Clothespin – or – When I took the red pill

“We’re going to prove to you that you don’t exist,” the teacher told us with a twinkle in his eye. “At least not in the way that you think you do.”

At a younger age I would have geared up to prove him wrong. But at 34, having just hired my replacement in my company and in so doing unknowingly abdicating the crux of my identity, sitting in lotus position in the main Gompa of the Vajrapani Monastery at the end of a dirt road two hours drive zigzag up a mountain from San Francisco, about 30 minutes beyond where Uber’s maps don’t go, I was open to listening.

“Think about this clothespin,” he said. “It’s a clothespin, plain as day. Nobody would say that it does not exist, right?” The Brit in our group, Amy, caveated to say it was actually a ‘clothespeg’, explaining that she and her brother used to launch them at one another as children. Regardless, everyone agreed the wooden clothes-hanging utensil did, in fact, exist.

“But I simply do this,” he took one of the wooden sticks from the clothespin, hiding the other stick and the still-attached metal spring behind the lectern, “and tell me, what is this now?”

It was a wooden stick, shaped with divots that would enable a clothespin to be formed if joined with an identical mate and fitted spring. But while it still had a hint of clothespin, kind of, I wasn’t sure it would have been any more than a stick from the distance I was sitting, had I not seen it in its previous condition a moment before.

“What about this?” He held up the other side of the clothespin. “Is this a clothespin? Would you be happy to purchase a bag of these?”

No. Just another stick. And a spring.

He prodded, “is the spring a clothespin?”

We shook our heads.

“So a moment ago we all agreed we were looking at a clothespin, and nobody would argue that it did not exist,” he said. “You didn’t have to think about it, or consider it at all. You simply knew innately what it was called, and what it was for. It had ‘CLOTHESPIN’ written all over it, as if its very essence was that of clothespin.

“But now, I only have to look at it a little closer–I have moved my hands and that is all–and now you say it’s no longer a clothespin. Well then, I ask you, what is it?” He held up the two sticks and spring.

Someone answered it was two sticks and a spring.

“Hmm… I think you are right,” he said. “No use to hang clothes.”

He put the sticks next to one another, and wrapped the spring around them to once more create a single object. “And again, what is this?”

A clothespin. Its essence returned as if by magic.

“So this clothespin now exists once more, but a moment ago it did not,” he said. “So now we have agreed that a thing can both exist, and not exist, at the same time. In other words, a thing can be what it is, and also be only its parts, its causes and conditions as one might say, at the same time.

“So what makes this, then, a clothespin?”

Someone said that we labeled it so. Someone else said that it could hang clothes.

“I see,” the teacher said. “So we are saying that there is nothing about this object that makes it internally ‘clothespin’, apart from our giving it a name and a purpose. Is that right?”

We nodded.

He bowed his head. “I would like to suggest to you, humbly, that you exist in the same way, and in only the same way.”

I felt numb.

“I would further suggest,” he continued, gesturing toward Amy. “That it could as easily be called ‘Clothespeg,’ and be used as a projectile, if you so chose.”

How leaning in to my greatest fear enabled me to make better decisions

Fear drives much of our lives. Neutralize your fear by leaning into it, and free yourself to make better decisions.

I’m convinced that everything I do is either to A) steer myself toward feelings that I interpret as positive or good, or B) avoid feelings I interpret as negative or bad. There really isn’t more too it than that.

I will go to incredible lengths to curate the feelings I’m exposed to. I have ended relationships rather than face my own failings within them. I have blamed others or the world rather than confront something I’ve done wrong. Most often, I will imprison myself and everyone around me in my own personal tunnel-vision, diminishing everything that is not the Goal with a wave of dismissal in an effort to avoid my deepest fear: shame, stemming from my deep recognition that I’m Not Good Enough.

Usually this means making knee-jerk, fear based decisions in reaction to feeling Not Good Enough, that seem right in the moment but that I often regret later on. I’ve sent so many emails that enabled me to check a box, get that dopamine hit of productivity in the moment, but that actually did more harm than good in the long run (sometimes I see this as quickly as 5 seconds after hitting send–#grateful for the ability to un-send these days).

It took me forever to realize what was going on, and develop an alternative.


I learned that I wasn’t good enough early in life, sometime before I can remember, and when I learned that I made the decision that I would do anything, literally anything, to prove otherwise. My whole life from that point forward has been one long series of achievements without end, each one seeming like the most important thing in the world until I attained it, at which point it was and had always been irrelevant. I was still not enough, and only the next achievement would prove otherwise. Etcetera, ad infinitum.

It wasn’t until I stopped achieving, forced through failure (providence?) to slow down, that I had the amazing opportunity to really take stock of the operating system through which I was living. I wouldn’t have chosen to stop achieving, because frankly it pays well, offers tons of positive feedback (the US consumer culture reinforces your worth as a function of your possessions / achievements), and it was painful as all hell to confront the feeling of my own inadequacy head on, rather than continuing to run away from them with the next gold star. But I’m so glad I gutted through it because through that process I was able to see the pattern of my mind’s machinations in a way that demystified it, and offerred me a choice I never knew I had:

Rather than achieving to run faster away from my own inadequacy, I could simply stop. I could stop putting myself through such ambitious hell, and simply deal with what was there.

Moreover, by dealing with what was there rather than running, I could avoid making the kinds of fear-based decisions that I usually regretted. By simply looking at reality without trying to fix it, I could see more clearly what there was to do, and make better decisions.


The thought of confronting my fear and my shame was terrifying, but so was the prospect of jumping back on the treadmill of achievement and simply pretending that I still thought hitting that next milestone would make me happy. So I did it. I simply stopped, taking two months off of work (not all of us are so fortunate, I recognize), and confronted it.

And crazy enough, I didn’t die.

Oh it hurt, for sure. There’s a reason I was subconsciously pushing so hard to avoid these feelings. Swimming in inadequacy was a kind of exquisite torture that I could never have prepared for, but thanks to many psychological and spiritual tools and mentors I was able to stay with the emotions, negative as I perceived them to be, and simply be. And in that, there was a freedom.

I didn’t have to reflexively jump into action and check an item off my to-do list. I didn’t have to mentally diminish myself or someone else in an effort to right-set some mental social hierarchy to make myself feel better. I didn’t have to do anything, in fact. I could just do nothing, and as Trungpa Rinpoche says, “Lean into the sharp points.” Feel what there was to feel, what I had been running from for so long, and let it pass.

By sticking with the feeling without succumbing to the intense urge to do something productive in response, I was able to develop a familiarity with it.

For me, fear of not doing enough feels like:

  • Tight chest, like when I smoked too much. I can’t get a full breath
  • Eyes feel wired, like I haven’t slept
  • My heart beat is audible, particularly when I see success in others
  • My mind spins, playing a loop of how my achievements compare to those who are more accomplished than me
  • Intense feeling that there is something wrong

I have no way of knowing if that’s the feeling for others, but now that I’ve stuck with it a number of times, really made it a point to taste the flavor of the feeling rather than running from it, I know the characteristics of that particular fear for me. I can recognize it when it comes, enabling me to actively avoid jumping into action as would be my reflex. And I know from experience that it always goes away, even if it feels like this time it’s going to last forever (it always does).


I’ve become familiar with my primal fear, that I’m existentially Not Good Enough, and will never be Good Enough. Certainly I’m not friendly with it, but I’m acquainted enough to recognize it for what it is. The fear that I’d jumped through hoops of fire to avoid, when you really boil it down, is simply a series of bodily sensations combined with a reflexive urge to achieve.

For a long time I’d unknowingly let that feeling drive so many of my actions, forcing me into suboptimal, fear-based decisions, and unproductive, repetitive patterns (and also, to be fair, into some success, albeit at the cost of relationships and consciousness).

The feeling still comes up regularly, but now when it does I’ve learned that there’s a choice. Most of the time, when I’m at my best, I simply sit with the feeling and appreciate how its intensity reminds me that I’m alive.

Then look at the situation with a clarity of mind that used to be inaccessible, and do the next right thing (HT my 3 year old).

Sit with the question

My mind is an answering machine. It comes up with answers, meanings, conclusions, theories all day, every day. It’s automatic.

It likes the solidity. To feel like, in the immortal words of the narrator of Fight Club, that whatever else happens, I’ve got that sofa problem handled.

Humans like solidity in general, I think. We build things constantly, taking ephemeral things like trees and people and making them into solid things like houses and businesses, each time answering an unspoken question. Each time we do this, we take something alive and full of potential–a question–and stamp an answer on it.

My brain tries to stamp my life solid as well. What am I? Well, I’m an entrepreneur. There, answered. Don’t like that? Well, I’m a basketball player. A leader. A good looking guy (with a growing bald spot). My brain can do this forever.

It stamps other people with labels, too. This woman is good, this one is mean. This guy is more successful than me. This one is not interesting. Over and over, all the time.

But none of that is real. All the answers are made up, and only exist to limit my experience. Humans (and all of reality) are really one big question, and we’re just trying to make ourselves less anxious with all our stamping answers on everything. Stamping someone with a label doesn’t change the person, only limits our relationship to them to a relationship with their label.

I find the alternative, when I remember to do it, much more rewarding (not to mention fundamentally, unavoidably, more accurate). I find I pay much closer attention to the amazing, detailed, massive, changing aliveness of my life, and all the people in it, when I simply sit with the question.

Every rose has its thorns

The deeper I go into the nature of things, the more I see paradox.

Where there is light, there is darkness. Where there is good, there is bad. There’s a reason that the Yin/Yang symbol has withstood the test of time. It’s a map of reality. I’m learning there is no such thing as Good or Bad, really. It’s perspectival, in that one man’s food is another man’s poison (I think that’s how the Bible puts it), or one being’s poop is another being’s fertilizer, if you like. It’s also a blend, in that everything good has within it something bad, and everything bad has a redeeming aspect within.

As deep as I can dig, this seems to be always true. There is nothing purely good, or purely evil. Purely light, or dark.

I have done things that, depending on who you are, may make you think I’m a downright bad person. Probably many people I happened upon in college, during the throes of my drinking days. We won’t go into specifics on this post, but suffice it to say I didn’t much care about other people, except in as much as they could help me get what I wanted. I sometimes do that even now, but people who know me now can (I hope) attest that at least I’m not PURELY an asshole. Most people who know me now, I think, think I’m quite a good person. This would no doubt shock some people in my earlier lives.

Depending on which part of me you are familiar with, you think I’m mostly good or mostly bad, but either way it’s nuanced. Which brings me to today.

Today I was confronted with how one of the things I like most about myself, the aspect of my personality which has gotten me so much, which I’ve always found so positive, also has a dark side.

And it’s because of that dark side that, after publishing a post every weekday for some time now, I’ve decided to ratchet down the pace of this blog to 2x/week.


One of the things I know about myself is that I keep my word. When I say I’m going to do something, I do it. End of story. It took a lot of work to develop that relationship, a lot of trying to keep my word, failing, confronting that failure, trying again, pushing past whatever is in the way, succeeding, trying again, etc., but for the last 10 years or so I’ve been enjoying a relationship with my word which is essentially iron clad. When I tell myself that I’m going to do something, then I will move heaven and earth to do it. It’s even more effective when I tell someone else, because then there’s the social pressure of letting them down as well. Can’t chance looking bad in someone’s eyes, so better hustle and get it done.

This is probably the single biggest character trait responsible for whatever success I’ve had in business. Once I say I’m going to do something, it doesn’t matter what life looks like, that thing gets done. I’ve tried to pass that trait down to our employees because it’s been so valuable to me, and for the most part I think we do a great job, and our business has flourished on our collective commitment to DWYSYWD (do what you said you would do). From my experience, developing a habit of giving and keeping your word is among the most powerful things you can do for your career and life, hands down.

It’s from this framework of unquestioning DWYSYWD that I started writing a month ago. I didn’t really know if there was a point to the writing, as I had nothing to accomplish by being open online. I didn’t have a goal, and in fact resisted the idea of a goal out of principle. I just liked to write, and something deep inside me made me feel like now was the time, after 10+ years, to finally get back on the horse. So there was really no outside reason for me to write so much, but it didn’t matter. I had told myself I was going to write every day, so everything else beyond that was immaterial. I would simply write every day, and life could work its way around that fact.

And, as per usual, I did. Every damn day, including many inconvenient days waking up earlier than 4 in the morning. And now I have a bunch of writing, some of which might be ok, and more importantly than that I have gotten back into the swing of the writing, which in retrospect was probably the point.

But like everything, there’s a Yang to this Yin. There’s a downside. And for me, I have recently learned that one of the reasons I’m so black-and-white about my relationship with my word is tied up very deeply in my habit of measuring my self-worth based on my accomplishments (which I’ve written about here and here). As I’ve peeled back the layers of my thinking, I’ve seen that in the same way I valued myself by the success of my business, I also valued myself based on my ability to stick to my word. In the case of this blog that manifested in the belief that I was somehow unworthy if I missed a day.

Ah crap, I thought when I recognized it. That’s that same pattern again.

As effective as I know that framework to be as a means of getting shit done, I have over time become unwilling to consciously anchor my mental, emotional and spiritual well-being to my accomplishments. It’s not worth it, because I know the end of that story. You do and get a lot, but there is never, and can never be, enough accomplishment to satisfy that craving. So you chase gold stars your whole life and die feeling unworthy. No thanks. Self worth can only come from inside, not from any amount of gold stars (even though America would have you believe otherwise).

So, as I’ve started doing when I notice my mental machinery in action, I am letting go. I still very much like writing, and imagine I’ll continue to do it a lot. I still very much like that it’s normal for me to keep my commitments to others and myself, and I imagine I’ll continue to do that as well. But it’s become unavoidable to me that the framework of “I will write every day,” while effective, has become toxic for me at this point in my journey.

So I’m letting go.


What does this mean? Well, due to my nature to overachieve I’m already writing weeks ahead of the present date, so I’ll let those run their course coming out every Tuesday and Thursday, instead of every day. Or maybe Monday and Wednesday. Who knows. And we’ll try the 2x/week pacing and see if it works. Or maybe three times per week, or one. We’ll see. I can feel a weight being lifted in writing that.

I’ll continue writing, and my hope is I find myself in a spot where I do so not because I’m committed through a structure that has become a proxy for my sense of self, but because writing is simply an expressive action that I am called to do.

That’s why I started writing a month ago, after 10 years letting the habit languish. To express things, not to get somewhere. And I think that’s where the work I’m meant to do–maybe even the words I’m meant to write–will come from as well. There’s no end to a life built on achieving, despite what media tells us. There is always someone with more.

As Thomas Merton put it, “the life of riches, ambition, pleasure, is in reality an intolerable servitude in which one lives for what is always out of reach.” I want off that treadmill, and that means giving my writing space to become something organic (again), even at the risk of “success.”

My word is my bond, I’ve always thought. And I’ve always been proud of that. But I’ve seen that my word can become my prison as well, every bit as much as the mental patterns through which I interpret the world.

More than any amount of success, I want to be free.


So henceforth, look for a post around twice a week from me. I’m guessing subscribers’ inboxes will be better for it anyway.

Joseph Campbell and the Power of Myth


“You must give up the life you planned in order to have the life that is waiting for you.”

Joseph Campbell

I got off the plane, vibrating.

On my way back from retreat in California, I had spent the flight between SFO and MSP immersed in Joseph Campbell’s The Power of Myth, a Netflix special with Bill Moyer that, while comically underwhelming in production value, contains a truly remarkable presentation of content. It was that content that had me buzzing.

For most of my life I’d had this vague hunch that, since most religions seemed to rhyme with one another (that is, contain much of the same content, even through their differences), that even though the individual tribes fought one another to the death more often than not, and even though any religious person would disagree with the assessment, there ought to be some core truth that guided them all. It seemed to me inevitable, or at least likely, that each religion started with the same truth, but then over history man got in the way and bastardized that truth to suit his various ends, distinguishing each religion from the others in the process. From my Western viewpoint, this assessment was I’m sure helped along by my understanding of the Abrahamic Tradition, the accepted belief among Christianity, Islam and Judiasm that each stemmed from the same guy: Abraham.

So it seemed to me at the time that there had to be a core truth that had in effect caused each religion, some piece of wisdom so important that religions were founded to pass it down over generations, but that each religion had forgotten or obscured it over time in their own way, so caught up they were in their own “rightness.”

Then I watched that Netflix special and Joseph Campbell opened the doors to that core truth for me for the first time (or at least the first time I was ready to hear it, as I’ve found is the way of wisdom). There was in fact a core truth, a core message that was present throughout all the major wisdom traditions and religions. This truth was beyond words, so there was no way for him to state it directly and instead he resorted to pointing at it from a number of perspectives, so that while it wasn’t made explicit, you got the gist of it.

The essence of that core truth, such that I can explain it now, was the overwhelming importance of presence to the moment. Of letting go of all the mental constructs we create over and over again, and coming back to the awe-someness of the fact that we exist, and that anything exists. The various traditions, according to Campbell, were all gesturing in their own way at the importance of letting go of your interpretation of reality, or what reality should be, some solid thing created out of all your thinking, and instead connecting with what actually is. And then living there, in, and as, the Universe, rather than trapped inside the noise of your mental constructs (I want to say “as a part of the Universe” to help it go down easier, but that wouldn’t be accurate). The practical way to do this being to stop thinking, planning, scheming, remembering, and everything else, to simply let go of it all. To live without reference points.

He did a much better job than I of explaining it, obviously, but having just come off a profound retreat in a monastery in the mountains, what I remember thinking getting off that plane was, “holy shit man, I get it.”

I walked through the airport in a pink cloud of having gotten it. Me, Ryan Vaughn, had somehow stumbled on the secret that all these millions of people were missing. And it was so simple! What a feeling.

I stayed in that space for a good hour before it dawned on me that I had lost it long before. I’d sacrificed presence to the awe-someness of each moment through the very act of understanding the significance of that presence. I understood it (thanks to Joseph Campbell then, but again and again through so many teachers since then), but the price for that understanding was everything.

So I gave up my understanding, for the first of hopefully millions of times, at a urinal in MSP, and returned to the moment. To the amazing reality of the universe, of you, of me, and of now. Yes, even the now that happens in the restroom.

These days, I endeavor not to understand. I try to remember that I haven’t learned anything. And anytime I think I do, or I have, I know I’ve lost the way.

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.

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 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.