I watching the kids getting their faces painted.


I think it was when I woke up to ethereal piano notes drifting across the forest and, after climbing from my sleeping bag and crunching up the bark covered path to the main field, strolled to the group of six people practicing capoeira as the dawn sunlight filtered through the redwoods.

Or maybe it was when I screamed at the top of my lungs, joining a mob of 50 or 60 people named things like Nacho Supreme and Chupa Chup in urgently imploring a person named Sunset to “let’s go,” as she brought the full weight of her army of groupies to bear in a life or death game of Rock Paper Scissors Rockstar.

It could have been when I was lying down at the end of a day, my head propped up on a pillow shared with Nacho Supreme in a tea yurt itself shared by dozens of prone people while a live band dressed somewhere between traditional Native American and traditional Hippie pranced around us singing (we were all fully clothed).

But really, the most incredible part was the rules:

Rule #1: No technology
Rule #2: No names
Rule #3: No “work talk”
Rule #4: No time

These created a structure ensuring that, whether you were competing in nose jousting, writing fiction on a typewriter overlooking a river, or doing standup for the first time on stage, whatever you were doing, you were 100% there. No expectations on who you were supposed to be, nothing to do, nowhere to go. Just here, just now, just us.

Laura (Nacho Supreme, who did standup on stage) and I (Skittles, who learned Capoeira, at least a little) call this magical place deep in the redwoods of Mendocino, California, “Camp.” Others call it Camp Grounded. We went for my 30th birthday in 2015, and had the honor of meeting its amazing founder, Fidget Wigglesworth, AKA Levi Felix, along with so many incredible people who we will only ever know as Honey Bear, or Chief.

In those 72 hours without time, I lost myself for the first time in a long time, in the pure joy of being. As Fidget said: “We’re all fucked. We’re all going to be fine. We’re all in this together.”

Laura and I were devastated to learn in the years following that Fidget was battling brain cancer, and later that he had passed away at 32 years old. I was 32 then as well. I was heartbroken that the world lost such an amazing human being, but will forever be grateful for the magic that he gifted to all of us.

I imagine he’d be smiling now, underneath that great big bushy non-ironic mustache, to learn that Camp Grounded has been rebooted.

Maybe I’ll see some of you there. Although neither of us will know it.

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