Last Friday, I left my job as a lawyer. Many readers may not even know that’s something I did because it’s not pertinent to what I do at MacStories. Over the course of many years, that job became less interesting and challenging. Eventually, I recognized that I needed a change, but nothing felt quite right. That is, until the day I decided to make an app. I’m not much of an app developer, but I wouldn’t be where I am now, writing this, if I hadn’t built one. This is my app story.
I started as a corporate bankruptcy attorney. I didn’t work for failed companies, though. I worked for banks owed millions of dollars by those failed companies. My job was to help navigate the process and collect what I could from what was left.
It was interesting for a long time. Each case meant learning a new industry, reverse engineering failure, and unwinding complex relationships between the parties. It was demanding, and the fact that failed companies’ debts rarely get paid back in full imposed a practical, ‘do-more-with-less’ constraint that required creativity.
Over time though, the market shifted. For a variety of reasons, the complex, interesting, hard problems were largely replaced by tedious, boring, monotonous ones. I knew I needed to try something different, but had no idea what.
Fast forward to the fall of 2013. I was sitting in the window at my local Starbucks on a Friday writing ideas into a notebook stream of consciousness-style, filling pages with nonsense and looking for a spark that could start something. It’s a practice that leads to interesting ideas when I make the time to do it.
That’s the day Blink was conceived. Blog posts by David Smith and Dr. Drang about Apple’s new affiliate linking program had lodged in my brain. There wasn’t a good way to create affiliate links on iOS devices even though they are how many links get shared on social media. I figured it wouldn’t be hard to look up App Store URLs and add affiliate credentials onto the ends of them.
I had no idea what I was getting myself into, which was good. Okay, that’s not entirely accurate. If you rewind even further, I’d spent the better part of the preceding five years helping my oldest son find the resources he needed to become an iOS developer. In the process, I’d learned a little myself, but hadn’t gotten beyond the most rudimentary of projects.
I got to working evenings and weekends in fits and starts studying the iTunes Search API, figuring out a way to bend it to my will, and learning Objective C. By WWDC in 2014, I had a mess of spaghetti code that, to my surprise, worked.
When I got to San Francisco, I showed off Blink to a few people and asked every writer I could find what they thought of the concept. Reactions to the app were mixed. There weren’t many people writing on iOS yet, and there were plenty of doubters.
As discouraging as the lukewarm response could have been, the negatives were eliminated by the announcement of share extensions in iOS 8. I immediately recognized that a Blink share extension could remove much of the friction of using the app and the complexity of relying on URL schemes. I also wanted to adopt size classes to make Blink Universal. The only trouble was, my code was a mess. What I had accomplished was a good learning experience, but it was fragile, so I burned it to the ground and started over.
I also picked an ideal customer for Blink so that I would have a concrete goal in mind. That customer, of course, was Federico. I didn’t know Federico then, but I’d read MacStories for years and listened to his podcasts as he moved more and more of his work to iOS. The idea was simple. I figured that if I could make an app that worked for him, it would work for others too.
I learned a couple of valuable things about myself that WWDC. First, being stubborn has its advantages. I’ll listen to a handful of people close to me who I trust, but I’m good at tuning others out, which came in handy when the initial reactions to Blink were mixed.
Second, the long, frustrating weeks and months of teaching myself Objective C were also incredibly satisfying and fun. I realized what I enjoyed about it, and my job as a lawyer, was the challenge and the constant change that kept me on my toes. As those qualities waned in my law job, Blink filled the gap.
As the end of 2014 approached, I made a mad dash to finish Blink. By this point, I had managed to get Federico’s attention when I’d posted a late-night teaser video on Twitter of my URL schemes in action. Five minutes later, he sent me a direct message:
Oh man, wow. Please make this universal and let me in the beta as soon as possible! ❤
@viticci November 5, 2014
I took Federico up on it and sent him an embarrassingly buggy beta. He tried it and came back with a laundry list of things he thought Blink should do. I knew I was on the right track.
I don’t mind working by myself, but by this point, I had started to feel the isolation of working solo for months. About the only person outside my family who knew what I was trying to pull off was Myke Hurley. We’d become friends after meeting at WWDC in 2013 and shared similar corporate job backgrounds that helped us relate to each other’s struggles as Myke worked to become a full-time podcaster and I developed Blink. I don’t know if I’d have made it through those early months and launched Blink without Myke’s encouragement.
The isolation faded though, replaced with a blur of sleepless nights sending out betas to a small group of testers and working on the icon and interface design with Frank Towers. My strung out state of exhaustion was preserved for posterity by Myke in his Behind the App series1 of the since-retired Inquisitive podcast.
Finally, on March 19th, I launched Blink. The feeling is hard to describe. I was exhausted and elated at the same time. I also knew immediately that something had changed. I had discovered how much making something matters to me.
Most lawyers don’t make anything except hours. As a bankruptcy lawyer, it was even worse because the best result I could achieve was that my clients lost less money than they might have otherwise, which isn’t very satisfying.
Something about building a product, as ephemeral as the bits that comprise apps are, and seeing other people use it to get their work done opened my eyes to something I didn’t even know I was missing. I sensed that I was immediately and forever ruined from cranking out hours for someone else. It was time to make a change, but it would require patience.
Blink followed the usual trajectory of most apps with several good days of sales followed by a steep decline. With a day job, I had the luxury of pouring most of the money I made back into promoting the app. Based on the goals I’d set for myself, Blink was a success, but it was clear early on that it was never going to pay my bills. I felt like I was onto something with Blink, but there were still pieces of the puzzle that were missing.
A few months later I was sitting outside on a beautiful summer day at a law firm function held at a stuffy country club. I was by myself with nothing but a pen and a notebook, just as I had been at that Starbucks nearly two years prior. A lot of crazy ideas were hatched and discarded that day, but one took hold: I would keep pushing Blink forward to see where it led by writing a guide to iTunes affiliate linking.
The article was still more concept than reality when I found myself at the first Release Notes conference walking along with Myke catching up on life. I told him about the article and how I was struggling with how to attract the biggest audience possible for it. Before I could finish, he interrupted and said ‘Send it to Federico.’ I started explaining why I thought Federico wouldn’t want to publish it, when he interrupted again, 'Just send it to him.’ Myke’s one of the handful of people who can get through my stubbornness, so I did.
I didn’t expect much to come of pitching my story to Federico and was thrilled he agreed to publish it. That evolved into what I do now at MacStories quite organically. I didn’t set out to write for MacStories, but I quickly realized I’d stumbled into something special that had the same sorts of challenges and satisfying sense of making something that I’d found in app development, but is better suited to my talents.
My experience with Blink is also why AppStories means so much to me. I knew as soon as Federico suggested it that the concept was perfect for us. As much as I like playing with all the apps I see each week, it’s the stories of the people behind them that resonate with me the most. There’s more than meets the eye to every app, even a modest little utility like Blink.
Blink gave me the confidence to walk away from my legal career without feeling like it was wasted time. It helped me understand what I liked about being a lawyer wasn’t the lawyering part of it at all. It was solving difficult problems that I enjoyed, which I could find elsewhere with something more in line with my strengths.
Friday, I made my last trip to Chicago as a lawyer. It was a strange feeling, but a good one.
Today, I’m free of the mental overhead of trying to juggle my law job and MacStories. I’ve looked forward to making this leap for almost four years, but it still feels like I’m only half prepared and just got started. I’m not sure that things will work out as I hope either, but I’m excited to see where this path takes me and fortunate to have the support of my family and friends along the way.
One thing is certain though, I’m glad to have finally told my app story.