A more joyful business

My plan for un-sabotaging my business, and becoming more human

"Joy is a meeting place, of deep intentionality and of self-forgetting, the bodily alchemy of what lies inside us in communion with what formerly seemed outside, but is now neither, but become a living frontier, a voice speaking between us and the world." - David Whyte

There's a video essay from Matt D'Avella I've watched multiple times in the past few weeks. It touches on something deep and resonant for me. If you don't know Matt, he's a filmmaker who made a pair of documentaries for Netflix, and built a popular personal development YouTube channel, which now has close to 4 million subscribers. Over the years, Matt did everything you're supposed to do as a YouTuber. He scaled. He hired. He diversified into online courses. He hired more. By all external standards for what's possible and desirable as a creator, Matt had made it.

But then he burned out. He lost the spark, and woke up one day realizing he'd created a job for himself he didn't particularly enjoy. Matt's video tells the whole story, along with what he's doing next. It's absolutely worth a watch.

Ever since I closed down the Ungated membership last year, I've had a handful of questions rattling around in my brain, along with this hazily defined term: joyful business. What would it look like if we optimized our businesses not around endless growth, but around feeling nourished, connected, and joyful in our day-to-day lives? And what is it about the defaults handed to us from creator/marketing culture that reliably lead us away from feeling that way?

These questions aren't hypothetical or academic for me. I'm officially on my third attempt at building an online business that feels nourishing and alive. My first two attempts suffered a similar fate to what Matt describes in this video. They felt draining, like I was slowly trapping myself in a job I didn't want. And I know countless other creators, some small and some incredibly successful, who have experienced this and are asking these same questions. How can we keep the spark of joy in our creative work alive? How can we structure our businesses so that they nurture our humanity, instead of squeezing the life out of us and making us more machine-like?

I don't have many answers, but I am devoted to living the questions and leaving behind artifacts from my exploration in The Forest. That said, I've done an awful lot of reflection about my past businesses, why they failed, and how I can move forward. There are two principles I've landed on, which I believe will help my new business grow into something joyful and sustainable over time. I don't know if they'll help you, but they're the exact advice I need right now.

Principle one. Cultivate present moment awareness, and be radically honest about what you're experiencing.

The biggest mistake I've made, again and again, is living in hypothetical, idealized versions of my businesses, instead of being truthful about how they felt in the present moment. My businesses weren't built on me trusting myself, but rigidly following goals and strategies I'd picked up from other people who appeared successful. As a result, working in these businesses often felt unnatural, forced, and stressful. That was my default state.

But instead of feeling and acknowledging how shitty my present moment experience was, I daydreamed and dissociated. I thought about how great I'd feel once I pushed through the resistance and made a bunch of money. "Once I make six figures, I'll be joyful" was a constant refrain in my head, keeping me focused miles ahead instead of attending to what was right in front of me. Not surprisingly, this strategy led to massive, debilitating bouts of burnout. Twice.

Ever since my stint at the French monastery, I've been practicing slowing down and noticing what's here now. I'm learning to stay attuned to myself. To listen. If I frequently find myself stressed and out of integrity, that's important data. Instead of forcing my way it, I'm treating dissonance as an invitation to get curious about its origins, be compassionate towards myself, and perhaps try something new in my business. And on the flip side, if I find myself feeling joyful and connected in the present moment, or experiencing deep resonance, that's a sign to get curious as well. To double down.

Basically the strategy is to pay close attention, do more of what feels good, and less of what doesn't. It sounds embarrassingly obvious when I type it out, but I've never operated my business (or life) like that. Excited to try, though!

Principle two. Treat your business like an ongoing conversation, rather than a scripted monologue.

Another way I've sabotaged past businesses is working towards some vision I decided early on, without listening to myself or paying attention to the signals I was getting from the world as I built. I got fixated on an ideal image of what my business should be, and then barreled towards it with tunnel vision, as if deviating from the path would be a failure.

For instance, I figured that because Ungated was so focused on 1,000 true fans, the appropriate business model had to be a membership. I'd get 1000 people to pay me $100 a year, because it was the purest, most straightforward version of the model Kevin Kelly laid out. I never even considered anything else. As it turns out, I don't particularly enjoy running memberships or charging subscriptions as a creator. Recurring revenue is seductive in theory, but in practice comes with all sorts of downstream tradeoffs and troubles. I'm working on another essay about that, but the short version is that the membership model left me feeling like an overtaxed machine, delivering certain membership benefits on a fixed schedule, instead of a creative human.

As I write this, I'm on a huge David Whyte kick, hence the quote at the top of this piece. One of the constant themes through his poetry and prose is "the conversational nature of reality." In his first podcast with Sam Harris, he says, "Whatever a human being desires for themselves will not come about exactly as they first imagined it or first laid it out in their minds. Equally, whatever the world desires of you will not happen, no matter how coercive that world is." In other words, it's going to be a conversation, no matter how much we might resist it.

One of the things I've realized is that I want my business to feel like a supportive, life-giving relationship. A marriage, perhaps. And relationships tend not to work when one party dictates all the terms and refuses to listen. Conversations are the essential building block of healthy relationship. They're the meeting ground for give and take, back and forth, where two parties come together to support each other, while making sure their own needs are met. The magic happens in the constant dance between asserting and listening, adjusting and pivoting, growing and evolving, together. That's how I want to relate to my business.

Going forward, I am striving to be in deeper conversation with my own needs and desires, for those needs to be in conversation with my business and its needs, and for my business to be in conversation with the world around it. Basically, it's conversation all the way down. I'm learning to break my patterns of rigidity, where I prioritize feeling certain and in control at all times. I'm learning how to soften into uncertainty, and be flexible when the chips don't fall as expected. I'm learning to enjoy the dance of conversation, knowing it'll almost certainly lead somewhere I can't see yet. Basically I don't know what my business will look like in two years, or how it'll evolve. But I trust that whatever shape it takes, it'll emerge through deep listening and conversation.

There are a whole bunch of practical changes I'm making to my business as I step into this new chapter. But these two internal shifts—from dissociation to presence, and from stubborn rigidity to conversational fluidity—feel far more important than the tactical changes.

More and more, I believe the state of our inner world gets woven into the fabric of our businesses. It creates a self-reinforcing environment. If we build from a place of insecurity, always feeling like we're not enough until we hit some arbitrary goal, then our businesses will keep us trapped on that treadmill, forever chasing the next milestone. Whereas if we can attune to what feels joyful and connective right now, and build from that place, our businesses create the conditions for even more joy and connection going forward. The environments we inhabit, both physical and digital, matter a great deal to our development and wellbeing. And businesses are environments that we get to create. As Derek Sivers says, "When you make a business, you're making a little universe where you control all the laws. This is your utopia."

There's one moment from Matt's video that feels particularly important here. It's when he talks to Ali Abdaal, who started a similar channel around the same time, and has also grown like wildfire. Unlike Matt, however, Ali says he's happier than ever after having scaled his business and hired people. He created a role for himself in his business that he genuinely enjoys more than his days as a solo creator.

It's a great reminder to me, as someone who tends towards idealizing small business. Scaling isn't wrong. Chasing growth isn't bad. For some people, that game feels vibrantly alive, while for others it comes with tradeoffs that aren't worth making. There are no right answers for how to build a joyful business. There's no playbook, no template. Every human is different. And it's up to each of us who embark on this journey to answer these questions for ourselves, so that in two years, or five, or ten, we wake up absolutely loving the business we've built, and the life we're living. That, in a nutshell, is the work we're all doing in The Forest.