I have plenty of role models in terms of people who've done wonderful things as part of regular careers and entrepreneurs who've created products or services. I even have a few role models who've explored alternative paths: simple living, writing, arts, crafts, trades… I love having such a diversity of life paths illuminated for me, with so many examples of people doing well.

I've been thinking about the path that I might take. The path of growing outwards – self, household, close relationships, and beyond – seems unusual, or at least harder to find information on. It feels a little feminine, I think, skewed towards domesticity. I think that's part of the appeal for me. I want to take the skills I've learned in the mostly-male world of the technologies I've learned, and apply those skills in areas that might not be gender-balanced for a long time. This way I can maximize learning and difference-making.

2015-04-10b Reflecting on paths for living a meaningful life – index card #experiment #evil-plans

The impression I sometimes get from stories of startup founders is that they jump so quickly to imagining and building a service or product instead of developing deep understanding of needs, people, systems, opportunities… I know that doing things is a great way to learn things – fail fast and fail often – but I'm also curious about developing my understanding by other ways. I imagine that if I do this well, I'll gradually develop the relationships and insights that would help me make a good difference. In the meantime, I can focus on improving myself, helping and connecting with people, and taking and sharing my notes.

2015-04-20e At peace with a small life – index card #experiment

It's getting easier and easier to not be tempted to shortcut this process. At a recent party, I was talking to a serial entrepreneur who was looking for a successor he could mentor. He seemed to derive a great deal of pride from having created a wonderful product, and it was well-deserved.

He asked me if I had created any products that could be identified with me, and if I wanted to. Reflecting on the conversation, I realized that no, I don't particularly need to work toward that kind of significance right now. I'm happy to continue my experiment to at least the 5-year mark that I had initially set for myself, and possibly longer.

2015-04-19c 5-year plan vs 5-year experiment – index card #experiment

The 5-year experiment thing boggled him too. I think he was thinking of it more as a 5-year plan: have a certain goal, get there with actions and the occasional workaround. I think of this 5-year experiment as creating a safe space for me to explore and learn, and the timeframe is there to prevent me from running back into my comfort zone too early.

I guess I could describe my aims this way: I work towards cultivating happiness/equanimity and producing understanding as my first two priorities. At this point, I'm not working towards wide impact, fame, influence, or money. I might get to that someday, but I'd like those first two things well-covered first.

2015-04-20f Experiment timeline – index card #experiment

When might I move on from this phase? It's not that I don't think I'm ready, that I'm waiting for the stars to line up, or that I feel constrained to do this right now. I'm stacking the deck, and I'm collecting people and ideas.

2015-04-20h Conditions for considering a startup – index card #experiment #startup

What will likely happen is that, after I figure out a little more about life, I'll have these relationships with people I strongly want to help as a business partner or as a provider (preferably both). For example, if W- wants to start a business, or if I resonate strongly with a friend's idea, I might dig into it more deeply. But I'd still want to see if we could build a company without making the personal health or relationship sacrifices that you often hear about in entrepreneurship circles. I'd want people to still get good sleep and spend time with other people who are important to them.

So that's how my Evil Plans might unfold…

I enjoy an awesome life in general, so it feels a little indulgent to focus on making it better. But for the next few weeks, I think I'll experiment by being even kinder to myself. It's not just a matter of spending the entire day reading or playing video games… (On the plus side, W- and J- are avid players of the Persona RPG series too, so we get to joke about the game and swap notes.)

2015-04-17b Being extra-kind to myself – index card #self-care

I think it's about paying attention to the kinds of things that give me (and other people) joy, and finding a great balance. If I read too much without writing or trying things out, I feel disconnected. If I play too much, my brain feels buzzy. I enjoy other things too: cooking, taking care of things, cuddling the cats… I derive a lot of pleasure from creating a good life for myself and for the people closest to me. Oh, and there are little splurges that aren't actually all that expensive: strawberries while they're sweet, seeds and starters, 100% cotton fabric. (Maybe as an extra treat, I'll buy a yard of a Liberty print and see what all the fuss is about).

Mm. Yes, I think I'll cultivate these as my favourite ways of self-care:

• paying attention to and appreciating life
• making things, imagining them, tweaking them, improving my skills

in addition to the other ways I've been keeping my life relaxed and open.

2015-03-25a Learning about taking care of myself – index card #self-care

I changed my mind about the e-mail thing, by the way. I rather like this relaxed approach to e-mail. I want to see if I can continue doing it, maybe even quiet that occasionally guilty part of me that worries about messing up other people's plans.

2015-04-17e Slowing down e-mail – index card #email #slow #relax #experiment #semi-retirement

I figure it's as good a time as any to get even better at self-care. Dig your well before you're thirsty, after all. Build your skills and habits before you need them.

2015-03-25b Why have I focused on self-care – index card #self-care

I came across an interesting exercise in Barbara Sher's I Could Do Anythng If I Only Knew What It Was: to pick a scenario and try fully committing to it, even just for a little while.

Let's say that this current lifestyle is the thing that I'm going to fully explore. I've started thinking of it as blending technology and non-technology interests, building a little on the idea of exploring that future where tech is more integrated into the home. I'm not the only one exploring it (yay!), but there aren't that many people with the opportunities to do so yet, so maybe I can bring some useful ideas and insights to it.

So: laser cutting and sewing, Emacs and cooking, days with the abundance of time that science fiction writers used to predict we'd enjoy.

What would this life look like, carried to its fullest extent? What steps can I take to move towards that? How would this life evolve as technology advances and my skills improve?

One direction people go with lives like this is that of homesteading: building up more independence by growing and making more things. I like being close to the library, subway, and supermarket, so maybe that lifestyle isn't quite for me yet.

Another direction is to stay where you are, but improve the way you do things.

• I want to make more customized things, like the way I like wearing the tops I've sewn. Who knows, I might even get good enough to sew things for other people. As I get better at imagining and constructing things, I might also be able to apply those skills to laser-cutting, 3D printing, and other manufacturing technologies.
• I want to get better at repurposing things, getting more value out of stuff before we recycle or trash them.
• I want to gradually swap out more of our consumables with reusables. For example, I can make produce bags out of mesh. Then we won't need to use plastic bags for fruits and vegetables.
• I want to cook a wider variety of recipes, and I want to prepare each recipe better. I also want to get better at transforming leftovers.

I feel a little odd about a life that seems so focused on such a small area (of interests, of geography, etc.). I feel some internal resistance around that. But hey, Emacs is a pretty niche thing too. Besides, it might be interesting to take notes and see where this goes.

Related sketches:

• 2015-03-27b Resistance to different dreams – index card #resistance
• 2015-04-16a Imagining a week of taking it easy – index card #relaxing #life
• 2015-04-16b What does my Resistance sound like – index card #resistance
• 2015-04-16d What if I extrapolated this rest to awesomenss – index card #life
• 2015-04-16e How can I cross-pollinate interests
  

The impression I get from people's descriptions of their lives or careers is that many people (or at least the ones who talk about stuff like this) go for a big goal. They want to influence lots of people. They want to make a big difference. Sometimes it works out really well, but there are plenty of cautionary tales too: people who get what they strove for, but who've sacrificed their health, happiness, or relationships along the way.

It seems, based on the prevalence of these cautionary tales, that it's quite rare to find healthy ambition. This is an assumption, though. Is it true or false? I think it might be false. There are probably lots of examples of people who dream big and have wonderful, happy lives, but they don't get written about as much. (Something about news and schadenfreude, maybe?)

Anyway, an alternative might be to start small and build a solid foundation along the way. If I look around, I can see lots of good examples of this, although people some are more deliberate about it than others are. Instead of moving towards a specific, large goal that's a big jump from your current positions, you develop capabilities and gradually expand in interesting directions.

2015-03-06c Growing slowly from a solid foundation – index card #purpose #influence #success #growth

You start with a solid foundation of self-care. You cultivate a good community around you, and then you grow at a sustainable rate.

I used to have hang-ups about opportunity costs or wasted potential. Now I reason that if I don't get around to figuring out XYZ because I'm growing too slowly, someone else is probably going to figure it out, or it wasn't needed anyway.

Another danger, perhaps, is complacency. After all, if you're growing outwards from a strength or a position of comfort, it's easy to say: "Why not just stay here a little longer?"

I think it helps to think of some skills or areas you can improve at each stage, since you'll be making progress on multiple stages all the time anyway. It's not like you'll master self-care and then move on to relationships. You learn a little of one, you try a little of another, and you build up different areas gradually.

2015-03-06d What does that progression look like – index card #growth #success #purpose

For example, I'm pretty happy with my self-care skills of understanding, being happy, learning, and reflecting. If I get better at health, everything gets better too. I'm getting the hang of enjoying vegetables, and I'm back to biking – yay! Similarly, I can practise getting better at thoughtfulness in close relationships, and at asking for help in terms of connecting with a small community. For expanding the communities I'm in, I can practise sharing tips and lessons learned.

Another thought about slow progress: it might be okay even if I'm taking things more slowly than I think other people do (or that a hypothetical Sacha might do). If I'm accelerating, I can do interesting things later on. So, that leads to these questions: Am I accelerating? If so, how?

2015-03-06e Am I accelerating – If so, how – index card #growth #success #acceleration

Compared to myself from five or ten years ago, I think I'm improving my self-care skills at a faster rate. Learning more about tools for thinking has helped, and I'm picking up life skills too. In terms of close relationships, I'm accelerating in terms of W- and local friends, but not in terms of family and friends in the Philippines. In terms of a tribe or small community, I think Hangouts accelerate things a little, and so does asking questions or thinking things through out loud. In terms of community, I accelerated more over the past few years (experiments with publishing and knowledge management) than I have in the past few months, but there might be ways I can play with that.

Back when I was a whiz kid (probably like most people who were into programming at an early age), I occasionally thought about those fast-growth success stories like 30 Under 30 (or 40 under 40, or Young Presidents' Organization, or…). There's something to be said about being on the fast track, demonstrating momentum. The narrative is clear. The goal burns bright. It's easy to prioritize.

This other path of slow growth and neighbouring possibilities has its own challenges. It's easy to get distracted and drift. I'm curious if I can do it well, and what I can learn from the process. I imagine that if it plays out beautifully, I'll have a rich tapestry of a life while being able to trace the threads that connect the different sections. People are great at rationalization, so I can connect the dots going backwards.

In the meantime, looking forward, I imagine that I'll grow steadily and solidly, with the occasional leap enabled by trust and safety nets, and with a community of people I admire, learn from, and help. I imagine that my impact will grow as I develop my capabilities, so I don't accidentally end up screwing up thousands of people's lives or wasting millions of people's time. It might feel embarrassingly slow at moments (or even most of the time), as I take tiny steps or cover the same ground. But it's a life, and it might be an interesting one.

If I'm curious about this path, how can I explore it more effectively? I've sketched a few areas to focus on, so I can work on those. And then there's reminding myself that it's okay to write about the small steps, the lessons learned, the reviews… Let's see how it works out!

Related:

• Big dreams and small dreams can coexist (2009)

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.

Sometimes I feel a little duller around the edges, not quite as alert. It’s a little harder to think, to reason. I feel slightly out of focus. I talk more slowly, move more slowly.

And yet, living more slowly, I feel like I live more gracefully as well. None of the sharp jitters when my mind works at its fastest, none of the zigzags and interruptions, none of the words tumbling over themselves in their haste. More meditative.

I know why this is so and I don’t seek to avoid it. The real question is: How can I embrace this state? How can I make the most of it? It is natural, and will only become more so over time.

Coding currently feels better with a sharp mind, but there are still a myriad tasks to do and things to learn even when I don’t feel at my peak. Over time, I’ll learn to code in a reflective state instead of the intense one I carried over from competitions and quick prototyping. I think this will be good for my growth as a developer. After all, speed is not as useful as insight and care.

Reflective writing feels better than rapid writing. I don’t feel brilliant, but I feel methodical: following threads slowly, watching my own thoughts.

Cooking has become something that gives me pleasure. It’s one of those activities that I can indulge in, knowing that I can reliably create value where sometimes writing or coding does not. There are no blocks when it comes to cooking, only the steady slicing of ingredients and the textures and tastes of alchemy.

This slowness is perfect for listening, for talking. When I was younger, I felt an almost physical itch to be elsewhere, to be away, to be within the world of a book or a computer instead of in conversation.

Tidying benefits from deliberate thought. I organized my closet and my drawers by colour, and suddenly the patterns are visible. It takes just as much effort to maintain this order as it would to mess it up, and so I keep it.

Most days, I get very little done. But somehow, looking back over the week, I find that I’ve covered more ground than I thought.

I have the perfect foundation for learning how to live slowly. Few commitments, few expectations. I’ve lived this first part at a speed that other people have found remarkable but also, perhaps, uncomfortable: speaking, reading, coding, enthusiasm. It might be interesting to experiment with the flip side of that: the kind of stillness that the nuns in my grade school carried with them, the calm of late-night relaxed conversations, the serenity of quiet. I think I can translate the things I’ve loved about my faster life. Enthusiasm and delight don’t need to be breathless. The world is frantic enough. Let me learn how to be contagiously restful. =)