Curiosity Slipstreams & Conversations | #177

April 9th, 2022: Greetings from Austin. It feels like summer here already, with most days in the 70s or 80s. Hoping to get out and paddleboard on the river sometime in the next week.

I was on The Deep End with Marshall Kosloff this week. He was such a great interviewer! We talked about empty media narratives about work, the word “sacrifice,” finding work worth doing, traditional success metrics such as homeownership & more. Listen here.

Next week I’m going to do a mailbag issue. If you have questions for me, reply and I’ll answer them next week.

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#1 Finding Your Conversation

The poet David Whyte’s idea of the “conversational nature of reality” is one of the most powerful ideas I’ve stumbled upon. It’s an idea that helped me make sense of my journey over the past few years and helped me release my grip on the “getting ahead” mode that dominated the first thirty years of my life.

In the “getting ahead” mode you are never present. Life is experienced as a continuous calculation, doing things in the present for future payoffs. You aren’t working in a job because you like it. You do it and keep doing it because it helps you achieve or buy things you want in the future.

There’s nothing wrong with this way of orienting in the world and it’s probably pragmatic to orient in this mode early in life. But it’s the default mode. We don’t need to try that hard to get tap into it. Decades of schooling set us up to think this way. The underlying assumption in school is that good grades will help us in the future. We never know how eactly but we trust that it’s true.

The problem is that eventually life gets trickier or the payoffs never quite satisfy. Whyte argues that ultimately, we realize that “we don’t get to choose so often between things we hope we can choose between.”

The getting ahead mode tricks us into thinking that life is a series of clear and simple choices. You either do what everyone else is doing or you’re a bum. If I had a quarter for every time someone said “Paul, surely I can’t follow your path because then I will be broke” I’d have at least $10.

Embracing Whyte’s conversational nature of reality, I’ve been able to detach from this way of thinking. I’ve been able to slowly gain comfort with not having a plan and be okay with it. Yet this does not mean rejecting common paths. It means being skeptical of the pull towards the most popular goals, aims, and metrics of success as starting points of how to orient my life.

Instead Whyte’s “conversational nature of reality” really just comes down to trying to do one thing: paying attention.

Pay attention to the things that energize you

Pay attention to the things that you do that excite others

Pay attention to the things you can’t stop doing

Pay attention to the places, people, and ideas that nourish you

Pay attention so you can find clues about what you should do next.

From a work standpoint, we are going through a shift from the industrial economy to a tech economy. This will upend our work beliefs, work norms, and ways of living. Paying attention is not only a woo-woo life strategy, it’s a practical way to stay connected with how the world is shifting.

One place worth paying attention is the internet. I believe it’s still a wildly underrated place for searching for clues in the conversational mode. If you can learn to mute, block, and filter the outrage, there is a wonderful long tail of hyper-curious people and incredibly interesting niches that have emerged. By sharing, replying, and engaging we can begin to notice what kind of curiosity rabbit holes we are being pulled toward.

For the last five years, I’ve been exploring the topic of work and our relationship to it. I’ve talked about this topic with hundreds of people and engaged with thousands through my writing and musings on Twitter. If I had to rely on talking about these ideas with the people I knew in real life, I would have run out of people in a month.

Twenty years ago, I would have had to find refuge in Academia or journalism. Within those worlds, I might have found people willing to engage in the kind of conversation that might light me up but I likely would not have had as much freedom to craft my ideas in an original way.

I’ve been genuinely surprised at the positive reaction to my book online. I’ve sold nearly 2,000 books in less than three months and have had incredibly strong responses from many people. I’ve been getting messages like this every few days.

Yet maybe I shouldn’t be surprised.

With my writing, I’ve just been trying to pay attention to what I was experiencing and testing these ideas in literal conversations with others. I’ve been riding a curiosity slipstream aligned with what people are really experiencing and iterating on those ideas over and over.

If I was playing “getting ahead” with my writing and trying to fit into the current models of how to succeed, I would have paid much more attention to what “authorities” had to say about the idea. I might have gotten more clicks in the short term but I definitely would have short-circuited my curiosity.

The internet has created a long tail of curiosity that has made it much easier to find your own personal “conversation” with the world. Not only that, it enables people to go much deeper on topics and for much longer.

Four years ago in Taipei, I had no idea what came next. Yet I sensed that I should be writing and sharing ideas online instead of doubling down on my freelancing work. I couldn’t have made a convincing case that this was smart yet every bone in my body told me it was the way forward. This was about a year into my self-employment journey and that was about how long it took to unlearn the automatic tendency of shiting into “getting ahead” mode - the mode that does financial calculations and figures out what everyone else is doing so that you don’t look too silly.

Yet when we first are presented with clues, they are hard to decipher. There is no plan and while I had a strong pull towards writing, it was only the beginning. I had to continue to pay attention and tweak my approach and mindset continuously over the past several years. Do this long enough and you start to trust the journey.

This is also what makes it so hard to give advice about these sorts of things. Just quit your job and wait a while and clues will start to show up, trust me. I think this is likely true for most people but it sounds like insane advice.

Nearly all the money and all the good things that have happened to me in the past four years can be traced back to daring to begin that new conversation with the world in the fall of 2018.

Will I still be writing about these topics in ten years? I don’t know. Will I write another book? No idea. I sense I’m at the beginning of a new conversation but I’m not quite sure what it is yet. Ten years ago, this uncertainty would have nudged me to pick a path, one that could be understood by others. Yet now I know that the key is really to just continue to pay attention. And this is likely a better strategy for more and more people.

Look for clues. Observe your energy. Listen to others. Find your curiosity slipstream.

With the “conversational mode,” I sense that I might arrive at the same destination that I would otherwise but it feels a bit slower, more deliberate, and ultimately, more fulfilling.

I’ll close this one out with Whyte’s poem which is even better if you listen to it here.

Everything is waiting for you

Your great mistake is to act the drama
as if you were alone. As if life
were a progressive and cunning crime
with no witness to the tiny hidden
transgressions. To feel abandoned is to deny
the intimacy of your surroundings. Surely,
even you, at times, have felt the grand array;
the swelling presence, and the chorus, crowding
out your solo voice. You must note
the way the soap dish enables you,
or the window latch grants you freedom.
Alertness is the hidden discipline of familiarity.
The stairs are your mentor of things
to come, the doors have always been there
to frighten you and invite you,
and the tiny speaker in the phone
is your dream-ladder to divinity.

Put down the weight of your aloneness and ease into
the conversation. The kettle is singing
even as it pours you a drink, the cooking pots
have left their arrogant aloofness and
seen the good in you at last. All the birds
and creatures of the world are unutterably
themselves. Everything is waiting for you.

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#2 YouTube fun

I made a video about my Maslow article (the one where I show who really invented the pyramid). It was a fun process and I’ve been dabbling in Premiere Pro trying to get better at video editing. If you have any topics you want me to create a video on, I’d love to hear them.

I also made this video for my other channel on “A REAL day in the life of a consultant.” I wanted to have some fun and show the behind-the-scenes of what a consultant really spends their time on.

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