Solo Success Stories Edition #4

Featuring: David Pennington

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Feb 23, 2024

Hi there! 👋 My name’s David - I’m a writer and solopreneur from Northern Ireland. In this publication, you’ll find a growing archive of resources (created by myself and a collection of valued guests) for those hoping to become - or grow as - solopreneurs. While you’re here, you should also check out:

My other publication,How to Write for a Living
This course I created (included in my paid plan)

Thanks for stopping by! Now, back to the article.

Happy Friday, and welcome back to Solo Success Stories! Each week, I’ll feature a fellow solopreneur with an instructive story to share about how the pursuit of solo business success has shaped their life so far.

So without further ado, let’s hear from

David T Pennington

I like to tell people that it was three lines of code that put me out of a job.

For years, adTech (the code behind things like Facebook’s ad platform) was putting newspapers and magazines out of business. One day I was pulling levers and pushing buttons to optimize campaign delivery for the world’s largest brands. The next, I wasn’t.

The layoff didn’t surprise me. I never cared for the work - the digital ad industry was (and still is) rife with bad actors, fraud, and missing money. Also: really bad ads.

My manager, who also had plans to leave the company in the following weeks, made no secret that my position was being eliminated after the big corporate acquisition/ tech update/ quarterly downturn. This was enough time to update my resume to see if I could land another job in an industry I was growing to hate. Layoffs, bad jobs, shitty paychecks - for over a decade I suffered through a garbage job market.

The day I graduated college was the same day Bear Stearns dumped off $20 billion in bad debt and ultimately triggered the entire 2008 financial crisis. The post-college transition was, quite literally, from the frying pan and into the fire.

Plus, the thing I was doing was no longer a thing that was done. I couldn’t find a campaign manager gig at any agency or tech firm anywhere. The job didn’t exist, my door to the digital advertising industry had closed, locked, and set itself aflame. Good riddance.

Between the severance and the unemployment benefits, I had enough of a runway to figure out the next “thing” (also, I should say, the support of my wife and the amazing benefits she gets through her rock-steady corporate insurance career). After I spent months submitting thousands of applications and resumes that led to dozens of milquetoast and uninspired interviews, I gave up on the idea of traditional “work.”

I spent my life writing stories. Since childhood, books have been my refuge. I went to school to study journalism (before the university shut down their journalism school my junior year, pushing me into an English degree) and I loved to tell stories.

The question became: “what do I want to make?” A far easier question to answer than “what do I want to do?” I don’t want to do anything. But I’ll make things all day long.

The early days of self-employment were picking at a lot of low-hanging fruit. Jobs from Upwork that I could turn around in a day or two. Guest articles here and there. I dusted off my old camera and did headshots for $50 a pop. In my entire “career” I never worked as hard as I did in that first year and I made a mediocre pile of peanuts.

Slowly, it built up. Some of the photo projects I composed on the side were put up in shows. I made a few bones self-publishing a short fiction collection. The gigs got bigger, more routine, and there was eventually income I could count on.

I was writing a LOT of copy. Every client loved it, but I hated every word I put down. Nothing felt genuine. Then, over one too-hot July evening I couldn’t sleep and found myself in the middle of a Jerry McGuire moment. I was pissed off at the idea of advertising and how online “brands” were opting to present themselves and talk to their audiences. I was tired of the garbage demands of “direct response” campaigns and how every other “copywriter” out there fancied themselves an armchair psychologist/ master manipulator. I set my thoughts down on the page.

Two hours of sweaty, aggressive typing led to the manifesto that would serve as the foundation of OutWord.

Over the next year OutWord would evolve into an antagonistic brand that forces its clients to think very, very critically about their presence in their consumer’s lives. We introduce chaos into the foundations of a company, testing the stability of their mission and upsetting how they market themselves. In the end, all of the garbage is stripped away and they move forward with a raw confidence no one can touch them with.

What’s next? Less, probably. I am getting picky about who I work with through OutWord. Even in a merciless market that demands bold ideas, I see companies cowering in what feels safe and familiar. The way I market the OutWord brand requires clients to finally admit that their shit does stink, and something needs doing. In the meantime, I am reading, drawing, and writing across all manner of mediums to make OutWord a stranger, more chaotic place to be.

People rarely do anything with advice, so I avoid giving it out even when it’s asked for. I am the kind of person who will suggest you stay in your safe, reliable job and not drop out of school or invest big in a sure thing. But when someone says “I’m thinking of starting my own thing.” I smile and nod and know they will probably never do anything outside of the job they’ve always done.

If you want to do your own thing, make sure it is YOUR OWN THING. Otherwise, you’re toast and three years from now you’re back looking for a job. Bring something wholly unique and interesting and different - the world has enough of what is already out there. Surprise us. Don’t worry about “researching your audience” or following trends. Make the thing you want to make, if it is uniquely yours people will want it.

Also: ignore the folks who talk about business on social media. Ignore the coaches and the gurus. Block out the passive content full of “advice.” If you need to know something, ask specific questions to paid professionals. Everything else will fail you.

Look alive out there.

David Pennington is a writer and artist living in Western North Carolina. He is the brains behind OutWord where he consults with brands about all the dumb stuff they do. Find out more at outwordcopy.com and dtpennington.com.

Thanks David!