No creative effort is wasted. There are many times when it feels like you’ve wasted your time drumming up an idea that doesn’t come to fruition. The more time I’ve spent in the creative field, the more I’ve learned that those supposedly wasted ideas eventually, inevitably come around to have their moment. When their time comes, whatever effort you put into them before helps you bring them forward quickly.
As part of my series about “authors who are making an important social impact”, I had the pleasure of interviewing Will Cady.
Will Cady, Reddit’s Global Brand Ambassador and founding head of Reddit’s KarmaLab creative strategy team, is in a unique position to listen to the real-time needs and concerns of thousands of media-driven communities today, while predicting tomorrow’s trends for culture. In his role as strategist, Cady has leveraged his uniquely blended approach of creativity and mysticism to counsel business leaders toward impactful, empathetic marketing of powerhouse brands in Tech, including Apple, Google, Samsung, T-Mobile, AT&T, and Adobe. He has worked with major household brands such as Toyota, LEGO, McDonald’s, Chipotle, and Coca-Cola. In addition, he has consulted with entertainment leaders at Netflix, Disney, Amazon Studios, Paramount, and more. Will Cady has appeared on stage in front of thousands at SXSW, the Consumer Electronics Show, Cannes Lions, and The Gathering. In 2020 he was named in AdWeek’s “Top 50” for Tech, Media, and Marketing. He is the author of the forthcoming book, Which Way Is North: A Creative Compass for Makers, Marketers, and Mystics (Matt Holt; October 10, 2023).
Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?
Glad to be here! Thank you for having me. As I’ve gotten older and broadened my horizons, I’ve learned to appreciate the unique elements that made me. We tend to take for granted what makes our homes special when we’re young because it’s all we know. It’s easy to assume the rest of the world is like your version of ‘normal’. Then you grow up and see how different the rest of the world can be, and therefore how special your home is.
What I’ve learned to love about where I came from is how much I grew up alongside history. I could jog to the Old North Bridge where the ‘shot heard round the world’ sparked the American Revolution just outside of Boston, Massachusetts. The stories about the people and the land I grew up with gave me some pretty powerful myths live within. The family I was raised in was, in a lot of ways, inspired by the spirit of writers like Thoreau who questioned the merits of modern society from his cabin on the banks of Walden Pond, where I happened to swim every summer. For my family, that countercultural spirit presented itself in wacky ways: with tie-dye t-shirts and Grateful Dead blasting out of the stereo in our house in the woods. It was a very Aquarian upbringing, which cemented in me a love of music, philosophy, and cultural curiosity from an early age.
When you were younger, was there a book that you read that inspired you to take action or changed your life? Can you share a story about that?
When I was very young, my mother used to read William Blake to me for my bedtime stories. How’s that for an odd upbringing? ‘Tyger, tyger burning bright’ was her favorite line to recite to me. My parents had a wonderful collection of books and music. It was like a little Library of Alexandria in our own house. The rule was, I could ‘check out’ anything, but I had to talk with them about it. It proved to be a powerful way to expand my mind from an early age and a wonderful way to feed a dialogue of shared curiosity with my parents.
As far as what book comes to mind first when I think of a single book that inspired me, it has to be Zen and the Art of Motorcycle Maintenance by Robert Pirsig. Whatever curiosity my parent’s library had sparked in me, Pirsig’s writing stoked the flame and it blasted me off in my early twenties into a voracious dive into philosophy for my own search for meaning. I think what impacted me so much about Pirsig’s writing was how well he described the experience of falling into your own internal world of thoughts, often at the cost of paying attention to what’s around you. In Robert Pirsig, I found somebody outside the walls of my home whose curious mind seemed to work the same way as mine and who had left a trail of exploration within it for me to follow. I felt, if not less crazy, less alone in being so.
It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
I love this question. It’s so important — especially right now — for us to cultivate a relationship of compassion and reconciliation with the lessons given by our mistakes. Like many of the young people today who have access to all the world’s information, I was often told that I was wise beyond my years. The pitfall of believing you are ‘wise beyond your years’ is that you haven’t yet had the years to fall short of your own wisdom. You will. Everyone does.
An early mistake that comes to mind for me has to do with learning how to be a musician and performer. I was a quick learner on the bass guitar, and I was a bit overly impressed with myself about how well I felt I could play. It was an ego thing. I was often so fixated on showing off my skill that I could forget to make music other people enjoy listening to. One night, my band had a huge show. We were fortunate enough to open up for a big band on a big stage at a very young age. It was one of our first gigs and it was in front of an audience of thousands. During soundcheck, I wasn’t paying enough attention to the stage crew who had pointed to a couple of pieces of electrical tape on the floor and told me to ‘stand on the X’.
When it came time to take the stage and play, I was so focused on trying to be an impressive bass player that I forgot to stand on the X. After the show, all my friends and family told me that they couldn’t see me the whole time. I’d literally missed my spotlight because I was so focused on the wrong thing. The irony!
The lesson? Don’t miss your spotlight from being too focused on the wrong thing. Also, always listen with full attention to the crew that is there to support you.
Can you describe how you aim to make a significant social impact with your book?
My book is the first step to a longer conversation. It starts with a reframe of our relationship with anxiety because I can see how paralyzed our culture is right now because of this. The idea I offer is that anxiety is creativity ready to be transmuted. This means that all this anxiety we’re feeling…It doesn’t mean there is something wrong with us. It means there is something for us to do. Anxiety is stagnant energy that wants to move. Energy in motion becomes e-motion. It’s the catharsis we crave. It’s also an invitation to empathize with each other, because we all have it.
We are all so blocked up with and being fed with so much anxiety every day that we can barely see each other, let alone communicate clearly. We have to come together as a humanity. Our capacity for creative collaboration has always been our gift. We can do amazing things when we come together. Finding the stories in the heart of our anxieties and using them as fuel for creation over destruction will get us through. I believe that.
More practically, my book offers some lessons carried over from my music education that I think will be very useful for establishing more coherent cultural dialogues. For example, one chapter spends a lot of time exploring how to think beyond polarized thinking, which asserts that for one idea to be true, another idea must be wrong. Getting more people to consider broader ways of thinking about each other’s perspectives will hopefully be an impactful contribution.
Can you share with us the most interesting story that you shared in your book?
Well, of course, I feel like my book is full of interesting stories! Readers will be the judge of that though. I had to cut quite a few stories I love in the editing process. Ultimately, I tried to focus the stories I included on a theme, which is the moments where I made a mistake and learned something from it because someone else was there to compassionately but firmly be my teacher in that moment. I feel like it’s critical to model both sides of these situations: how it looks to graciously accept when someone is correcting you and how it looks to gracious offer a lesson to someone when they’ve made a mistake. Talk about turning anxiety into creativity!
One story from the book I feel is especially important to this theme came after a group sharing session at the end of a retreat. I had been on a bit of an ego trip in my share, talking about all my grand plans and big ideas about myself. Afterwards, one woman in the group came up to me to chat privately to support my big visions by gently bringing me back down to earth. She was all heart and gave me such a powerful lesson I am so grateful for that I chose to recount our conversation as a critical scene in the book. It’s called ‘bad ass grounding’ and it’s about how being a leader for people means always thinking about what you can do for them over what they can do for you.
What was the “aha moment” or series of events that made you decide to bring your message to the greater world? Can you share a story about that?
My interest in writing a book stemmed from my love of books. I have built my own little ‘Library of Alexandria’ like the one in the house I grew up in. My happy place is when I’m surrounded by books in every direction all around me. I think artists have a need to not just surround themselves with what they love, but to contribute to it. Simply put, I wanted to place a book of my own on my shelf.
The ‘aha moment’ for this book came in 2020 when I was asked to start teaching meditation amidst all that incredible anxiety of those times. As an executive at my company, leading the creative strategy team, there were a few people that knew my calendar and were curious about the daily reminder I openly kept on it to meditate. That led to other people joining me for weekly meditation sessions where I began to share my private methods that I had developed to work with the relationship between anxiety (which I have a lot of) and creativity (which I also have a lot of). The response was so overwhelmingly positive that it signaled to me I had something worth sharing that just might help people. That is why my book, Which Way Is North is structured off my meditation system, the Seven Directions.
Without sharing specific names, can you tell us a story about a particular individual who was impacted or helped by your cause?
Eventually, I also began to teach the Seven Directions meditation online in various audio and video chat forums. These were social spaces, so it made sense to open it up to group discussions after the meditations for people to share whatever came up for them during that session. Some of what people shared in those discussions was incredibly vulnerable and filled my heart with affirmations that this system really works.
One story that comes to mind for me is someone who shared their personal breakthrough about a major life change. The Seven Directions meditation asks people to notice the stories that come up for them internally in response to seven different questions. For this person, a story came up with the question of ‘what is in front of you?’ It was a replay of all the odd, outsized anxiety they’d been feeling recently every time they were looking for a parking space for their car. In the meditation, they were able to reconcile that this anxiety wasn’t about the parking spots. It had been coming up for them in these moments as a metaphor for their fear of not fitting in to the new city they had just moved to. They were able to clock the meaning of the anxiety that had been bothering them and then relax into a creative expression of it that brought them peace. It was a beautifully clear example of exactly what the Seven Directions meditation is designed to do.
Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?
Prioritize the easing of suffering above all else. By putting anxiety on one side of a spectrum and creativity on the other, I’m offering an axis of consideration for leaders to work with. If you are someone with a voice people tune into and trust, my challenge to you is this: is your voice adding to the anxiety that is breaking down our culture? Or to the creativity that is helping it renew? How are your messages helping to ease suffering?
This does not mean ignoring hard conversations. It does mean entering those hard conversations with a spirit of compassion and reconciliation for all who are suffering within it — even and especially when you disagree with their point of view. Repair what is broken so we can create a better world. These are difficult times. Humanity can and must come together to make it through.
How do you define “Leadership”? Can you explain what you mean or give an example?
Leadership is a service, not a throne.
In a management context, social structures need individuals to be leaders because decisions need to be made by someone who has a vantage point across all points of view. This means being comfortable with the loneliness of a position that often asks you to make decisions not everyone understands because not everyone has access to all the information you do. This also means constantly investing in building trust and cohesion not just for you from your team members, but also for your team members with each other. Keep the information flowing so decisions and adaptations can happen quickly with a high rate of success. That’s the job.
In a cultural context, people need voices to articulate visions that move the dialogue forward. Your job as leader is not to uphold an illusion of your perfection. Nobody is perfect. Your job is to speak from the authority your honest reconciliation of your imperfections gives you. The greatest leaders are the ones who have experienced challenges others can relate to and have found a way through it other people can follow. It’s not about you as a person…it’s about your path. That’s what truly inspires people, I believe.
What are your “5 things I wish someone told me when I first started” and why?
- No creative effort is wasted. There are many times when it feels like you’ve wasted your time drumming up an idea that doesn’t come to fruition. The more time I’ve spent in the creative field, the more I’ve learned that those supposedly wasted ideas eventually, inevitably come around to have their moment. When their time comes, whatever effort you put into them before helps you bring them forward quickly.
- The people at the bottom often see as much as (or more than) the people at the top. When you’re at the bottom of the hierarchy at a company, you’re typically tasked with managing documents that track all the workstreams across projects and teams. Guess what? That means you see (almost) everything. Pay attention and you’ll learn something. Don’t just enter the information, make sure you understand the stories that information represents. Be curious and ask people questions about the work. They’ll appreciate you for it too. If they don’t…well, they might not be the best people to learn from.
- Learn the seasons and cycles. Both business and culture operate in cyclical patterns. Most pronounced is the calendar year which offers its quarterly fiscal cycle that determines when investment decisions are made and therefore what kind of work you’ll be doing when. There are also multi-year cycles that influence larger cultural trends. A new innovation emerges, start-ups begin to form around it, some of them start expanding after investments, then there are mergers, acquisitions and failures until the massive conglomerates absorb or invest in the companies that mature. The cycle repeats. People find their way as individuals or as teams that stick together throughout each phase of change in the cycle. Regardless of the approach, learn to notice which phase of the cycle you’re in for the industry or cultural movement you’re a part of. It’ll help you make smarter decisions, especially after you experience a few and can start juxtaposing cycles with each other. I’ve been through maybe five or so.
- Be good to people always; and own up to it where you learn you aren’t. People remember how they’re treated. Every industry, every scene is smaller than you think. If the moral appeal to kindness isn’t enough to persuade you to be good to people, at least recognize that the more trust you build among your peers, the more you become capable of. Here’s the catch though…You’re not going to play life perfectly. There are countless ways to lift people up just as there are to countless ways to make people feel down; even with the best of intentions and often in ways you never even knew you could. It’s okay. What’s not your fault can still be your responsibility…and surprisingly, an opportunity if you approach it with courage and heart. If the opening is there, acknowledge what you could have done better, ask for learning, and people will remember well. If the opening is not there, well sometimes it’s best to reflect on your own, take the lesson, and move on. Some of my most trusted allies are people for whom I’ve owned up to a mistake or who have owned up to a mistake to me. Integrity is a synonym for strength and it is built from trust.
- People buy opportunities, not ideas. As a creative, this has been a tough one to learn. In the marketing space, I have rarely ever seen a client buy an idea as it was pitched to them. Even when that does happen, the final output ends up morphing to something much different by the end. I have also rarely seen anyone react well to being presented with an idea ‘off the shelf’ that isn’t unique to them. Creative pitches are for starting conversations, not ending them. Similarly, in music, I had to learn that a good song is not about how you sound when you sing it, but how your listener feels when they play it. People want opportunities, not ideas. The art is in leading them to your ideas through the opportunities you give them.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
I asked my dad what he thought the meaning of life is. He said, ‘pass it on’. Now that’s what I say when people ask me too.
Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂
Killer Mike. I admire the brashness and boldness with which he conveys his messages while also being an honest community builder. I think I could learn a lot from him about how to be more fearless toward my creative purpose. Also, I’ve seen those restaurants he’s been opening so I know he’s got access to some legit food.
How can our readers further follow your work online?
I’m accessible on Instagram/Threads as @willcady and on LinkedIn as, well, Will Cady.
This was very meaningful, thank you so much. We wish you only continued success on your great work!
My pleasure! It’s a privilege to be here.
Social Impact Authors: How & Why Author Will Cady Is Helping To Change Our World was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.