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... Mat Cashman!
Do you know Mat Cashman? He's Head of Options Education at the Options Clearing Corporation (OCC), a saxophonist, a trader, a teacher, and one of the most thoughtful people I know about the relationship between practice, performance, and what it means to build a life worth living.
If not, allow me to introduce you. Mat has spent decades thinking about mastery - first as a professional musician, then as a pit trader, and now as an educator helping thousands of people understand options markets. But what makes him truly exceptional is his refusal to compartmentalize any of these identities. He brings the discipline of practice from music, the high-wire intensity of trading, and the vulnerability of a lifelong learner to everything he touches.
I wanted to connect with Mat because he embodies something I value deeply: the willingness to dissolve the armor of who you thought you were supposed to be, so you can become who you're actually meant to be.
Our conversation is LIVE now on the Cultish Creative YouTube channel (and this Just Press Record playlist). Listen and you'll hear Mat and I working through the difference between practice and performance, why mastery requires both, and how to stop calcifying the same skills over and over again when what you really need is to put yourself into discomfort.
THREE: That's The Magic Number of Lessons
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Mat 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: You Get To Decide What Makes You Uncomfortable
"The real interesting part about this is the actual knowledge of that. The idea of self, in that way. It is really important because you get to decide how you spend your time practicing and what you practice, and that can be a musical thing, it can be in your personal life, it can be in your work life - whatever it is. And, constantly pushing yourself into those parts of it, that are uncomfortable, is the way that you get bigger. Right? It’s the way that you expand your capabilities."
Key Concept: The distinction Mat is drawing here is between practice as comfort and practice as growth. Most of us practice what we're already good at - it feels productive, it builds confidence, but it's actually calcification. Real practice requires choosing your own discomfort. You decide what domain to enter where you're incompetent. You decide to be the beginner. That decision - that act of choosing - is what separates people who expand from people who just repeat.
Personal Archive Note-To-Self: I remember a point in middle school where, I was at this nerd summer camp for a week, doing these late 80s/early 90s robot experiments, and thinking, “This is something I could be OK at, but I’ll never be good at it, let alone great at it.” The fantasy of what was cool was meeting the reality of how good some of the other kids were at making these logic-programmed bots do stuff that, while I could appreciate, I knew it was corny.
For me. Not for them. I bet some of them are rich and running the world now. But it wasn’t me. If I tried to force it, I’d have calcified in and on that practice. But since I didn’t, somebody else gets to, and I can still appreciate the reality of my own limitations.
When Mat talks about the choice of spending your time and where you practice, I can’t help but think about how great a role our own intuitions play. There’s only so much overriding we can do. It’s important to know how to override a little, so you don’t just quit or tap out in the face of resistance, but it’s also important - because the world is a full of people and we all get a shot to be ourselves.
Work question for you: What are you practicing right now that's actually just comfortable repetition? What would happen if you intentionally chose one domain where you're genuinely bad at things?
LIFE: Don't Put That Part of You in a Closet
"It occupies a different space for me. The horns, my saxophones, stay on stands out of their cases for a very specific reason - if I put them in cases and put them in closets, what I have done is put that part of me in a closet and I don't want to do that. But I also have to recognize that it occupies a different space now than it did previously. I need a certain amount of liquidity that saxophones didn't provide. That's part of the reason why I got into trading in the first place. I was a professional saxophone player for a while, and it's a rough life and it's hard to make money. But sax occupies a different space for me now, just within my personality.”
Key Concept: This is about honoring the evolution of what matters to you without abandoning it. Mat's saxophones aren't on stands as a performance statement - they're there as a daily reminder that this part of him still exists, still feeds him, even if it occupies different real estate in his life than it did 30 years ago. The insight isn't about choosing between old identity and new identity. It's about refusing false choices. You can be less invested in something and still refuse to put it away.
Personal Archive Note-To-Self: I had a guitar out in my office until winter set in and I found out that my dog, Jack, really wanted to chew the guitar stand which was bad both for the stand’s standing qualities and Jack’s intestinal qualities. But, while it was out, I loved the reduced friction of “you can just pick this guitar up, now.”
Like Mat, I want the reminder that a part of me still exists. It’s part of why I like being surrounded by books I’ve read and haven’t read yet too. Life is full of broad reminders of where you came from, where you are, and where you might go.
The guitars, the art, the books in my creative space in the house are all calls to who I’ve been, what I love, and what else keeps me on the track in the direction I’m going. Not because I know where I want to end up, because I love the slashes that constantly remind me to be more me.
Life question for you: What part of you are you considering putting in a closet? What would it mean to keep it visible, even if it's not your primary focus anymore?
LEGACY: The Joker Scars Were Never Intentional
"There's a certain amount of this which is interesting that you and I share - we were both musicians first and then work in finance second, and we have to kind of create the slash. Whether we like it or not, whether it was intentional or not. So we have some joker scars. It's fine. We're smiling. I didn't do it on purpose. I just did it. There's a certain amount of it that wasn't intentional, but it's there. And there's a part of it too, that's based on how people react to their own hang-ups about whether you're a slash artist, or whether you're a jack of all trades and a master of none. That saying exists for a very good reason! But it's also not quite as relevant now as it used to be."
Key Concept: Mat is saying something radical here - that the unconventional path you didn't plan for, that happened to you by circumstance and necessity, might actually be your greatest asset. The old saying about jacks of all trades is losing relevance precisely because the world is getting weirder and more specialized simultaneously. A person who brings a musician's discipline to finance, or a trader's intensity to education, has a fingerprint nobody else has. The scars aren't evidence of failure. They're evidence of interesting living.
Personal Archive Note-To-Self: Mat gets bonus points for the Batman reference. And the more I replay his idea in my head, the more I think that the Joker scars can’t be seen as failures. Or, at least, if you think those scars are failures, then you also think that the Bruce Wayne complex that leads him to be Batman is also a failure, and it’s a hall of mirrors all the way down from there.
We have pasts that we don’t need to apologize for or be embarrassed about. We don’t have to talk or think about or dwell on them all of the time. But, we have to accept how they’re here with us. And the reality of showing up as yourself, that’s the reality of “we’re smiling.”
Legacy is the weird combination of experiences that make us, us, and how it effects how others become themselves. We can’t control most of it. We only control what we do with it. So if the little bits that make us special are our not-so-secret ingredients, why not lean into the best bits of all of them, to leave this world (unlike Joker) a little better than we found it.
Legacy question for you: What "joker scar" from your own path are you still apologizing for? What if that unexpected combination is actually your edge?
BEFORE YOU GO: Be sure to…
Connect with Mat Cashman on LinkedIn or X
Learn more from Mat via his bio at the Options Industry Council
Explore the Options Clearing Corporation's educational resources at OptionsEducation.org
Take a moment to sit with the difference between practice as comfort and practice as growth in your own life
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
