Two weeks ago, I found myself leaving a CTO role at a small startup and back on the job market during a unique up-cycle of tech hiring. My past job hunts came during economic down-cycles or in locations outside of the Bay Area – so this was something new.

There is an opportunity to express my sense for adventure while finding my next position.

In down-cycles and smaller job markets it can be pretty easy to decide what to do next: “Hey, I got a job offer. I’ll take it!” In a booming tech economy, there’s an opportunity to something new and a lot of potential career paths to take. More opportunity…and more potential for “analysis paralysis.”

To add to this, the code stack I’ve been working in the last 10 years, Java/J2EE, was starting to feel stale. Java/J2EE is far from dead, but there are other languages shaking things up. I decided maybe it was time to check out Python.

With these two factors in mind, I had to come up with a plan for trying something new in my tech career. If you’re in the same boat, I recommend five easy ways to sharpen your skills while looking for a new job:

  1.  Take a easy intro class. I found Google’s Python class online(, it was hard to make myself watch the videos, but the programming assignments were a lot of fun.
  2. Throw up website, figure out a framework. It was really exciting to do my first Django website: Will Aristotles ever become anything? Who knows, the point is to have something to play with.
  3. Join StackOverflow and start answering questions ( Over the years StackOverflow has saved my bacon, but I never had an account. Finally I have time contribute some answers. More importantly, teaching and troubleshooting for others has turned out to be a great way of learning more Python.
  4. Start working on something totally unreasonable. For that would be taking on some Python based Machine Learning problems ( I’m not likely to become a master in algorithmic perspective recognition in the next few weeks – but I’m having fun trying.
  5. Networking. San Francisco offers a huge number of groups and people to network with. I just swung by a “Python Twisted Hackday” (via and was pretty inspired seeing teams creating useful projects in day. I can’t wait for the next meetup.

Will all the above end up getting me the career change I want? Not sure, but it’s definitely fun to try. Find yourself in the same situation? Make your own plan.









by in A-Players, Career Development, Hackathon, hiring, Technology