Blog » Neither Working Nor Not Working, Part III (Task Management)

Many problems with distraction and productivity are a matter of accountability. Team working situations and imminent or well-structured deadlines are good antidotes to not-working. Peer and client pressure can provide a good kind of stress that filters out many distractions through simple necessity.

Much of my freelance life, however, is devoted to solitary work on projects with vague, nonthreatening, or flexible deadlines. The freedom to do just about anything during a day is why many of us freelance. But this very freedom can be paralyzing without some structure or system that lets us make meaningful choices about how to spend our time.

So once you apply some simple time-management ideas to clear time for work ... what do you do with it?

It’s the rare freelancer who has too little to do. In addition to the main goal of delivering good work, the entrepreneurial tasks of drumming up business, maintaining relationships with clients, and invoicing and bookkeeping take up a significant percentage of the freelance life. And then there’s all the stuff too-often relegated to back burners or bottom drawers. Creative freelancers always have personal work that needs attention. Techies always have some new development framework or software version to learn.

My approach to managing these many demands is unsurprising. Lists. Making lists solves two problems for me: my spotty memory means that things fall between the cracks once in a while, and having good lists means I can quickly figure out what to work on next.

Many freelancers are daunted by their to-do lists, commonly by tasks that are either intimidatingly large and complex or simply too numerous. The former is a common problem, and I endorse the common solution: break large projects down into stages and parts, repeating this process until you are working with items that can be considered on the scale of hours or days. I find that lists are also great for approaching a plethora of tasks that seem more or less equally demanding, for the simple problem that listslike the workdayare linear. Something has to be next on the list. And if there aren’t clear reasons to choose one thing over another, make an arbitrary choice: roll dice, flip a coin, choose alphabetically, whatever.

Much like using a Pomodoro timer, creating a list can externalize and simplify messy matters of decision. This separation of functions is a key aspect to taking control over your work life. If you can separate the managerial aspects of your work (make a list and order it) from the messiness of doing it (gah! I have sooo many things to do!), then it frees you to pay professional attention to the tasks at hand.

I use a few different tools and approaches to keep my lists of tasks up to date and useful:

Simple lists

These are plain old paper or digital lists. My examples are this awesome pad of week-at-a-glance planning sheets and Google Keep.

I love the pad of paper pictured above: it has just enough room for reasonable number of items per day, and I really appreciate having an overview of the week, which is largely how I plan out my work life. Paper lists are simple and intuitive, but have some serious drawbacks: they are not always close at hand, they cannot be easily shared, and they are sometimes illegible. Seriously, my handwriting is *terrible* and an unfortunately high percentage of the time I just plain lose notes and ideas and reminders because I can’t decipher them again.

Thus, Google Keep. This is where my partner and I keep our day-to-day household lists: groceries, household to-dos, etc. We were already in the habit of using Google tools like Maps and Drive to plan vacations and budgets, so Keep was an easy choice for shared simple lists. Unfortunately it’s a little too simple for my work life because it isn’t really made for categorizing and prioritizing things. It’s tough to manage multiple lists, and impossible to move items between them. If you just need a simple, shareable digital list tool, though, then Keep is great, and is fully cross-platform, so I find myself using it regularly from both my laptop and my phone.

Structured lists

I’ve experimented with a couple of more structured (and necessarily digital) list tools. I am currently using an Android app called Wunderlist. It allows me to create multiple lists and move items from one to another. For instance, I typically have several categories of items, including “Personal,” “Household,” “Writing,” “Web Work,” and so on. I add items as appropriate, and then come evening or morning I (tentatively) plan my day by browsing through the categories and moving items to the “Inbox” where I can prioritize and check them off. It offers some integration with my computer (there's a Firefox plugin to add items) and is generally a pleasant app to use.

Lifehacker has a good round-up of list apps here.

Project-management tools

In my life as a web developer, I had good experiences working with Agile project management and its “sprint” concept. This involves breaking up large-scale projects into sub-tasks, each of which should take between, say, an hour and a day to accomplish. They are prioritized into a list, called the “backlog,” of work that needs to be done. Each week an appropriate number of hours worth of tasks is moved from the backlog into the “sprint board" (or "kanban" board) which consists of a series of statuses such as “To-do”, “In progress”, “To proofread”, “Done”, and so on.

sprint board small imageA sprint board can be managed with an app or website, or even non-digital(!) methods involving whiteboards or a matrix of post-it notes. In my case, I use TinyIssuea very simple open-source task tracker that I modified to add a sprint board (pictured). If you are competent with installing web software, you might give it a try ( There are other commercial, hosted tools that do much the same thing: JIRA and BaseCamp offer sprint board functions and there are a whole bunch of open-source options.

In addition to this sprint board approach, the Gantt chart is a popular method of dealing with inter-related tasks. I've played around with some apps (like Planner) that use Gantt charts, but have never made them part of my personal suite of tools.

Time estimates

Specific tools aside, taking the additional step of estimating how long tasks will take is amazingly helpful, if initially intimidating. It's great for two reasons: 1) it obliges you to keep breaking down your tasks until you reach a level of detail where you can actually estimate how long something will take, which means you've arrived at the most helpful level of detail, and 2) being able to look at your work in terms of how long each step will take makes it immediately more manageable. If "write article" is too vague and intimidating, consider how easy this looks:

  • research concept / markets / outlets (1 hour)
  • initial research (1 hour)
  • informational interview (0.5 hour)
  • write & send query (1 hour)
  • outline / rough draft (2 hours)
  • detailed interviews (1 hour)
  • edit and revise (2 hours)

Voila: the work will take a few half-days, which is both a reassuring fact and convenient to schedule. Time estimates not only help with the psychology of making work manageable, but they let me do short- and medium-term planning, and ideally prevent surprise deadline or budget problems.


Whatever approaches or tools you use, the process of task management involves the helpful reduction of large matters into their manageable component pieces and the prioritization of those pieces. This will not only equip you with a ready answer to the question “what shall I work on now?” but it means that you have taken time to consider your ongoing projects from a strategic and structural point of view that will help you define and relate various parts to the whole.

Taking time for this meta-work can defuse the anxiety and indecision involved in dealing with either intimidatingly large or dismayingly numerous to-dos. This is because stepping back and dealing with the work on the level of labelling and ordering is automatically more manageable than actually setting about doing the work in question. And having named and ordered the work, proceeding with it demands only a linear progression through a set of specific tasks. (It doesn't, of course, solve the inevitable unplanned crises that arise in freelance life. But it does give you a basis to assess those demands, and cultivates a certain amount of resilience in prioritizing even urgent requests when you're beset with them.)

Effective project management demands particular aptitudes and skills by and large independent of the skills you bring to bear directly on doing your work. The solo freelancer can cultivate them to some extent by simply realizing that getting organized is real work, and that it should be part of every day and every week. For my web work, I long added a blanket 15% to every quote to cover “project managementwhich includes communication, meetings, and decision-making with clients, but also my own time spent on making sure I know what to do next and why. Much as setting aside time to work will help with attention and intent, choosing to spend some time on the specific managerial labour of sorting and defining and ordering work in progress will free you to just do the next thing instead of fretting about what the next thing ought to be.

Be your own manager once in a while, and you’ll free yourself up the rest of the time to just do what needs to be done.


Neither working nor not working

Add new comment

This question is for testing whether or not you are a human visitor and to prevent automated spam submissions.