Hi there! It’s been a while since I wrote anything. There are reasons for that, but they’re all rather nebulous and hard to pin down. That’s sort of what this article is about. It’s also a retrospective of sorts; a look back at the last year and a bit, which has been wacky and wonderful and horrible all at once. It’s about some career decisions I’ve made in that timespan, and how those have collided with and ricocheted off of the rest of my life, and where I’ve ended up for the moment.

Truthfully, this one’s largely for and about me, and I don’t think there’s going to be any sort of Going Indie-esque lesson or a perfectly relatable story to take from this one, but I would be absolutely thrilled to have you read along anyways — maybe you’ll see parts of yourself reflected in whatever it is I’m about to write. Onwards!

Setting the scene

In July 2019, I quit my job. I had been at that job for 3 and a half years, and I cared deeply about it and the people I worked with. I was in a leadership role and had been a big part of significant company growth and change over the years. And yet, I was wickedly anxious and deeply unhappy. There were a variety of complicated reasons for that, but I think the best shorthand we’ve got for what I was feeling is “burned out.” And when I got into a scary car accident at the end of June (everyone was okay, thankfully; the cars were not), my camel’s back gave out, and all the straw it was carrying went everywhere.

Straw breaking a camel's back

“The straw that broke the camel’s back”, in case that wasn’t abundantly clear.

So I left, without really knowing what I was going to do next. Part of me thought what I needed was to simply do nothing for a little while, but I just wasn’t able to stomach that idea – irrationally, I was too afraid of somehow missing out on my next big opportunity, or falling into some sort of perpetual pit of unemployment.

Part of me thought maybe I just needed a different job to shake things up and challenge myself in new ways. But after putting a ton of effort into several take-home projects for one prospective employer, only to be told quite plainly that my implementation was “poor,” I realized I was nowhere near the right frame of mind to be applying for jobs, and immediately cancelled the other interviews I had lined up.

Part of me liked the idea of picking up some freelance work, which would allow me to set my own pace and schedule. Through sheer luck and happenstance, I stumbled into a few flexible, long-term contracts pretty early on, and so…that’s what I started doing. I was now officially a freelance iOS developer!

But meanwhile, part of me also really wanted to commit time to building my own apps, and wondered if there was some reality that existed in which I could make some semblance of a living off of work that belonged entirely to me. So after a few months of focusing solely on part-time freelance work and my mental health, I endeavoured to “become an indie developer” at the start of 2020.

Doing the indie thing

This part is well documented, so no need to rehash most of it. Here it is in broad strokes: at the beginning of 2020, I established a 3-pronged approach (patent pending) to getting some independent work off the ground. I started participating in iOS/tech/design Twitter, I started writing some stuff for this blog, and I started building an app.

This was really great for a while. It was exciting to try to establish something of an online presence and see my writing gain a bit of traction, and the continued freelance work prevented me from going into full panic mode financially while also making it a lot easier than it might otherwise have been to carve out time for the personal writing and app development work I was doing.

Once the pandemic landed, I came up with a new idea for a silly little app, and decided to put the in-progress indie project on hold to pour my energy into getting that idea out the door. That idea became Oh Bother, and quite suddenly, a bunch of the things I had been pursuing with this indie work – some real press coverage and recognition online, some non-negligible download numbers, some pocket change, and ultimately, proof that I was capable of designing and building something that I was proud of and that people were into — all became realities.

That was pretty rad, and I’m so dang thankful to have had that experience.

Losing momentum

Here’s the thing about accomplishments: the warm glow that follows is fleeting, and inevitably, that nagging question — “What’s next?” — rears its head. Practically speaking, I thought what I wanted next was to keep working on Oh Bother and on the blog, and see if I could build off of the momentum and grow them each into more significant projects with wider audiences. That’s still my goal today, but a good chunk of time has passed now since I last did any writing or released any updates, so…what happened here? Where’d all that momentum go?

Me napping on the path from Oh Bother 1.0 to Oh Bother 2.0

That’s a loaded question, but let’s try to sort it out. First of all, I’d be remiss not to mention a weird truth about humans, which is that it can be hard to stay motivated to work on something once you’ve received validation for it. By my own very modest standards, Oh Bother succeeded, which meant that after release, the onus was right back on me to set brand new goals for this thing. But when you hit your targets and receive a bunch of praise in the process, it can be tough to set new targets that you’re just as genuinely hungry to hit. It’s easy to get complacent and start wandering off toward some other shiny new project. Truthfully, I don’t think this has been a huge concern for me over the past few months — I still love Oh Bother and so badly want to make progress on it — but it’s definitely tricky to avoid this feeling entirely.

The bigger, often paralyzing issue I started to have after releasing the app was the question of how much of my time Oh Bother really warranted. I always thought of it as a pretty silly little project, but clearly my work had found some sort of audience, which left me really unsure of how much of myself to commit to it. There’s definitely a part of me that wonders if, after the surprise momentum the app built on launch, I should have put everything else on hold to focus on the indie work full-time. Ultimately, I never considered that as a serious option, because of my lack of belief in the app’s ability to maintain users’ interest, and because of my aversion to scrapping the freelancing stuff (a.k.a. the only stuff actually paying the bills).

So, this left Oh Bother as an evenings-and-weekends kind of side project. Totally viable in theory, but here’s the thing about side projects: in my experience, at least, they’re the first thing to get thrown out the window when life gets shaken up in any way. And while I grappled to figure out how much time I should be putting into this side project, everything around me was shifting just slightly as a new reality started to set in: in a few months, I was going to be a dad.

To be clear, this was not unexpected, and was quite thrilling. But I also knew my life was about to get turned upside-down in ways I couldn’t really understand or predict, and I felt my priorities start to shift out from under me. The months since I had left my last job had been all about experimentation and change and figuring out what I really wanted to do next, but with a baby on the way, it started to feel urgent that I “get my shit together”, so to speak. What exactly that meant was, and continues to be, vague and ill-defined, but ultimately, I wanted to feel settled and confident — at least for a time — in my career, in order to give myself the mental space to really focus on and appreciate this new chapter in my family life.

What’s next?

So I decided the lofty, long-term dream of making a living off of indie work would definitely have to wait a few years. I started dedicating more time to freelancing work as I tried to figure out if running my own little iOS consulting business was something I could settle into longer term, but found the more I leaned into it, the less happy I felt. I found that at its worst, freelancing meant doing work I didn’t really have ownership over, while missing out on all of the important social, educational, mental and financial benefits a great job can provide.

I needed a new plan. And although it probably wasn’t wise to be putting all this pressure on myself…I needed it pretty quick. The baby wasn’t going to wait for me. Suddenly, after months of me strolling along, casually wondering “Hmm, I wonder if I could turn these freelance gigs into a proper business!” or “Hey, I’m a pretty good writer, let’s spend a bunch of time on that!” or “Huh, maybe this indie thing could turn into something some day!”, or even “Wait, am I a designer?”, I had to turn all those thoughts into My Next Big Career Move.

And when you’re a bit neurotic and regrettably career-obsessed like I am, this career move pretty quickly starts to feel like a career- defining move, which immediately turns into a personal identity-defining move. And just like that, I found myself pretty frantically trying to figure out who I am and what on earth it is I even like to do.

Job hunting

The play here was simple, in theory: find a new job as an iOS developer. I’ve got lots of experience at this point, and I had a good story to tell about the independent work I had done in the time since my last full-time job, so the rational side of my brain was pretty confident I’d be able to get some interviews lined up and find the right job.

Unfortunately, I found myself feeling very unsure about what “the right job” actually was. My career up until now had consisted of jobs at startups, on fairly small teams, all of which I ended up leading in some capacity. I’m thankful for those jobs, and there’s a lot to be learned by taking full responsibility for a team or an app, but I’ve also never had much of an opportunity to be mentored or learn about my craft from more experienced peers. I’ve been a big fish in small ponds for a while now, and eventually, I realized that I wanted to try moving to a bigger pond — or at least, one with lots of bigger fish.

Big fish in small pond

Here’s the thing about “big pond” jobs – they’re typically pretty tough to get. Successful companies full of talented people attract talented, successful people, which, as a job applicant at one of these companies, usually means two things:

  1. You’re competing against a whole bunch of other very qualified folks.
  2. The application process is…not trivial.

Long story short: I applied for a few of these jobs, and found the process to be intimidating, frustrating, and most importantly, really not aligned with my identity as a software developer.

Who am I?

Some backstory: I was never one of those kids who, you know, learned how to program when they were eight, and spent a bunch of their free time taking computers apart or building elaborate mods for their favourite games or whatever. I thought computers were interesting, and I eventually took a computer science course in high school, but I didn’t think too much of it, and only continued the following year because the music course I wanted to take ended up getting cancelled. I got the hang of it, and did well when I ultimately studied it in university, but it was more or less just school to me. I wasn’t a “great hacker,” like so many of my classmates seemed to be; I was just good at writing exams.

This is all to say that while I’d like to think I’m pretty competent at writing code at this point, I’ve never really been passionate about it for its own sake, and I’ve always felt like a bit of an outsider to the “computer science”-ness of it all. What’s kept me going in this field is the idea that code is a tool that can be used to create things that are beautiful and joyful and meaningful and empowering – not unlike a song or a book or a piece of art.

So while I am definitely a “software developer” on my LinkedIn page, I don’t think that really captures how I think of my work. I’m a designer and a writer and a teacher and, heck, even a marketer on some days, and one of my most strongly-held beliefs about our industry is that all this stuff is way more important than we give it credit for; the best software comes from teams of developers with diverse non-technical skillsets and equally diverse backgrounds.

Long story short: in applying for jobs, I don’t love being reduced to a timed LeetCode solution or an architectural decision in a contrived take-home challenge.

I won’t belabour the qualms with interviews – I’ve been on the hiring end of many, and recognize the challenge of crafting a good technical interview – but some of these things really started to throw me for a loop. I thought I wanted these jobs, and yet, I was being tested on things that, frankly, I didn’t care much about, and that, in my mind, had very little to do with what actually made me a good candidate. One company, two interviews in, suggested a whole list of study materials (“Cracking the Coding Interview”, etc.) to prep for interview three…and I just cancelled it. None of it felt like me.

With the stress of these technical interviews weighing on me, I seriously started to question whether this was the kind of work I wanted to pursue. The excitement and positive feedback around my indie work had everything to do with my creativity and product thinking, my design skills, and my ability to communicate effectively. Meanwhile, most of these interviews weren’t really interested in any of that; these were purely technical evaluations that stripped away everything that makes me uniquely effective as a product creator, and pitted me against a slew of other folks who I can only assume care a whole lot more about big O notation than I do.

Of course, this is all an emotional oversimplification; each interview process was different, and it’s quite possible — probable, even! — that in each of these cases, I was simply not the best candidate for the job. But in general, the misalignment between how I see myself professionally and how I was often being evaluated felt significant, and it really made me wonder whether software development is the field I’m actually “supposed” to be in. Would I be happier looking for design jobs? Am I better suited to some sort of “product owner”-type role, perhaps? Should I be seeking out professional opportunities to write or to teach? ShOuLd I jUsT bE aN iNdEpEnDeNt ApP dEvElOpEr??

Me, as an artist, showing off my painting

Can someone just pay me to do bad drawings please?

Anyway, it was a stressful summer. And to bring this back around: all my indie work certainly suffered for it. Freelancing, job hunting, and impending parenthood — not to mention this little pandemic we’re having — left me intellectually and emotionally drained.


At the end of August, I finally received an offer from a company whose interview process felt quite a bit more aligned with my values and strengths than some of the others, and I accepted it. Amidst all my hand-wringing about struggling to find the “right” job, I was extremely lucky and relieved to have found this opportunity as quickly as I did. It’s very much a “big pond” job that I think will challenge me in a bunch of new ways and as more than just a code monkey, and I can’t wait to see where it goes. Ultimately, my professional identity is still “software developer,” and I’m feeling good about that. Landing an exciting job — effectively being told “hey, we value what you do and we want you here” — has a funny way of resolving career uncertainties and insecurities, for a while.

A couple weeks later, my daughter was born. Suddenly, the whole parenthood thing was real, and we had to figure it out on the fly. Everything about this was (and continues to be) strange and stressful and surreal and wonderful, and I’m more grateful than ever for so many of the people in my life — especially my little family.

A couple weeks after that, I started the new job. This was also right around the time the baby started to get suuuuper colicky (an imprecise term that just means “screams always, inconsolably, for no reason”). Suffice to say, the past couple months have been a hilariously overwhelming blur, but we’re starting to come out the other side, I think. Thankfully, my wife (like so many moms) is, quite literally, a superhero.

This year has been an absolutely wild ride. Everything has happened, and everything has changed. Inevitably, there’s lots I wanted to do this year that I haven’t — namely, the indie stuff that has ground to a halt since the summer — but I think the main reason I wrote this rambling piece is to remind myself of two things: 1, to be kind to myself, and proud of the stuff I have managed to do in this crazy year; and 2, to recognize and appreciate how lucky I am to have been in a position to do any of this stuff at all — in 2020, of all years.

I’m still really optimistic that once I settle into my new normal — hopefully in the next month or two — I’ll be able to ramp up the independent work again. I’ve got so much more I want to do with Oh Bother and beyond, and I’m feeling bullish on having barely scratched the surface of what I can accomplish on the indie iOS scene. I’m also as eager as ever to keep getting more involved with this community and build relationships with the ridiculous number of you that inspire me every single day. Let’s keep building cool stuff together.

I’ll be back soon – stay tuned! 📻