Which Way Is North

Where do you look to find humanity? What is the purpose of creation? How can we find our place within or beyond technology’s reach? Questions start conversations. Answers end them. This podcast takes the quest in questions to explore the infinitude of human experience by welcoming guests to discuss what arises for them when asked seven strategically open questions from the book, ’Which Way Is North: A Creative Compass for Makers, Marketers, and Mystics” by author and host, Will Cady. Join for conversations with artists, entrepreneurs, cultural leaders, mothers, fathers, authors, models, speakers, strategists, and good human beings who are each given the opportunity to choose their identity: speak their truth underneath their given name or stretch out behind the anonymity of an archetypal name. Which of these do you suppose yields a conversation with more humanity? Listen and decide for yourself. Learn more at willcady.com

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Episodes

Tuesday Apr 15, 2025

There’s a question keeping the scientists up at night. 
 
Are we aligned?
 
You’ve most certainly heard of alignment before. Maybe from an auto mechanic talking about your tires. Maybe you heard your chiropractor mutter something about aligning your spine before cracking your neck. Or maybe you’ve got some core childhood memories of your mother, eyebrows raised, asking “are we aligned?” at the end of a stern talking to.
 
Well, the ‘alignment problem’ as its known in scientific circles probably resembles that last context of stern parenting the best, but with a dash of auto-mechanic and an extra helping of profound existential dread. 
 
The short of it is this: if we are to develop a super-powered artificial intelligence (referred to as AGI) that is not aligned with humanity’s values, wants, and needs; we stand to risk total destruction of the human species. The long and dry of it is this proper definition: “alignment aims to steer AI systems toward a person's or group's intended goals, preferences, or ethical principles. An AI system is considered aligned if it advances the intended objectives. A misaligned AI system pursues unintended objectives.”
 
The alignment problem is often articulated with a story about paper clips. Seemingly benign, the task is given to a super-powered AGI to ‘manufacture as many paper clips as possible’. Given that simple set of instructions, it arguably would inevitably consume all available matter, including human flesh, as means to achieve its end goal to ‘manufacture as many paper clips as possible.’ We should have known it would be Clippy to bring about humanity’s doom in the end. It was always Clippy. The alignment problem was always there as a warning every time we tried to resize an image in Microsoft Word.
 
Anyways. This is a real problem! It’s one that has quite a lot of the brightest minds in the scientific community darkened by deep, urgent concern. It’s quite sensible given the daily yield of new headlines from the rapid acceleration of AI technology; a march of progress propelled by developers whose profit motivations match - perhaps exceed - researcher’s concerns. One technology spanning two communities at the spearhead of human development. One moves at the speed of business growth, the other at the speed of scientific certainty, which leads me to what I believe is the true core of this issue:
 
Alignment is a technology problem second and a culture problem first.
 
How can we build AI to be aligned with humanity when humanity can’t even align with itself?

Episode 6: The Calibrator

Tuesday Apr 08, 2025

Tuesday Apr 08, 2025

Change is a constant. I remember learning this very young, but what life has taught me since that I didn't expect is that change doesn't just happen constantly on the outside, it also happens constantly on the inside.
Just as much as your circumstances change, who you are as a person changes with them. Just as much as the people, the environment, the events in your life continue to evolve and unfold, so too does your inner journey of discovering who you are.
So how do you navigate that? How do you navigate two turnings, an inner and an outer, at the same time? There are people that are here to help. Our next guest is one of these people.
They refer to themselves as "The Calibrator" in this conversation. I think it's great because I take that as like the tuning of a musical instrument, which fits because the best that we can do amongst changes is to find harmony. I asked them how they want to share a bit of what they do with our audience and they sent me a text with a gorgeous bit of writing about the role of communication in the process of really uncovering who we are and how we learn to navigate the environments and the people that are around us. They wrote:
"We've all had the experience of saying the wrong thing to someone and getting a response we weren't looking for. This happens every day in our work lives and in our personal lives. Why is this? And more importantly, is this a foundational truth of being human? That we can't reliably and predictably communicate to each other and that we will sometimes just plain miss?
This is the question that initiated a journey into human discovery, development, and bespoke individual qualities that has brought me to the present day. I started with a relatively simple premise. We are all personas that are crafted from a set group of native qualities that are baked into us. We all have the same four types of qualities and we all have different unique qualities that are reflection of us as individuals. Since we are all different, we all communicate and receive communications differently. If we want to always get through, connect, and reach our fellow humans, the solve is to start by understanding how everyone receives communications on an individual level.
I created a system for this, which evolved into an algorithm and code for unpacking people. If we can understand how to communicate with each other, we can also learn how to do so strategically. So we can actually motivate each other and put our entire community into flow. With this challenge, the journey unfolded."
And unfolded did. This person, The Calibrator, is, I would say, a master of navigating change through grace, with grace, and communicating through change to hold people together brilliantly.
As you'll hear in the conversation, we met at a time of, you know, changing environment. They had just moved from their family home for years into a new environment, a new chapter. We were looking around the house and talking about all of the things, all of the stuff, and the stories that that stuff carries. We talked about what it means to stop and then start again, to transition from the old into the new.
What you'll also hear is that house is in the Pacific Palisades. Where we sat and had the conversation is gone. It's ash now - and everything that we were talking about burned with it. In the days and weeks that followed, we communicated. We communicated about how that experience was, how this person, The Calibrator, was doing. What I saw is somebody that deepened their well of strength, deepened their connection and their communication with the people around them through an incredibly arduous journey.
So listen closely to what this person has to say because their story and their wisdom is going to be valuable for you whenever you face some of the hardest trials in your life. The most important thing that you'll be reaching for then is...how to communicate with others.
 

Episode 5: Jenny Boyd

Tuesday Apr 01, 2025

Tuesday Apr 01, 2025

Culture is the output of community.
Few people understand what this means better than our next guest, Jenny Boyd.
To explain who Jenny is, it's best to actually just read the bio from the jacket of her book, Icons of Rock. It reads, "Jenny Boyd is a former 60s model and the younger sister of Patty Boyd, who was married to George Harrison and Eric Clapton. Married to Mick Fleetwood twice. Jenny has been immersed in the world of rock and roll since her teens. As a rock star muse, Jenny even inspired Donovan and Mick Jagger to write songs about her, including Donovan's famous hit, 'Jennifer Juniper'. A good friend to The Beatles, she worked at their retail venture, Apple Boutique in London. In 1968, she accompanied sister Patti on the band's visit to Rishikesh in India, where they studied transcendental meditation with Maharishi Mahesh Hiyogi. Jenny co-wrote two songs for the band Fleetwood Mac, although the group's manager gave the writing credits to her husband, Mick Fleetwood. She earned a PhD in psychology and spent many years running an addiction treatment center in England. Jenny's critically acclaimed memoir, Jennifer Juniper, was published in early 2023."
We came together around the release of this book, Icons of Rock, because we share an interest in the inquiry of this question: Where does creativity come from? As Jenny has shared her story with me, that has been a bit of a through line for her. So in this conversation, I'm digging into the community level - the human level elements - of the creation of a culture that is absolutely mythic to me.
I grew up as a musician with a band striving for rock stardom. That entire story is one that was really burst into being by the story of the Beatles, by the story of Fleetwood Mac. And Jenny was there. That trip to India is the trip that created the white album. I mean, that is a monumental piece of art and culture. Her sister, Patti, is supposedly the inspiration behind the song, 'Layla'. That is my sister's name. So there is something deeply synchronistic in our coming together and having a conversation.
But for Jenny, these are her friends, her family. For so many around the world, the idea of these things as culture creates a distance from the humanity of what it is that created these inspirations for us. For Jenny to be a part of these scenes, a part of these communities throughout all of her life, and then have the wisdom to pursue a PhD in psychology, to do clinical work for addiction, and to then become an author asking these questions is an absolute gift to all of us.
She is providing us with a North Star to understand how does this happen? How do great art and great culture get made? And in this book, Icons of Rock in Their Own Words, is transcriptions of many conversations that Jenny herself has had with incredible luminaries asking them, what is it that's taking place for you on stage, in the studio, in the writing process? Where does that creativity come from?
That is her gift to all of our benefit. So drop in, give this conversation a listen.
This is Jenny Boyd.

Tuesday Mar 25, 2025

How do you get to the place where knowledge is power, when so much information is poison? Well, it starts with how you start your day. How quickly do you reach for your phone and start scrolling through the feeds? At which step from bed to bathroom to kitchen to stepping out in the world do you tune into the news?

Episode 3: The Artist/Wizard

Tuesday Mar 18, 2025

Tuesday Mar 18, 2025

I was at a gathering recently at the home of our next guest where someone said something so stimulating to my ears. They said, "a wizard knows the hidden paths." That was really interesting to me because this event itself was what could best be described as a 'gathering of wizards.'
 
Now, 'wizard' is a term that has been eclipsed in recent years by the term 'shaman.' When people are trying to describe a person of magic, they are talking about somebody that brings that magic and humanity to bear in service to their community and to the culture that they're a part of. Our guest for this conversation is a tremendous teacher of people like that...wizards.
 
What makes them a tremendous teacher is in the way they speak, the way they teach, the way they offer their knowledge. They share with a sense of childlike wonder, not with the cumbersome, burdened by the weight of authority sort of voice of a teacher that I think too many of us have grown accustomed to or have experienced in our paths through academia or our careers. No, this is somebody that exists in a state of awe and holds that awe for you. One who shares awe with you is a true teacher. That is the kind of teacher who can show you what an idea like 'hidden paths' really means.
 
An idea like 'hidden paths' is describing truths to life that don't have signposts, at least in the ways that we understand them. They're not drawn in the kinds of lines that you might see on a sign or on a screen or on a page. They're not so visible as much as they're...felt. By being in that place of awe, that place of wonder, a teacher of wizards is holding a bit of a compass for others to help them understand how it is that they feel and how they can behold the paths that might become apparent to them and guide them through their life. The way that I experience some of these hidden paths, is in the in-between of the perceiver and the perceived. It's a forgotten scent in a perfume as somebody walks past that brings you back to a core memory. It's a symbol, a color, a place, a breeze, something that evokes a deeper recognition of where is it that you come from and where is it that you're trying to go.
 
To the artist and wizard, these paths are out in the waking world. They are in the pages of books. They are in the master strokes that they see on paintings. This entire conversation that you're about to be a fly on the wall for is a teaching from one of the greatest wizards I know, sharing their awe about how they followed the hidden paths in their life, how they interact with the masters and the paint strokes that they have left behind for us to learn from. Through their sharing of their awe, they invite me and through me as you listen to this conversation, they invite you to be in that reverence of life with them.

Episode 2: The Madame

Monday Mar 10, 2025

Monday Mar 10, 2025

What you're about to hear is an intimate search for humanity. In particular, it's a lot of me trying to understand the feminine part of humanity. This conversation took place at the very end of my almost decade run playing my role in building Reddit into the business that we know today.
 
On my very last day, I had taken a trip to London to speak at an event in Soho, and my last words as an employee of the company were, "my name is Will Cady, I'm from Reddit, we remember the human." Then I walked off the stage and basically hopped on a train from London down to Paris where I met this woman.
 
We spent the next few days just falling into each other in the potential of the question mark of whatever it is that comes next. Paris is an astounding city to do that in. It is a living museum of humanity. It in particular has this profound feminine undercurrent of love, eros, for humanity has this nurturing and sensuous perspective on the human story. That love for you humanity is captured in stone. It's captured in monuments all over the city.
 
Between lavish meals, we were running, we were walking, we were skipping, we were dancing, an we were riding bicycles all around the city. I have this one incredible memory of the two of us together, navigating through the rain, hiding under one umbrella. We had walked down the Champs Elysees towards this obelisk that we saw in the distance and it led us to this Atlantean looking fountain and this woman, she stepped out from the umbrella, she started twirling in the rain and as she was twirling we saw down an avenue from that strange Atlantean looking fountain, this Greek temple building. It was the church for Mary Magdalene. We walked up the steps to this to get out of the rain, which was getting heavier. When we stepped inside, there was a string quartet that was performing Vivaldi's Four Seasons. So we sat in the pews, we listened to this incredible musicianship and just absorbed the power of the architecture and the way that those sounds resonated within it.
 
When it was done, we stepped out of those front doors and there was a massive rainbow right in front of us. It was a moment that felt like synchronicity and blessing for being human. It felt very Mary-esque (for those that are familiar with that archetype) not just the mother Mary, but the Magdalene Mary. There are so many esoteric secrets and journeys to go into the meaning of human archetypes like those and they're all there for you when you walk the streets of Paris.
 
After that we settled in, got a bottle of Margaux, and we had this conversation for this podcast. For me, this conversation was one of openness and discovery of the experience that I don't know about...how it is to be a woman in this world.
 
Give it a listen. Hope you enjoy.

Episode 1: About The Podcast

Monday Mar 10, 2025

Monday Mar 10, 2025

See the best in each other, get the best in each other. That's the simple principle at the core of the Which Way is North podcast. Join me and my guests in a search for our humanity as we do what humans do best...talk.
 
This episode shares an overview of the seven questions structure of the podcast along with some stories about the podcast's creation and intention. As you listen, think about how you yourself might answer these questions right here and right now:
 
What is in front of you?
What is behind you?
What do you rest upon?
What shines upon you?
What do you receive?
What do you give?
What is in your heart?

Episode 0: About The Book

Saturday Mar 08, 2025

Saturday Mar 08, 2025

Where does creativity come from? The answer is unique for each of us—our True North—and this book that inspired this podcast will help you find yours.
As artificial intelligence gains an increasing foothold in our work and our lives, the need to find and maintain our uniquely human creativity is growing more urgent. This guide will ensure that you stay on course as you navigate through the complexity of modern times. It will help you open new pathways to creativity and equip you with tools for your personal and professional journey to becoming a conscious participant in creation.
Through a combination of essays, meditations, and memoir, Which Way Is North offers an illuminating journey into the interior of the human heart and mind, revealing how your inner experience informs who you can be and what you express out in the world.

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