The Five Year Plan

It's a brand new year. Our house has toys strewn across the floor and there's a giant bin of laundry sitting right next to me that I 'm' attempting to ignore. It feels like the perfect time to think about long-term things.

Early in my career one of my managers told me that I was the most goal-oriented individuals she had ever worked with. After working in an organization with quarterly OKRs, I have come to find that while I have always had clear goals in mind, I amm generally terrible at achieving them because I hardly write them down. (See the New Year's post)

Today I decided to sit down and sketch out a Five Year Plan to concretely answer the "where do you see yourself?" question. My goals largely follow a few themes.


I found my love for writing (and reading longform pieces) in a somewhat odd way. One of my high school English teachers would give weekly vocabulary quizzes. I would try to tell a story every week with all of the words. Ever since then I thought I might have the creativity to publish an actual work. I have dabbled in creative writing over the years, writing small stories, dabbling at being a consistent blogger of some sort. I am hoping this year's goal of writing 500 words intended for publishing a day will help not only improve my writing but add to some writing goals. A convenient by--product of this is writing almost 200,000 words and having enough posts to seed a bunch of "actual works".


I love building things and seeing them come to life. This is one of the key reasons that despite being a pointy-haired manager I can not seem to stop writing code. But there is a curse in all this in that I can never decide on a language or framework and stick with it. I have a bad case of shinynewitis when it comes to these things. Looking at the Five Year Plan should remind me that there is a lot of time in life to master specific technologies, and hopefully I can actually stick to a technology on an annual basis.


As a kid growing up in the South, I would go to church on Sunday and spend the afternoon watching NASCAR races. My favorite games growing up were Rad Racer on the original Nintendo and Ayrton Senna's Super Monaco GP II on the Sega Genesis. I started going to track days after I finished college and spent a couple of years autocrossing before getting married and having young kids ate in to both time and money. Now that I've established some roots it's time to go back to one of my early passions.


  • authoring 500 words x 365 days
  • weigh in under 155 pounds
  • attend at least 5 HPDEs and get solo sign off at at least 2 tracks
  • launch a Slack App in the App Directory


  • publish a book on [insert something here]
  • teach my daughter how to ride a bike
  • buy a dedicated track car
  • spend at least 10 days on the track and graduate to the equivalent of NASA HPDE3
  • learn and ship a side project in Ruby on Rails


  • reach 1000 users for my indie software project
  • teach my son how to ride a bike
  • spend at least 10 days on the track and graduate to the equivalent of NASA HPDE4
  • learn and ship a side project in Swift


  • publish a book on [insert something here]
  • start training my daughter for go-kart racing
  • start teaching the kids to code
  • become a HPDE instructor


  • throw a shindig for our 10th wedding anniversary!
  • start training my son for go-kart racing
  • obtain my wheel-to-wheel racing license
  • move south to Millbrae or Burlingame

This isn't comprehensive and I bet some of these will change. Somewhere in there I would love to reach the next level up at work, though this will largely depend on business need. You have goals. I know you do. And I know a major step to reaching goals is writing them down at all. Can't wait to see yours!