I've been thinking about what I should prepare for during the fourth year of my experiment. The first year was about exploring business. The second year was about digging deeper. The third year focused on self-care. I still don't know what shape my life will take in my fifth year and beyond, but I can plan for the probabilities.

Here's what I know:

• The stock market has been doing well. This is not likely to continue, but I don't mind investing for the long term, and I should be able to weather dips.
• I continue to provide good value through consulting, even though I've reduced my hours. It's nice to know that it's doable.
• This year I've had excellent quality of life, and I like it. I learned a lot about cooking and thinking. I revisited sewing and yoga. I loved having the space to deal with complex thoughts and issues.
• I want to tackle health. It would be great to move on from the fourth year of my experiment with good habits, strength, flexibility, and stamina.
• I want to collect good people and interesting ideas.

What signs should I watch for to know when I'm ready for a transition? How can I prepare?

I'm reasonably certain that I'll move to the next phase. I'm just not sure when. In the meantime, I can prepare by keeping my eyes open for people and ideas, developing skills, and learning more about what makes me energized.

What kind of business would I like to build next? I like our life too much to sacrifice it needlessly, so any business needs to either fit around this lifestyle or be worth it in terms of making a difference.

Businesses sometimes develop lives of their own, so I want to be careful about the patterns I set up for myself. As tempting and straightforward as it would be to follow the usual plan of working intensely over a short period of time, I wonder if there are other ways.

I suspect a business makes sense for me to build if there's a problem that I want to solve at scale, and if solving that problem involves money. There are lots of problems I can work on for free or pay-what-you-want, so I might want to lean towards working on those while I can.

There are different ways to come up with ideas or recognize opportunities. I respond better to specific individuals than to abstract markets, concepts, or even personas, so it makes sense to be on the lookout for people to work with or serve. I can also start cataloguing strengths, resources, and needs (for myself and other people) so that I can play a large game of connect-the-dots. Here are some of the strengths and resources I might be able to build on.

I'm particularly curious about the strengths outside technology. I feel like I'm getting better at being specific about language, teasing out differences and organizing thoughts while learning out loud. I enjoy exploring different scenarios and identifying adjacent possibilities, reining in perfectionist tendencies or analysis paralysis with satisficing. I like making small improvements, organizing things in sequences for easier flow and learning. I haven't invested as much in supporting other people or building relationships outside the household, but it might be interesting to try that.

So, if I were to apply myself with more ambition, what could that look like?

I can improve my physical habits to increase energy and joy. With a solid foundation of self-care, I can connect more deeply with more people, helping them grow. This will help me develop empathy further, making it easier for me to write, draw, and share things that are more useful to more people. It will likely also involve getting the hang of writing, finishing, and spreading books/courses, since people benefit from organized paths. I might run into ideas for tools and platforms along the way, so I can build those if my capabilities catch up to my wants and my wants outpace existing technology. If that generates additional cash, I can look into converting that into more advantages.

Mm. I think that could work. Bringing it back down to the level of things I can do right now:

I'm making good progress on doing a bit of yoga every day. (~30-90 minutes over the past 6 days so far!) To improve our quality of life even further, I'd like to get better at transforming the meals that we cook. As the weather warms up, I want to enjoy more park time and shared reflections with friends, and to use my focus on quality of life to help friends who are going through difficult times. (Friendfeed indeed.) I'll continue saving up so that the next steps will be easier – but I'll probably get even more out of a deliberate effort to catalog people's people's interests, skills, and needs, especially if I can practise helping people accelerate.

Mm. Sounds like fun.