How to turn my web application into a lifestyle business?
adammichaelc: Start charging. 3 plans -- good better best. use the money to hire another developer. maybe eventually build an iphone app; charge $5 for it. build an iPad app. charge $15 or $20 for it  -- you're still selling to early adopters who have money so they will buy. i think the Getting Real book would be a good read, as @steveklabnik mentioned.How many visitors do you get to the site currently? With a decent landing page with the paid option you could probably start out around a 0.5% - 1% +- conversion rate, and improve from there with some intense A/B testing. What's your free conversion rate?Other random ideas:
1. Partner with a small company that has a popular paper day-planner but no technology. Grow together and cross-pollinate. 
2. Partner with a huge company that has a popular paper day-planner but whose technology is lacking. 
3. Partner with another planning company, Apiggo (ToDo) and work out a deal to play off each other's strengths somehow
4. Add team-tasking and sell that version to businesses
5. Partner with somebody that sells to people that love productivity stuff, like David Allen. There's probably somebody at HN that knows him, or knows somebody that knows him.Anyway, you're an awesome designer! Great work. Good luck.