Male, Early 30s, American.
Plan: Retire into low-key business(es) by 2023.
1) Complete my two-year AAS degree as Computer Support Specialist by 2013. Find better paying jobs as a result.
2) Simultaneously work on online-content website/business to build passive income. (this is experimental until it becomes reality) My hope is to reach some key milestones before I get my degree in 2013.
2a) Income milestones would be $750/mo, $1500/mo, 2083/mo, and $5000/mo.
2b) If I reach 2083/mo I would start to think about quitting my job or school. If I reach 5000/mo, I definitely would quit my job or school to focus on my other projects.
3) Assuming my online content business doesn't work, I would take my income from my IT work and buy rental houses, anywhere from 4-10 houses. Similar income milestones would apply as to when I'd depart the job market.
4) I would continue to save money and diversify investments to expand income and enrich my life with my hobbies, interests and activities.
Pretty simple. If it happens sooner than 2023, I won't protest. :)