Starting from a small life

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

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

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

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!


What do I want to get ready for next?

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.

2015-03-28b Imagining the fourth year of my experiment -- index card #experiment #vision

2015-03-28b Imagining the fourth year of my experiment – index card #experiment #vision

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?

2015-03-25c When do I move to the next phase, and how -- index card #experiment #plan

2015-03-25c When do I move to the next phase, and how – index card #experiment #plan

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.

2015-03-25h Imagining my next venture -- index card #experiment #vision

2015-03-25h Imagining my next venture – index card #experiment #vision

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.

2015-03-29b What strengths and resources can I use to help others -- index card #strengths #experiment #business

2015-03-29b What strengths and resources can I use to help others – index card #strengths #experiment #business

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?

2015-03-29d What would more ambition mean -- index card #ambition #experiment

2015-03-29d What would more ambition mean – index card #ambition #experiment

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:

2015-03-28c How would I like to take things to the next level -- index card #improvement #experiment

2015-03-28c How would I like to take things to the next level – index card #improvement #experiment

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.

Sketched Book – Self-compassion: Stop Beating Yourself Up and Leave Insecurity Behind – Kristin Neff

I read Kristin Neff’s Self-compassion: Stop Beating Yourself Up and Leave Insecurity Behind (2011) on the recommendation of a friend who’s been working through many of the issues addressed by the book. I liked the book’s differentiation between self-esteem and self-compassion, and its exercises for acknowledging your inner critic and becoming kinder to yourself. The website ( has MP3s for guided meditations and a hyperlinked bibliography of related research.

I’ve sketched the key points of the book below to make it easier to remember and share. Click on the image for a larger version that you can print if you want.

2015-03-24a Sketched Book - Self-compassion - Kristin Neff -- #sketched-book #self-help

2015-03-24a Sketched Book – Self-compassion – Kristin Neff – #sketched-book #self-help

I’ve been thinking about self-compassion and self-care over the past few years, ever since I decided not to set up that taskmaster dynamic with myself. Instead of trying to force myself down one path or another, I chose to go along with myself, focusing on understanding and then slowly guiding myself. It seems to be working well. I can tell the difference between that and the approach many people seem to take (decision, guilt, shame, force), and I like the kind approach more.

It’s good to be able to look at your negative internal monologue or the parts of yourself that you’ve been avoiding thinking about, become aware of what’s going on, and work on reframing or transforming those thoughts. It’s good to look at what you’re resisting and figure out how you can embrace and move through that pain.

I’ve had a very easy life so far, compared to other people I know. I’m glad this book exists; the techniques will help me through the challenges that are sure to be ahead, and I hope they’ll help other people too. Good book if you often beat yourself up, judge yourself harshly, or feel lost and frustrated.

Haven’t read the book yet? You can buy it from Amazon (affiliate link) or get it from your favourite book sources.

Like this sketch? Check out for more. Feel free to share – it’s under the Creative Commons Attribution License, like the rest of my blog.

Weekly review: Week ending March 27, 2015

I started yoga again, and I think it might be a good habit to build. It’s been good to spend time with people, too. =) Next week, I’m looking forward to sewing some box cushion covers, cooking more, doing more yoga, and spending more time with folks.

2015-03-29f Week ending 2015-03-27 -- index card #weekly output

2015-03-29f Week ending 2015-03-27 – index card #weekly

Blog posts


Link round-up

Focus areas and time review

  • Business (33.0h – 19%)
    • Earn (7.2h – 21% of Business)
      • Earn: E1: 1-2 days of consulting
    • Build (10.8h – 32% of Business)
      • Drawing (8.2h)
      • Packaging (0.6h)
      • Paperwork (0.3h)
        • File payroll return
    • Connect (15.0h – 45% of Business)
  • Relationships (4.6h – 2%)
    • Check on project F4
    • Hang out with Eric on Friday
    • Drop gift off at Jen’s
  • Discretionary – Productive (12.8h – 7%)
    • Emacs (2.2h – 1% of all)
      • 2015-03-18 Emacs Hangout
    • Research yoga places
    • Research private yoga lessons
    • Writing (2.5h)
    • Review Createspace
  • Discretionary – Play (6.0h – 3%)
  • Personal routines (31.6h – 18%)
  • Unpaid work (15.3h – 9%)
  • Sleep (64.6h – 38% – average of 9.2 per day)

Quantified Self: How can you measure freedom?

At a recent Quantified Self Toronto meetup, one of the participants shared his key values (freedom, health, happiness, purpose) and asked for ideas on how to measure freedom. I gave him some quick tips on how I measured:

  • Money:
    • Long-term freedom through a theoretical withdrawal rate: expenses vs net worth and investment returns
    • Short-term freedom for discretionary expenses: opportunity fund for tools and ideas, connection fund for treating people
  • Time, particularly discretionary time (my own interests and projects)

In addition to those two easy metrics, there are a few other things that contribute to a feeling of freedom for me.

2015-03-06b What makes me feel free - What can I measure -- index card #quantified #freedom #independence #feeling

2015-03-06b What makes me feel free – What can I measure – index card #quantified #freedom #independence #feeling

  • How often do I have to wake up to an alarm clock, or can I sleep until I feel well-rested?
  • Am I starting to be stressed because of commitments? Do I have to juggle or cut back?
  • Can I follow the butterflies of my interest/energy, or have I promised to do a specific thing at a specific time?
  • Can I share what I’m learning for free, or am I restricted by agreements or by need?
  • Am I getting influenced by ads to want or buy things that I don’t really need? Do I experience buyer’s remorse, or do things contribute to clutter? Is it easy to remember my decisions or my values in the din?
  • Do I have the space to enjoy a great relationship with W-?
  • Can I make the things I want? Do I have the skills to create or modify things?
  • Am I reacting or responding? How reflexive is my ability to see things in the light that I would like to see them in, and to respond the way I would like to respond?
  • Can I learn about what I’m curious about? Do I use it in real life?
  • Can I make small bets and learn from them?

I think it’s because I tend to think of freedom as freedom from stress and freedom to do things – maybe more precisely, to live according to my choices without having to choose between deeply flawed options. I’m in a safe, rather privileged situation, so I’m not as worried about freedom to live or move or speak or learn; those are more important freedoms, for sure! So with the definition of freedom I have, I feel pretty free. Based on my impressions from conversations with other people, I think I’m probably in the top 10% of freedom in terms of people I know. Or at least a different sort of freedom; I’m more risk-averse than some of my friends are, for example, so they’re freer in that sense.

2015-03-06a How can you measure freedom -- index card #freedom #independence #quantified

2015-03-06a How can you measure freedom – index card #freedom #independence #quantified

If you break down the abstract concept of freedom into different types of freedom, you can figure out which types resonate with you and which ones don’t. You might then be able to think of ways to measure the specific types of freedom you’re curious about, and that will help you get a sense of areas in your life that you may want to tweak.

Philosophy has a lot to say about freedom, so that’s another way to pick up ideas. The biggest freedom, for me – the one I most want to cultivate and keep – is the freedom that comes from choosing how I perceive the world and what I do in response. I like the freedom described in Epictetus’ Discourses. How could I measure this or remind myself about this? Since it’s entirely self-willed, I can keep track of whether I remember to take responsibility for my perceptions and responses and how easy it is to do so. I imagine that as I get better at it, I’ll be more consistent at taking responsibility (even if I realize uncomfortable things about myself) and that I’ll do it with more habit. I can also track the magnitude of things I respond to. I know that I can maintain my tranquility with small events, and I’ll just have to wait and observe my behaviour with larger ones.

What does freedom mean to you? How do you observe or reflect on it?