✍🏼 Leadership: an invitation to connection

The most important parts of our human experience are elusive: impossible to describe. In attempting to do so, we lead, and generously offer an invitation to connection

Happy Friday to the 47 of us. We’re up from 36 just on Monday, which fires me up. I’m so glad you’re here.

Often, I find that the ideas that excite me most are the most challenging to describe, let alone discuss with another person.

I also see some of smartest people out in the world navigating the same challenges in their own ways - in their books, interviews, talks, and work more broadly.

Some do so artfully, but it can still feel curiously indirect.

Sam Harris. Rick Rubin. David Whyte. Paulo Coelho even wrote an entire novel, The Alchemist (one of my favorite books of all time), to paint a picture of his ideas.

Hell, I struggled coming up with the title of this essay. This stuff is no joke.

I explored why this is, and what it means.

And it eventually brought me to some thoughts on how the elusive makes us human and in fact might be the foundation of true leadership.

I also want to call out that at the bottom, I’m throwing some links to the most interesting things I’ve devoured recently, so if my droning bores you to tears, at least scroll to the bottom to check out some of those links before you ✌🏼 out.

I hope you enjoy - and if if you do, I’d be grateful if you shared this with a few people you think would also enjoy it.

Cheers,

Devin

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Leadership: a generous invitation to connection, through the elusive lens of our humanity

The most important components of our uniquely human experience - like our emotional, psychological, spiritual layers - are impossible to describe directly.

To clarify (like last time), when I refer to our “uniquely human” experience, I am not talking about scientific, quantifiable truths of our physical bodies and the external, observable world.

What I’m exploring, and am far more interested in, are the subjective, visceral layers of our internal experience. The most important parts of our reality. The ones that add depth, complexity, and texture to our lives. The ones that ground and comprise our humanity.

Part of the reason that these internal layers can’t be described directly is that they’re subjective. They’re felt more than they are observed.

By definition, then, we can only come to fully know and understand our particular individual context, since we can’t possibly inhabit the full-contact, all-consuming, embodied nature of others’ lives - especially these uniquely subjective, visceral human layers like emotion, psychology, spirituality, etc.

The best we can come to hope for is as close to a complete understanding of our own experience as we can get. Then, we can extend an invitation to others to engage in dialogue to share our humanity with each other.

What we feel is the most real

It’s important to call out that just because these are visceral, bodily phenomena, it doesn’t mean that they aren’t real or true.

Also important - just because we can’t use language to precisely pinpoint, describe, or analyze these experiences, it doesn’t mean that we’re all alone. It doesn’t mean that our perspective is singular and unique.

It doesn’t mean that these realities aren’t shared, more universal experiences of being human beyond our specific, interior corner of human life.

But because we must struggle with language to precisely pinpoint, describe, and analyze these experiences, it can certainly feel that way.

In fact, because they’re felt viscerally, I believe they’re the most real.

Experience isn’t theoretical. Truth is felt in the body, viscerally.

People, above everything else, are searching for the feeling of being alive.

This is why stories are so powerful.

Stories are one of the mechanisms we use to convey these bodily sensations. To point at the truth and validate the realities of our what we see, think, and feel. To let others know that they’re not alone - and to feel less alone ourselves. To connect.

They’re powerful in a way that facts and statistics aren’t.

Facts and statistics are self-evident. They can be proved by those impersonal external forces, like science and logic.

Facts and statistics are intellectual. Stories are emotional.

Both matter, but intellect is everywhere. We spend so much time in our heads, immersed in thought, that feeling is what adds richness, depth, and texture to our lives.

To borrow from what Paul Graham said about ambitious people, when you give people story and emotion, they “bloom like dying plants given water.”

What we feel is the most real, and the most elusive

So many of these conversations, books, talks, and tweets that work to convey these layers of experience can feel frustrating.

The messaging can feel so slippery, like we can’t quite pin the thing down.

It’s because we can’t.

Spirituality, mindfulness, awareness, growth, development, creativity.

They can feel so elusive. Mystical. Magical. Mysterious.

The best we can do with these sorts of topics is to point at them from different angles.

To try to approach the essence of the thing, to get as close as we can, until we hit this invisible wall of the limitations of language. Then, we move over a couple steps, try again, and see if we can get any closer - or at least get a slightly different perspective. Repeat.

It’s sort of like a riddle.

We get an indirect, fuzzy, opaque silhouette, and all we can do, before we know, is explore. We work to use our most dependable tools, as well our most unusual. We try to see as much surface area as we can. We imagine its implications and possibilities, start guessing at what it’s trying to evoke, then repeat, repeat, repeat until, finally, something clicks. That’s when our deep intuition stirs up a triumphant, invigorating, peaceful energy of understanding and knowing. It resonates. We got it.

I use the term resonate very deliberately. Since we’re talking about visceral, bodily sensations of our inner lives, when we resonate with an idea or story offered by another person, we feel it.

It feels like a jolt of energy, an ignition of excitement. Like the tempo of the world speeds up. Like we entered the field of a magnetic gravity that’s pulling us to the core of some truth of the reality of our world.

There is something triumphant about the way this all works. Because it’s impossible to be spoon-fed understanding of these things, there’s work that’s required on our part.

When we connect, we earn it.

“Yes” people, “no” people

When it comes to these ideas, there are two types of people: people that resonate, and people that don’t.

People that say yes, open the door, and invite more, and people that say no, slam the door shut, and turn away.

Symptoms of the “yes” people: a head nod, a lean forward, quicker breathing, louder talking.

Symptoms of the “no” people: an eye roll, sheepishness, judgement, criticism, doubts, even anger.

Or, the most disheartening, nothing at all - an unfazed disinterest, as if nothing even happened.

As if that thing that is so core to our being doesn’t even matter. As if we’re the only one.

At least with doubt or anger, there’s an acknowledgement that something is there. That even if they disagree, we’re not alone.

Disinterest can feel the most deflating, especially since leading into this mystical territory is vulnerable. Because it’s subjective and emotional, it’s the stuff that makes you, you.

It’s personal. It takes courage.

For these reasons, it’s the most important dialogue we can have.

We must be unfazed by the “no” people.

We must keep leading these conversations.

A freeing realization to simply start

Because these conversations mean so much to me, I can find myself feeling deep anxiety and fear that I’m not perfectly describing what these sorts of experiences and ideas are like for me.

If I’m going to risk the vulnerability, I want to make sure I serve the invitation to these things up on a silver platter, accurately articulated, perfectly presented, so that it minimizes the risk of bringing forth the “no” people.

But over time, I’ve realized that it doesn’t actually matter how we describe these things. The two types of people are who they are.

People will either get it, or they won’t.

These layers of understanding are like strange forces that inhabit us all the way to our core. If it’s there, it’s always there, and it’s deep.

Like a tuning fork whose sound rings forth, seemingly from nowhere, when surrounded by the right frequency and pitch of another sound, the “yes” people will resonate and connect regardless of how perfectly we can conjure its reality.

Relatedly, a “no” person will never get it, regardless of how we try. They just aren’t set to relate to our tone of experience, no matter how many versions, angles, pitches we offer.

This frees us up to simply lead - to initiate the conversation. It’s either going to work, or it’s not, so we simply start.

Leadership: a generous invitation to connection

I’ve also come to realize that this anxiety and fear is about me, and in fact isn’t the point.

I believe connection is the goal.

And if connection is the goal, it’s about more than just one person. Connection isn’t a single-player game. It requires another to engage.

With this in mind, I realize that narrowing the focus to my own fears is not going to help. This approach will only hold back the possibility of connection.

Plus, a self-centered, fear- and scarcity-based perspective makes us feel worse along the way, regardless of the outcome. Whether the invitation for connection is accepted or not, the outcome is the same. Any fear just makes it more miserable for us.

If connection is the goal, the point shouldn’t be to get someone else to understand or validate us.

If connection is the goal, we’re better off coming from a place of generosity.

If we first scour our own experience for those experiences and ideas that stir up that energy, excitement, and curiosity, and offer them as an invitation, then we’re on our way to connection.

This, to me, is leadership. An invitation to connection.

Leadership is taking the first step.

Extending an offer of ourselves, from our core. Our experiences, feelings, ideas, and questions - the ones that make us who we are. Doing so from a place of generosity.

This approach also frees us from the anxiety and fear around whatever response we receive. If we offer an invitation, a gift, then it is done for its own sake - without expectation for anything in return.

True leadership and connection are fueled by that intrinsic, intuitive, optimistic, abundant energy of excitement that we all have, in our own way, deep in our core.

But we must work to uncover that in ourselves before we can lead.

As the leadership trope goes, “we can’t lead others where we have not been ourselves.”

Stories are the vessels of connection

I so strongly believe that stories matter.

Stories are the stuff of our humanity - the mechanism by which we share who and how and why we are, and connect with others who feel that way, too.

I know how alive I feel when I find (or maybe it finds me?), deep down, that invigorating energy of being in that “yes” person zone.

I also know how alive I feel when I connect with other “yes” people - the most alive.

Through connection, we deepen and strengthen our feeling of aliveness, and it has an afterglow much stronger and longer than the single-player version.

We search so often for these things called purpose and meaning. What are they, but connection? Offering to others, generously, that which matters to you. Invigorated. Alive.

Feeling.

Connection may be the tool for igniting and sustaining these feelings we’ve been searching for.

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Curiosities

• John O’Donohue on the On Being podcast. A lyrical, poetic conversation about beauty and our humanity. An incredibly pleasant Irish accent to boot. Some favorite quotes:

  • “I don’t think we’re less capable at all. I think we’re more unpracticed at it, and therefore more desperate for it. I think it’s a matter of attention really. That if you realize how vital to your whole spirit and being and character and mind and health friendship actually is, you will take time for it. The trouble for so many of us is that we have to be in trouble before we remember what’s essential.”

  • “In most workplaces there is huge imagination but it’s practical imagination that’s dedicated to productivity and looking at the bottom line. And I think that when they stand back a little and see that the spirit and soul dimensions are not luxury items, but are actually the very origins and sources which will enable everything to flow and unfold in a new way, that then they realize that the invisible world is a secret hidden resource that can be released, and excavated for the huge resources of spirit, guidance, for areas of ourselves that we’ve forgotten.”

  • “Eternal vigilance is the price of liberty.”

  • On how to find/pursue beauty: “When is the last time that you had a great conversation? A conversation which wasn’t just two intersecting monologues, which is what passes for conversation a lot in this culture. But when did you last have a great conversation in which you overheard yourself saying things that you never knew you knew. That you heard yourself receiving from somebody words that absolutely found places within you that you thought you had lost. And a sense of an event of a conversation that brought the two of you onto a different plane…A conversation that continued to sing in your mind for weeks afterwards.”

• Bryce Roberts from Indie.vc on a different type of entrepreneurship and investing. I’ve been thinking about this question for the last several years: is there another way to fuse ambition and impact as an entrepreneur or investor in a way that doesn’t dilute our humanity at the expense of economics? Bryce’s perspective is one that resonates

• What’s the difference between transformation and evolution?

• Naval Ravikant on The Knowledge Project podcast. One of the most intelligent people out there, in my opinion. I’ve listened to just about every one of his interviews. He has incredible insights not just on business and life, but also spiritual pursuits and happiness

  • I also recommend this book, which is a master compilation of all his publicly available insights

• I’m loving this performance. Vibey, low-key background track for working, plus stunning visuals