What's in a Name?

The point of this publication

The story behind the name of this Substack is also, by accident, the story of what it has come to stand for. 

When I unearthed my latent love for writing, I decided to start sharing my work online. It followed that I might want people to read it. This desire led me into the world of ‘audience building’, where well-known bloggers shared seductive promises that I’d gain swaths of followers if I applied their strategy. All I had to do, they said, was create a niche for myself. Get specific. Really specific. The only way to grow readership was to present myself as the purveyor of a singular type of content—sales advice for middle-aged plumbers, for instance, or software development guides for divorced cat owners. This would allow me to carve out my own space in the vast expanse of the internet. I needed to become something specific, they advised, or else I would be nothing at all. I believed them.

I thought about what sort of niche I could create. My expertise and experience, to the extent that I had any, were spread out across a bunch of random and mostly inconsequential fields, from software sales to concert tickets to buying businesses. There wasn’t a clear through-line. But after thinking more about the sales angle, it occurred to me that one thing I found to be important and was pretty good at was asking questions. It seemed unique; I couldn’t find anyone who had built a blog or product around this particular thing. I could become The Question Guy.

The first order of business was to come up with a name. One day, ‘A Questionable Life’ popped into my head, which I thought had a nice ring to it and captured the spirit of the enterprise. I bought the domain straightaway.

The audience building gurus preached that the best way to get started was to post Twitter threads. I found myself in a group with other adherents of the Niche and Pitch faith, and we used each other for feedback on our thread drafts and engagement once they were shared. I bought the best thread-writing software, picked a great Twitter photo, wrote a clever bio. I had everything I needed. It was time to get to work.

The only problem, it turned out, was that trying to write a Twitter thread about questions felt like dunking my head in a vat of acid. It was excruciating. I tried writing about different scenarios where asking the right questions was important, about how to ask better questions, about examples of questions I had found useful. Everything my keystrokes produced was gross. I sent a few drafts to the group for feedback, which were met with generic regurgitations of the same advice about how to write better hooks, how to be more punchy, whatever. 

This inspired me to try asking myself a question:

What the fuck am I doing?

I thought back to why I started writing in the first place. It had nothing to do with becoming The Question Guy, or any other type of Guy. And it had nothing to do with Twitter. I wanted to write because I loved doing it. When I thought about it, confining myself to tweeting some kind of meta, abstract commentary on the act of asking questions—or writing about any other niche topic for all eternity—sounded like a great way to stop loving writing before I even started.

Instead, I started a Substack and wrote what I wanted. The subject matter was all over the place. I wrote about sobriety, agency, creativity, smartphones, an addiction to buying books. But over time, a theme slowly revealed itself. And that theme happened to be captured perfectly by the misguided name I had originally chosen.

"Every man ought to be inquisitive through every hour of his great adventure down to the day when he shall no longer cast a shadow in the sun. For if he dies without a question in his heart, what excuse is there for his continuance?" – Frank Moore Colby

Brilliant figures throughout history, from Euripedes to Rilke, have talked about the importance of ‘living the questions’. But what does that actually mean?

The nature of human life is such that we rarely, if ever, arrive at any definitive answers about our existence. Our cognitive capacities are incapable of reconciling the paradoxes, contradictions, and ambiguity that course through our consciousness. But there is something about the act of asking the questions in itself that endows our lives with a sense of meaning, of aliveness. We start living our way in the direction of an answer. In the process, we become more of ourselves. We show up better for others. We act with intention. And this, I believe, enables us to make the most out of our time on this spinning rock.

Continuing to question this one life we get is my promise to you with this publication. Whether those questions are about the existence of free will or oppressive gym cancellation policies, the objective remains the same: to examine our lives such that we might live just a bit better.

That’s how this thing started, after all—by questioning why I was writing in the first place. By living A Questionable Life.