The following is a list of events from my past that have helped make the principles of 4HWW resonate so strongly with me:

  • 1980’s: My elementary school is the first in the state to switch to a “year-round” schedule. I learn the value of, and become accustomed to, shorter bursts of focused work with vacations spread throughout.
  • 1993: I spend 2 months at a summer camp in rural New York called Camp Rising Sun. I work and play with 100 boys and girls from around the world, gain a real love for people and languages of other cultures, and make lifelong international friends whom I promise to visit someday.
  • 1996-98: I volunteer for a 2-year service mission to central Canada through my church, which changes my perspective on life. Related to 4HWW, I learn two valuable lessons: 1- Serving other people really does bring happiness. 2- It’s possible, and quite liberating, to live for two years out of two suitcases and on a minimal budget.
  • 1999: For a class assignment, I read “E-Myth Revisited,” (one of the books Tim references in 4HWW) and it changes my perspective on entrepreneurship.
  • 2000- I watch my best friend’s father retire from decades of working in the public school system. A year later he returns to the school system where he continues to work today.
  • 2000- My college Economics professor instills in me a strong understanding of the concepts of opportunity cost and sunk cost. I never look at time, money, nor material possessions the same again.
  • 2001- I decide and begin to declare that I want to be semi-retired at age 45. I qualify the statement with “semi” because I recognize that another 50 years of not working at all is ridiculous. I also get used to answering the question of “what will you do with your time?”
  • 2002- Much to my delight, I discover an article entitled “Retire at 45,” which I write about. Thus begins my quest to avoid large homes, particularly the millstone-collar mortgage that accompanies them.
  • 2002- Upon moving to Chicago for graduate school, Chelsey and I sell our car and move into a studio apartment; two things considered very unconventional for a married couple (especially to our friends back home). This allows us to enjoy the city lifestyle we want without incurring significant debt.
  • 2003- I take a semester off from grad school to spend time on my own business endeavors, and I consider transferring to CMU. The counselor at school asks me if I’m stupid. After spending the semester building up my Flash skills and developing one of my muses ( WebSort ), I return to school. Chris Conley and John Grimes become my mentors.
  • 2005- As graduation approaches, I form my favorite conversation-starting question: “So, if you could work from anywhere for one year, and have the same job you do now, where would you live?”
  • 2006- With a new baby, the worry of health insurance, and a very sexy-sounding project waiting for me, I take a “real” job and we move to the Boston area. At first things are fantastic. Eventually, the call of entrepreneurship becomes too strong.
  • 2007- I resign, giving longer-than-usual notice in order to help finish the project. A week later I come across 4HWW via 43Folders. Chelsey and I listen to Tim’s presentation from SxSW, and we decide to really go for it.

Finally, here are some past entries from my personal site that came to mind as I read 4HWW: