22 May 2020
A friend of mine worked as an investment banker right after college. As he described it to me, in i-banking you essentially have a very fixed career that comes with well defined roles. You start as a summer intern and (usually) from there you get an offer to come work at graduation as an analyst. From analyst you progress through associate, vice president, director and then managing director.
15 May 2020
When an individual contributor becomes a team lead or manager one of the hardest challenges to overcome is removing yourself from the critical path. I’ve failed at this multiple times but I’ve found that there is a pattern to my failures. They’ve all come from a slow burn rather than trying to take on something large from the get-go.
My biggest failure was becoming the de-facto data analyst after our original data analyst left the company. Don’t get me wrong, I’ve enjoyed learning about the data stack and being part of the data community (shoutout dbt!) for a while now. The failure is that it came at the expense of the time I should have been dedicating to people management.
07 May 2020
I believe in estimation of software projects because I’ve found it works well when you do it for the right reasons. I know estimation is a controversial topic so I thought I’d add my own opinion to the chorus of voices advocating the pro side. My only disclaimer is that my experience is entirely based on startups so this may not apply to larger companies or other industries.
30 Apr 2020
When I took over my first engineering team I thought deeply about my core philosophy for an engineering team and how that might impact my decision making. I try (and occasionally succeed) at being as consistent as possible so that engineers on my team have a good sense of what they can expect from my thought process. Most of these thoughts are not original but I think they form a good basis for how to approach thinking about startup engineering.
24 Apr 2020
Reflections on my time at Wonder
Today is my three year anniversary at Wonder.
I won’t go into the entire story of how I
fell ass-backwards into became the head of engineering but as I’m leaving Wonder soon I thought I would take some time to reflect on many of the lessons I’ve learned and record them here.