I'm almost half-way through this 5-year experiment with semi-retirement. Every so often, I like reflecting on the possible outcomes and whether I want to influence things one way or another. (Totally unscientific here!) Thinking about this will also help me figure out what I need to try so that I can properly discriminate among the options. Here are some of the ways this experiment could work out.

• A. “I want to go back to a regular job.” Let's say that at the end of five years, I've learned what I want to learn to have a smoothly-running, wonderful life, and I want to go back to working within someone else's business so that I can take advantage of its scale and infrastructure. I'd rebuild my network and dust off my resume, likely working my way back into a technical position in a team I enjoy working with. Life would be pretty similar to what life was like at IBM, except perhaps I'd be fitter, cook better, and write more.
  • Factors that would nudge me towards this: Possible job satisfaction, scale, learning experiences, team I like; also, if W- downshifts to part-time or takes a break
  • What would a typical week look like? Work, cook, read, write. I might use the extra cash to outsource chores or buy conveniences. Hmm, danger of lifestyle inflation here?
• B. “I want to keep freelancing.” Let's say that I like the flexibility and usefulness that consulting a few days a week gives me. I'd probably expand my consulting practice slightly so that I don't have to worry about being classified as a personal services business. During my free days, I might continue to do the kinds of things I'm doing now: writing, learning, tinkering with stuff.
  • Factors that would nudge me towards this: Happy clients, continued growth; also, if W- downshifts to part-time
  • What would a typical week look like? Much like my current weeks, but maybe consulting for different companies for a good balance.
• C. “I want to build a lifestyle business.” This would be if I'm curious about building other types of businesses. Maybe I'd learn more about web marketing, for example. I'd still keep it low-key so that I can do other things with the rest of my time.
  • Factors that would nudge me towards this: Curiosity about businesses that go beyond time-for-money exchanges; commitment to make products or automated services
  • What would a typical week look like? Responding to people's questions, creating new things, improving old stuff. Occasionally learning new skills and trying them out.
• D. “I want to ‘lean in' in terms of business.” This would probably be the next stage after building a small lifestyle business that's focused on products or automated services. Assuming I've got the rest of my life sorted out, I might channel my curiosity and energy into building the business so that I can help more people and apply what I've been learning from business books.
  • Factors that would nudge me towards this: Finding a good market that I really want to help
  • What would a typical week look like? I'd probably learn how to manage a small team, do lots of research and customer service, and make stuff happen.
• E. “I probably don't have to work, at least for a while.” Stock market growth and savings might mean that I'll have lots of flexibility, so I could choose to work or not. Depending on our circumstances, I might decide to focus on building up skills, making our lives easier, learning things, and sharing whatever I can. It'll be an interesting challenge figuring things out. I'd like to get really good at writing. I'd still be open to going back to work (even in a non-tech job) if the market plummets or W- needs me to cover things.
  • Factors that would nudge me towards this: ~3% withdrawal rate, good cash buffer for market corrections, productive things to do with my time, questions to explore
  • What would a typical week look like? Read, write, garden, exercise, cook. Occasionally get together with other people.

I'm the most curious about E (financial independence plus writing), but C (lifestyle business) that might eventually transition to D (larger business) could be interesting too.