Category Archives: planning

Thinking about what wild success at 29 looks like

One of the brainstorming exercises I picked up from our workshops at IBM was the idea of a “wild success story” – imagining a great future and backtracking from there to the present. It’s useful in personal life, too. For example, this is what I blogged in 2009:

I wake up at 5:00 AM to opera, light, colors, cats, kisses, or whatever gives me a great start to my day. I exercise a little to get my blood flowing, and I have a healthy breakfast of steel-cut oats or fresh fruit. Then I gear up for a morning of creative work, settling into a comfy chair or setting up on the kitchen table for a four-hour session of brainstorming, writing code, and preparing articles and presentations. I snack on fruit and nuts along the way. I have a light lunch or head out to lunch with friends. Then I tackle more routine tasks: responding to mail, following up, editing and formatting documents, testing code, taking care of chores, reviewing delegated work, and other things. I make dinner and enjoy it with people I love, and spend the rest of the evening reading or enjoying people’s company. After tidying up and taking care of other things, I go to bed, happy with the work I did that day.

I’m close to that, but I’m not quite there yet. My Fridays are shaping up that way, though, and we’ll see how things go in September.

On a larger scale, what would a wildly successful 29th year look like? Looking back on the eve of my 30th birthday in 2013, I’d like to be able to say:

  • I have even more wonderful relationships with family and friends.
  • I regularly stay in touch, and have good notes on what people are interested in and are up to.
  • I survived my first business tax return, yay! I’m now investing in building skills while giving back to the community, eventually turning that into income from mobile apps, illustration/animation, and other ways to create value.
  • I’ve got lots of sketchnotes of meetups, books, and product reviews. I’ve organized them into a blog and an e-book. My sketchnotes have colour and depth and interesting layouts. =) I help people find out about useful stuff and good get-togethers.
  • I’ve updated my Stories from my Twenties e-book with what I’ve learned from my 29th year, and I’ve shared the updates with the people who bought the book and sent me their receipts.
  • I’ve gone through Lingua Latina Per Se Illustrata, and I understand it. =) I’m also picking up Cantonese.
  • I’ve been having fun gardening. We’re growing more greens and have actually gotten into the habit of eating them. (I know!)
  • My finances are on track for my 5-year experiment; this might even be extended at least a few more years.
  • I’m ready to rock my thirties!

Thinking about the next mini-experiment

The consulting engagement I’m working on is great. It takes advantage of a hard-to-find combination of different skills and experiences, and I’m having lots of fun. I’m glad I can help make a difference.

What do I want to do when it wraps up in around three months? I’m leaning towards experimenting with concentrating on some projects, which means not committing to any large, regular chunks of outside work. The Quantified Self conference in September will give me lots of reasons to work on Quantified Awesome. I’ll probably harvest enough ideas from it to be busy for quite a while afterwards.

I keep thinking about writing a book, too. If I clear the space for it, dedicate the time to it, then I’ll have some clear answers. Either I’ll emerge with a book (the first book is often the hardest, they say; after that, you know you can write), or I’ll know that I’m not yet in the right space for writing a book, and maybe I’ll have an idea of what I need to work on before I am.

I haven’t had such a large chunk of time to myself in a while, structured and directed mostly by me. The closest I can think of was the time after I returned from my technical internship in Japan and before I left for my master’s degree in Canada. Fortunately, I blogged back then too, so I can try to remember what I did and what it felt like.

March 2005: Spoke at a conference, worked on open source, practised poi April: Worked on open source, spent lots of time with family May: Worked on open source, wrote flash fiction, wrote about hipster PDAs (index cards) June: Took driving lessons, worked on open source, wrote flash fiction, moved to Canada

Right! Open source, that was what I was focusing on – that, and spending time with family, and exploring productivity tips. I’ve been working on far less open source than I thought I would be, but that’s because I’ve been focusing on non-programming things like writing and drawing. It was fun working on open source. I was maintaining Planner Mode (another organizer for Emacs) at the time, and I had a lot of fun working with the community. Time to re-subscribe to mailing lists and see if I can stay sharp by helping out.

That should be a good balance, eh? Writing and drawing to exercise creativity and share what I know, Quantified Awesome and open source software so that I can make better tools. Should be fun. For the business side of things, I might explore e-books and icon design as a way to use the writing and drawing skills I’ll be developing. Quantified Awesome and open source software might be more of a stretch for business, but let’s see where that takes me.

By that point, I’ll have been consulting for six months. I’ll probably give this self-directed learning and working a try for six months as well, and we’ll see how other factors influence our scheduling.

Looking forward to it!

Planning my life

I often think about what I want in life. What do I want to learn? What do I want to be able to share? What do I want to try? What do I want to do?

I think about life a lot because:

  • I want to make better decisions: Planning my life allows me to deliberately try things instead of being limited to chance or what other people want
  • Looking back makes it easier to go forward: Reviewing my life helps me decide what I want to continue doing, what I want to stop doing, and what I want to start doing
  • Planning ahead helps: You can’t plan for everything, but a little foresight can make things a lot easier

Gaps are great for thinking about these things: biking to work, waiting in line, getting ready for bed, relaxing during a long weekend. I review my key priorities and brainstorm ideas for the next steps. I make lists in my notebook, tap ideas into my phone, type thoughts into my laptop, or think out loud (good for bike rides!).

Most of my notes are in scattered places, and that’s okay. I don’t need a perfect record of everything. I don’t need a well-organized outline. I don’t mind covering the same ground again. Every time I make a list, I learn from what I add, change, forget, or remove.

I revisit my plans regularly. Every week, I review the things I’ve accomplished, plan what I want to do the next week, and check how I feel about how I’m doing. Once in a while, I flip through my old mindmaps and notes, crossing out things I’m no longer interested in and adding new ideas.

Every so often, I sit down and flesh out the plans further, sharing them on my blog or adding them to my private notes. I think about what I want to learn, and I plan my curriculum for getting there. I think about the experiments I want to try, and I take the first step. I think about what I want, and I dig deeper to find out if I really want it or it’s something I think that I want. These plans change, and that’s good. The changes tell me more about myself.

I don’t have a firm plan for my life. I don’t have goals like “I want to be ____ by ____” or “I want to _____ by ______.” Many people have these bucket lists – things they want to do before they die. It’s easy to get carried away by these goals, though. Many people plan themselves into unhappiness by saying, “I’ll be happy when I…”. I try to not give in to the temptation to think that happiness is something external, something caused by events or reached when you get to a threshold.

I like to think that I plan out of curiosity. I’m curious about certain things, and I can make certain decisions that get me closer to understanding. For example, I’m curious about entrepreneurship and parenting. With a little planning, we can give ourselves as good a foundation as any. I can’t dictate the cards that are dealt, but I can stack the deck.

How would I like to get better at planning my life?

I’d love to learn more from other people’s lives. I read voraciously to learn about other people’s patterns, and I also ask people about their lives and their decisions. The more I learn about the different paths people have taken, the more I can explore and prepare for possible futures, and the more ideas I can pick up and play with.

I’m working on getting better at documenting and reviewing my decisions. I read a lot about decision science and decision management. I like the way that the practice of thinking through my decisions helps me understand future ones. I’m looking forward to writing about more decisions.

I’m looking forward to testing more of these plans. Many things take time. The wait is fun because I can periodically tweak my plans to try new ideas, understand things better, and get closer to what I want. Besides, there’s always the chance I’ll be surprised, and that helps me learn to think on my feet. (Many of these surprises are awesome!) Life is good.

Thanks to Soha for the nudge to write about this!

Learning more about what I want to learn

It’s hard to get better without knowing what better is.

I want to draw better. What does better mean? For me, “better” means having a wider visual vocabulary for both individual concepts (icons? shapes?) as well as layout (graphic organizers? metaphors?). “Better” means cleaner lettering and more font or design choices. “Better” means being able to draw more things more recognizably, and to design pages so that they’re visually appealing as well as informative. “Better” means becoming more comfortable with colour and shade, and using them to emphasize what’s important. Someday, “better” might even include working with animation.

How can I learn how to draw better? Practice is a big part of it, of course. I can revise my previous sketches, and I can make new ones. I can also look at sites like Sketchnote Army for inspiration. I can collect graphic organizers and visual metaphors. For deliberate practice, I can draw lines, circles, and other shapes, and I can work on lettering.

I want to write better. “Better” means adding more vividness to my writing: picking just the right verb, noticing little details and fleshing them out, adding more specifics and more data. “Better” means pushing beyond clichés. “Better” means writing so that other people can learn more effectively – digging deeper to find things people might be curious about, organizing my notes so that other people can learn more from them.

How can I learn how to write better? Again, practice and inspiration. I can revise my posts and organize them into a coherent e-book or blog series. I can challenge myself to research and share a topic I’m curious about. I can read other people’s work and play around with their styles.

I want to connect better. “Better” means knowing more about people’s lives – it’s easy to know about mine, but I think it would be interesting to know more about people too. It boggles my mind wonderfully that I now have old friends here in Canada (by golly!). I’d like to cultivate more friends and build deeper friendships both in person and online.

What does your “better” look like?

From maker time to learner time

It turns out that when I have more control over my schedule, I don’t fill it with development. I haven’t been working on open source or personal projects, much less client websites or applications. This is a surprise to my 2010 self, who figured she would spend the whole day coding if she could.

I spend most of my discretionary time learning instead: drawing, writing, Latin, business, life. Maybe it’s because I’m in the fledgling stage of business and there’s so much to learn. Maybe it’s because 3-4 days of consulting a week takes up a large chunk of brainspace. Maybe it’s because development won’t get me where I want to go in this short-term search for a business that can survive unpredictable schedules and the primary care of young children.

Learning time. Yeah, that seems like the focus that fits me. If I imagine days and weeks stretching ahead of me – maybe in half a year, after this consulting engagement – I can easily see myself spending time exploring ideas and sharing my notes. I’d want to plumb this, deepen my understanding of this, before I focus on something like development.

Self-structured learning time is intimidating, but I want to see if I can get past the initial anxieties and figure out things that work. Writers have been able to do so for millennia. Things will be okay.

I’ll still build things, of course. Code is a powerful way to crystallize learning and make it easier for people to do better. It also helps me ask questions that would be hard to answer manually.

Okay. I give myself permission to focus on learning after this. I know I’ll probably feel that itch to do something that creates immediate or measurable value for people. That’s okay. I might feel insecure at some point. That’s normal. But there’s so much I want to learn, and I think I’ll be able to stay motivated even without outside drivers. Worth trying it out and sticking with it through at least the initial bumps.

This will be fun!

(Thanks to Mel Chua for the nudge!)

Why I’m temporarily unhireable

The consulting work I’m doing now is a wonderful fit for who I am at this moment. In the past two months, I’ve been able to do a lot. They’d like to keep me, and I can see how I could make a good difference here. But I didn’t leave one wonderful job just to start another wonderful job, did I?

My primary reason for experimenting with entrepreneurship is to build something more flexible and more scalable than employment. By flexibility, I mean that it should be able to accommodate the unpredictable schedules and irregular demands of raising young children if W- and I have more kids. By scalability, I don’t mean the mind-boggling aspirations of venture-backed startups. I mean the ability to create more value with less time, and possibly by involving other people.

My secondary reason for experimenting is to learn what I can learn so that I can share those lessons with as many as people as possible. Thanks to frugality and other factors, I enjoy the privilege of being able to learn about entrepreneurship without immediate financial pressure. Thanks to a great network, I can learn from people’s experiences instead of struggling in isolation. Thanks to a keen interest in both technology and business, I can try things out instead of waiting for the missing piece. With all these advantages, maybe I can make things easier for other people.

With these reasons in mind, it becomes easier to say no, even though I also really want to say yes. Full-time work doing what I’m doing now? It would probably be awesome, but it doesn’t follow my reasons, so I’d prefer to help people learn how to do what I do. If I could be in more than one place, I would be in so many. Since I can be in only one place at a time, I’ll focus on training people, and I’ll work on the questions that I most want to ask.