Choosing Measurement and Leverage
I’ve spent almost my entire software development career in Chicago. I say “almost” because the seeds of my career were planted during the years before and after college when I lived in Seattle. It was in Seattle in 1999 that I taught myself HTML to get a side-gig at About.com. It was near Seattle in the 1980’s that I watched Microsoft work its way from a little building near Burgermaster, to 4 buildings across the highway, and eventually took over a huge, ever-expanding campus in nearby Redmond. It was in Seattle that I watched Amazon shape the world of ecommerce. I did some temp work just before I started grad school in 1997 and remember seeing notices in the temp office about warehouse work for something called “Amazon”. Watching these technologists’ ideas come to life and generate wealth for so many people in the Seattle area made an impact on me.
10 years ago my wife, my daughter and I moved to Chicago from Seattle. I love Chicago. I was born here, I went to college here, I have a lot of extended family here. I feel connected to this city and love walking around the Loop on a weekday. It just feels so alive. Much more than Seattle. But Chicago does not love technology and innovation like Seattle does. One of the great aspects of Chicago business is that it loves many things. Its business interests are incredibly diverse, which helps it weather economic storms better than most. But without much love for technology and innovation, Chicago’s best technologists are typically drawn to the most lucrative businesses to support. The most lucrative businesses for technologists in Chicago has been, and remains to be, finance. I quickly learned that most of the best and brightest of Chicago’s technologists gravitated to finance, and were making some great money there. Naturally, and especially as my family’s sole-income-provider, I was attracted to Chicago’s financial industry, just like so many others.
In 2005, I was working for ThoughtWorks. For the first half of the year I consulted at Chicago’s Huge Hedge Fund™. It was amazing. 3 kinds of coffee. As much soda, juice, fruit and ice cream bars I wanted, any time I wanted. Catered lunch every day. Even afternoon snacks. Great equipment too, nice big dual monitors and comfortable chairs. I worked on a team of smart people, led by Jim Northey, a great mentor. I audibly said to myself everyday, “don’t get used to this.” Good thing too. The company did some housecleaning in mid-2005 and pushed out many of its consultants, including ThoughtWorks. I landed at my next ThoughtWorks gig just a couple blocks away at Monster National Bank™. The first week I was there I went through withdrawal for the first time in my life (no more Dove Bars). But it was another great opportunity to work with some great people, like Derek Groothuis, Paul Julius, Mike Ward, Paul Hammant, Ross Niemi, and Ross Pettit.
The upside of these gigs was that I was building my finance resume and setting myself up to permanently join the ranks of Chicago’s finance geeks. The downside was that I didn’t really enjoy much of the work. The most interesting stuff I worked on was building tools to help improve the productivity of those who had to work with these huge legacy software systems. I enjoyed this because what I built was helping people who I was directly working with. The software systems that actually facilitated the businesses were an absolute mess and incredibly difficult to work with. The customers and users of these systems were far removed from me and my teams, so the feedback loops were always very slow and weak. If we screwed up, we fixed it, but it didn’t really bother us. We were still billing our time and working a normal work week. If we blew an estimate, we simply adjusted our velocity. If we did well, no one really noticed. To be fair, these layers and weak feedback loops aren’t always characteristic of Chicago finance IT. My friend Gareth Reeves told me about his days at a small financial firm where he ran an awesome XP shop with tight feedback loops and close collaboration with the business.
Knowing that I wasn’t going to stay at ThoughtWorks long-term (they love weekly travel and I hate it), I started considering my options. By the spring of 2006, I had told ThoughtWorks I was moving onto greener pastures. My manager at Monster National Bank™ caught wind of my departure and offered me a full-time position. I was also considering joining a 3-person, 8-month-old agile consultancy based in the town where I live (Wheaton, IL). The bank was offering a big salary, tons of benefits, 4 weeks vacation, and a hefty bonus. The little company had 2 weeks vacation and I got reimbursed $400 for medical insurance. I had about 24 hours to make my decision. I turned the bank down and joined little Obtiva.
Why?
Well, in 2005 I started reading a lot of Paul Graham. Probably because Hackers and Painters had just been published. This was also the year that Rails exploded. For me, mixing Paul Graham with Rails meant big dreams. Paul’s How to Make Wealth essay had a huge impact on me. Particularly ideas such as…
The people most likely to grasp that wealth can be created are the ones who are good at making things, the craftsmen. Their hand-made objects become store-bought ones. But with the rise of industrialization there are fewer and fewer craftsmen. One of the biggest remaining groups is computer programmers. A programmer can sit down in front of a computer and create wealth.
and
To get rich you need to get yourself in a situation with two things, measurement and leverage. You need to be in a position where your performance can be measured, or there is no way to get paid more by doing more. And you have to have leverage, in the sense that the decisions you make have a big effect.
Therefore, when I was given the option to join the global foreign exchange division of a large financial institution, it didn’t make any sense to me to say yes. I believed that I was talented and hard-working enough that joining a 3-person consultancy would be a better career move than supporting a bunch of filthy rich investment bankers. If I were talented but didn’t like to work hard, then the bank would have been a good move. I could grit my teeth, collect my paychecks and bonuses, look for ways to make more money, yearn for retirement, and try to find some happiness along the way. But, I do love to work hard, and I love taking on audacious tasks, and I love crafting software, and I love being measured, and ultimately, I love making a difference. So Obtiva made perfect sense.
That was 3 years ago. Obtiva is now a 20 person company and I own part of it. I live in a world of incredibly tight feedback loops and deploy software every day to my customers. I believe Paul Graham’s advice about measurement and leverage were bang on. For me it came down to a decision between a large financial institution and a little consultancy. Finance isn’t inherently bad, but I still believe that large is. Consultancies aren’t inherently good, but I will always prefer little companies. These tendencies of mine were formed 2000 miles away, in Seattle, where I watched little companies change the world.
My hope is that this post will offer some insights to people who come to a similar crossroads. Believe in yourself and let yourself be measured! Take the red pill!
