Observations from one year of solo work

8 hours ago 2

May 5, 2025

When I set out as an indie consultant, a peer of mine gave me advice I find myself returning to:

“For the first year, you take everything and do anything to make the business work. For year two, you use that information to figure out your unique perspective and offer. In year three, you finally know what clients you like to work with and can even scale.”

As I enter year two this month, I can report they were right.

That’s why today I’m announcing a new website for Gate Check Studios, more focused positioning (see the site for the full story!), and availability to take on new clients for the first time in 2025.

(I also will start saving this space for more personal updates. Head to the new Gate Check Studios newsletter for bi-weekly takes on content, marketing, media, and the internet. Subscribe here.)

But perhaps more interesting to you, dear personal newsletter subscriber, is the role identity has had in my solo journey. I entered this phase of my career with some reluctance and trepidation. Depending on when you spoke to me, I was going to leave the client game to go back in house. Or start my own thing. Or something else.

I have had a wandering eye — which in my case, means roughly six domains were registered with good intentions and I was late in the process with a few companies for full time roles before backing out.

But then a friend challenged me: “What if you took the energy you spent exploring other things and put it into your business? Into your clients?”

Working alone on your own business is like sitting in a hall of mirrors everyday. You see all of the best and worst parts of your psychology reflected back to you.

And I realized that while my various explorations and side projects taught me something, my business — the actual thing paying my bills — was reactive. The market was telling me that my consultancy was the most valuable thing I was doing.

And yet, I was protecting my ego by not committing to one thing. Especially something as difficult as growing a service business. If something didn’t work out, I could always shrug and say “well, I didn't give it 100% of my mental commitment, so no big deal.”

What is the point of going through all of this trouble if I’m not going to make my business, my career unique to me?

I also have this spidey sense that a few things are happening in my world of content / marketing / branding are worth betting on (more there in the Gate Check newsletter).

I still may, no, scratch that, will one day yet evolve this into something else. But for right now, I'm focusing on making the best business for me, betting on the future of the internet I see coming, and doing the best work for my clients and their teams.

Wish me luck. (Or better yet, let’s make cool things together).

The right level of emotional involvement as a consultant.

Working at a startup means you likely have some equity. And when you have equity, it helps to think like a shareholder at work. If any part of the company isn’t doing well, it’s a determinant not only of your “time investment” (working each day) but your “growth investment” (your equity).

I didn’t realize it, but I had the habit of getting emotionally invested in the companies I worked for. But when you’re a “hired gun” your clients usually don’t want you poking around in areas outside what they hired you for. They hire you to solve a specific problem. This has taken some rewiring.

Sweet Jesus, I’m so glad I’m not on Zoom all day.

Going solo has softened my anti-remote work position a tiny bit. I realized that while I still would take a creative, collaborative office any day… a small percentage of my issues with remote work were because of my aversion to Zoom calls. With those drastically reduced, I’ve been more content to embrace the remote life.

The Internet’s Tower of Babel moment and the end of Internet monoculture

Whether you came of age during Homestar Runner, “The Dress”, or cancel culture, you know what it feels like to have most of the internet talking about the same thing. As audiences splinter and the platforms offer each user an algorithmic experience, those days are over. The lack of this town square makes the internet less fun but it also makes it more difficult to observe what is occurring in various subcultures. This is making Americans feel even less connected to one another, which has profound impacts culturally and politically.

Embracing my late-30s with late-30s media habits

Speaking of the decay of the Internet’s town square, after 18 years, I deleted my Twitter/X account (please clap). Thinking of doing the same? I used Replit to archive all my tweets so I can search them if I want to find something I posted in 2012.

As a result, I’ve been mostly consuming news via The Economist, The New York Times, The Philadelphia Inquirer, and Polymarket. I regret to inform you that the social media haters were correct and that this has made me feel less anxious about the state of the world.

Pods I’ve been on: I appeared on Nick Bennett’s "1,000 Paths”