What Do I Want To Do Next?

One of the reasons I was really amped about joining the team at EducationSuperHighway was because the problem we were setting out to solve was one that I felt could be solved rather easily. We’ve already made great strides towards solving that problem (more info about that in Wired), and we know that in the next maybe two years we’ll be winding our work down.

Funny enough, this is the first time I’ve been hoping to be out of a job sooner rather than later, since that will mean we’ve achieved our goal and made schools in the US places where digital learning can thrive. But the recent release of our report, as well as my upcoming anniversary at ESH, has got me thinking - what next? I mean, I might reasonably be able to say “job well done” and move on to my next challenge in less than a year, so this question has been on my mind.

I wanted to write down some of my thinking on this both to help me organize my thoughts, but also so I can share it and get some input from others who have a deeper pool of experience and have worked more jobs than I have. So, here goes!

What do I value?

One of the big things that I’ve learned over the last couple of years is what really is and isn’t important to me when it comes to a work environment. So I guess I’ll just list what I’ve found to be my needs and my wants as a good benchmark for thinking about what to do next.


  • Remote friendly
  • Great colleagues I can learn from
  • Spending a majority of my time coding / reviewing code
  • Livable salary
  • Good healthcare, including dependents


  • Remote-first or all-remote team
  • Option to pair if desired
  • Tech stack that includes Ruby, Go, Elixir and/or Clojure
  • Focus primarly on backend work
  • Ability to spend time teaching/helping less experiened colleagues
  • Good code review culture
  • Adherance to agile development practices
  • Work that focuses on refactoring and/or scaling (I’ve built enough CRUD apps - now I want to work on really gnarly problems that require difficult solutions)

Deal breakers

  • Having to pair 100% of the time (wish I could do it, but it’s just not great for me)
  • Frontend only work (I’m just not super interested in that stuff)
  • Expectations that I am ‘on call’ to work all the time (I have a family who I love spending time with and I don’t want work to take away from that)

I listen to a ton of podcasts, and everytime someone from GitHub is on one of them it makes me think that I really want to work there. First and foremost, I love the product. It’s a spectacular way to share code and manage working on it, and now that they have deeper integrations with other services (most notably, the Pipelines feature on Heroku), it’s becoming a HUGE asset to us. We used to have our code hosted on BitBucket at ESH, and I can’t even imagine doing that now. Plus, I don’t think open source would be a fraction of what it is now if it weren’t for GitHub, and I strongly believe in open source.

But beyond loving the product, I think the culture there would be awesome for me. Being able to work remotely is a really big point for me, and their remote-first culture is super appealing. I especially liked hearing Sam Lambert on the Ruby on Rails Podcast talk about how they choose the right systems for their projects really reinforced the idea in my mind that it’s a wonderful place to be a developer. Also, Kyle Daigle is a co-host of that show and talks about all the awesome things that working for GitHub entails, and I’d be lying if I said that his testamonials aren’t really swaying me to want to work there.


The idea of working for a consultancy like thoughtbot is super appealing to me, and again their podcasts have really sold me on the idea that it’s a spectacular place to work. I’m not sure that there are any consultancies that are remote-first, though, which is kind of a dealbreaker for me. If they would be cool with remote workers then I think I’d really like to work there. Or if there are other places like thoughtbot that are cool with remote workers, that might work, too. I’m not sure there are many like them out there, though, so I’m not holding my breath on that one.

Autonomous vehicles?

I’m blind in one eye because of a car accident I had when I was a kid. It was caused by nothing more than me being an inexperienced 16-year-old driver and not knowing that I shouldn’t over-correct when my car slips a bit on the ice that is so commonly on back roads in Connecticut in January. This would never have happened if my car could drive itself, and now that I have a son I want to make sure that he never has to drive in his life. I’m not really sure how to break into this industry since I have a feeling it might require more CS knowledge than I have since I’m mostly self-taught, but I might be wrong! I just don’t know anyone in the industry so I haven’t been able to ask the kinds of questions that I would normally ask.

Being a consultant?

A lot of folks manage to do really well for themselves as independent consultants, but I’m not sure that’s for me. Sure, it nails two of my five needs (remote friendly and majority of my time spent coding), but I’m fairly sure the other three wouldn’t be possible, or at least not easy, if I went this route. Plus, this would mean I’d have to spend a good amount of time on marketing and sales, neither of which I’m really excited about. Again, though, I might be wrong, so if anyone has any feedback on this, let me know!