I elaborated these first two year goals on my personal website:
1) Create a website that solves some problem, no matter how minor. I have notions of a variant on mortgage calculators that I could work on.
2) Use Python and learn to program some physical device: a camera-wielding drone over a swim meet? A cat-tracking GPS device? MakerFaire was awesome. Go to it with a product. Or just be able to make cool birthday presents for my kids.
3) Make a program that will optimize some element of TriplePoint’s business.
4) Be able to volunteer as a tutor/coach for some class of kids at the end of the two year path.
5) Stretch Goal: a comprehensive analytics and reporting engine for the communications industry.
6) Five-year goal: Become deeply knowledgeable about fields outside of where I gain technical competency to be able to properly incorporate the trends into a larger work of history.