I'm always most proud of the next thing I'm working on but never what I've done. My latest project is Everdwell but I'm most proud/excited about what we're going to be doing next with the product, not what it does today.
It took me a really long time to get to a point where I was somewhat content with my sources of inspiration. TheNews.im and Dribbble help me get past writers block or designers block but the best inspirational feedback usually comes from close friends.
I've been seeing a lot of Wikipedia redesigns. Someone needs to build a brand new Wiki platform from scratch. I don't think Wikipedia could update anytime soon but the millions of other sites currently using Wikis (and millions of sites that will) could take advantage of a more well-designed platform.
I'm making this up as I go and haven't decided on a definite path yet. I want to build companies and products and grow teams. That's something I've always enjoyed.
Many times I was 90% sold on an idea but didn't commit the last 10%. All of those times someone else was able to execute and build an awesome product or multi-million dollar business. I think Slack is my new favorite "I could have done that" idea. But as they say, "hindsight is 20/20."
I've always loved design and strategy so, if I couldn't work in tech, I would want a job that allows me to be creative and strategic. A CEO of a non-tech company could be fun. If anything, I do love to write.
Secret. It's my new addiction.