The Programmer Entrepreneur Dilemma

For the first 12 years of my programming career I became successful due to my work ethic.  Not only did I work long hours, but I worked off hours learning new technologies and programming languages.  For any programmer to be successful and maintain a high level of success, they must do this.

My ritual tended to go in year long cycles.  At the beginning of the year I would reflect on what I had learned the year prior, what I was using, what I wasn't using and figure out what exactly I wanted to learn in the coming year.  I would then buy a book and spend my nights and weekends going from cover to cover and doing exercises along the way.  If I had done my job right, I had picked something that was applicable to my current job and I could use it in practice.  Sometimes I would get halfway through a book and realize I wasn't enjoying it, put the book down and buy a new one.  I'd say over those first 12 years, I learned at least 1 new language a year and would throw in programming theory and concept books along the way.

Then nearly 2 years ago something happened.  I had an idea for a new website that I became excited about.  So excited that I spent nights and weekends (and an entire thanksgiving vacation) building and successfully launched what is now known as redditgifts.  This was one of the most exciting projects I had ever worked on.  For starters, it was my idea, my execution and its success or failure rested on my shoulders.  I was immersed in the community behind it and was taking constant feedback and iterating at a rate I had never done before.

Redditgifts was not my first foray into entrepreneurship but it was my most successful.  The effect of this success was interesting and unexpected.  Instead of spending my nights and weekends learning programming stuff, I was now spending my nights and weekends coming up with and experimenting with new ideas and projects.  With every idea I would experiment with, I would get 10 more ideas that I wanted to experiment with.  Luckily I happen to work at a company (Focus.com) where they realize the value and power of programmers having business ideas and have fully embraced this.  Not only do I spend my nights and weekends coming up with cool shit, I now get to do it during the day and get paid for it!

I'm sure that up till now this all seems like a good thing, and don't get me wrong it is a good thing.  It does however cause me to look to the future and wonder if what I am doing is the right thing for my career.  I am still programming, just as much as ever in fact, but I am not learning at the same pace as I was.  Let me rephrase that a bit, I am not learning programming at the same pace I was, I am in a steep learning curve of product design and business strategy and that is great.  But what does this mean for my future?

I'm not going to pretend I know the answer to this.  I think this could easily transition to me doing a startup and owning a good stake in a product's vision (and implementation).  I also think this could easily go away and I could go back to my old learning ways, but if this is the case, what does this say to the year or two that I have slowed my learning?  I haven't had the time to learn node.js or clojure and i'd love to mess around with scala and the Play framework.  True, I could do my next project with node.js but it would be much quicker for me to just do it in python and get it out the door!

So, that is my current dilemma.  I know there are plenty of people out there who have dealt with this, how should I look at this?  Please advise!