Indie Diary - Day 100

I’ve had an eventful and mostly positive first 100 days of independence. This update is way overdue, so it’s a long one... here goes!

Fun Times


I attended three great conferences: Çingleton in Montreal, CocoaConf in Seattle, and CocoaLove in Philadelphia. Going in, I was anxious about overcoming my shyness enough to meet new people, especially some of my heros. I ended up doing ok, definitely better than I had worried about. I met a lot of nice, interesting and smart people, which was great… but I mostly chickened out of introducing myself to the “big name” people. I think the best recipe for getting better at this is to keep at it, and to work on doing a little better each time.

Coaching with Jaimee Newberry

One of my favourite podcasts is the currently on hiatus, Unprofessional, co-hosted by Jaimee Newberry and Dave Wiskus. In a couple of episodes, Jaimee touched on the idea of life design, treating everything about your life and career as something that can be designed, using techniques that are similar to how we design software. This made a ton of sense to me, especially in this new phase of my life. I did some more research, and found out that Jaimee had started doing life design coaching. I worked up the courage to write to Jaimee to learn more, and the more I learned about it, the more certain I was that it was going to be a huge help for me.

I’m six sessions into working with Jaimee, and it’s been awesome. We’ve been working through who and what’s important to me, and ensuring that that’s where I’m investing my time. We’ve talked about dealing with burn-out, and I did an exercise that has really helped in moving past the baggage I had from my last job. We’re working on building confidence and new habits, and on how I can share my voice.

If that sounds interesting and helpful to you too, get in touch with Jaimee, she’s the best!

Friends and Family

In the last couple of years, I’ve been lousy about spending enough time with friends and family… but I’ve had a great time catching up. As I start to get busier again, I need to remember to not sacrifice this important time.

Toronto International Film Festival

Colleen and I have talked about going to TIFF for a long time, but we made it happen this year. I really enjoyed the festival, it was refreshing to see a bunch of films that I knew almost nothing about before the screening. I would definitely go to TIFF again, the only thing I’d change is that I’d stay closer to downtown the next time. It would have been nice to have a place for a quick power nap and a healthy snack on the days we saw 3 or 4 films. (P.S. Go see Jon Stewart’s directorial debut, Rosewater, which is in theatres November 14th)


Travel vs Momentum

I’ve done a lot of traveling, which has been fun, but it has made it difficult for me to build and maintain momentum on my product design work and coding projects. At times, it has been pretty discouraging to have a couple of quiet days where I could make progress, and then to not make as much of the time as I wanted to.


I feel like I’ve fallen into a pattern of consuming way more than I’m creating. It’s so much easier to devour podcasts, blogs, books, etc. than it is to create and release things… but it’s way less satisfying.

I’m back at home at my desk for the next six weeks, so I need to focus on projects that I can finish and release so I can start reversing my ratio of consumption to creation.

What’s Next?


I’m a couple of weeks into a side project where I’m re-implementing some of the UI interactions from the iOS SpringBoard application in Swift. The idea was that by working from an existing design, I could focus on learning Swift and some iOS frameworks that I hadn’t used before. I still feel that was a good idea, as I’m not having to make design and product decisions as I go… but I may be trying to learn too many things at the same time.

I’m going to keep at it, with the goal of being done by the end of the year. I feel like there’s a lot of lessons still left to be learned by finishing it up, and also by releasing the code. I definitely suffer from the fear of “being wrong on the Internet”, but I think I need to get over that fear if I’m going to be successful as an independent.

Product Design / Research

I have a product idea that I suspect could be viable and interesting for me, but I’m working on building more certainty. Unfortunately, this is the kind of work that’s hard to measure, and it risks being an excuse to go consume more blog posts and books. To make it more concrete, my plan is to pretend that I have decided to build it, start making some design and implementation decisions, and estimate the cost to build and operate it. From there, I’ll take a step back and see if it still feels like a good bet. My goal is to know by the end of my next 100 days whether I’m going to go for it or drop the idea.


Releasing code or products is always going to be on an infrequent schedule, so I feel that writing regularly is going to be important for maintaining creative momentum. My goal is to publish something on this blog every week from now on. Please sass me if I’m not doing it!