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. 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.

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... Naomi Win!

Do you know Naomi Win? She's a psychologist and behavioral finance analyst (working alongside prior guest on Just Press Record, Daniel Crosby), specializing in decision-making under uncertainty and the psychological factors that drive financial behavior.

If not, allow me to introduce you. She brings a rare combination of clinical psychology background and financial markets expertise to help people understand how they actually make decisions when the stakes are real and the outcomes are unknown. I wanted to connect with her because she embodies something I value deeply: the intellectual courage to sit with uncertainty rather than rushing to false certainty.

Our conversation is LIVE now on the Just Press Record YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear her thoughts on why uncertainty is the only condition where learning happens, how relationships require the same kind of risk management as investments, and her fascinating take on American individualism's impact on community.

THREE: That's The Magic Number of Lessons

In the meantime, I wanted to pull THREE KEY LESSONS from my time with Naomi 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: Repair Ability Trumps Compatibility

Key Concept: In professional environments, the ability to acknowledge mistakes, address misunderstandings, and repair working relationships is more valuable than initial compatibility or chemistry. Teams that can navigate conflict and miscommunication effectively outperform those that avoid difficult conversations. The skill of repair creates psychological safety and resilience.

Personal Archive Note-To-Self: My experience with working in small businesses/playing in bands/etc. up to the age of 25 can be summarized as learning to say and figure out, “This is f*****d up, are we still cool?” Contrast that against my experience of working for large corporations/trying to climb ladders, “This is f*****d up. Are you cool with actually fixing this or are you getting out of the way?” Well, f***.

Workplace repair and workplace abandonment show up differently at different scales. In small organizations, relationships stack on top of each other - you need Gary for his trombone skills AND his sense of humor AND because he's the only one who lives close enough to Anthony to drive him to band practice. When Gary screws up, you repair the relationship because losing Gary means losing all three things at once.

In larger organizations, relationships become interchangeable building blocks. You need someone who can do financial modeling - it doesn't matter if it's Aaron or Liz or whoever. When Liz screws up, the repair question isn't "how do we fix this with Liz?" It's "should we replace Liz?" The contribution matters more than the individual contributor.

Because in smaller communities, you usually join because you know how you fit in. You probably even know why you fit in, or, at least, somebody else is saying, "hey, we need you to do this because you're awesome at it." That's a magical formula for signaling mutual commitment to a relationship AND a mission.

The larger the organization, the bigger the gap between who you are and what the job description needs. When something breaks, the only repair that needs to happen is, “if you can't get it done, who else can?”

This is why Naomi's insight about repair mattering more than compatibility hits so hard when you think about where you want to work. If you value being seen as a whole person rather than a replaceable function, you need to focus on organizations that understand the significance of relationship repair. It's an attitude as much as an operating system for well-being.

In the eternal words of Too Short, “Get in where you fit in.”

Work question for you: Think about your most productive working relationship—how did you both handle the first major disagreement or mistake?

LIFE: Uncertainty Is Where Learning Lives

Key Concept: Instead of viewing uncertainty as something to avoid or quickly resolve, we can reframe it as the natural state where growth happens. Our brains are literally designed to gather more information and stay alert when facing the unknown. The discomfort of uncertainty signals that we're in a position to learn something new, if we can sit with that discomfort rather than rushing to false certainty.

Personal Archive Note-To-Self: The need to get in where you fit in above, it's not just my normal Short Dog appreciation PSA, it's me genuinely calling out this point of failure that I see Naomi saying you can learn from. She's right. I've learned from failure many times.

One of the worst feelings I've ever had, is doing work, on a "team," where people talked about "we’re like a family" and all those types of “but, are we? really?” values, and they manifested in me feeling way way way uncertain about where things were actually going - because what they saw as a fit and what I felt as a fit seemed off.

It seemed f****d, honestly. But, when people want you to get a job done and you're at least mostly getting that job done, they can and will ply you with certainties about the quality of your work and where things are heading. It's good large-company strategy, you can't get mad at it, but you can learn, as I had to, to respect what is and isn’t “you.”

Here's the thing though - that uncertain feeling? That's your neurological system doing exactly what Naomi described. Your spidey sense starts tingling. The off feeling is the out-of-alignment you know to be true, even if you can't verbalize it yet. When the off feelings start, your brain will start purposefully taking in more information, staying alert, trying to figure out what doesn't match and why. At a multisensory level.

You can get crazy good at overriding these emotions too. You're not in the jungle, there aren't snakes, so you can talk yourself out of it. I'm crazy good at this evasive logic. But it's a mistake to totally outsource your judgment to other people's certainty. People can and will tell you that's not a snake on the ground and to just chill and go back to work, but it doesn't mean the person isn't a snake, or even in a lesser way, that they don't have your alignment as part of their ambitions.

You can fail to honor what you're feeling and fail to learn a life-changing lesson. Their certainty isn't your certainty. But feelings tell you when that's happening. Feelings will tell you when you got it right. Learning to notice that alignment, when it's out of whack, has changed my life. It hasn't perfected it, but I've learned - and continue to learn - this lesson, deeper and deeper.

Life Question For You: What uncertain situation in your life right now might actually be an opportunity for learning rather than a problem to solve?

LEGACY: Self-Trust Is Our Only Real Certainty

Key Concept: In a world where we try to micromanage everything from Uber arrival times to social media feeds, the fundamental truth remains that uncertainty is the only guarantee. The antidote isn't more control or prediction, but developing deep self-trust—the confidence that we can handle whatever responses life gives us. This self-trust becomes the foundation for taking meaningful risks in relationships and life.

Personal Archive Note-To-Self: When you feel like you're bad at everything, because nothing is going your way and nothing is working out, and everybody else seems to have an easier time with everything compared to you, your self-trust is running on empty and you'd better do something about it.

I ended up in therapy which, in hindsight, is a lot better than a lot of other places I could have ended up when I found myself there. I got help, I started rebuilding and recharging all sorts of relationships in my life, I changed jobs, I started having fun again, and - it can be done, but it starts in self-trust.

Here's the thing though - I still don't entirely trust myself(!). I know my track record. I've gone through the shame and embarrassment of processing it with the help of professionals (and I still will pick through it from time to time, but, OK, so what, I know it's the past too). The point is, my self-trust today doesn't get to resolve things I did previously, which means it also doesn't solve for everything that happens next.

And that's exactly Naomi's insight about uncertainty being the only real certainty. I fully expect life to deal me some more blows even though I really hope it doesn't. But the lessons learned, the ties to knowing what good and bad alignment feels like, I now have a basis for why I trust myself more. And that makes all the difference as I run into the next rounds of rejections and unexpected face plants.

Self-trust doesn't eliminate uncertainty - it gives you confidence to handle whatever responses you get. Those friends, and work people, and spouses that we find (yeah, seriously!)- I know this very personally - your alignments and their alignments are built on your self-trust like a system of bridges. The mutual support becomes possible because we're all betting on our ability to handle whatever comes next together.

My life today is the closest to OK I've probably ever felt because of this reason. I just had to get in where I fit in. I should have listened even closer to Too Short all those years ago, eh? (OK, not everything he was saying, but, self-trust, you know?)

Legacy question for you: Where in your life are you avoiding action because you can't guarantee the outcome, and what would change if you trusted yourself to handle whatever happens?

BEFORE YOU GO: Be sure to…

• Connect with Naomi Win on LinkedIn (her preferred professional platform)

• Consider how uncertainty shows up in your own decision-making

• Take a moment to practice sitting with one uncertain situation instead of rushing to resolve it!

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.

Last thing: 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.