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May 30 '10 10:02pm

Reflections, One Month In

It’s been a month since I turned over a new leaf in my working life, and I’d like to share some thoughts.

First, I am writing this on my personal blog and not on my business site because, when I created that site, I knew that every business website nowadays has a blog, and that seemed a good reason to leave one out. That’s not a permanent decision: I’ll probably start a blog there when I have a unique and coherent point of view, as a business, to share with the world, but that’s not quite yet.


It’s been a very busy month. I wanted to hit the ground running, so I deliberately took on a larger work load for the immediate term than I probably want to sustain. (I was also a little surprised and very encouraged by the amount of demand there was so soon out of the gate.)

I’ve [re]-learned a few things about time. Halfway into the month, after working most of my waking hours for two weeks, I left my laptop at home and took my Kindle to a coffee shop in Cambridge to read Seth Godin’s Linchpin for an evening. My work involves constant mental energy by its nature, but I got more thinking done between the lines of the book in an hour there than in the previous week. Being head down in work all the time may be good for productivity but is not conducive to new ideas or reflection. (If hygiene didn’t matter, idea-generation alone would be a reason to shower every day.)

Valuing Open Source

I decided early that certain principles should be deal breakers. One in particular that’s been challenged several times already is respect for open source. I work primarily with open source software that is valuable because so many developers and organizations released their contributions for free to the community. Learning and adhering to best practices and new techniques (in any context) involves reading what other people have done, and that’s only possible because they share it. “Giving back” skills and code to the ecosystem makes the world richer for everyone. (As a side benefit, it can also be good for marketing.) Most businesses still think in zero-sum terms - open source saves money, but don’t let anyone else benefit or add to anything we created - and I think that’s short sighted. It’s one of the reasons I left my corporate job.

So it’s been interesting, in nearly every client agreement I’ve been involved with, to have to defend my right to re-use or release any original code serving a general purpose back to the community. The standard consulting contract still has absurd intellectual property clauses - everything you bring to the project, even if it was yours before, is now solely ours, etc. That’s a 20th century mentality and the lawyers need to catch up with the times. On one project I decided to conduct a requested audit/review of a site but not write any original code because the client (or their lawyers) were so adamant about code ownership. (My thought: if a brand-new competitor could beat you simply by using the same general-purpose additions to an open-source framework as you’re using, you should rethink your value proposition.)

(If you’re dealing with the same issue, check out CivicActions’ contract template, released under a Creative Commons license, which is a great model for upholding open-source values.)


I spent a little time today reflecting on a failure of mine at the job I recently left (in the context of Linchpin). One of the company’s sites that I worked on was an old site on an old server and the code wasn’t version controlled. Deploying new code involved downloading, modifying, and uploading in duplicate to the staging and production servers, hoping no one else was working on the same files. I thought this was backwards and insisted on putting the code in SVN like the rest of the sites, and took it upon myself to do so.

Only a fraction of the code could actually go into SVN, however; the vast majority of the site’s many static files (accumulated over years) were generated by a separate application in a way that would make SVN unusable. Separating and deploying them became a nightmare, the solution to which was more about office politics than systems administration. Editors and designers had to change their workflows so files would be tracked and in the places they belonged. But they were comfortable with the way they’d done things for years, and the sysadmin team didn’t want another automated process to worry about.

So I got the technical work done, but the “process” stuff (the human part) lagged, and deploying code became a full day’s work that only I could do. Months went by, we had meeting after meeting to figure out a long-term solution, I proposed a complex solution that was rejected, then simpler ones; the sysadmin proposed a solution no one understood; the editors didn’t show up at the meetings. I likened the situation to walking through a swamp - you’re better off on the other side but drowning if you stay in the middle. A week before I left, I took the code out of SVN, and left it to the other developers just as it was when I came in.

I did a lot of good work at that job, but that was one failure worth reflecting on as I develop my business. Being good at the actual work is critical, but it’s not the whole game. The “art” as Godin calls it involves the social/emotional work as much as the technical. I made the conscious decision (in leaving) that corporate politics were not the best investment of my time and energy, and I don’t regret not staying around to fight more battles with entrenched cubicle dwellers. But I do need to constantly work on my inter-personal skills, and think about the human side to infrastructural change, and be sure I can follow through on both sides of the coin if I commit to something.

Working at home

I’ve been working mostly at home. Pro: the cats like having me around. Con: I don’t have an ergonomic setup yet. (I’m looking into getting an adjustable sitting-standing desk, preferably before I develop tendinitis or carpel tunnel. The MacBook Pro is a beautiful thing but the sharp front edge tend to pinch the nerves in my arms and make my wrists numb.)

I really enjoy working at good coffee shops, and being a T ride away from some amazing ones in Cambridge and Davis Square is great. Over the next few months I’d like to explore working at least part-time in a coworking space. I do miss the camaraderie (and Nerf gun fights) in the office, though I don’t miss the cubicle.

Well this is quite a long post. Congratulations if you’ve read it all the way through. Thank you, and stay tuned.

May 2 '10 12:09am

Discomfort and Showing Up

Craig Harper offers the following hypothesis: "There is a positive correlation between how uncomfortable an individual is prepared to get and their likelihood of success – irrespective of the field of endeavour." 

There's definitely truth in that.

I was listening to an interview on Fresh Air the other day with the actor Sean Hayes, and heard this great exchange:

GROSS: So if singing scares you a little bit, and you're out on a Broadway stage singing, that's got to be scary with a capital S.

Mr. HAYES: Yeah, that's what life's about, though, isn't it? Isn't it about getting out of your comfort zone and getting off the couch and challenging yourself and forcing yourself to do things you wouldn't other do, otherwise what are you living for?

GROSS: Comfort.

(Soundbite of laughter)

Mr. HAYES: Well, actually, I'm realizing that now. Comfort never sounded so great.

Friday was my last day at my "day job" with a corporate employer. Monday I officially begin my new era of freelancing. (In practice the era started a few weeks ago, but this is the clean break.)

Someone told me today, switching from a job to freelancing means you go from working some time to working all the time. Definitely truth in that too. It'll be a few months until I get a good work-life balance back, and that's fine. Maybe I'll work for 6 months and take a month off. I couldn't do that before.

A colleague asked me the other day how I've gotten work so far. I didn't have any particular secrets to share. Mostly I just showed up. (As Woody Allen said, that's 90% of life.) I show up at Drupal meetups, share what I'm learning and working on, we get pizza and beers afterwards, and I get work. I saw a proposal for a panel discussion at DrupalCon that I wanted to participate in, I "showed up" and asked if I could join, that led to a gig with ImageX Media. I laid down the cash to show up at DrupalCon, and it was exhilirating. None of these were calculated, "if I show up here, I'll get this gig." It just works out that way. Showing up just seems like a good idea in itself. (What's the worst that can happen? I'll decide not to show up next time because it's a waste of time, lesson learned.)

I've noticed several people recently who don't seem to be getting anywhere, because they don't show up anywhere. Because it's sometimes uncomfortable to meet a bunch of strangers or write something on a subject in which you don't have a PhD, or try to get involved with something unknown.

One thing I'm worried about for the next year is that I'll get into a comfortable groove, establish steady habits, feel like I'm doing really well, and stop learning from others. That'll be one of the biggest challenges over the next year, maintaining that open-mindedness and humility. That, and maintaining a work-life balance. I have to make sure not to ever get [too] comfortable.

(Added: I Google'd "90% of life is showing up" to find the source of the quote and stumbled on this great blog post by P Morgan Brown.)

Apr 11 '10 9:21pm

Launching New Leaf Digital

Last week I wrote that I was turning over a new leaf in my life, leaving my corporate job at the end of April to become an independent/freelance web developer. A combination of factors, including turning 25, reminded me that this was something I wanted to do eventually, and there's no time like the present.

So today, I officially launched the website for my new business, New Leaf Digital, at

I've also joined the development team at ImageX Media in Vancouver, starting May 3rd. ImageX will be a pillar of my new track, and in the rest of the week I'll be working for my own New Leaf Digital clients and pursuing other interesting projects.

The good news is, I'm already swamped for the next few months. The last few weeks have been exhilarating (and exhausting), as I take on new clients and set up New Leaf Digital, while still working 9-5 an hour from home.

Next weekend I'm headed to San Francisco for DrupalCon.

Apr 6 '10 11:52pm

Big News For Me

I've got some news about a major change I'm making in my career. I've been doing web development in various capacities for around a decade now. My last two jobs on this track included a year with a Drupal consulting shop and the last seven months with a large publishing firm.

I've recently decided to leave my job and go independent. The next few weeks will be very busy, transitioning out of my day job (ending April 30th), attending DrupalCon in San Francisco (April 19-21), speaking to potential clients, and freelancing in the evenings.

I'm turning over a new leaf in my life, going in a direction I've wanted to pursue for a while. So it makes sense to call my business New Leaf Digital, and I'll have more details about that soon.

I've been inspired by so many people and ideas lately. By Jason Calacanis' talk about "Samurais and drones," Andrew Warner's incredible interviews, 37Signals' ReWorkSeth Godin's Linchpin, and so many others. (I'm going to devote part of the soon-to-launch to these inspirations.)

I want to thank all those who have encouraged me and given me great advice. I also want to thank everyone who has not encouraged me: those who have my best interests at heart, because they care, and those who don't, because they brought clarity.

This is an incredibly exciting and (in a good way) terrifying move. Really the only thing to fear is failure, and fear of failure is a terrible reason not to do something great. James Cameron said it right at TED:

Don't bet against yourself. Take risks. Failure is an option. Fear is not.

Stay tuned.

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