A first look at new process: creating an optimum list of tasks. But what does “optimum” mean?

After writing my kickoff post, I wondered what to do next. I started by jumping into email and checking significant mailboxes:

• contacts – This contains emails from people who have written to me via the blog contact form. There are 10 unanswered emails that I haven’t had time or energy to review yet.

• amazon business folder – What sold, and outstanding alerts or complaints. Nothing actionable, though this reminds me that I have a lot to do to make more sales by making better materials, figuring out non-US fulfillment, etc. Blargh.

• client business folder – A combination of automated alerts from an email system I built, and updates to the various project management tools. Nothing actionable, but there are plenty of things for me to do from a Trello list that has a prioritized list of projects to work on when I have time.

• business networking folder – Updates from linkedin and companies that have products that I use. Safe to ignore, but it reminds me of all the things I want to learn and build.

I could answer the emails now and get them out of the way, but I’m looking for something meatier and process-driven to do. In other words, I want my daily big task to be clear and actionable. My gut feeling is that I want a nice optimized list to work from so I know what to do. However, I don’t feel particularly enthusiastic about putting that list together. Partly this is because none of the tasks I’d put on that list will lead to a Big Reward or an Exciting New Opportunity. At least, not yet. Intellectually I know that anything I can produce will, by the very fact that it exists, provide new opportunities if I choose to share it. Sharing sparks ideas and builds bridges for future cooperation. However, this is a promise of an unspecified benefit that is certainly not guaranteed to happen any time soon, plus it requires actual work. Therefore it doesn’t entice the lizard brain into pumping serotonin. “Meh” is my primal reaction. Creating a nice optimized list, though, is what I need to do. My lizard brain, though, is telling me that all the items on my list are equally unlikely to produce a Big Fat Juicy Reward in the very near future. I’m attempted to trick myself into doing it by engaging my Writing Power: when I write, I tend to solve problems and become engaged by the desire to run an experiment because then I get to see what happens. This blog post is the experiment! I am being productive by procrastinating on the actual work of making that optimized list, a time-honored tradition practices by academics around the world. Where was I? Oh, that list.

What is Optimum?

The ideal list would come from an easy process that the lizard brain AND the rational brain can agree on. I have plentiful sources of tasks: the trello board is the canonical source of Dave projects, a holy shrine of everything I have done and ever shall do. I am also deluged constantly by my own thoughts that give rise to new ideas, though for the last few weeks I’ve been suppressing them because I have a huge backlog of projects that aren’t getting done. Fortunately, this doesn’t bother me because I no longer allow project backlogs without deadline to bully me into feeling bad. Which is a good reminder to look at what that ideal optimized list is all about: being more awesome by making things and sharing them with the world. My frustration stems largely from my lack of superpowers to will amazing things into existence, though I know they would (probably) be very cool. I’m very much in the bootstrapping phase of this dream. Step 1 is making enough money through product sales and a handful of related side-projects with paying clients. Step 2 is to use the time save from not working on other people’s projects to forward my own ambitions. In reality, there are other external commitments that I have that pop up every day, and they must be scheduled in. I need to have my car looked at, book appointments for health, deal with two boards of directors I’m on, do laundry, blah blah blah. You get the idea. Some of these need to be on the list. I’m not alone in having a giant list of potential projects, lots of chores, and lack of certainty in how to handle it. There’s a natural desire to want to handle it all and handle it efficiently, because the act itself is incredibly uninspiring. And yet, it is on the other side of this fog of un-inspiration and un-certainty that our next opportunities await. What is optimal? Three practical approaches come to mind:

• Apply discipline, and do everything systematically. This is the way of Getting Things Done. If you were not the type of person who started your homework the moment it was assigned, GTD itself is a kind of mental overhead, and requires external energy and periodic rewards of some kind to maintain. I find it hard to maintain because the tasks I have to do generally are not rewarding or well-defined.

• Timeblock and hope for the best, vigilantly harvesting useful output and converting efficient patterns into principles as they appear. This is what I largely have been doing for my own projects. It’s liberating to assign 15 minutes to a hairy project, and just see what happens. However, it still is an effort. While time blocking frees me from having to do a complicated project breakdown prior to starting the work, it still demands a measure of faith to keep going. It also requires much more flexibility and assessment on the part of the worker, so it is not for everyone.

• Do less by reducing scope to the essentials, and let go of everything else. Or outsource it to trusted partners. If you have a gigantic project list like me, it’s probably because you want to do a lot of things. And you are a control freak who doesn’t trust anyone else to do it well. If you can let go of these impulses, you can get a lot more done because a lot more gets finished. It requires patience and discipline, qualities that I tend to have in short supply unless I am mindful about it. That is what I’m doing now.

Summarizing these approaches, you end up with this:

1. Discipline and systematic engagement of tasks.
2. Dissolving big hairy tasks into manageable slices of time, trusting that the imperfect knowledge you start with will be improved as time goes on.
3. Doing only what really matters at any given time, reducing resource requirements.

As much as it pains me, #1 doesn’t come easily to me. I’m great at analyzing tasks systematically, but I find the execution through systems tedious. This even applies to computer programming, which promises to automate systems so you don’t have to do it yourself anymore. So I’m going to focus on #2 and #3. For that I need a process. You’ll notice that I haven’t mentioned PLANNING as an approach. That’s because I already tend to overplan (this blog post is a good example of that). I suppose another way of looking at overplanning is to say that I already plan more than adequately. My desire for a new or improved process is to craft a solution that fits my own proclivities: I find routine boring, I have a surplus of interests and ambitions, and I have a tendency to dislike starting tasks that aren’t known or guaranteed to deliver a reward in the near future. So another element of my optimum system is that it has to be one that I can follow with minimum friction. That is shadow directive #4.

The Process of Creating A List

The elements of an optimum process are, so far:

• time blocking
• scope reduction
• built-in rewards

I also know that the following skills are cheap and essential for me to function well:

• writing to think things through
• daily writing
• experimenting to see what happens
• sharing what I do

Aspects I need to avoid:

• feeling trapped – negated by keeping number of tasks and size time commitment low.
• being bored by routine – helped by scheduling more happy bubble time than work time.
• over-committing to other people’s projects – helped by not committing to projects that take more than they give back to me.
• going too long without reward – this is handled through the sharing act, since a blog post is produced and I like sharing what I’ve learned.

The process itself would look something like this:

1. Identify current scope and desired deliverables, and narrow it down to just a few projects.
2. Do some writing about the scope with a 15-minute morning burst, every day.
3. Create experiments to drive the initial exploration stage, writing about critical or interesting developments and sharing them online.
4. Time block in small amounts, 15 minutes at a time, until flow is achieved. Get this done first thing after waking up, before checking email, for at least one of the projects.
5. Find something to deliver and test (another experiment)
6. Assess and deploy what was created.
7. Write about what happened
8. Reassess, and go back to 1 to start the process again.

This is a familiar process, but I haven’t formalized it before. The most challenging item is the first one, identifying my current scope. I know that all of the tasks available to me are useful and will deliver some kind of tangible future benefit. The near-term benefit is getting to write about what I’m learning and sharing it on the blog. The process for identifying scope is simply choosing three things to work on every day, and not worrying about everything else. That’s incredibly important. A supporting process is managing idea capture. I’ve had five or six ideas while writing this article, and I have chosen to ignore them. I trust they will come back if they’re really important. Alternatively, I could capture them intro Trello. Whatever I decided, I have to be sure the decision does not create anxiety. This is a mental stance I am developing; a big part of focus is putting everything else that doesn’t matter in the moment out of mind. Only a few tasks are allowed to be critical at one time, and I decide this arbitrarily if life-or-death is not involved. At this point, there are some administrative things I can do:

• Print out the process and put it somewhere I will see it. Since I’m using my laptop again to work in multiple locations, I need to revisit my traveling office.

• Make a summary sheet for my current scope of tasks. I could put this in my daily planning text file, which is accessible everywhere through DropBox. It’s the easiest thing to do, since that planning file will be reviewed every day since it’s my brain.

• Create accountability for my daily tasks and achievements. Trello is the primary way that I keep track of tasks, and I’ll continue to use it. It’s viewable from desktops and mobile devices. I’ll also post progress notes on the blog. If I’m doing things, I’ll certainly have something to write about.

OK! I have the semblance of an approach. Here are the tools I’ll be using:

• Text Editor for the daily continuity notes I maintain as “first in the morning” activity. The text editor I’m using is Sublime Text. I’m saving the files, which use Markdown syntax.

• DropBox (referral link) is used to synchronize both my daily continuity notes and my working project folders, with the exception of websites and other projects that have source code. For those projects, I’m using Mercurial for source control, as it is a little friendlier than Git while having the advantage of distributed source control. That’s a topic for another day.

• WordPress for my Stream of Consciousness blog, where I will maintain some daily continuity notes to myself. I have WordPress configured as a network, which gives me plenty of space to write without cluttering up the main blog. Writing about what I do is my interim reward…sharing is caring! :-)

• Trello (link) is where I’m keeping all my projects and tasks. It’s essentially a jumble of everything I want to do (and shall do) spread across a couple of boards. The main board is where I keep a priority queue of tasks that need doin’, and the supporting board has a week-by-week archive of what got done.

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p>I feel the need for some kind of tool or form that captures my thinking in some useful structure. Perhaps this is a modification of the Emergent Task Planner merged with the Concrete Goals Tracker, but it’s too early to say. I’ll try getting along with my text editor first.

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I’ve been writing non-stop about this topic for the past six hours, so I’m going to call it a day and enter Happy Bubble Time. Tomorrow I will formally kick-off the new process.

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