Experimenting doesn't have to be about coming up with conclusive answers. It can be about reducing uncertainty and increasing understanding. For example, compared to where I was at the beginning of this 5-year experiment with semi-retirement, I'm more comfortable with business. There are fewer unknowns in my life. No, actually–there are just as many unknowns, I think, but I feel more confident about handling them.

The original questions for this 5-year experiment were along these lines:

• Would I be able to build a viable business that fit my goals and needs?
• Would this kind of lifestyle be a good fit for me (and by extension, for us)?
• Would I use the additional time well?

If life continues along its current path, I'm reasonably certain that the answers will be yes, yes, and yes. So I've been thinking: what other uncertainties do I want to explore? What other unknowns do I want to learn more about? Does it make sense to structure those as experiments as well?

2014-08-29 Considering the time after the experiment

Thinking of these things as experiments seems to work well for me. Not the high school sort of experiment where we dutifully rolled marbles down inclines or mixed various chemicals to note their reactions, but rather a time-bound trial that you prepare for, observe, learn from, and reflect on. Before I started framing things as experiments, I usually limited myself to small ideas and occasional improvements. Thinking of this as an experiment helps me say to myself, yes, it will take a bit of time to really unfold, so don't worry about evaluating it too early, and don't worry too much about messing up because you'll learn something along the way.

Anyway… What other experiments might I run after this? Are there experiments that would make sense in parallel? I'm somewhat curious about trying out different business models to see what they're like. I'm curious about building an even more solid foundation for future experiments in terms of health, skills, and other intangibles. I'm curious about learning and adapting to a changing world. I don't have a clear experiment yet, not like the way I delineated my current experiment, but I'm sure that will come to me.

In the meantime, I have two years left in this experiment. Having the basics covered means that I can try bigger and more interesting things. Maybe software as a service? I've been avoiding this because of the risks and the support commitments, but maybe it's time to learn more about building products and services that people might find useful. I know where to find the markets for some of the ideas I'm interested in, and I know some people who'd be willing to give me feedback and help me build things for them and others. There are a number of other non-business things I want to learn more about, too.

2014-08-29 Tweaking my experiment

I like looking at other people's lives in order to pick up ideas for things to try in mine. It's useful to look at the life paths for both typical people and exceptional people, since all those paths sketch out different possibilities. If I can imagine myself clearly at different ages and on different probable paths, I can get a better sense of what I want to do in the near future. It's a little like bringing those possible future Sachas together so that I can ask them how they got to where they are, and maybe adjust my current path a little. It's a strange mental image, I guess, but it's handy for me. And there are tons of other people to learn from, too–role models from so many different walks of life.

2014-08-29 Re-planning my life – #experiment

Hmm. Let's see how things work out…

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.

As an experiment, I decided to work a lot more last week than I normally do. I made work my default activity. If I didn't have something particularly interesting in mind to write or draw or read, I'd log on to the network and check for requests, work on prototypes, and follow up on things I needed to do.

2014-08-13 Nudging the balance toward work – #experiment #consulting

The result was a very productive week. I made a few interesting Javascript-y prototypes that we're considering for use. On the the non-technical end, I worked on some marketing materials.  The momentum and focus felt great.

One of the things I realized about consulting when I was at IBM was that consulting is as much a learning opportunity for you as it is a way to create value for clients. At a little over two years, I think this is the longest I've ever worked on a single engagement. I want to make the most of what I can learn from this, while I'm immersed in the API and the environment and the experience. I'd like to get even deeper into building user interfaces, maybe even analyzing and tweaking performance.

2014-08-13 Discretionary work – #consulting

These are skills I can build on that for future products, services, or consulting engagements. Because I haven't been blogging or keeping copies of my code (didn't feel right based on the IP agreement of my engagement), I'll have to trust that the fuzzy recollections of my brain are enough for me.

My track record for remembering isn't too good. I can only vaguely remember some of the details the projects I worked on at IBM, and I suspect I've completely forgotten at least one. (And t's only been two years since I left!) But confidence and a certain sense of where things are or how I can go about doing things–those things stay with you, even if the specifics go.

Still, focusing on work makes me feel a little like I miss giving myself long stretches of time to tinker with non-work code, write blog posts, and figure out questions. It feels like my brain is a little buzzier, a little more tired. I usually sit down and write for an afternoon or two, when my brain is clear. In a few months, I'll have plenty of time to follow my own interests, so I guess I can wait until then. But it's good to know what I'm postponing so that I don't get too used to not having it. From Daniel Klein's Travels with Epicurus:

And Epicurus saw this opportunity for old age as one more benefit from leaving the world of commerce and politics behind us; it frees us to focus our brainpower on other matters, often more intimate and philosophical matters. Being immersed in the commercial world constrains the mind, limiting it to the conventional, acceptable thoughts; it is hard to close a sale if we pause in the proceedings to meditate at length about man’s relation to the cosmos. Furthermore, without a busy schedule, we simply have the time to ruminate unhurriedly, to pursue a thought for as long and as far as it takes us.

Incidentally, I really like this ability to change my work schedule on a week-by-week basis. This is the weekly variation in all the time I spent directly related to earning since I started this experiment in February 2012:

I started off working a lot, aiming for about 4 days a week. I tapered off a little to 2-3 days, and took a month off from time to time. Last week was more like the focused days of early in the experiment. I've gained a lot from learning to relax and use my time for my own interests, so we'll see how that plays out against these desires to learn and create a lot of value.

As an experiment (and because the timing works), I have a three-month break coming up. It'll be quite a different experience from the 1-month breaks I've been taking so far, probably as different as the way that having an entire weekday to yourself is different from squeezing your activities into an evening. So I have a few questions to think about:

• How can I make the most of that time?
• With the answers to that question in mind, how can I make the most of the weekdays I have until then? How do those activities compare with working a little more from August to September?
• Considering the most likely situations, how would I like to adjust my work/discretionary-time balance?

It got me thinking about what I actually do during my leisure time, and why. Oddly enough, despite the ability to spend lots of time reading and writing, I still end up writing at roughly the same rate I did back when I was working full-time. Some days the words flow freely and I queue up a few posts, other days I'm casting about for ideas. My reading has shifted a little, and for the better (I think). I doubt I'd have had the patience to read philosophy and reflect on it slowly back when I read in the evenings and the occasional weekend.

Aristotle writes in the Nichomachean Ethics on the topic of why we choose what we choose:

But that [virtue and vice] are concerned with the same things might become manifest to us also from these considerations: there being three objects of choice and three of avoidance–the noble, the advantageous, and the pleasant together with their three contraries, the shameful, the harmful, and the painful–in all these the good person is apt to be correct, the bad person to err, but especially as regards pleasure. (1104b30)

It might be useful, then, to reflect on these leisure activities and figure out how they stack up against Aristotle's objects, along with some notes on how adding more time to these activities makes sense. This will help me make a decision about the months leading up to November, and for after the break (depending on how things turn out).

Legend:

• T: Well-served by additional time
• N: Noble
• A: Advantageous
• P: Pleasant

Hmm. Tabulating and sorting it like this is actually pretty useful. I can see why work is so tempting for me, despite the opportunity to do other things. It is an opportunity to work towards and practise nobility/excellence through work; it is advantageous in terms of resources and reputation, which contributes to safety; and it's pleasant, especially when I get a chance to do some rapid-prototyping magic or some custom analytics.

Writing and drawing are less clear and more self-directed. But they are useful techniques for working towards nobility; they are advantageous both in terms of the content and the skills I develop; and both the process and the results of figuring things out are pleasant. If I spend more time and attention on these things, I can improve my ability to observe and articulate. It may take me years to get the hang of these skills, but they are good to develop.

I can develop both writing and drawing in the afternoons and evenings, but I do notice a difference in attention. I usually watch movies in the evening as a way of spending time with W-. This is okay for slow and light writing, but does not lend itself well to study, deep reflection, or application. When I worked full-time, I generally wrote in the evenings (sometimes before dinner, sometimes shortly after) or on one of the weekend afternoons. I like writing on weekday afternoons, now. I like the pace. Would I pick that over consulting? Yes, actually, depending on what kinds of tasks I'd work on. I can put off writing when there are important and time-sensitive tasks to be done, but writing is also important to me long-term, and I'm willing to take on a little risk in order to experiment with it.

Hmm. If I do two to three days of work a week–maybe even four–from now to October, while leaving at least one full day for writing, that's probably good. I can front-load the writing, since that's important to me. If I feel it could use more time, I might adjust what I work on. I'll spend the usual time cooking and taking care of house-things, although I might spend a little more time during the week to cook fresh dinners. I can use the three-month break to experiment with more writing and drawing. In the meantime, I can avoid getting used to the additional income by stashing it all in a safety net, opportunity fund, or similar budget. If we keep our lifestyle the same, it's easy to evaluate work for its own sake.

Are there some smaller-value activities that I should spend more time on instead of reading, writing, and drawing? Spending time with people is nice, but it can be a little iffy in terms of energy, so I might take the occasional opportunity and use the rest of the time on other things. I can review my notes instead of reading lots of new books, and use those notes for material for blog posts and experiments. When I find myself looking for non-writing activities, this table might be handy to review.

Let's see how this works out.

I've been reading a lot about early frugal living. I read Henry David Thoreau's Walden (1854), and I followed a link in a blog post to Ralph Borsodi's This Ugly Civilization (1929) and thence to his Flight from the City (1933, during the Great Depression – particularly poignant bits in the chapter on security versus insecurity). Both authors provided detailed breakdowns of their expenses and descriptions of their methods, fleshing out philosophies of simple living. There's much that I don't agree with, but there are also many ideas that I recognize and can learn even more from. I'd probably get along with the authors, and their mental voices will be handy to keep in my mind. I found both of them somewhat more relatable than Ralph Waldo Emerson in his essays, but I'm sure Emerson will yield additional insights on re-reading.

Both Thoreau and Borsodi emphasized the freedom you get (or keep!) by minimizing your wants. Thoreau wrote, “… for my greatest skill has been to want but little.” Borsodi points out the artificiality of many desires as products of a factory-oriented culture that must have people buy the things that factories produce. By questioning your wants and becoming as self-sufficient as you can be, you free yourself from the restrictions many other people have. In a way, it's a follow-up from what I'm learning from Epictetus. I like how the Greeks tend to be more about living in society instead of going away from it, though.

Homesteading is a big thing for both Thoreau and Borsodi. I'm not particularly curious about exploring homesteading at the moment. City bylaws ban keeping chickens, and I still struggle with garden productivity. The city is all I know so far. W- and J- both have reasons to be here. Besides, the Toronto Public Library system and a decent, reliable connection to Internet are doing amazing things for my learning at the moment. Perhaps someday, but not now. In the meantime, despite Borsodi's disdain for the stock market, I like the fact that it's doing well. The gains are much less than Virginia Woolf's five hundred a year (about US$45,000 these days; mentioned in A Room of One's Own), but I don't need that much to live well, anyway. Still, I'm going to keep working on some skills for independent living (cooking, sewing, repairing, making, etc.), since I can do that wherever I am.

Onward!

I've been holding back from experimenting with new businesses. I'm not sure how the next few months are going to be like, and I don't want to make commitments like sketchnote event bookings or additional freelance contracts. Besides, focusing on my own stuff has been an interesting experiment so far, and I want to continue it.

Still, from time to time, I get the itch to build systems and processes for creating value for other people. For example, when I talk to people who are struggling to find jobs or having a hard time building freelance businesses, I want to support and encourage them by helping them see opportunities. Talking about stuff can feel a bit empty, but actually doing stuff–and showing how to do it–is more helpful, especially since I seem to be more comfortable with sales, marketing, and business experimentation than many people are.

So, depending on how these next few months turn out, what are the kinds of businesses that I'd like to build?

• E-books and other resources: I like the way free/pay-what-you-want information makes it easy for people to learn without friction and still be able to show their appreciation through payment, conversation, links, or other good things. I also like the scale of it: I can spend some time working on a resource, and then people can come across it when they need it. No schedule commitments, either.
• Software, maybe?: Someday. The upsides of working on stuff that other people use: feature suggestions, warm-and-fuzzies. The downside: dealing with bugs. I think the first step would be to build tools for myself.
• Visual book reviews?: People seem to like these, and I enjoy reading.

Let me take a step back here and break that out into the specific characteristics I like. If I identify those characteristics, I might be able to recognize or imagine other businesses along those lines. What attracts me?

• Scale: Build once, help many. I don't mind lower sales at the beginning if I'm working on the kinds of things that people will find useful over a long period of time.
• Accumulation: I like collecting building blocks in terms of content and skills because I can combine those in interesting ways.
• Generosity: I like free/pay-what-you-want because it allows me to reach the most people and feel great about the relationships.
• Flexibility: I like minimizing schedule or topic commitments because that reduces stress and lets me adapt to what's going on. Self-directed work fits me well.
• Distinction: I like doing things that involve uncommon perspectives or combinations of skills. I feel like I can bring more to the table.
• Value: I like things that help people learn more, understand things better, save time or money, share what they know, or be more excited about life.
• Other things I care about: I care about making good ideas more accessible, which is why I like transcripts, sketchnotes, writing, and websites. I also care about helping good people do well, which is why I help friends with their businesses.

Writing fits these characteristics pretty well. If I can help friends through process coaching and things like that, I can learn more about things that other people might find useful too. It's entirely possible to build good stuff around just this learn-share-scale cycle. Anything else (spin-off businesses? software? services) would be a bonus.

I have a little more uncertainty to deal with. I can see the timeline for it, so I'm okay with giving myself permission to take it easy for the next couple of months. After that, I'll probably have a clearer idea of what the rest of this experiment with semi-retirement (and other follow-up experiments! =) ) could be like.

What would more focused writing or content creation look like? I might:

• Pick a subject people are curious about and write a series of blog posts that I can turn into e-books
• Revisit that outline of things to write about and flesh it in
• Organize blog posts and other content into downloadable resources
• Create courses so that people can go through things at a recommended pace and with multimedia content
  • Ooh, more animations

I think that would be an interesting life. =)

I still want to do something to help all these awesome people I come across who are having a hard time finding jobs or building businesses for themselves, though. It's odd hearing about their struggles while at the same time watching the stock market keep going up – businesses seem to be doing okay, but it's not trickling down? Maybe I'll spend more time listening to people and asking what could help. Maybe I can spend some time connecting with business owners and seeing if I can understand their needs, too. Knowledge, ideas, and encouragement are easy, but there are probably even better ways to help. Hmm… That gives me a focus for networking at events. Looking forward to helping!

I set aside Tuesdays and Thursdays for consulting. Fridays are for meetings and getting together with people. Saturdays are for spending time with my husband or having the rare party, and Sundays are for cooking and chores.

Mondays, Wednesdays, and Fridays are discretionary time. I could spend those days working. My consulting clients would love to have more time, and there are all sorts of other things I could work on as well.

I've been making myself find good uses of that time on my own, though. Depending on the projects I'm focusing on, I might spend those days coding, drawing, reading, or writing. Lately, I've been working my way through a stack of philosophy books from the library. Histories give me overviews and show me the relationships between thinkers, while treatises give me the context for all these quotes that have been floating around.

Hmm. Maybe that's what fascinates me about philosophy at the moment. I've picked up bits and pieces of wisdom through quotes and summaries. Now I want to learn more about the context of those sound bites and the thought processes behind them. I want to reflect on the maxims, choose the ones I want to apply to life, and learn how to observe and improve. At some point, I'll probably feel that I can learn more from experience than from books, and then I'll jump back into the fray. In the meantime, it's amazing to be able to condense centuries of thought into afternoons of reading. Not that I fully understand everything, but there's enough to spark awareness and recognition.

I'm not particularly interested in the big questions of metaphysics, epistemology, or logic. Ethics, maybe–small “e” ethics, not as much the Ethics of What Everyone Ought To Do. I want to get better at choosing what's good for me and doing it. The ancient Greeks have a lot to say about that, and some of the later philosophers also do.

I'm not an entrepreneur, or at least not yet. I'm using this space and capital to improve myself (or at least theoretically improve myself) instead of building a business. I'm not even focused on learning a marketable skill that I can list on my résumé, although I'm sure my interests will turn towards that at some point. In the meantime, it feels good to lay the groundwork for more clarity and better decisions.

What's the next step? Well, since I'm interested in applied philosophy, that probably means testing these ideas out in everyday life. On the personal side, there's living simply and thoughtfully. On the social side, maybe practising more loving-kindness. I don't think I'm cut out to be a pure philosopher, so I'll likely use my time to learn, code, write, and draw. I wonder what I'll be curious about after I build a good foundation in this area. Useful skills, perhaps? Design and aesthetics? Business? We'll see.

In the meantime, I'll give my mind enough space to unfold questions and learn from the notes that people have left for us.