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Planning my next little business

I’ve been holding back from experimenting with new businesses. I’m not sure how the next few months are going to be like, and I don’t want to make commitments like sketchnote event bookings or additional freelance contracts. Besides, focusing on my own stuff has been an interesting experiment so far, and I want to continue it.

Still, from time to time, I get the itch to build systems and processes for creating value for other people. For example, when I talk to people who are struggling to find jobs or having a hard time building freelance businesses, I want to support and encourage them by helping them see opportunities. Talking about stuff can feel a bit empty, but actually doing stuff–and showing how to do it–is more helpful, especially since I seem to be more comfortable with sales, marketing, and business experimentation than many people are.

So, depending on how these next few months turn out, what are the kinds of businesses that I’d like to build?

  • E-books and other resources: I like the way free/pay-what-you-want information makes it easy for people to learn without friction and still be able to show their appreciation through payment, conversation, links, or other good things. I also like the scale of it: I can spend some time working on a resource, and then people can come across it when they need it. No schedule commitments, either.
  • Software, maybe?: Someday. The upsides of working on stuff that other people use: feature suggestions, warm-and-fuzzies. The downside: dealing with bugs. I think the first step would be to build tools for myself.
  • Visual book reviews?: People seem to like these, and I enjoy reading.

Let me take a step back here and break that out into the specific characteristics I like. If I identify those characteristics, I might be able to recognize or imagine other businesses along those lines. What attracts me?

  • Scale: Build once, help many. I don’t mind lower sales at the beginning if I’m working on the kinds of things that people will find useful over a long period of time.
  • Accumulation: I like collecting building blocks in terms of content and skills because I can combine those in interesting ways.
  • Generosity: I like free/pay-what-you-want because it allows me to reach the most people and feel great about the relationships.
  • Flexibility: I like minimizing schedule or topic commitments because that reduces stress and lets me adapt to what’s going on. Self-directed work fits me well.
  • Distinction: I like doing things that involve uncommon perspectives or combinations of skills. I feel like I can bring more to the table.
  • Value: I like things that help people learn more, understand things better, save time or money, share what they know, or be more excited about life.
  • Other things I care about: I care about making good ideas more accessible, which is why I like transcripts, sketchnotes, writing, and websites. I also care about helping good people do well, which is why I help friends with their businesses.

Writing fits these characteristics pretty well. If I can help friends through process coaching and things like that, I can learn more about things that other people might find useful too. It’s entirely possible to build good stuff around just this learn-share-scale cycle. Anything else (spin-off businesses? software? services) would be a bonus.

I have a little more uncertainty to deal with. I can see the timeline for it, so I’m okay with giving myself permission to take it easy for the next couple of months. After that, I’ll probably have a clearer idea of what the rest of this experiment with semi-retirement (and other follow-up experiments! =) ) could be like.

What would more focused writing or content creation look like? I might:

  • Pick a subject people are curious about and write a series of blog posts that I can turn into e-books
  • Revisit that outline of things to write about and flesh it in
  • Organize blog posts and other content into downloadable resources
  • Create courses so that people can go through things at a recommended pace and with multimedia content
    • Ooh, more animations

I think that would be an interesting life. =)

I still want to do something to help all these awesome people I come across who are having a hard time finding jobs or building businesses for themselves, though. It’s odd hearing about their struggles while at the same time watching the stock market keep going up – businesses seem to be doing okay, but it’s not trickling down? Maybe I’ll spend more time listening to people and asking what could help. Maybe I can spend some time connecting with business owners and seeing if I can understand their needs, too. Knowledge, ideas, and encouragement are easy, but there are probably even better ways to help. Hmm… That gives me a focus for networking at events. Looking forward to helping!

Realistic expectations, ruthless elimination, and rapid exploration

“You’re pretty organized, right? Do you have a system for productivity that I could use?” someone said to me. She sounded frustrated by her lack of progress on some long-standing projects. I shrugged, unsure how to help.

I don’t consider myself super-productive. I am, however, less stressed than many people seem to be. I’ve been learning to keep realistic expectations, get rid of less-important tasks, and work in quick, small, useful chunks.

Realistic expectations: We tend to overestimate how much we can do, particularly if we’re looking a week or two ahead. Even if last week was derailed by interruptions, we hope next week will be a smooth ride. I’m guilty of this myself. I compensate by expecting little of myself – just one to three important tasks each day, moving forward a little bit at a time. If I find myself with spare time and motivation, I check my other tasks for something to work on. It’s okay if I end up procrastinating something. That usually means I spent the time on something I valued more.

Ruthless elimination: “But how do I motivate myself?” This is another thing that people often struggle with. I use different strategies depending on what I need. For example, I’m currently working on a project with a high risk of failure and a fair bit of work. For me, it helps to amplify the perceived benefits, downplay the small pieces of work that I need to do (it’s just a small task), and downplay the risks (failure isn’t all that bad). On some other projects, I might decide that my lack of motivation is a clue that I should just wrap up the project, get rid of specific tasks, delegate work, or transform those tasks into things I might enjoy more.

Rapid exploration: After I adjust for realistic expectations and get rid of tasks through ruthless elimination, I think of tiny tasks that will help me move towards my goals. That way, I can explore and get feedback faster. Then I try to get as much value as I can from those steps, usually ending up with blog post ideas and lessons learned in addition to the thing itself. This also means that I can squeeze work into 15- to 2-hour chunks instead of waiting for a 4-hour span of uninterrupted, energetic time.

There are a bunch of other things that help me out (keeping outlines of projects and tasks in Org Mode, documenting as much as I can, knowing my tools well), but those three behaviours above seem to be different from the way many people around me work. Hope that helps!

Three productivity tools

Kosio Angelov asked: “If you could use only three productivity tools for the rest of your life, which three would you choose?”

2014-05-14 Which three productivity tools would I use if I could use only those for the rest of my life #emacs #productivity

2014-05-14 Which three productivity tools would I use if I could use only those for the rest of my life #emacs #productivity

I’m totally cheating with my answers. I can’t imagine using only three tools. What counts as a tool, anyway? Is the Internet a tool? What about the scientific method? Are we talking about apps, applications, platforms, systems, frameworks? =) Anyway, these are the answers that came to mind. They’re not your usual suspects, but I’ll explain why I like them a lot.

Emacs: This arcane text editor from the 1970s is capable of far more than most people think it can. It’s not an application, it’s a platform. I use it to code, write, plan, connect, automate, calculate, and so on. People get intimidated by its learning curve, but for me, it’s well worth it. I’ve been learning and blogging about it for more than ten years. Based on what I’ve seen, I could probably keep going for decades. I love the way you can dig into how things work, tinker with the code to make it fit what you want, and combine different packages. Great user community, too.

I’m not sure what to say to productivity newbies considering Emacs. It takes a certain kind of person, I think. If you’re someone who likes constantly learning and tweaking, you’re good at learning from what other people have written, and you’re not afraid to do a little worse in order to do even better in the future, this might be for you. You don’t have to be a programming geek, although it helps.

Linux: Again, I’m cheating by including an entire operating system, and probably I mean all the little tools I’ve gotten used to rather than the operating system itself. But I love being able to use utilities like grep and find (thanks, GNU!), stitching programs together, scripting things, installing other tools… People have suggested that I look into Mac OS X, but it gets a little on my nerves. I like Linux more. There are some programs I want to run on Windows, though, so I end up using Linux in a virtual machine so that I can do my development in a proper environment.

Ruby:  I use Ruby for little automated scripts as well as special-purpose web-based tools like QuantifiedAwesome.com, which helps me track my time. It feels like the way my mind works. I used to use Perl for scripting and I’m learning Python, but Ruby has the least friction for me. This may change as I get deeper into other languages, but in the meantime, Ruby is a good language for the kinds of things I want to do.

—-

All of these tools take effort to learn. They’re not like, say, Boomerang for Gmail or ScheduleOnce, which are easy to pick up and have clear benefits. My favourite tools require imagination, but they open up infinite possibilities. I’m not locked into one way of doing things. I still have limits, but they’re the limits of my own ideas and skills. I think that’s what I like about these tools. They have depth. Whenever I reach for some new capability, I almost always find it.

So, if you’re a newbie and this sounds intriguing, how do you get from point A to point B?

I think I got here by being interested in learning, being unafraid of tinkering, and having the space to do both. When you’re learning a complex thing, you might feel frustrated and intimidated by it. Good games design that learning experience so that people enjoy small wins as they develop their skills, but not all topics are like that. Sometimes you have to enjoy the learning for its own sake.

… which is an odd message to share with people who are looking for productivity hacks, maybe, but it’s something I’ve been thinking about lately. There’s a cost to picking general-purpose tools that are perhaps not the best at one specific thing, but experience results in compounding benefits. There’s a cost to keeping both your schedule and your eyes open, but perhaps it can lead to surprising things. There’s a cost to choosing the path of learning rather than the quick fix, but who knows what the true cost is down the road?

On why frugal me is cool with paying other people to do things

I am frugal by nature. I do the mental calculations almost reflexively. Food is my favourite measure of equivalent value, since I rarely buy books these days. If I bike instead of taking public transit, that’s three Vietnamese sandwiches. For the price of dinner for two at Pho Hung, we could buy and roast two whole chickens. I hardly eat out, since I know I can make my favourite meals for $2-$4 a serving.

2014-03-06 Our frugal life #finance #frugality

2014-03-06 Our frugal life #finance #frugality

Many people who are working on financial independence take pride in doing as much as possible themselves. It’s a great way to save money and build a variety of skills. I usually do the same. It’s great knowing that fixing a washing machine doesn’t have to be a scary thing.

But there are some areas where I spend more than most people do, like outsourcing.  For example, even though no one expects transcripts for podcasts and even though I can transcribe my own posts, I pay other people to transcribe them for me. I pay people to research, draft, code, experiment, learn. I’m slowly getting the hang of passing on tasks even if I feel like I could learn a lot by doing things myself. If I outsource those tasks, then at least two people learn: my assistant and me. In fact, since they write down things I might otherwise just skim or take for granted, I can usually take what they send me and share that with other people.

For me, outsourcing is so much more than just a money-for-time trade off. I think of outsourcing as a way to help other people build up assets and skills as they figure out flexible work that fits their needs. It’s a way for me to learn from different perspectives and experiences, too. I don’t need stuff. I don’t crave experiences: no exotic vacations, no once-in-a-lifetime memories. I’d rather take advantage of the abundance to scale up and help others.

2014-01-28 What do I get out of delegation

2014-01-28 What do I get out of delegation

(See more in Ramping up delegation)

Independence matters to me. So does interdependence. If I can carve out enough to provide reasonable security for myself and I have the skills to go and earn more money if I need to, then I’ll use the surplus to make the world a little bit better. I had thought about focusing on stashing away more money so that we might have a greater margin of safety. (Who knows, maybe W- might even be able to retire.) I’m slowly adding to that stash, but that doesn’t rule out helping other people along the way.

I don’t want to become dependent on outsourcing. I make sure all my tasks are documented so that I can take over if needed. I establish financial limits so that outsourcing doesn’t encroach on my other plans. (This is one of the reasons why I like working with assistants on an as-needed basis instead of committing to a specific number of hours or tasks a month.) I learn from small experiments before I move on to larger ones. I prefer outsourcing to people who can learn from the experience instead of to established companies with polished solutions.

I don’t have to spend the money on this, but I decide to, and it’s worth it to me.

Thinking about my TODO keywords

It’s been twelve years since David Allen published Getting Things Done, with its geek-friendly flowcharts and processes for handling tasks in an interrupt-driven life. The way I manage my tasks is heavily influenced by GTD. I think in terms of next actions, waiting, and someday, and I have weekly reviews. I modified the TODO states a little to reflect what I need. It’s time to think about those states again to see what I can tweak and what reports I could use.

I use Org Mode in Emacs to manage my tasks and my notes. I can customize it to give me different kinds of reports, such as showing me all of my unscheduled tasks, or all tasks with a specific category, or even projects that are “stuck” (no next actions defined). Thinking about my processes will help me figure out what reports I want and how I want to use them.

Here are different types of tasks and how I track them:

  • Things I can work on right now (next actions): TODO
  • Things that I can work on after a different task is finished: currently WAITING, but probably better to implement with org-depend
  • Things I will revisit at a certain date, but I don’t need to think about them until then: TODO, scheduled (I used to use POSTPONED)
  • Things that would be nice to do someday, but maybe are incompletely specified or understood: SOMEDAY
  • Things I have decided not to work on: CANCELLED
  • Things I have asked someone else to do: DELEGATED
  • Things I can ask someone else to do: TODELEGATE
  • Things I am waiting for (usually not based on date) and that I need to follow up on: WAITING
  • Things I can write about: TOBLOG. These are pretty optional, so I don’t want them in my TODO list…
  • If something is a duplicate of something else – remove TODO keyword and add link?

I use the following code for an agenda view of unscheduled tasks:

(defun sacha/org-agenda-skip-scheduled ()
  (org-agenda-skip-entry-if 'scheduled 'deadline 'regexp "\n]+>"))

(add-to-list 'org-agenda-custom-commands
   '("u" "Unscheduled tasks" alltodo ""
     ((org-agenda-skip-function 'sacha/org-agenda-skip-scheduled)
     (org-agenda-overriding-header "Unscheduled TODO entries: "))))

So the to-do process looks like this:

  • Every week, review my evil plans and projects. Check my agenda without the routine tasks to see what new things I’m working on. Schedule a few tasks to encourage me to make regular progress.
  • Every day, go through my Org agenda (C-c a a) and do all the tasks that are scheduled.
  • When I’m done or if I feel like working on something else:
    • What do I feel like doing? If there’s a specific activity that I feel like:
      • Go to the relevant project/section of my TODO list, or check the TODOs by context (drawing, writing, etc.)
      • Clock in on that task.
    • If there’s a specific task I feel like working on:
      • Find the task, maybe with C-u C-c C-w (org-refile) and work on it.
    • If there’s a new idea I want to work on:
      • Use org-capture to create the task, file it in the appropriate project, and then clock in.
  • If I have an idea for a task, use org-capture to create the task and file it in the appropriate project.

How do I want to improve this?

  • Maybe get more used to working with contexts? I have all these Org Agenda commands and I hardly ever use them. I tend to work with projects instead. Actually, working with projects makes sense too, because that minimizes the real context shift.
  • Get better at reviewing existing tasks. I started tracking the number of tasks in each state (DONE, TODO, etc.), which nudged me to review the tasks and cross old tasks off. If I streamline my process for capturing tasks, filing them, and reviewing them by project/context/effort, then I can get better at choosing good tasks to work on from my existing TODO list.
  • Estimate effort for more tasks, and use that more often I have some reports that can filter or sort by estimated effort. I don’t use effort that much, though. Does it makes sense to get into the habit of choosing tasks by estimated time as an alternative approach? I usually have fairly large, flexible blocks of time…
  • Tag things by level of energy required? I want to take advantage of high-energy times. So, when I feel alert and creative, I want to focus on coding and writing. I can save things like paperwork for low-energy times. I can tag some tasks as :lowenergy: and then filter my reports.

Hmm…

How Org Mode helps me deal with an ever-growing backlog

If you’re like me, you probably have a to-do list several miles long. I like thinking of this as the backlog from agile programming. It’s a list of tasks that I could choose to work on, but I haven’t committed to doing everything on the list. This means I don’t have to waste energy feeling guilty about not getting everything done. Instead, I can treat it like a buffet of projects to choose from depending on what I feel like working on.

2014-04-28 Dealing with an ever-growing backlog

2014-04-28 Dealing with an ever-growing backlog

I think I add tasks faster than I cross tasks out. (Hmm, I should track this!) It never ends. Most tasks suggest next steps I could take after I finish the first ones. You might think that an ever-growing to-do list is a bad thing. This is okay. In fact, this is good. It means that I’ll always have a variety of tasks to choose from.

People manage tasks in different ways. For my personal tasks, I use several large text files in Org Mode for Emacs. Org Mode is an outline-based tool which makes it easy for me to organize my tasks into projects and projects into themes. It also supports tagging, links, agendas, dynamic views, and all sorts of other great ways to slice-and-dice my task list. Here’s how I deal with some of the common challenges people face with a large task backlog:

  • Making sure important, urgent tasks don’t fall through the cracks
  • Making sure you don’t neglect important but not urgent tasks
  • Keeping track of what you’re waiting for
  • Catching procrastination

Making sure important, urgent tasks don’t fall through the cracks

If something has a deadline, I add the deadline in Org using C-c C-d (org-deadline). This means that reminders will appear on my daily agenda for the 14 days before the deadline, counting down to the deadline itself. (The number of days is controlled by org-deadline-warning-days.) In addition, I usually schedule the task for a day that I want to work on it, so that I can get the task out of the way.

I’m careful about what I commit to, erring on the side of under-committing rather than over-committing. I’m selective about my client work and my volunteering. I keep my schedule as open as I can, and I’m not afraid to reschedule if I need to. Hardly anything I work on could be considered urgent. If an urgent request does come in, I ask questions to determine its true urgency, including potential alternatives and consequences of failure.

You might not have as much choice about what to work on, but you might also be surprised by how much you can push back. Be careful about what you allow to be urgent in your life.

Making sure you don’t neglect important but not urgent tasks

I have plenty of space to work on things that are important but not urgent because I manage my commitments carefully. This means that I can usually finish a few important-but-not-urgent tasks every day.

Which tasks do I consider important? I like thinking in terms of projects. Important tasks tend to be associated with projects instead of standing in isolation. Important tasks move me toward a specific goal. I have many goals and projects, but because they’re fewer than the number of tasks I have, I can prioritize them more easily. I can decide that some projects are in the background and some are in focus. Important tasks are the tasks that help me make more progress on the projects I consider important.

Because I like having two or three projects on the go, it helps to make sure that I make regular progress on those projects instead of getting carried away on just one. Tracking my time helps me stay aware of that balance. I also review my projects every week and schedule specific tasks for each of them, so I can make a little progress at least. Once I switch context and start thinking about a project, it’s easy to pick another couple of tasks in that area and get even more done.

If you’re struggling with creating enough space to work on important but not urgent tasks, you might be able to partner up with someone so that you can block off time to work on non-urgent things. Many teams have a rotating schedule for dealing with customer requests or urgent issues. One person covers the requests for a day, allowing the rest of the team to focus. Then the next person takes on that duty, and so on.

Keeping track of what you’re waiting for

One of the useful tips I picked up from David Allen’s Getting Things Done book was the idea of marking a task as WAITING. I usually add a description of what I’m waiting for, who’s responsible, and when I want to follow up. This makes it easier to follow up. When I’m waiting for a specific date (ex: the library makes a DVD hold-able after a certain date), I schedule the task for then.

I use the Boomerang for Gmail extension when I’m waiting for an e-mail reply. Boomerang lets me pop the message back into my inbox if I haven’t received a reply by a specific date, so I don’t have to keep track of that myself.

Handling less-important but still useful things

There are tasks on my to-do list that have been on that list for years. This is okay.
I’m getting better at noting names and contact information in my tasks so that I can follow up with people even after some time. This is particularly useful for book recommendations. I get a lot of book recommendations and I get most of my books from the library, so there’s usually a delay of a few weeks. Because Org Mode lets me add notes and links to the body of a task, I can look up information easily.

I work on less-important tasks when I don’t feel like working on my major tasks, or when I’m looking for small tasks so I can fill in the gaps of my day. Org Mode gives me plenty of ways to look up tasks. I usually look for tasks by projects, navigating through my outline. I can also look for tasks by effort estimate, so I can see everything that will probably take me less than 15 minutes. Context is useful too – I can search for various tags to find tasks I can do while I’m on the phone, or out on errands, or when I feel like writing or drawing.

I like thinking in terms of low-hanging fruit, so I often choose tasks that require little time or effort and have good impact. It can be overwhelming to look at a long list of tasks and decide which ones have good return. It’s easier to tag these tasks when you create the task, or to think in terms of projects instead.

Some tasks grow in importance or urgency over time. If I want to make sure that I revisit a task on a certain date, I schedule it for then.

Catching procrastination

I still end up rescheduling tasks multiple times. (I’ve been putting off redoing my business cards for a few months now!) I’ve noticed that there are different kinds of procrastination, including:

  • Procrastinating because you don’t have time today: It’s easy to reschedule things a few weeks or a month in advance. In fact, Org has a built-in command for bulk-scattering tasks. From the agenda view, you can type m to mark multiple tasks, then type B and then S to scatter tasks randomly over the next N days. (Call it with a prefix argument as C-u B S to limit it to weekdays.) If I catch myself procrastinating because I don’t have enough time, that’s usually a sign to be more cautious about my estimates and commitments, so I adjust those too.
  • Procrastinating because it’s less important than other tasks: This is related to the time reason. I have no qualms about pushing less-important tasks forward.
  • Procrastinating because you don’t feel like working on it: Is the task actually important? If it’s not, I usually get rid of it without feeling guilty. If it’s still useful, I might unschedule it so that I see it only if I’m looking for tasks in that project or in that context. Alternatively, I can just mark the task as CANCELLED or SOMEDAY. If the task is important, I think about whether I’m likely to feel like working on it at some point in the future. If I’m likely to not feel any different about it, I might delegate it, or I might just sit down and do it since procrastination doesn’t add value. On the other hand, if I’m likely to feel like working on it at some point, then I tag it with that context and push it out to some other date.
  • Procrastinating because you forgot about it: I usually check my agenda every day and Org shows forgotten things in a different colour, so I catch these quickly. If the tasks are more important than the tasks I’ve already scheduled, I might work on those first. Alternatively, I might schedule it for sometime later.

I procrastinate based on my to-do list, not based on my inbox. The inbox is a terribly unstructured way to manage your tasks. I use Boomerang for Gmail to defer some mail to a later date, but that’s usually so that I can pop it back into my inbox the day that I meet someone so that I have context and so that I don’t have to copy the link into the calendar entry or my TO-DO list.

Wrapping up

So that’s how I deal with having a large backlog. I focus first on the stuff that I need to do, and I make sure that shows up on my agenda. Then I make it easy to look for stuff that I want to do using Org’s support for projects, tags, time estimates, and so on. I don’t feel guilty about having lots of tasks to choose from. I view my backlog positively. It lets me do good stuff without worrying too much about how I spend my time.

How do you deal with your backlog? =)

Sneak peek! Writing this post prompted me to start tracking whether my backlog grew or shrank each day. Check out my preliminary results and the code I used to analyze my TODOs.
2014-04-27: Fixed typo in keybinding – thanks, Sujith Abraham!