Digital To Do List + watch

If you are like me you may have been caught in this trap some time in the past. You are in the middle of a difficult transition and have a long list of items that need to be completed. Some are small, task-based items and other items are more complex and time consuming. You end up going for those task-based ones because it feels so good to check something off the list. With each check mark it feels like progress and it’s a wonderful endorphin rush. And occasionally that’s OK. The problem is these are seldom the type of tasks that create meaningful change; in either your life or your career.

Periods of transition are intimidating. You want to make progress and you want to make it now. We’ve all been instructed to create To Do lists or project plans to document the daily work toward that goal. Check marks equal progress, right? Yes… and sometimes, no.

Not all check marks are created equal. Neither are all items included in the plan. Those task-based ones, necessary as they are, provide a limited return on the investment of your time and energy. This despite how good it feels to check them off. And it’s too easy to favor them for their illusion of progress. But do they really create the type of meaningful growth needed?

The items that create a real value-add return are more complex — requiring a deeper level of thought and commitment. However for them the value is more in the process of doing than the having done. By this I mean that rushing through the work to check the item off usually results in decreasing the value returned by your efforts. Yes, the item is done. But has it been done well? Has it been done sufficiently? If the answer to these questions is not ‘yes,’ how much value can really have been created?

So the problem becomes to find a way that works for you to create a sense of progress when working on something which includes these dense tasks. The most common advice is to break down complicated items into small, manageable chunks that can be regularly checked off. And for most people that works. So try it.

Unfortunately for me I’m a big picture, gestalt kind of person. And despite having done some project management in my career I frequently find the whole process of breaking things down more frustrating than helpful. And after a certain point it often feels entirely artificial to me. So these days my process is to break the items as much as makes sense to me and then put the task on my list each day [that I plan to work on it.] At the end of the day I ask myself to honestly answer this question: ‘Today did was enough¬†effort put in to deserve a check?’ If my answer is ‘yes,’ I get one. If not, I don’t. It works for me*.

So when in a period of transition remember:

  • Not all items on your list are created equal
  • Be sure each workday includes a mixture of task-based items and deep work
  • The more complicated, time consuming the task, the more potential value can be created from its completion
  • Rushing through deep work to get to done only cheats yourself
  • Find a way to note progress on complex tasks that is meaningful for you

Remember, check marks don’t change lives; only real, meaningful effort does.

*And is less expensive & time consuming than the type of project management software used during my years on IT Projects; where tasks were broken down, estimated and at the end of the day the number of hours put in was entered and the estimate of the hours remaining compared with the original task estimate hours. Flashback…. shudder

Post Script: just as I was completing this post received a newsletter which seemed to agree with me.