One of my biggest "oh shit" moments last year was when I realized I'd been deriving my sense of self-worth from being perceived as intelligent. I wanted people to think I was smart so I could feel good about myself.

On its face, that might not seem like a big deal. I mean, nobody likes to look stupid. But the negative ripple effects this caused throughout my life are hard to understate.

This single desire, combined with lousy self-esteem, is at the root of my perfectionism, my tendency to over-complicate things, my imposter syndrome, my years of intellectual inflexibility and closed-mindedness, and so on.

So to help break out of these old patterns, I'm trying on three new labels for myself. Imperfectionist. Learner. Explorer.

Looking smart vs. being smart

There's a stark difference between what it takes to look smart and be smart. Each leads to a totally different set of behaviors, and a totally different destination.

When the goal is to look smart, people generally...

  • avoid messy, complex problems
  • overcomplicate simple advice
  • surround themselves with people who praise them for their intelligence
  • put on an authoritative, confident mask, even when it's not warranted
  • get defensive about ideas and people that challenge them
  • buy into and perpetuate simplistic worldviews and ideologies
  • consume a lot of information, but do very little with it
  • give lots of advice and ask very few questions

But when the goal is to develop genuine intelligence, those behaviors get flipped. Being smart requires that people...

  • dive head first into messy problems
  • try to simplify and clarify
  • surround themselves with people who make them more intelligent
  • treat every person they encounter as an opportunity to learn and grow
  • move through the world with humility and curiosity
  • realize that no single worldview or ideology has all the answers
  • consume information as needed, then put it to use
  • ask lots of questions and give very little advice

It sucks to admit, but I took the former path for years. My first business, though somewhat innovative in the filmmaking space, basically amounted to me sharing uncontroversial marketing advice like "find your niche" and "have a clear value proposition" and "seriously, you should build an email list." I projected all of those things out into the universe authoritatively, with a clear sense of "I've figured it out and you should listen to me." And it felt great. Until it didn't.

I ended up trapped in an intellectual prison of my own making. I became the Niche Guy™ loudly proclaiming to anyone who'd listen that This Is The Way for creatives to build an online business. It was bordering on zealotry.

But here's the funny thing. Once I left behind my first business and started working on Ungated and Citizen Within, I repeatedly found that I didn't resonate with my own advice anymore. And for awhile there, that tension paralyzed me. After years of being Niche Guy™ it was genuinely painful to admit that things were more complicated than I had made them out to be. It felt akin to demolishing the very thing that helped me feel good about myself for so long.

In the culture of online business and marketing, crafting a persona of expertise and authority is widely agreed upon as a best practice. But having played that game for years, all I can say is if you travel far enough down the road of trying to look smart, and you end up in some dark, frustrating places.

Experiments in crafting a new identity

As I wrote in a piece about why I'm not targeting a specific niche anymore:

One of the things I've learned about myself this past year is that I'm allergic to labels. In this season of life, my goal is exploration and personal evolution. I enjoy being a cultural and intellectual chameleon. I value the ability to upgrade my beliefs as I move through different corners the world and learn new things.

Even though I'm wary of rooting my identity too firmly in any one place, I've been playing with the idea that certain labels can help me adapt to a changing world, help me be more prolific, and actually become smarter over time.

Which brings us back to those three labels I mentioned earlier. Imperfectionist. Learner. Explorer.

Each of these get me way out of my comfort zone in a healthy way, all while having more fun and taking myself less seriously. Here's how I'm conceptualizing them.

  • Imperfectionist: I strive to ship imperfect things (like this essay you're reading now) frequently, because I get better and iterate faster the more I hit publish. I know that perfection doesn't exist, and trying to achieve it is a fear response rooted in insecurity. When I'm a perfectionist, I'm operating from a place of "I'm not enough, but this work might validate me." But when I'm an imperfectionist, I live from a place of "I'm enough just as I am, and this work has no bearing on how I feel about myself."
  • Learner: Every encounter with unfamiliar ideas is an opportunity to stretch beyond my limited conception of how the world works. I start from a place of intellectual humility, admitting that in the grand scheme of things, I know next to nothing. But I strive to constantly learn new things, and document those learnings in public along the way.
  • Explorer: There are no maps for where the world is going. So I follow my curiosity and intuition, then run little experiments to see how those instincts play out in the real world. For instance, transitioning into the Gift Economy, and then back out. Or writing everything in lowercase. I don't strive for a theoretical understanding of the ideas I talk about, but an intuitive knowledge derived from repeatedly stepping into a new arena and playing full out.

I don't talk about this much, but I have a vision for Ungated that could be characterized as laughably ambitious. Simply put, I want to help change the internet for the better, and make it an unrecognizably friendly, diverse, creative, delightful place compared to where it is today. All with the understanding that when the internet flourishes, so do other, non-digital aspects of the human experience.

It's a lot like this banger of a tweet from Visakanv:

Ten years from now, maybe twenty, I believe the citizens of the internet and the world at large can be in a healthier relationship with themselves, with others, with the planet, and so on. I believe that any meaningful change in that direction starts from within, and that if we play our cards right, each of us individually, then humanity as a whole, can get out of our own way, solve some messy problems, and flourish.

Whether that's true or not, I don't know. Only time and continued effort will tell. But I'm confident that adopting these three labels will help me be a force in the movement toward that future.