Lone Wolf, Letting Go

In pursuit of the question I cannot answer alone

“Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”

―Rainer Maria Rilke

I

Eight months ago, I was certain of my path. I’d spend my life as a solo creator, making my living as a lone wolf with a small, but mighty internet business. For the better part of a decade, I’ve reveled in that feeling of being unemployed and unemployable, a feral free agent who’d resist getting a Real Job with all his might. I sincerely believed the only way for me to give my gifts, and enjoy my life, was to go my own way.

Yet here we are, mere months later, with me heading up marketing and storytelling for Foster. Full time. My own business is on the back burner. And who knows, I may not return to it any time soon. If ever. In this emerging season of life, I’m all-in on Foster. It’s work that brings me alive, and I’m doing it alongside a handful of my closest internet homies.

There’s another life update that’s relevant to this story. Just as I’ve long worked alone, so too did I believe I needed to live alone. Yet as I write this, I’m packing up the one-bedroom apartment I’ve called home for four years, and getting ready to throw everything in storage. After that, I’ll be heading off to a semi-monastic co-living hub in the south of France. I don’t know when I’ll return.

It appears my Lone Wolf Era is coming to a close. The stories of self I’ve been standing on my entire adult life are dissolving beneath my feet. That ground has been shaky for awhile, but this summer I said “fuck it” and began making leaps of faith into my next chapter.

When I reflect back on these seismic changes, I can trace their origin back to a single question I began exploring three years ago. Questions, I’m beginning to learn, often have latent transformational magic buried within them, waiting to be harnessed by anyone who devotes themselves to living said question fully.

II

Over on Foster’s new Substack, we’ve coined a term for those big, ambitious questions that defy easy answers, yet still captivate and compel us to explore. We call them Frequently Unanswered Questions, or FUQs (pronounced “fux”).

Our contention is that FUQs, when we begin to live them instead of merely intellectualizing them, can snap us out of the patterns of sterility and malaise that often accompany modern life. Inhabiting our FUQs provides an abundant source of fuel for creative and career pursuits, of course. But it also puts us on the path towards individuation, or the process of becoming most fully ourselves. Inhabiting questions can help us come alive, find new allies, and begin rewriting the stories that keep us stuck.

Without quite realizing it, I’ve spent the last few years turning myself into a case study for this hypothesis.

There are a few big FUQs that have long lurked beneath the surface of my work. Chief among them, “How can I be the change I want to see on the internet?” That question has spurred every big leap I’ve made in my work life over the last decade. It’s been the impetus for side projects I’ve launched. And it’s at the heart of a book I just started writing (more info soon!) 

But there’s another FUQ that’s been fueling my journey this year—the one that’s currently helping me close the door on my Lone Wolf Era. 

III

One of the beautiful things about ambitious questions is they beget more questions. You follow the trail, staying open to whatever crosses your path, and then boom, there’s another question, and another—each more specific and finely grained than the last.

Even if you’ve only followed me for a bit, you probably know I have a bone to pick with the marketing industry. I’ve long been inquiring into how marketing might feel less like a zero-sum war of attrition, and more like a delightful infinite game. From that line of inquiry, new questions emerged. How would marketing strategy change if it wasn’t rooted in endless short-term growth, but instead in the disciplined pursuit of enough? How might I have to change and grow to implement such a strategy?

Somewhere along the way, I became fascinated by the mechanics of trust. Our world is caught in a downward spiral of escalating distrust, fueled in part by culture wars and a fracturing media ecosystem. This dynamic is paralyzing our institutions and making it harder to address the many interrelated crises facing our species. My hunch is that rebuilding our capacity to trust is at the core of what heals individuals, communities, and civilizations. How can trust be regenerated after years of atrophy? How might we rebuild trust both within ourselves, and at scale? What role could marketing play in all of this?

By following that trail, I ended up at the doorstep of the question that would change everything for me. What would marketing look like if it regenerated our ability to trust?

IV

Like most big questions, this one started out as an intellectual puzzle. I was compelled by the question, captivated even, but I wasn’t ready to live it yet. But still, I started my way down the path, reading far and wide at the intersections of psychology and sociology and relationships.

And then, my questions evolved in unexpected ways once again, this time leading me into the realm of spirituality and religion. Trust, I began to learn, isn’t so different from faith. We can never know with 100% certainty what’s in another’s heart, nor can we ever be unconditionally safe and in control. Nothing in the universe works that way. At a certain point, we have to let go, surrender, and choose love in spite of the risk that we might be hurt. That’s trust.

Despite believing all of this intellectually, what I didn’t see at the time was that my own life was radically out of integrity with those beliefs. As a lone wolf, my life was a shrine to distrust. I spent years actively choosing to cut myself off from the world because I was too scared to trust anyone else with my wellbeing. And I didn’t just choose the lone wolf path. I lionized it. I told myself a story that my way of living was good and righteous and true.

Looking back, this pattern makes perfect sense. As a kid, we moved around a lot. My stepfather managed high-end hotels, so we jumped from state to state, and even to Russia for a few years, as he got new gigs. I was never really able to form deep, lasting connections or feel a sense of rootedness. Somewhere along the way, I began telling myself a story that I didn’t need other people in my life. After all, they’d just disappear like they always had. For me, it was always easier not to trust than to risk getting hurt.

V

My habit of distrust goes one layer deeper, right down into my relationship with myself. For the last 15 years, I’ve used food to numb myself, and to run away from things I don’t want to feel. Everybody’s got their coping mechanisms, and mine has always revolved around consuming copious quantities of unhealthy food. 

Through all those years of binge eating, I developed a belief that I was fundamentally untrustworthy, that something in me was broken and twisted, and that it needed to be controlled by force. So that’s what I did. I allowed my “higher self” to put extreme dietary restrictions on my “lower self,” and enforced them as militantly as I could. It never worked, though. Not for long. Eventually the part of me that hates being distrusted and controlled would rebel, leading me back into binging. And the cycle would repeat, again and again. So it goes.

Last year I had what can only be described as an Oh Shit Moment. I realized one of the biggest underlying drivers of my binge eating has always been loneliness. Go figure, right? I’d long told myself a story that I didn’t need people, and I was great at rationalizing that story and living it. But some deeper part of me was always screaming out for connection and companionship and intimacy. This dynamic created a toxic stew of loneliness and cognitive dissonance, which instead of acknowledging and resolving, I ran from. I used food to numb it away and ignore it for well over a decade.

Whether with myself or others, I’ve learned that distrust only ever begets more distrust. It creates a self-fulfilling prophecy that, if left unchecked, leads to a life of disconnection and bitterness and apathy. The only thing that can break this cycle is choosing to trust again. Choosing trust when you have little reason to feels naive and dangerous. But increasingly, I believe it’s the most courageous thing any of us can do. The modern world makes it seem so sensible to double down on distrust, and further isolate ourselves in our comfortable little bubbles. But, as I’ve learned the hard way, that’s no way to live.

VI

A little over a year ago, I published a comprehensive essay about the philosophy of non-coercive marketing.

This was my first real attempt to articulate an answer to the question of what marketing would look like if it regenerated our ability to trust. And let me tell you, it’s one of the scariest things I’ve ever hit publish on. I expected people within the marketing industry to hate it, to rip it to shreds, to laugh at my naivety. I went out of my way to hedge by saying it was specifically aimed at solo creators like me. Not for anyone doing “real marketing.”

But then, the damndest thing happened. The essay caught fire, and started to spread. Within a week, it was featured in a pair of popular newsletters, racking up tens of thousands of views in the process. Marketers of all stripes started emailing me and sending DMs. Some were independent, or working on their own businesses. Some ran agencies. Some worked in startups and tech. Hell, some of them even worked in B2B enterprise marketing.

All of them said some variation of the same thing. “I love the philosophy you laid out here, but how do I implement it in a larger company like the one I work for?” To which the only truthful way I could respond was, “I have no clue. I’m just a lil solo creator guy lol.”

Hard as I tried over the next few months, I couldn’t shake that question. It stuck in my brain, nagging at me. What would non-coercive marketing look like in larger organizations? How might it scale?

It would have been so easy and convenient for me to keep doubling down on the creator space, and on applying non-coercive marketing to the paradigm of 1,000 true fans. That’s my bread and butter, and something that would have resulted in a wildly lucrative little business for me. But that line of inquiry lost its spark somewhere along the way. I felt myself being pulled to engage with the larger, scarier question. Resonant FUQs are like that. They’re seductive, magnetic even. They’re like an intriguing glowing doorway you walk past every day, trying to ignore, until one day your curiosity gets the best of you and you can’t help but crack it open and take a peek.

Once again, I started reading widely, this time diving into the depths of developmental psychology and organizational design. But it quickly dawned on me that if I wanted to fully inhabit this larger question, it wouldn’t be enough to just read and write about it. I needed skin in the game. Nor would I be able to do it alone. 

The time had come for me to choose between my Lone Wolf Era or stepping onto a new relational frontier. The time had come for me to choose trust.

VII

I’ve been part of Foster since its early days in the summer of 2020, back when it was a bootstrapped Slack community for writers. Since then, I’ve been along for every step of the journey as it’s raised money, pivoted, and veered into software and cohorts and retreats. There was even a crypto phase where we started laying the groundwork to become a DAO. It’s been a wild ride.

But one thing has never changed; Foster serves writers much in the same way I always aimed to serve creatives with Ungated. It’s about helping writers come alive, and express what is uniquely true and resonant within them. I’ve long been curious about the link between authentic expression and individuation. Foster is inhabiting that same question, but exploring it with more resources and collaborative firepower than I’d ever have on my own.

It’s not just the what of Foster I find magnetic, though. It’s the how. As an organization, Foster lives on the frontier of developmental culture, decentralized coordination, and collective ownership. Foster is actively weaving more trust into the foundation of its work culture, and working to rewrite the underlying story of how companies and institutions are built. It’s inhabiting another one of my favorite FUQs, “What would business look like if it nourished the human spirit instead of degrading it?” I can’t imagine more fertile soil in which to plant the seeds of non-coercive marketing.

When Dan Hunt, Foster’s founder, opened the door to me potentially taking ownership over the company’s marketing earlier this year, I was both thrilled and incredibly anxious. It felt so resonant, yet I was carrying a decade’s worth of accumulated distrust on my shoulders and in my body. I was still wrapping myself in a tapestry of stories lionizing my own individualism. Besides, my Lone Wolf Era wasn’t just an aesthetic choice. It was an emotional protection strategy, designed to keep me safe. I knew I wouldn’t be able to snap my fingers and change this dynamic in an instant.

All of which is to say, this summer has not been fun. In many ways, it’s been one of the more stressful, emotionally fraught seasons in recent memory. With each passing month, I found myself being pulled closer into the heart of Foster, and wanting to devote myself to it, all while there were constant warning sirens blaring through my head and body. Turns out, it’s not easy shedding the comfortable confines of longstanding stories. It’s not easy untangling the ways distrust and fear live in the body, wreaking havoc on new relationships. But I’ve been doing the work—emotional, somatic, spiritual—to step into this new era gracefully and compassionately.

Six weeks ago, I made the official leap to full time.

VIII

These last few weeks of full time work for Foster have been a whirlwind. It turns out, inhabiting big questions together can be even more enlivening than inhabiting them alone. The creative potential gets amplified to a remarkable degree. As such, I’m happy to report our non-coercive marketing efforts are off to one hell of a good start.

So far, we’ve replaced our website with an ever-evolving, collaboratively-written google doc called The Book of Foster. This is exactly as insane of a marketing decision as it sounds, while also being the highest integrity way for Foster to communicate its essence. We’ve started running free, artfully-facilitated writing groups, which are quickly becoming one of my favorite parts of the week. We’ve decided to be the change we want to see on Substack by fostering an intimate conversational scene instead of presenting ourselves as Experts with Answers. And as I write this, we’re gearing up to run one of our signature cohorts—this time focused on the power of inhabiting questions as a writer. Having been on this journey myself, I’m so excited to help guide other writers through the process of discovering and living the questions that matter to them.

And of course, over on the personal side, I’ve begun packing my entire life into boxes, and I’m getting ready for an extended stay at a co-living hub in the south of France. While there, I plan to make new friends and visit old ones who live across Europe. I plan to meditate a lot, specifically focusing on somatic awareness and coming into a more trusting relationship with my body. I plan to write more than I ever have, and make huge progress on my book. My biggest goal, though, is to work on developing a healthier relationship with food. I’m so excited to discover how living in community changes how I approach eating, and see how healthier eating ripples through every other facet of my life.

In other words, I’m no longer just thinking about the questions that matter to me. I’m living them as directly and ferociously as I can. After a decade of being stuck in my head, and rationalizing away my basic needs as a human, I’m ready to take care of myself and embody my values more fully. Of course, I don’t know where any of this is leading, which is rather uncomfortable at times. But even in my moments of doubt, I can’t shake the sense that I’m on the right track. I trust my questions will continue guiding me down the path of becoming the man I know I can be.

Onwards.