Ten Years Indie

A decade ago, I made a major announcement:

I’m leaving my 9-5 job to work on Relay FM, 512 Pixels and my freelance business full time.

This anniversary snuck up on me, and I think that’s a sign of how well things have gone since I published that blog post.

Had you told me ten years ago that I’d still be making things on the Internet with my friends, I’m not sure I would have believed you.

This Is Probably Too Much History, but I Wanted to Chronicle It All Somewhere, and This Blog Post Seemed Like the Right Place for It

In the beginning, there was 512 Pixels, which launched as ForkBombr almost 17 years ago. I wrote a lot about the site a couple of years ago, so will point you to that post, and simply add this: while blogging is not as cool as it once was, the fact that I can write and publish whatever I want, whenever I want, is still something I find incredibly dear. This site still feels like my home base on the Internet, and always will.

On June 5, 2013, Federico Viticci, Myke Hurley, and I launched The Prompt, and it changed our lives. The Prompt’s success on 5by5 gave us the courage and platform to start Relay. We renamed the show Connected at that point, but, aside from 512 Pixels, it’s the longest-running project of my career. If something were to happen to Relay, I suspect the three of us would find a way to continue discussing Apple and other things that interest us.

I am extremely thankful to Ticci and Myke for our ongoing partnership, and to Dan Benjamin for giving us the space to explore all those years ago.

When I stepped away from my previous job, Relay wasn’t generating quite what I needed to support my family, so I took on a variety of freelance projects. At the time, I was writing at The Sweet Setup and monthly at iMore, and would have stints at MacStories and Six Colors as well. What I didn’t elaborate on was my in-person freelance. In 2015, a friend and mentor of mine named David Madison¹ was retiring from his Apple consulting business here in Memphis, and I took over a significant portion of his clientele.

I’m extremely thankful to Shawn, Rene, Serenity, Federico, John, Jason, and Dan for allowing me to publish on their sites, and to David for trusting me to serve his clients as he transitioned into retirement.

Additionally, I was providing consulting services to several large clients in Memphis, including The Children’s Museum. I put a mountain of time into helping the organization design and implement the space that houses the 1909 Grand Carousel that is now enjoyed by thousands of kids a year. I built websites for a range of smaller non-profits, churches, and even a couple of companies.

All of this let me pay my bills, but it was exhausting to be available to so many people while also trying to grow Relay. After a few years of seeing my work week fragmented into more pieces than I wanted, I scaled back some of my outside work. I turned my attention to new podcasts on Relay, and at one point, was hosting or producing half a dozen shows. Beyond Relay, I also hosted a couple of shows on The Incomparable.

I’m extremely thankful to Serenity, Mikah, Tiff, Quinn Rose, and Quinn Nelson for helping make those shows with me.

Some of these shows ended of their own accord, while others were retired when I had the opportunity to join Mac Power Users in January 2019. Becoming a co-host on MPU changed the trajectory of my indie career, as it replaced several smaller projects on my “Yearly Income” spreadsheet.

I’m extremely thankful to David Sparks for choosing me to help shepherd such an important show in our space.

My remaining freelance ended when the world shut down in 2020 with COVID, and Myke and I had to turn our attention to Relay with a renewed sense of urgency as we saw ad sales evaporate in front of our eyes. Along with our team of Kathy and Kerry, we were able to pivot our existing membership system into what it is today.

I am extremely thankful for our team at Relay, and for the thousands of people who have become members to support their favorite Relay podcasts. For the last couple of years, my personal income from Relay has been split pretty evenly between ads and membership.

These days, my work life is much simpler than it was in those early years. The core components in my Content Creator world include helping run Relay, hosting MPU and Connected, and writing 512 Pixels. I’m fortunate to write and talk and think and debate about topics I love, all in front of a vibrant, caring, and generous audience.

I am extremely thankful for each of you.

Even Dream Jobs Come With Nightmares

Being a content creator the way I do it has its downsides. Publishing endlessly can lead to burnout. Social media can poison your opinions. The Internet can be unforgiving when it comes to mistakes. Working virtually can become lonely. Relevance can fade.

Even ten years later, these challenges remain on my mind. Sometimes, I worry that my expertise in Apple won’t be as valuable to people as it is today, especially as some think the company’s reputation is on a downward swing. Sometimes, I fear that Relay’s style of podcasting will fall out of favor — with both listeners and sponsors. Sometimes, it feels like we’re all one dumb social media post away from it being taken away.

The severity of those concerns ebb and flow over time, but in late 2023, I got a phone call that would help quiet those voices in a new way.

A New Challenge

In late 2023, my buddy Underscore David Smith informed me that he was looking for help with his business so he could focus more fully on developing his iOS apps at Cross Forward. As is his way, David was extremely gracious when discussing this opportunity with me, saying he didn’t have another name on his call list.

That meant a lot to me, and it came in a season of reflection on my career. My podcast output was sustainable, and Relay felt like it was on stable ground. However, I was in a funk. I wasn’t learning and pushing myself as I once had, and I knew joining David would mean new types of work and new areas to explore. After conversations with Myke and my wife Merri, I said yes.

The last 18 months of working on Widgetsmith, Pedometer++, Sleep++, and his other apps with David have been a true joy. What could have been some freelance hours spent taking care of basic administrative tasks has blossomed into a true creative partnership, just as I have with my cohosts on Relay. I’ve learned a great deal about various aspects of developing and maintaining iOS apps. While growing at this scale can be dizzying, I’ve had more fun doing so than I ever imagined.

My work at Cross Forward has been all upside. Growing my expertise in the iOS app ecosystem has made my commentary better, and being able to think clearly about Apple has made me a better team member for David. It’s also given my family a greater sense of stability and financial security, which I’m grateful for, as media advertising continues to be a rollercoaster.

I am extremely thankful for David for trusting and mentoring me over the last year and a half. If you use any of our apps, I’m thankful for your widgets, counted steps, and nights of sleep tracked.

Thinking About Legacy

When Relay turned ten last year, Myke and I talked a lot about legacy. To be clear, we don’t plan on going anywhere for a long time to come, but big round numbers mean something. (Just look at how many words you’ve read to get here!)

Merri and I had little kids when I went out on my own; our youngest son was born a month after Relay launched.

I am extremely thankful to Merri for always believing in me and being the best partner in life I could have imagined. She’s the best gift I have ever been given, and I would not be the man I am without her beside me.

Today, we’ve got two teenagers and a 5th grader. I’ve been able to attend more school programs, go to more doctor appointments, and be present for more everyday moments than would have been possible had I stayed in a traditional job. Those things add up to something special. To be clear, I have prioritized work over family life way too many times over the last decade, just like other parents, but I like to think that when my kids reflect on their upbringing, memories of Merri and me both being present will be at the forefront of their minds.

Of course, our family life is intertwined with St. Jude, as our oldest son is a survivor of pediatric childhood cancer. Since 2019, Relay’s community has given over $4 million to St. Jude. That money is the true legacy of Relay and its listeners, and I couldn’t be prouder of it.

More than anything, I want to leave a legacy of gratitude to those around me. The world is a cruel and broken place, but I don’t accept that it always will be. I may just be talking and writing about computers while working on a handful of iPhone apps, but if that effort makes someone’s day brighter after reading a blog post about an old Mac, through swiping past a widget with a photo of a loved one, or hearing a joke on a podcast, then the day’s headaches are worth it.

Getting to deliver a little joy to the world is what I’m thankful for most of all.