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Rethinking my time categories: the blurring of business and discretionary activities

I track my time with medium-level categories (not detailed enough that I’m tracking individual tasks, but not so high level that it’s hard to make sense of the data). From time to time, I notice categories drift, or they stop fitting. Consulting is definitely business, but does working on Emacs really belong there? Why is coding classified under business but writing is classified as discretionary time? Most of my categories still make sense a year or two later, but some of them could use more thinking about.

What is business, anyway? I suppose it can include anything related to the earning of money, including support such as paperwork or delegation. Packaging (by which I mean creating e-books and other resources) is part of business, since I earn a small income from that (and pay taxes on it, too!). So is responding to e-mail. Technically, Emacs is related to money, because people have actually booked and paid me for help sessions online ( I consider programming-related activities to be part of maintaining my technical skills and network. In that sense, coding, web development, system administration, and other geek things are business-related. I distinguish between sketchnoting for client engagements and drawing on my own. Many of my drawings are more along the lines of personal or business planning. Perhaps I should track more under those categories now that I’ve established drawing as a way of thinking, and shift to using “Business – Drawing” when I’m specifically working on illustrations or improving skills.

Discretionary time includes the stuff I do just for fun and the things I learn about just because (Latin and Morse, for example). Probably the only weird thing in here is that I classify writing as discretionary time. It’s fun. Coding is fun too. Coding is more obviously valued, though, so I guess that’s why I consider it business time. And also, if I classify writing as coding time, I’ll tip over way too often into the “working too many hours a week” zone, when I’m not really doing so.

Maybe a better approach is to classify coding, drawing, and other fun things as discretionary time instead, even if they occasionally result in money. Benefit: I get to celebrate having more discretionary time and a lighter workload. (Yeah, it’s all mental anyway…)

Or maybe I need to take a step back and ask myself what kinds of questions I want to be able to answer with my categorical data.

In general, I want to make sure I don’t spend too much time working, because I want to force myself to work on my own projects. That’s why I track the time spent consulting, doing paperwork, and connecting with people (including responding to e-mail). I usually keep a close eye on my Business – Earn subcategory, since that’s the one that can creep up on me unawares. That’s fine with my current categories.

I also want to look for patterns in time use. How does spending more time on one activity (and less time on other activities) influence what I do and how I feel? How bursty am I when it comes to different discretionary projects? As long as I’m tracking at the subcategory level, it doesn’t really matter what the root category is.

Hmm. Since I’m not actually using the distinction between discretionary and business for reports or visualizations that nudge my behaviour, I can probably leave my categories alone if I remind myself that those ones have fuzzy boundaries. It would matter more if I wanted to set goals for investing X hours a week on business things (or, conversely, spending Y hours on discretionary non-business related things, which is oddly harder). Since I don’t care about that at the moment, I’m fine. Also, it’s easy enough to reassign the parent categories, so I still leave the door open for analyses at a later date.

As long as I can keep things clear enough in my head so that I feel confident that I can explain to any auditors that yes, my  business expenses make sense, I should be fine. I feel a little weird about not having a proper business plan for lots of things I’m working on. I mean, I can write them (or draw business model canvasses, more likely), but I prefer this pay-what-you-want model. Oh, hey, there’s an assumption there that I can dig into. People can (and do!) build metrics around freemium or pay-what-you-want models. Maybe I can figure out how to approach this in a business-like-but-still-generous way.

What would a more business-y way look like? I would float an idea to see if it’s useful. Then I would make stuff (and sometimes I’d make it anyway, just because). I might actually track conversions, and try things out, and reach out to people and communities. I’d publish little guides and videos, and maybe add a tip jar for smaller pieces of content so that people can “vote” for things they like more.

All things to do in due course. In the meantime, knowing that the path is there means I can leave all of this stuff still filed under the Business category, because it is. Even if it’s fun. Writing still feels more discretionary than business-y (even posts like this, for example), so I’ll leave that where it is. So no change, but I understand things better.

Do you track your time and have fuzzy boundaries between categories? How do you deal with it?



Working fast and slow

When it comes to personal projects, when does it make sense to work quickly and when does it make sense to work slowly? I’ve been talking to people about how they balance client work with personal projects. It can be tempting to focus on client work because that comes with clear tasks and feedback. People’s requests set a quick pace. For personal projects, though, the pace is up to you.

It’s easy to adopt the same kinds of productivity structures used in the workplace. You can make to-do lists and project plans. You can set your own deadlines. I want to make sure that I explore different approaches, though. I don’t want to just settle into familiar patterns.

2014-04-07 Working fast and slow #experiment

2014-04-07 Working fast and slow #experiment

I work on personal projects more slowly than I work on client projects. When I work on client tasks, I search and code and tweak at a rapid speed, and it feels great to get a lot of things done. My personal projects tend to be a bit more meandering. I juggle different interests. I reflect and take more notes.

Probably the biggest difference between client work and personal projects is that I tend to focus on one or two client tasks at a time, and I let myself spread out over more personal projects. I cope with that by publishing lots of little notes along the way. The notes make it easier for me to pick up where I left off. They also let other people learn from intermediate steps, which is great for not feeling guilty about moving on. (Related post: Planning my learning; it’s okay to learn in a spiral)

Still, it’s good to examine assumptions. I assume that:

  • doing this lets me work in a way that’s natural to me: what if it’s just a matter of habit or skill?
  • it’s okay to be less focused or driven in my learning, because forcing focus takes effort: it’s probably just the initial effort, though, and after that, momentum can be useful
  • combinations of topics can be surprisingly interesting or useful: are they really? Is this switching approach more effective than a serial one or one with larger chunks?
  • a breadth-first approach is more useful to me than a depth-first one: would it help to tweak the depth for each chunk?
2014-04-02 On thinking about a variety of topics - a mesh of learning #my-learning

2014-04-02 On thinking about a variety of topics – a mesh of learning #my-learning

One of my assumptions is that combining topics leads to more than the sum of the parts. I took a closer look at what I write about and why. What do I want from learning and sharing? How can I make things even better?

2014-04-02 Evaluating my sharing #sharing #decision

2014-04-02 Evaluating my sharing #sharing #decision

Emacs tinkering is both intellectually stimulating and useful to other people. It also works well with applied rationality, Quantified Self, and other geekery. I can align sketchnoting by focusing on technical topics and  on making it easier to package things I’ve learned. Blogging and packaging happen to be things I’ve been learning about along the way. Personal finance is a little disconnected from other topics, but we’ll see how this experiment with the Frugal FIRE show works out.

If I had to choose one cluster of topics, though, it would be the geek stuff. I have the most fun exploring it, and I am most interested in the conversations around it.

What does that mean, then? Maybe I’ll try the idea of a learning sprint: to focus all (or almost all) my energies on one topic or project each week. I can work up to it gradually, starting with 2-4 hour blocks of time.

2014-04-02 Imagining learning sprints #my-learning

2014-04-02 Imagining learning sprints #my-learning

Because really, the rate-limiting factor for my personal projects is attention more than anything else. If I experiment with reducing my choices (so: Emacs basics, Emacs chats, open source, Quantified Self), that will probably make it easier to get the ball rolling.

2014-03-28 Identifying rate-limiting factors in my work #kaizen

2014-03-28 Identifying rate-limiting factors in my work #kaizen

So I’m still not adopting the taskmaster approach, but I’m reminding myself of a specific set of areas that I want to explore, gently guiding the butterflies of my interest down that way.

We’ll see how it works out!

Experiment update: Mid-term pre-mortem check

In the early days of my 5-year experiment with semi-retirement, I brainstormed ways it could fail. I worried that I might end up too distracted to make useful stuff, or that I’d end up being incapable of pursuing my ideas, or that I’d mess up somewhere–paperwork, people, products–and botch the whole thing. I worried that I’d finish the experiment with nothing to show and no compelling story for the gap I’d have in my resume. I worried that W- would get tired of this exploration.



I feel less worried now. Part of it was realizing that I can plan for only so much safety. Part of it was learning how to choose what I’m going to focus on, how to select my projects without managers and track my progress without annual performance reviews. (Well, I still have annual reviews, but they’re self-driven.) Part of it was trusting that I can handle things, a confidence which grew after each small step.

Looking back, I can see the things I found mentally challenging in the beginning, and how I worked around them.

  • The career gap doesn’t look all that scary now. I know lots of other people who have managed it. They’re fine, and I’ll be fine too.
  • Self-direction turned out to be good to learn, and it seems like I can come up with useful projects.
  • Paperwork? There were a few stressful hours as I learned more about the tax code – I amended my first corporate tax return a number of times – but I think that doing my own books was worth it. Besides, Canada Revenue Agency is surprisingly approachable. Hmm.
  • Opportunity cost? “Wasted potential” only
2014-02-21 What did I find challenging when I started #experiment

2014-02-21 What did I find challenging when I started #experiment

If you’re starting your own experiment or you’re well into one, I’d love to hear about some of the challenges you faced and how you worked around them!

Going fishing for three years

People often ask me if I could draw for them, or write for them, or code for them. I refer all that business to other people. Here’s why.

2014-02-19 Teaching people to fish, selling fish, fishing for yourself #experiment #sharing #my-learning #teaching #confederates #community

2014-02-19 Teaching people to fish, selling fish, fishing for yourself #experiment #sharing #my-learning #teaching #confederates #community

You see, some people want to learn how to fish. These are the people who want to learn more about sketchnoting or Emacs or other things I’m interested in.

Many people want to buy fish. They don’t want to learn things themselves, but they can build on what they buy.

Most people just want to buy sushi. (Or fish and chips, or whatever.) Already prepared, no work needed, yum. They’re too busy to cook. They don’t want to know the details. They just want good stuff.

I want to learn how to fish for rare fish. The kind of fish few people bother with because you have to go into uncharted waters. Interesting, elusive fish, almost too smart to get caught. I want to learn how to ask good questions and share what I’m learning.

I want to be part of a community of enthusiasts who swap tips and stories. I want to find other people who have gotten bitten by that bug, and I want to help other people discover the joy of exploration. That’s why I’m not selling any fish. I’m focusing on learning how to fish rare fish, and teaching what I’m learning. My top priority is to learn how to fish. But I’ll take the time to teach you to fish because I want to be able to learn from you someday.

Sure, I might be able to learn a little while catching fish for other people. I know from experience, though–both mine and others–that it’s too easy to get used to that. You forget there’s a world beyond the fishponds. Better to force myself out there, while I can.

At least for the next three years (the rest of this 5-year experiment), I’ll be out fishing. That is, drawing, writing, learning, playing – somewhere out there, where few people get to go. What would wild success be like? Plenty of stories, maybe a few mementos, and a great community to keep exploring with.

2014-02-19 Imagining wild success for this experiment #experiment.png

2014-02-19 Imagining wild success for this experiment #experiment.png

Thanks to Evan Smith for the nudge to explore this metaphor!

(Note: I don’t know anything about fishing, and I’m not planning to add it as a hobby. But I do like cooking, though, which might explain some things.)

Tell me what you think!

  • What can I help you learn how to fish?
  • Are you looking for rare fish too? Let’s learn together!

Reflecting on what I want to contribute to and how interested people might (semi-)work with me

From time to time, people ask me if I’d be interested in working with them to make something bigger happen. I’m getting better at saying no. I want to focus on learning how to direct my own life. Other-directed work is seductive. Clear tasks! Appreciation! My mind wanders back to it, thinking about whether it’s better to spend this hour doing something I know people want, or something that I think might help me and others grow.

2014-02-21 Untangling myself from client work #experiment

2014-02-21 Untangling myself from client work #experiment

But I have the space to explore more, and I need to learn how to use it. Sometimes, to remind myself, I flip through the spreadsheets of my finances and projections. I joke about this being an experiment with semi-retirement. I don’t know how close to the truth it is, since circumstances can always change, but I’m ahead of where I had hoped to be. If the numbers do work out, what difference would it make? Mainly the freedom to focus on things beyond what people are clearly willing to pay me for. People might be able to pay others to do the same work I would have done, but few people are in the position to do the things I can choose to do.

2014-02-24 Reminding myself of freedom #freedom #experiment

2014-02-24 Reminding myself of freedom #freedom #experiment

What do I care about, then? What do I want to work on building as part of this experiment? What outcomes do I want to support?

2014-02-28 What outcomes do I care about #experiment

2014-02-28 What outcomes do I care about #experiment

  • Emacs help is a self-serving interest. If I help more people learn about and get deeply into Emacs, I’ll benefit from a more interesting and more adaptable editor/platform/way of life. That’s why it makes sense for me to make visual guides, pair-program with or coach people, and record screencasts and Emacs chats. (On a related note, I also care about helping people with automation, scripting, data analysis, learning, and other topics I’m curious about.)
  • Other people’s useful knowledge and insights: People know all sorts of things, but they struggle with sharing. If I get better at asking questions and podcasting interviews, I can help people share what they know in a form that other people can come across.
  • Organized info: I want to take notes along the journey instead of waiting until the end – even if it means capturing detours and dead ends. Organizing, editing, and packaging those notes makes it much easier for people to catch up, though. I can add sign-posts to mark the trail. People can always wander through the side-trails if they want to, but at least they can choose.
  • Managed resources: I’d like to be able to confidently embark on the next experiment. Frugality and good decisions make that possible. Limiting commitments and needs will help a lot, too.
  • Delegation: I want to be able to delegate well, so that I can involve other people in making things happen without wasting people’s time or attention. I think it would be a good idea to build up a process library and paths for developing skills. It’s like applying open source principles to management and processes. I want to help my team members build their skills, and I also want to help other employers and potential employers delegate more effectively.
  • Community: I want to experiment with building communities based on generously helping each other, and I’m doing that by sharing as much as I can for free. I love how people reach out to me for questions and conversations.
  • Maps and resources: Topics can be intimidating to learn. I want to help people make sense of what they’re learning, and this is where drawing overviews and creating resources can help.

At least for the duration of this 5-year experiment, I don’t need a salary or a flow of clients. The only reason to work with an organization or enter into any new partnerships, then, would be to take advantage of the scale in order to do things that I can’t do as effectively on my own. So far, I’ve been referring all work to other people (except for previous commitments). Would there be reasons for me to connect with other people who are working towards similar goals, whether through a formal partnership or an informal relationship?

2014-02-28 Are there ways for organizations to help me scale #experiment

2014-02-28 Are there ways for organizations to help me scale #experiment

  • Money isn’t enough as a motivator. Yes, I can turn surplus money into delegated time or invest in learning, experimenting, and improving my tools (and there’s always using it for extra safety). Money is not a limiting factor, though.
  • Motivating needs, feedback: One of the benefits of working with clients or organizations is that people need stuff that I might not have thought of myself. They can also give me feedback on whether what I create works for them. This can be better than making stuff in a void and wondering if it will be a good fit for anyone else. That said, though, it’s tempting to focus on what people want instead of what I’m curious about that might turn out to be good anyway. I might be okay if I get a stream of ideas without any commitment to work on them, so I can choose the things that interest me.
  • Implementation support and leverage: This one is interesting for me. For example, I can help brainstorm a list of things that would be good to make (blog posts to write, videos to record, etc.). We can work on them, bringing different skills to the table. Or I might hand it off entirely; I don’t need to write the blog post or tutorial myself.
  • Mentoring and guidance: I can learn something from people who are further down the path (or who have traveled a different but relevant path). It takes a little translation to make sure I’m still following my dreams, though.
  • Co-authorship, co-hosting: This one is interesting for me too. One of my goals is to help people get stuff out of their head and into a form that other people can learn from. Asking people questions is one way to do this. I don’t always know who knows stuff I’m curious about, and it would be great to tap other people’s networks (especially if someone can go to the trouble of coordinating with guests, etc.). Talking to other people about the things we do differently will help us learn more, and there’s probably a book or two in there.
  • Audience and reach: Less interesting for me, mainly because I’m not focused on being more popular or reaching more people. I am, however, up for more confederates.
  • Bundling: This is related to audience and reach. Have people written about topics that complement topics I’m interested in? We can offer something more useful together, maybe.
  • Process / skill feedback and improvements: This is probably the most interesting for me. I’m happy to swap ideas about what could make something better. That helps me reflect on and communicate what I do differently, and I learn from other people too. I might pick up tips along the way, too.

So that points out a few possibilities for relationships:

  • Helping people who will try things out and share their experiences: For example, we might discuss a blog post. I’d show how I might do things differently or suggest some things to try. You give it a shot, and we discuss what that’s like and where you want to go next. Ideally, I’d work with people who blog about what they’re learning along the way, so those ideas get written up and shared too. If not, maybe they’re open to having the coaching in public, so I can just post that. At the very least, I can harvest the tips myself and put them into blog posts. I’m interested in scale, so helping people who help others might work out.
  • Brainstorming ideas and directing work: We might come up with a list of things that would be good to make. Then you or your team can make that happen, and I can give feedback. It’s kinda like the books I want to write or the things I want to fix. I don’t mind if other people get to it first, as long as it gets done.
  • Picking people’s brains together: We come up with topics of mutual curiosity, and you find someone who can speak about the topic. I’ll float the idea by my network too. We chat, and the whole thing gets recorded, transcribed, posted, etc.

I think I’ll do this on a free/pay-what-you-want basis as well, as an experiment. I want people to talk to me, because I learn a lot from the process. Comments, conversations, confederacies, and long-term relationships are awesome. If you’re charging people for stuff (directly, through sponsorship, etc.), it’s probably fair that you pass some revenue on as a way of indicating the value you perceive. That mostly translates into more experiments anyway, so you can indirectly encourage me to explore the kinds of stuff you’re also interested in.

Hmm. That might be a good way for me to focus on the stuff that I want to happen, while allowing other people to link up in case we can collaborate on shared goals. I’m not going to subsume my goals under anyone else’s, but if there’s low-hanging fruit that I can easily reach and pick for you while I’m on my way to what I want, I might as well – especially if it gives you a boost so that you can pick your own low-hanging fruit better. =)

So what this might look like in real life is:

  • Maybe you’re working on something that’s a great fit for an outcome that I’m working towards too, or you’re working on something that could benefit from short, commitment-less help from me.
  • Reach out with what you’re interested in. Pick something that we can discuss in 15-30 minutes. (As it turns out, you can cover a lot in 15 minutes.) I’ve committed to working on stuff that’s publicly available, so focus on things like blog posts, videos, resources, etc.
  • If it tickles my fancy, we’ll bounce around ideas or approaches.
  • Do something with at least one idea, and get back to me with your experiences and next questions. (And even better, a write-up about what you’re learning!)

That should be good for letting me give focused, specific help, while keeping my mind uncluttered so that I can focus on the things I want to do that are less common. =) Let’s see how it works out!

Reflections on infopreneurship

There’s a lot of information on how you can build an online business by selling what you know. Many people are looking for that dream. It feels a little weird to me, and I want to figure out why. I guess one of the things that rubs me the wrong way is that a lot of people talk about becoming an expert in some crowded topic, and building an audience somehow. I don’t want an audience. I don’t want students. I want peers and confederates: people who learn, act, reflect, and share.

2014-02-14 Reflections on infopreneurship and alternatives

2014-02-14 Reflections on infopreneurship and alternatives

Another thing that makes me uncomfortable is that there seems to be very little expectation of action. There’s a lot of talk about it. But when I go and follow up with people on the results of the advice I applied from them, they’re boggled that I actually did something. One person I talked to said that 80% of the people he talked to don’t end up doing anything. 20% is still a good number, but still…  Steve Salerno wrote in Sham: How the Self-Help Movement Made America Helpless that the people who buy new self-help books tend to be people who bought a similar self-help book in the past 18 months. I don’t want to give people something that just makes them feel like they’ve made progress instead of helping them actually do things.

I think part of my hesitation comes from this: People get stuck for lots of different reasons, but it’s rarely for lack of reading. I don’t want to pitch information as the magic pill, the silver bullet, the shortcut to making things happen.

When I read, I skip platitudes but dig into reflections and lessons learned. I like processes and workflows. I want what I share to be similarly useful. The stuff that helps me get unstuck tends to result in thoughts like this:

  • “Oh! That’s the name of what I’m looking for. Now I can dig into the details.”
  • “Hmm, what I’m dealing with turns out to be fairly common. I can try what other people have done.”
  • “Oh, I see, I was missing that particular piece. Let me try this now.”
  • “Interesting question! Let me explore that…”
  • “Okay, that’s less intimidating than I thought. I should just go for it.”
  • “I had no idea you could do that! Oooh…”

What can I write or draw to help people get those moments? How do I help people get unstuck – or better yet, how can I help them accelerate or expand their learning? And since I can code and tinker and dream… What can I make? Ideas are one thing, but tools are another. I’ll keep an eye out for places where people are consistently getting stuck, and I’ll see which ones lend themselves to automation.

2014-02-14 Building systems to help people do things

2014-02-14 Building systems to help people do things

As I explore packaging and publishing more, I want to focus on stuff that people can’t find in a gazillion other blogs and e-books out there. Keep me honest. =) I like making things free/pay-what-you-want, since it helps me act from abundance, widen the conversation, and make room for people’s generosity. I’ll also share the processes and tools I’m building for myself. If you find them interesting, tell me, and maybe we can find ways to tweak and expand them to accommodate your idiosyncrasies as well as mine. I like the conversations that grow out of this, too.

Some of my technical role models have published books (both self-published and traditional). I can see how that saves a lot of people time and helps people learn. They work on open source projects and commercial systems too. I think that’s the sort of information work I want: stuff that helps people do things.

Hmm… Aha! Maybe that’s it. If I focus on helping fellow geeks solve problems or try interesting things (mostly tech, some lifestyle?), then I don’t have to worry as much about wasting people’s attention. We’re used to trying things out and testing them against our own experience, and we’re used to telling people “Hey, that didn’t quite work for me” or “That saved me a few hours of figuring things out! Here’s something to make it even better.” =)

2014-02-24 Aha, a plan for the things I want to write #experiment

2014-02-24 Aha, a plan for the things I want to write #experiment

(No offense to life coaches, motivational speakers, and self-help authors. Hey, if it works for you, great. =) I don’t have the experience to give good, well-tested advice in that area yet.)

Technical guides, I think. My long-postponed book about Emacs. Short guides about Org Mode or automation or Evernote or information management. There’s a lot to write. These aren’t books people read for inspiration and the vague desire to do something someday; they address what people want to improve now. (Well, maybe Emacs is a little on the inspirational side. ;) )

It’s easy for me to connect with people who are already travelling similar paths. I can share my notes. I can reach out and ask questions. What about helping people who are just starting down those paths? Maybe that’s where packaging what I know can be useful, especially if I can help people accelerate their learning and diverge to follow their own questions. My selfish desire is to learn from other people’s perspectives. I don’t want to make people dependent on me, the way that people seem to become fans of one motivational speaker or another. I want people to learn from what I’ve learned, but I also want them to translate it to their contexts, test it against their lives, and add their own insights. I’m happy to spend extra time helping beginners who do stuff, think about it, and then go on to ask different questions.

2014-02-09 How do I want to manage my learn-share pipeline

2014-02-09 How do I want to manage my learn-share pipeline

So, what would the processes look like if I figured this out? I’d have a good balance of thinking, learning, doing, and sharing. I’d be able to work top-down from outlines, anticipating the questions people might have. I could work bottom-up from questions and blog posts, too. I might not notice that I have enough to publish, so I could establish triggers to check whether enough has accumulated that it needs to be chunked at a higher level of abstraction: Q&A or sketches into blog posts, blog posts into series, series into short books, short books into longer ones. I’d harvest all the generally useful Q&A from e-mail and conversations to make sure they’re captured in the pipeline somewhere, even if it’s an item in my Someday list.