From my 'mid-life-crisis' series of blog entries :-)
Open Source Work
Open Source Work has paid my bills for a long time. Starting with Plone in the early 2000s, to Django in the early 2010s, to now. And for this, I am very grateful. To be clear: it's not exactly the Open Source Work that has paid my bills, it's the consulting work I've been able to secure as a result of my dedication and devotion to open source software and communities. Which is great! (Even more clear: my dedication and devotion to open source software and communities has made learning new skills fun. And those skills have paid my bills for the past 8 years.)
TL;DR: Open Source Work is awesome. I'll likely spend my entire life doing it (in some capacity or another). And while Open Source Work does not pay, the experience is invaluable.
Along the way, I caught the "startup bug" and have been interested in building a SaaS offering that would at least pay my bills, if not make me fantastically wealthy. Enter 2012's: pythonpackages.com. The year I spent doing pythonpackages.com work was awesome. I learned a lot. Traveled. Met a lot of cool folks who seemed genuinely interested in my idea(s). But unfortunately, I never made a dime doing it. The lesson, among others, is that SaaS offerings are hard. I am now semi-focused on a "reboot" of the pythonpackages.com idea(s), but that's going to take a while to get going.
TL;DR: Consulting *was* the dream. Now building a SaaS offering *is* the dream (among others). So where does Open Source Work fit in?
Play as Work
I've been "working for a living" since age 14. Back then, I was a busboy and dishwasher in my family's Italian restaurant, where I first learned to work hard and have fun doing it. Since then, I've always worked hard, had fun, and taken few vacations (except for 1994-1998 when I was a full time CS student). I suspect I will always "work for a living" though as I get older, the line between work and play becomes even blurrier. Everyone wants to love or at least like their work. But very few are able to turn their play in to paid work. That's what I want to do. And I am very fortunate, I think, to know what I want to do in life. I know middle aged folk that still don't know the answer to that question.
TL;DR: liking my work *was* the dream. Now turning the things I like to do into paid work *is* the dream. In 2013, I would like to spend more time doing Open Source Work, working on projects like Buildout, DC Python, Pillow, Plone, django-axes, et al. If you have benefited from my work on any of these projects, directly or indirectly, please consider making a gittip donation to help me do more Open Source Work in 2013.