I wanted to like Adobe Illustrator CS6. I really did. I’ve been looking for a vector drawing tool that could fit into my sketchnoting workflow. Illustrator CS6 handled my tablet PC’s pen input more smoothly than Inkscape did, creating neat curves while still letting me work with the tight circles I use for lettering. Vector-based drawing meant that I could resize and move things around easily. I liked using the Navigator to keep a bird’s eye view of the image while zooming in on details. I was excited by the possibilities of building my own symbol libraries so that I could drop in visual elements quickly.

But it keeps crashing on me, which is frustrating. Even though I’ve rigged up some AutoHotkey macros to make it easier to save (triggered by a foot pedal, no less!), I don’t want to deal with that kind of mental friction and re-work. So, no Illustrator CS6 yet, and by extension, probably no Creative Cloud subscription. It’s like the way I ended up ditching Autodesk Sketchbook Pro on my Android tablet – it mostly works, except for when it doesn’t. When it doesn’t, it frustrates me.

I tried CorelDraw, too, but the eraser tool there doesn’t work the way I want it to. Artrage Studio Pro has a sticker library that might give me the ability to clip frequently-used images, but it’s not as responsive as Autodesk Sketchbook Pro is, so it’s a little frustrating too. Oh, well. I guess I’ll stick with Autodesk Sketchbook Pro for another year, and maybe use Inkscape to trace my drawings if I need to resize them.

I trust things a little more if I have backup plans. For example, I’ve messed up with Autodesk Sketchbook Pro on my tablet PC. One time, I accidentally moved my layer instead of zooming it. Fortunately, I’ve gotten into the habit of using Camtasia Studio to record my screen during the drawing process, so it was easy to go back in time and reconstruct the missing parts. Still annoying, but at least that was more my fault than the program’s.

It’s a little frustrating investing time into learning something that didn’t pan out, but knowing that these tools aren’t a good fit for what I want to do is valuable information as well. I’ll keep an eye out for other things!

As part of my resolution to spend more on learning, I went for one-on-one art classes in a nearby studio (Pamela Dodds’).

My first exercise was to draw shoes with lots of soft lines. The teacher said to focus on drawing each line in relation to each other instead of thinking about the whole shape. That makes it easier to defamiliarize yourself and draw what you see, instead of this preconceived notion of a shoe. I ended up making this shoe a little shorter than it actually was, but it was recognizably a shoe, hooray!

My homework was to draw more shoes.

Since I’m curious about translating abstract concepts to concrete images and vice versa, my teacher also suggested that I draw different kinds of shoes and the ideas associated with them.

The second class focused on negative space and chairs. On the left, you can see the chair I drew in class. On the right, here’s a chair that Leia (one of our cats) often likes sleeping in.

The third class was about lines, angles, and proportions. I started by drawing the scissors, then drawing the detergent bottle, and then finally by drawing the overlapping shapes of the coffee mugs.

At home, I practised by drawing the salt-and-pepper shakers, and by drawing the mouse.

My last session was one about faces and proportions (see above). Both of these were drawn from (rather odd-looking) mannequins. I like the profile likeness, although it was a little difficult getting the hang of the chin.

I’ve read many art education books such as Drawing on the Right Side of the Brain and Drawing by Seeing, so that sped up the teaching and gave us a shorthand for discussions. For me, the art classes were more of a meditative space where I could deliberately practise techniques, with feedback from a teacher who could warn me when I was getting too close to the paper (and thus shifting my viewpoint) or who could figure out where I was a little bit off in terms of proportions.

It’s a very different style of drawing compared to sketchnotes. I’m usually just focused on getting the gist of an idea across in a very simple, iconic form. In terms of getting better at sketchnoting, I’ll focus on broading my visual vocabulary by sketching different terms of concepts instead of focusing on drawing more realistic images. Still, it was fun discovering that even though I hadn’t been practising much “proper” drawing, I was getting better at seeing things!

Decision review: Good decision to experiment with art class, although I’ll keep looking around for other classes and I’ll keep practising on my own.

This is my Logitech H800 wireless headset. I bought it so that I could try dictating to my computer using Dragon NaturallySpeaking 11.5. The wireless headset that came in the NaturallySpeaking box never quite fit on my ear. It was always falling off. The Logitech H800 fits me well, and the voice recognition software has no problems with it.

The headset turned out to be pretty handy for other things as well. Bluetooth support meant that I could pair the headset with my phone. I started listening to classical music when working on my computer. I listened to podcasts while I tidied up the kitchen, watered the garden, or went for a long walk.

The headset charges using a micro-USB cable, and can be charged while in use. This is great, because I always forgot to charge my previous headset in time for me to use it. We use micro-USBs for so many other devices, so we always have cables handy. The downside? Between listening to music over Bluetooth and using my phone’s GPS to track exercise, I need to remember to charge my phone at every opportunity I get.

The Logitech H800 headset comes with a mini receiver that’s small enough to stay plugged into a laptop all the time. Unfortunately, it’s not a Logitech unifying receiver. Now I have two of those slim-profile Logitech receivers plugged into my laptop (mouse and headset). That leaves one USB port for flash drives, charging, and other things I want to plug in. I haven’t gotten into the habit of carrying around a powered USB hub, but I’m close to it!

Decision: Better than I expected, although FutureShop sold the headset for quite a bit more than the Amazon US price. I picked it up at FutureShop because I wanted to test the fit before getting it, and it worked out fine.

I thought that once I went into business for myself, I’d do the same kinds of money vs time vs enjoyment calculations that other people have done, and I’d probably end up making similar decisions such as signing up for a housekeeping service, eating out more often, or having either meals or groceries delivered.

It turns out that even though I know that:

• my time is worth $X-Y/hour
• my earnings are flexible (I can work more hours and earn more money)
• it’s possible to hire people to do some of the things I do for much less than X an hour

… I’m still pretty comfortable with doing many things myself. I think it’s because I enjoy those chores more than other people do.

For example, W- and I spent the Good Friday holiday doing our spring-cleaning. I moved my warm-weather clothes into my drawers and chose a few for donation. W- and I emptied the fridge and scrubbed the shelves. He made the glass doors all sparkly-clean.

Cleaning was social bonding time. We chatted, laughed, planned. It’s cheaper than therapy. I suppose we could hire someone to do it, but we would want to spend time together anyway, so it made sense to spend that time doing something useful.

Chores become fun when we do them together. Same with cooking. During our cooking sprints, the two of us chop and laugh and stir and joke. Picking up groceries is a good excuse to go for a walk together.

Because I get a lot of intangible value from doing these activities with W-, I’m not particularly drawn to the idea of outsourcing them so that I could spend more time on the business. I like the break from work, the space to breathe and play around with different ideas. I like the time we spend building relationships.

So yeah, it didn’t turn out to be a straight “I can earn $X/hour so I should outsource anything I can have done for much less than that amount” sort of decision. I’m happy to outsource accounting at least for this first year, and probably for later years as well – it can be complex, and I’m buying peace of mind as well as time. I’m investing more in tools that I like and webapps that I use. But I’m still looking for areas where I can practise delegation and management skills, and I haven’t quite found a good fit yet. No worries – maybe someday!

I’ve been thinking about getting an Android tablet so that I can draw more at conferences and around town. My laptop’s fantastic for drawing and writing, but it doesn’t have the battery life to get me through a day of conference sessions.

Before taking the plunge, though, I considered the different options. If the main thing I want is the assurance that I’ll be able to draw and write for a full day, there are a few ways to do that:

• Learn how to draw on paper. This is somewhat scary, but it’s useful, so I’ve bought myself another sketchbook for mindmaps, sketchnotes, and other sketches. I filled the last one over two years or so, and maybe I’ll fill this one faster!
• Get another battery for my Lenovo X220 tablet, and swap out batteries when needed.
• Get the extended battery slice for my X220 and enjoy way more battery life for some extra weight.

I decided to get the extended battery slice. More precisely, my business decided to get it, because I’m using it for sketchnotes, illustration (I do that professionally now, too!), writing, business correspondence, client meetings, and so on.

The battery slice is a large, flat battery that attaches to the bottom of the laptop. It extends my battery life by quite a bit, and is hot-pluggable so that I don’t have to interrupt my work. I haven’t tested its limits yet, but this power icon is pretty neat to see:

With this, I think I’ll be able to spend more time in libraries, cafes, parks, or conferences. Might be fun. =)

I remember now why I had stopped tracking time before. Breaking things down at the project level made me feel weird about my extracurricular interests at IBM, like the community toolkit and now the IBM comics. On one hand, I wanted to support our utilization goals and claim time as accurately as possible. On the other hand, I didn’t want to give up personal time, especially as I could use it to build more functionality into Quantified Awesome. I felt conflicted. I found myself slipping from the feeling of an abundance of time to the feeling of a scarcity of it, to be carefully portioned out among too many demands.

Today, brainstorming how to address my worst-case scenario considerations, I realized something: I’d been thinking about it the wrong way. It’s not extra time I’m donating or a hobby I might outgrow. It’s a live opportunity to test ideas with a massive, built-in internal market.

Comics on the intranet homepage? A fledgling artist couldn’t buy that kind of space. A community analysis tool that other people have come to rely on? Good practice in supporting disparate users and scaling up value.

No money might change hands, but a steady stream of thank-you notes helps my manager argue for a top rating, which often translates into a bonus.

So now I’ve got a couple of ways to rethink how this fits into my life.

I can promote these extracurriculars from the category “Work – Other” to “Discretionary – Other” or something similar, and budget myself four or five hours a week. It’s not work, it’s learning.

Alternatively, I can keep it under “Work – Other” and add an effective 10% overhead to my billable work. Many people have told me that I’m a fast developer, anyway, so scaling my output down to that of a somewhat above average developer will still mean that we do good stuff. The cognitive surplus goes into process improvement, self-development, and happiness, which is definitely worthwhile. I get stressed when I feel like I’m letting my other priorities slip, so spending time on them is important too.

These extracurricular interests can create a lot of value. I should adjust my measurements accordingly so that my measurements don’t lead to conflicting feelings.

How you measure affects how you manage.

I’ve been fiddling with Quantified Awesome, this personal dashboard that I’m building so that I can keep track of what’s going on in my life and use that data to make it even more awesome. For example:

• Tracking my time helps me make sure work doesn’t tempt me too much, and that I make time for both personal projects as well as connecting with other people. It also helps me improve my time estimates: How much time does it really take to walk to the subway station? How instant are instant noodles?
• Tracking library books reminds me before they’re overdue, helps me collect my reading history, and gives me a greater appreciation for where my tax dollars go.
• Tracking my clothes helps me remember to wear different types of clothes more often, makes it easier to donate items I don’t typically wear, and encourages me to try new combinations.
• Tracking the produce we get from community-supported agriculture helps us avoid waste.
• Tracking stuff helps me remember where infrequently-accessed items are.

It turns out that other people are interested in this too. 21 people have signed up through my “I’ll e-mail you when I figure out how to get this ready for other people” page, and my mom wants to use it too. That’s awesome!

Now I have to go ahead and actually build it so that other people can use it. That’s scary.

And like the way I deal with other scary, intimidating, procrastination-inducing things, I’m going to list my excuses here, so that I can shine a light on those assumptions and watch them scurry away like the cockroaches they are and, if necessary, squishing them with a well-applied flipflop.

• Excuse #1: Idiosyncrasy. The way I work might be really weird, and other people may not be able to figure out what to do.
  • What’s the worst-case scenario? “I have no idea how this works!” I end up with lots of crufty special cases because I can’t figure out how to reconcile different ways of working.
  • What’s the best case? I adapt the system to the way other people work, and I get inspired by what they do. I build a lovely, flexible web app and API.
• Excuse #2: Risk. I’m fine with loading my own data into an experimental system, but if I mess up and delete other people’s data, I’ll feel terrible. Also, they might trigger bugs.
  • What’s the worst-case scenario? Catastrophic data failure, nothing saved.
  • What’s the best case? Regular backups help me recover from any major mishaps, and careful coding avoids more common mistakes.
• Excuse #3: Support. I’m going to spend more time handling bug reports and feature requests, and less time building little things that might be useful only for me.
  • What’s the worst-case scenario? People get annoyed and frustrated because I’m currently focused on other things, like my work.
  • What’s the best case? I get the system to become mostly usable for people, and I use my discretionary time to build more features. People’s requests inspire me to build more stuff and create more value.
• Excuse #4: Documentation. I’ll need to write documentation, or at the very least online help. This means confronting the less-than-intuitive parts of the system. ;)
  • What’s the worst-case scenario? I describe what currently exists, get frustrated because I want to improve it, and end up cycling between updating documentation and improving the system.
  • What’s the best case? I describe what currently exists, and end up improving it along the way. I build online help into the system so that it’s easy to change. There’s a blog that helps people learn about updates, too.
• Excuse #5: Offline access. A web-based time tracker might be of limited use if you don’t have web access often. I’ve been working on an offline HTML5 interface, but it’s still buggy.
  • What’s the worst-case scenario? Early testers try it out, but get frustrated because of the lack of offline access.
  • What’s the best case? I figure out the HTML5 offline thing. Someone else might be interested in building a native app, and we work together on fleshing out an API.
• Excuse #6: Impatience. If I bring people on too early, they might get annoyed with a buggy system, and lose interest.
  • What’s the worst-case scenario? People give it a cursory try, and give up in annoyance.
  • What’s the best case? Early users are extraordinarily patient. We figure out a minimal viable product for each of them – the simplest thing that could possibly support what they want to do. Over time, things keep getting better and better. Also, I build a decent export interface, so even if people move on to a different system, they’ll still have their data.
• Excuse #7: Privacy and control. A bug might accidentally expose people’s information, which is not fun. I also don’t want to have to police the system for objectionable content, considering the thumbnail uploads.
  • What’s the worst-case scenario? Someone’s private notes get accidentally published.
  • What’s the best case? People sign on knowing that I might have bugs, and don’t save any super-secret or inappropriate information on the system.

Okay. I think I can deal with that. So, what are the smallest, least-intimidating steps I need to take in order to get closer to opening up?

• Write a quick test to make sure that people’s data will stay private. We’ll make people’s accounts private by default, although mine will stay mostly-public.
• Make a list of things that people should be able to do right now. (Not including new functionality!) Gradually write tests to nail down that behaviour.
• Make a list of things that people may want to do some day. Eventually set up an issue tracker.
• Enable Devise’s invitable feature so that I can set up accounts for people easily.
• Doublecheck backups.
• Bring one person on. Then the next, then the next…

It will still be better than nothing, it will be a good learning experience, and participation is purely voluntary anyway.

One step at a time.