For years, I've been connecting with interesting people and documenting insights that might help my clients and myself. What was once private is now (mostly) public.
People often ask: "How do you know all these people?" and "How do you connect these (re: random) ideas?" The answer is simple: consistent relationship cultivation and thoughtful note taking. My north star is trusting my instincts, my maps are the constellations in these reflections.
This approach to multidisciplinary networking has helped dozens of clients, colleagues, and friends strengthen their networks and unlock new opportunities. Feel free to steal these ideas directly - that's what they're for! I can't promise you'll learn FROM me, but I guarantee you can learn something WITH me. Let's go. Count it off: 1-2-3-4!
Introducing... Dylan O'Sullivan!
Do you know Dylan O'Sullivan? He's a writer, editor, and thinker who refuses to settle for surface-level understanding. Currently Senior Editor at Infinite Books and unofficially the author of Normy McDylan: Based on a Twitter story, not a Memoir, Dylan moves through the world asking the questions most people skip.
If not, allow me to introduce you. Dylan's the kind of person who can trace a conversation from flat characters in fiction to the atrophy of human attention caused by short-form video - and make it all feel connected and urgent.
I wanted to connect with him because he embodies something I value deeply: the refusal to accept easy answers, and the relentless pursuit of understanding what makes art, attention, and identity actually work.
Our conversation is LIVE now on the Just Press Record YouTube channel (and this Cultish Creative Playlist, and check out the write-up on Panoptica). Listen and you'll hear Dylan wrestle with questions about presence, constancy, taste, and what it actually means to pay attention in a world designed to turn you off.
THREE: That's The Magic Number of Lessons
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Dylan to share with you (and drop into my Personal Archive).
Read on and you'll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.
WORK: Make the Stone Stony
"It takes what we have familiarized to the point of becoming invisible to us, and it makes it strange. It kind of takes away that wallpaper sheen and makes us see it again. So his example is it makes the stone stony and then all of a sudden we're aware of the stoniness of the stone. And I think there's a remarkable amount of stuff that I'm particularly bad at this. Well, if you ask me what the carpet color underneath my feet right now is, even this is my bedroom, it would take me 20 seconds and I'd give my best guess. And there's just so much around us that we don't know and we are blind to."
Key Concept: Defamiliarization is the act of making the invisible visible again - taking what we've stopped seeing and forcing ourselves to really look. Dylan's pointing to a problem most of us have: we live surrounded by things we've completely tuned out. The carpet under your feet, the forest you walk past every day, the details that make up your actual life. The work is noticing what's become wallpaper. That's where real attention begins.
Personal Archive Note-To-Self: There’s the scene in Guys and Dolls, and it’s the scene with the greatest backstory but let’s just focus on the scene for a second, where a very desperate for cash to sponsor his craps game Nathan Detroit is pressuring Sky Masterson to make a quick money bet with him over numbers he already knows and therefore all but guarantees him with a sure win (“cheesecake or strudel?”). Sky, the consummate professional, recognizes the ruse and counters, “If you are really looking for some action, I will bet you the same $1,000 that you cannot name the color tie you have on.”
The familiar, the passive, the background noise of life - we all automatically suppress it. Artists and especially comedians make a living out of putting the smallest of details in absurd focus and, comedy or tragedy, it’s why noticing details in distinct ways is the core of the arts. Even in Guys and Dolls, Nathan ends up refusing the bet and then, “Polka dots! In the whole world, nobody but Nathan Detroit could blow a thousand bucks on polka dots!”
So what do you do about it? My only idea is to have an established routine of reflecting. If you don’t opt in to noticing the background noise, I think it only gets farther and farther away from us noticing as we get older. Especially if we’re busy, especially if our lives are noisy. All the more reason to have a Personal Archive (and rewatch Guys and Dolls for the billionth time, because the background detail attention makes every rewatch exciting).
Work question for you: What's one thing in your immediate environment that you've completely stopped seeing?
LIFE: Don't Turn Yourself Off
"I don't think TikTok, the platform, gives you a remarkable feeling of presence. I think it's the difference between self forgetting and self negation. I think those scrolling apps don't tune you in. They turn you off. And I think there are superficial similarities between those two things, but especially over long time horizons, they're chronically different."
Key Concept: Self-forgetting and self-negation sound the same on the surface - both involve losing yourself. But Dylan's making the crucial distinction, that self-forgetting is what happens when you're genuinely present and absorbed in something real. Self-negation is what happens when you're scrolling - you're not absorbed, you're just turned off. One is presence without ego. The other is absence disguised as ease.
Personal Archive Note-To-Self: There are so many examples of this contrast its almost impossible not get inspired to cite 15 quotes related to this gap. Joseph Conrad’s always near the top of my mind on this topic with, “Let them think what they liked, but I didn’t mean to drown myself. I meant to swim till I sank — but that’s not the same thing.” Ego plays such an important role in this, and I think that’s what Dylan was calling out.
Negating yourself is part of the picture, and seeing the situation as it is, rich with all of the naturally present details, and their context, and our raising levels of awareness once we opt to tune in - that’s a special type of turned on and tuned in ego-space. It’s where creativity comes from. It’s where self-actualization is - actually actualized? But forgetting yourself from the mix, drifting out passively into scarcely observant state of easy, that’s more biblical, and we all know who’s been in as many hotel rooms as the Gideon Bible, so it feels safe to quote Proverbs here, “Let him drink, and forget his poverty, and remember his misery no more.”
We all need breaks in life. This isn’t to argue against pauses that refresh. But we also need ways to step back and see what we’re living in, which includes testing ourselves, finding our limits, and coming to our own peace with the role ego plays in our own existence.
Life Question For You: When's the last time you felt genuinely present versus just passively turned off?
LEGACY: The Effort in Understanding
"How much of it is seed into bloom and how much of it is co-created with your will? It's a very messy picture with too many variables, but I think trying to hold onto who you are—and the effort in understanding it—that's what matters. I think a lot of people don't sit in silence and think to themselves or write to themselves and they don't try to answer those questions. It's easier to scroll and to not bother yourself with those kinds of things. But I think there's value in it, obviously."
Key Concept: We can't fully control who we become - that's partly nature, partly nurture, partly luck. But what we can control is the effort we put into understanding ourselves. That effort - sitting in silence, writing, asking hard questions about who you are - that's what creates continuity and meaning. Most people skip it. They scroll instead. But the people who do the work? They know themselves. And that knowing is where real legacy begins.
Personal Archive Note-To-Self: Dylan’s idea and encouragement to take more walks, and get short-term videos out of your life like sugar, it’s good advice. Silence, the old friend, is great for triggering reflection, even when it’s just thoughts skating across our minds.
Asking people when the last time is they stared out a window for a while, or just sat with a book, or basically did anything without a phone or a computer anywhere near them - it’s quality encouragement. I know it seems lite, but how often do you have a conversation with a friend about the last time you did nothing?
One of the best, legacy-adjacent moments in Guys and Dolls is watching people actually choose to open up space for each other. Adelaide and Nathan can't admit they already love each other. Sky and Sarah have to meet in a moment of genuine vulnerability. Nathan, Nicely, and Benny are friends because they show up. That's effort - not the craps game, but the showing up.
It’s about the effort we put in. And we need to both encourage ourselves and others, by nudge or example, that it’s worth it.
Legacy question for you: When was the last time you sat in silence and actually tried to answer a question about who you are?
BEFORE YOU GO: Be sure to…
Read his newsletter Essayful (and maybe your clicking on it will get him writing it more actively again)
Check out his work as Senior Editor at Infinite Books
Did you see Dylan’s original Just Press Record, when I introduced him to Luca Dellana? It’s so good.
Take a moment to reflect on all these ideas!
You have a Personal Network and a Personal Archive just waiting for you to build them up stronger. Look at your work, look at your life, and look at your legacy - and then, start small in each category. Today it's one person and one reflection. Tomorrow? Who knows what connections you'll create.
Don't forget to click reply/click here and tell me who you're adding to your network and why! Plus, if you already have your own Personal Archive too, let me know, I'm creating a database.
Want more? Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and listen to Just Press Record on Spotify or Apple Podcasts, and follow me on social media (LinkedIn and X) - now distributed by Epsilon Theory.
You can also check out my work as Managing Director at Sunpointe, as a host on top investment YouTube channel Excess Returns, and as Senior Editor at Perscient.
ps. AI helped me pull and organize quotes from the transcript, structure the three lessons, and sharpen the Key Concepts. If you're curious about how I use AI while keeping editorial control and my own voice intact, I wrote about my personal rules here: Did AI Do That: Personal Rules

