I migrated my blog last weekend. Over ten years worth of articles! (though I should say that I haven’t blogged regularly since 2013) Goodbye self-hosted static site with CSS from 2009. Hello Medium. It’s possible that I’m a little late to this party.
In the end, I didn’t end up importing everything. Because Medium appears to lack the ability to auto-import articles from Jekyll (preposterous! who would have thought?!), I had to manually migrate — or at least extensively edit — most of the content. Only the top 50 or so articles that were receiving significant traffic from Google Analytics made the cut. So I had an excuse to cheat a bit and discard a lot of the chaff.
Looking back on the rants and raves of 20-something me (the way that soon 40-something me will look back on 30-something me), even the best of those posts can still seem rather embarrassing. Misplaced enthusiasm for absurd tools, often impractical NIH-ism, and terrible grammar are among the many crimes of my youth. It’s also readily apparent that the tech industry as a whole has evolved a lot; 2007’s developer best practices were not what we would today consider practices at all, let alone preferential practices. Such is progress.
Reading through those old posts was also inspiring. It reminded me that at one time a regular writing schedule served a super important developmental function for me. It’s widely documented that there are a bunch of pretty great benefits that one gets from writing on the regular. It helps you organize and reframe your thoughts, it can be therapeutic during hard times, and improves memory recall. If nothing else, it’s a fantastically cheap type of external memory. Writing something down means you never have to ask “what exactly did I do yesterday, anyway?” or “how long did that crazy project take me and what did I actually learn from it?” (anyone who doesn’t manage their life through daily TODO lists is definitely missing out on an awesome party).
The most important benefit for me was that writing in public was a way of committing myself to certain things, on a certain schedule, at a time when my life was pretty much completely unscheduled. Knowing that I had to publish an article every week, or every month, or on any schedule really, ensured that I was continuously learning things that were worth talking about, and later, building things that had enough value to share… even if I was sometimes inventing those things just so I could share them. And even if no one was listening (which was frequently the case).
Not everyone needs this sort of framework for self-discipline. But it sure helped me when I needed it most.
I started getting serious about blogging sometime in early 2005. The startup I was working at had finally (painfully) failed. I’d then gone back to school and completed my MS (which is to say I opted out of the PhD). I didn’t really know what to do next. I knew I didn’t want another startup job just yet but I also didn’t really want to work for a living. I wanted to build things and dabble, but eschew long-term commitment. My rent was cheap. What was I to do? I decided I’d build a reputation as a software consultant, of course!
Ironically, it’d been awhile since I’d even written production software professionally — because school right? — so the blog became my public journal of experiments and explorations as I embarked on learning something new. At the time, this was Ruby on Rails. As a recovering C/C++ and Java developer, who had dabbled with (and hated) PHP, it had a lot of Smalltalk-ish things about it to love.
It seems that I lucked out, or perhaps just had a damn good pattern matcher; Rails exploded in popularity over the following 18 months. When I started getting involved (v0.9.x), the community was still bootstrapping its way into relevance. Through other blogs and IRC, I met a lot of other passionate people who were all far smarter than I was. They were building cool stuff! And talking about it on the Internet! I wanted to do that too. So I built things that I thought were worth talking about; some for myself, and some for clients, and managed to work alongside some really brilliant collaborators in the process. Many of whom I’m fortunate enough to still talk to on a regular basis.
Writing was the glue that tied it together for me at that time. A blog article was an expected outcome of the projects I was working on, a natural showcase for any learnings or discoveries, no matter how trivial. It was a forum in which to pose questions, to announce intentions that had to be followed through on. A short 3-paragraph link-laden post was often a challenge to elevate a clever piece of code into an easily digestible library I could talk about, or a chance to formalize my opinion on something by saying it out loud instead of merely thinking it (and often regretting it later). Writing in public helped me commit to learning. And it guilted me into following through. If someone else read what I had to say, agreed with it, or loved it, that was great. But it wasn’t for them; it was first and foremost a personal commitment to myself.
My blogging commitment encouraged me to become increasingly prolific in open source. This in turn led to hosting meetups, creating weekend hackathon events and launching critical infrastructure projects that are still in use today. It got me invited to speak at developer conferences. It got me paid as a monthly blog contributor to a developer magazine. It even ultimately got me a book deal. No one ever really read the book (thanks Apress), but no matter. I still wrote the damn thing. Mission accomplished.
I think I can quite confidently say that none of these things would have happened if I wasn’t writing about them on a poorly designed website with tiny fonts and bad art on a consistent basis.
Eventually the journey led me back to startups. Flash forward another eight years and I find myself working on the other side of the table in venture capital and wondering what the hell happened. How did I get here? What the fuck am I doing? And, honestly, why did I stop writing about it?
The truth is I’m not entirely sure when or why I stopped writing regularly. Was Twitter to blame? Was it that paid blogging gig, with the rigorous publishing scheduling and editorial oversight, that took all the fun out of it? Had it simply become a task? Perhaps I was just too busy with other things. Based on the archival evidence, my first time in the founder seat of a product startup in 2010 seems to have dealt the killing blow.
Maybe I was out of ideas worth writing about? (Gosh I hope not) Or maybe I had simply gotten what I needed out of it, and it was time to move on? The truth is it was probably a bit of all of these things.
It’s not like I went cold-turkey, but my writing output has certainly dwindled to drips and drops in the past few years. Yes, I’ve written several articles for SOSV’s Medium, and I’ve guest-posted in a few other places, but those writings have felt more like obligations; I wasn’t writing simply as a challenge to myself, because I had something I wanted to say (or commit to), or as a logical outcome of learning something new.
A colleague recently suggested that not needing these explicit “reward” or “motivation posts” might be a sign of maturity. I sure hope not. It seems to me that one great disadvantage to being a bit further along in ones career (other than arthritis) is that you can sometimes feel like you have less to prove. And more to lose. Looking back on this has made me realize that putting thoughts to words is important, if only to motivate oneself to follow through on the thing that was worth talking about in the first place. Somehow, writing about it — and making that writing public so you’re accountable for it — makes it all that much more achievable. Even if nobody else is listening.