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... Jenny Wood!

Do you know Jenny Wood? She's a former Google executive, bestselling author of "Wild Courage," and someone who turned chasing a stranger off a subway train into an 11-year marriage and a philosophy for living boldly.

If not, allow me to introduce you. She spent 18 years at Google before becoming an entrepreneur and author who helps people push through the three fears that hold us back: fear of failure, fear of uncertainty, and fear of judgment by others. I wanted to connect with her because she embodies something I value deeply: the courage to act when your gut tells you something is right, even when your brain is listing all the reasons why it might go wrong.

Our conversation is LIVE now on the Just Press Record YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear her explain why "no is just an opening offer" and how to turn your weirdness into your greatest strength.

THREE: That's The Magic Number of Lessons

In the meantime, I wanted to pull THREE KEY LESSONS from my time with Jenny Wood 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: Flip Your Perspective With FLIP

Key Concept: Jenny's FLIP framework gives you a systematic way to evaluate whether it's time to make a change in your career. Real growth happens when you're slightly scared - when you have emails you don't know how to answer yet. If you're just going through the motions without butterflies, you're probably in incremental learning mode instead of the step-function learning that actually advances your career.

Personal Archive Note-To-Self: Fun is underrated. Or, at least misunderstood. I remember being in college, in a rare opportunity to sit in on a class that Jackie McLean was teaching (the jazz legend), and he started to explain how a big part of the problem with being a professional musician were the words society stacked against you. Stuff like how everybody else goes to work, but we play music. Jenny reminded me of it.

Just because a word feels out of place, doesn’t mean it doesn’t belong. Likewise, just because you’re at work, doesn’t mean it’s supposed to feel like torture. The only path forward, i.e. the only paths that aren’t designed to keep everybody in a box, require us to start by framing them as a task we want to do (and not just in exchange for some money on payday usually!).

When you lead with fun, then mix in learning, in the name of an impact, with a personal connection - you tee up pro-social progress. If you can spread that energy throughout your community, or your college, or especially at work/at your company, so many positive things can follow.

Work question for you: When you look at your current role through the FLIP framework (Fun, Learning, Impact, Personal), which element is missing, and what would it take to get those career-advancing butterflies back in your stomach?

LIFE: Embrace Your Weird As Your Superpower

Key Concept: Your differentiators aren't weaknesses to hide - they're competitive advantages to amplify. In a world where everyone is trying to fit in and follow the standard playbook, the people who stand out are the ones who lean into what makes them different. Your weird isn't a bug, it's a feature that can set you apart in meaningful ways.

Personal Archive Note-To-Self: I used to not talk about music at work. I used to not talk about people like Jackie McLean, or even Miles Davis, or anybody I thought was too obscure or narrow. Even though they meant something to me, since most other people wouldn’t know them, I edited them out. I did that for a long time. I can’t even imagine how much farther along my life and career would be had I not done that.

When you start allowing your weirdness into the rest of your life, you start sparking deeper connections than you’d imagined were possible. The other day I text a buddy a funny thought I had over “when I see UGC, as in user-generated-content, it always makes me think of UGK.” I had a good laugh over it. I thought of a few other people I should send it to, too.

And the reason I wanted to tell them, rooted in how we became more than work acquaintances in the first place, was we could make a reference like that to each other. If I had to stop myself midweek to appreciate how a UGK reference (they’re an 80s/90s Texas hip-hop group, FYI) was one common musical bridge I had beyond otherwise work relationships, you should stop and think about this too.

Your weirdness is like a weed. It just spreads in unpredictable ways. If you let it go, it will grow, and - it doesn’t have to be some invasive, ugly weed either. UGK and Miles - they’re like my wildflowers. The more I put them out there, the more people I find who are my people, and the more fun I have collaborating with them.

Life Question For You: What aspect of yourself do you consider "weird" or different that you've been trying to downplay, and how could you start treating it as a strength instead of something to hide?

LEGACY: Play To Win What You Need Now

Key Concept: Success isn't about chasing someone else's definition of achievement or even your own outdated goals. Jenny's WINN framework forces you to get honest about what you actually need at this stage of your life, not what you thought you needed five years ago or what society tells you to want. Your ambitions should evolve as you do.

Personal Archive Note-To-Self: I simultaneously hate the alphabet soup of professional acronyms, and love the puzzle solving aspect of creating acronyms out of nothing. WINN is perfect in this way. Asking what I need now, and wondering about what you need now, is - a delightfully simple reminder of what’s going to grow the whole pie, for both of us, as opposed to just figuring out ways to divide it up.

Part of figuring out how to put one foot in front of the next is figuring out where you need to put each foot down next, in the name of progress. It’s such an obvious detail - how tactics, like steps, determine the success of any longer term strategy - but you have to think about it to not overlook it.

Whether we are helping ourselves or others, figuring out exactly where to put your foot down next, and keep moving in the right direction, is the smallest step in the largest, long-term outcome. When we act in service to micro motions in macro directions, we move mountains.

Legacy question for you: If you stripped away all external expectations and outdated goals, what do you genuinely need now at this stage of your life, and how might pursuing that create a more authentic legacy than following yesterday's dreams?

BEFORE YOU GO: Be sure to...

• Connect with Jenny Wood at ItsJennyWood.com

• Check out her book "Wild Courage" available everywhere books are sold

• Follow her work in keynote speaking and executive coaching

• Follow her on LinkedIn, Twitter, and Instagram

• 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.

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.