Check Your Parachute on the Way Down

I recently left my position as Director of Software and Web at littleBits Electronics, without a concrete plan, with 2 young kids in New York, and here is why I chose to embrace serendipity. This may seem crazy; popular wisdom would say to sign something before you leave, to always secure your next move, but that just felt disingenuous to me. Besides, I really felt like I needed to jump, and am convinced that every time you provoke life, you will be delighted and surprised.

Until a few weeks ago I was a founding member and the senior software leader at littleBits, joining shortly after its seed funding in late 2012 [more on my professional past here]. After pouring my heart and soul into this company for years, I couldn’t just “check out” and search for something new while pretending to be just as invested as always. I’m too passionate about what I do to pretend, and too honest and frank to play it cool.

I’m overwhelmingly proud and grateful; I’m extremely proud of everything I’ve done at littleBits, I’m proud of my friend Ayah Bdeir, and grateful for the years we worked together. I’m grateful to have known all the truly amazing people there, and proud to have played a major role in the company. But even in great circumstances there comes a time to move on.

I always thought “What Color is Your Parachute” [which I haven’t read] was about making sure you always had a plan of where you would go to work if you were to jump [or be pushed] out of your current airplane; which always seemed smart but rather mercenary. But apparently, beyond lots of practical job-hunting tips, it’s more about self-discovery, carefully figuring out what one is best at and what one enjoys most, which tend to coincide. So to do this, I write. Writing is an age-old technique to help externalize and process; as Joan Didion says:

“I write entirely to find out what I’m thinking, what I’m looking at, what I see and what it means.”

Background

I am a self-taught entrepreneurial technologist with an incredibly varied experience. I founded and ran a mostly digital design and production agency in Montreal for 10 years, working with startups, Fortune 500’s, big tech companies and individual professionals. We rarely did straight tech builds, because I believe that the collaborative relationship between Product, Design and Tech is more important than the individual pieces taken separately.

I have a heavy software tech background, but since “technology has moved from a vertical industry to a horizontal layer across our society”1, tech should be a vehicle for creating something great, not an end in itself. I have architected many complex software systems, built and ran many teams producing large-scale, global software, and with everything I’ve learned, there is always more to learn about people and the world.

Where I’m going

I want to go somewhere to help build a culture of Awesomeness. I am a high-performance socialist, which means I believe we live fundamentally in a society, not an economy, and that how we work is as important as the economic value we create. But don’t get me wrong, economic value is important to create.

I recently re-read the famous Netflix Culture deck, which is as relevant today as it was in 2009. There are aspects that seem a bit too Randian from afar, but overall it’s still so rare to find companies who live by simple lessons like “you don’t need policies for everything (there is no clothing policy at Netflix, but no one comes to work naked, so why would we need to track and limit time off?)”. Rare are organizations who specify what Judgement, Curiosity, Courage, Passion and Honesty mean. Who temper the potentially harsh “adequate performance gets a generous severance package” with the surprisingly human “Hard Work — Not Relevant” [echoing the increasingly popular sentiment that overwork is not a badge of honour]. Who aim to increase employee freedom and scope as they grow instead of decreasing it because of the belief that “process scales” and organic structures don’t.

Technology is Cultural

I am endlessly fascinated by the cultural side of tech. Tech choices — be they architecture, language, process or style — are inherently ideological, and steeped in cultural significance. So much of why projects and teams succeed is about cultural alignment first, rather than technical. So while I have worked very directly with lots of specific technologies, I am just as comfortable now working with a team who are experts in something I am not.

No, I don’t have to be the Best Engineer at Everything

I think of my role as a kind of multi-disciplinary, multi-lingual Director for the film we’re making of design & technology. Each contributor on a team is a creative expert in their own domain, responsible for their own part, and I provide guidance, clarity, vision and alignment to their individual contributions and pull the whole production together.

I have been fully invested in projects that bridge software and hardware in the quest of education, meaning and usefulness. I have written and spoken extensively about tech from the theoretical, philosophical, specifically technical and cultural. I also organize communities inside and outside companies.

I guess the purpose of this post is to reach out and hear thoughts, ideas, questions that you may have about firmware, hardware, software but also, what does it feel like to be out there, free in the open. I suppose the internet is this magical place where we write and connect. I hope to connect with you.