The Structuring Paradox of Productivity

An obsession with productivity tends to have causes.

When I was in high school, I got generally high marks whilst mistaking sitting in my room for working, and cursory glancing at pages for studying. Despite my best efforts at planning (being encouraged by my parents to set a daily studying schedule), it turned out I was able of squandering unconscionable amounts of time without getting almost anything done.
Essentially, I was coasting through tasks and assignments without any kind of system. This worked for me in high school and (with unsatisfactory results) in university.

It took me a while to fully identify my lack of structure as a weakness, as a lack of substantial progress can be hard to recognise amidst general (but non-significant) achievements.
For instance, when finishing my first major position in a student NGO, I was generally thought to have done a good job. However, when I looked back on the strategy I had set at the start of the mandate, I noticed that I had forgotten to implement many of the essential points and had generally not been able to manage complex projects.

This can always be useful to reflect on for yourself:
Are you really achieving what you set out to do, or do you find yourself compromising half-way due to time pressure and forgetfulness?

I realised I tended towards the latter, and so the search began for a program to help me structure my goals and areas of responsibility. This came in the form of Todoist.
Todoist helped me structure my work to an unprecedented level. Despite my graduation to more senior positions, I was effortlessly keeping track of the tasks and responsibilities in a variety of fields. Using it was also a lot of fun: it feels good to never miss a deadline and be able to give a good example to your team members. Plus, the dopamine rush of crossing off an entire project full of tasks is almost orgasmic.

BAP part 2I swear I can hear angelic voices in the background

My new  structure of task management had many ostensible benefits: I was finishing tasks well before my colleagues, noted down many achievements and was generally managing to satisfy the demands of my teams.
And so my productivity sky-rocketed. At least, according to the app.

Over time however, wrinkles began to appear: I would sometimes forget to sufficiently break down tasks (seeing it as “complete” while still missing important components) and whole areas of my life were sometimes forgotten to be worked on.
I noticed that I had begun to judge the success of a day by how many tasks I had fulfilled, not how much closer I was to my actual ambitions and dreams.
In a way, organisations suffer the same problem: it’s hard work to satisfy the daily supply and demand of the market, yet in this haze one can forget to deal with major structural problems or critical threats.

There’s a paradox here: the more structured your tasks and to-do list become, the more you’ll see their fulfillment as the fundamental KPI of your productivity in life. This is obviously problematic: you might cross off ten tasks a day and satisfy your dopamine addiction, but what if the tasks are mostly administrative and actually distracted you from critical obligations? (Organisations face the same issue when they get lost in operational tasks whilst heading for an iceberg.)

Stephen Covey from “The 7 Habits of Highly Effective People” refers to this as the failings of third generation time management: an over-reliance on structure and metrics of progress, rather than a more broad definition of effectiveness.
There is a very real “rush” and sense of accomplishment when crossing off tasks, and without constant vigilance this will can make you lose track of your actual goals. Covey tried to solve this by adding prioritisation as well as a focus on people to his time management.
I would add to this that to-do list can never fully capture your life: there is always work to be done in your life which defies the compartmentalisation of a to-do list. It is necessary to add an open, creative and divergent property to your task management.

I’m still dealing with this difficulty in task management, but here are my current solutions:

1) Frequent reflection 

Every week, I plan a moment to review my goals and my to-do list, both long- and short-term. (Yes that’s right: reviewing my to-do is on my to-do.)

Crucially, the basis of this evaluation is not the time pressure of upcoming deadlines, but rather on my personal mission statement (which contains my mid-term goals and long-term ambitions). This weekly review is a time to detail and refine goals that aren’t getting done, and set aside chunks of time for these.

In addition to the weekly check-ups, a larger re-evaluation takes place every month.

2) Personal 20 Percent Time

Every morning I try to spend about an hour working or reflecting on areas not on my to-do list. These are generally more open topics, such as continuous responsibilities, looking for new opportunities, quality-of-life improvements, or personal learning. These are areas notoriously hard to put in a to-do list (when exactly does one cross off “think about what to do next year”?).

Just like the 20 Percent Time concept at Google, this time gives you a chance to gravitate towards undervalued areas that are harder to push into a fixed structure.

3) Retain creativity 

Finally, I believe achieving any goal is partly a matter of convergence (finishing tasks, pushing your solution forward) and partly one of divergence (coming up with new ideas, thinking outside of the box). A structured to-do list does well with the former but poorly with the latter, so give it an outlet too.

I’m currently trying out James Altucher’s idea of coming up with 10 ideas per day. It has so far helped me train my idea muscle, and made me come up with very out-of-the-box ideas to improve my life.

In short: battle the structuring paradox by:
1) Weekly (and monthly) evaluation months
2) Daily unstructured time to work on continuous areas
3) Daily creative time to come up with divergent ideas

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