The Thorny Issues & Rubber Band Effect: My To-Do List Strategy

We often find ourselves looking at large to-do lists and trying to mentally gauge which tasks to prioritize and complete. Over the years, I have come across several prioritization frameworks and delved into procrastination tools & focus measures such as the Eisenhower matrix (Urgent/Important matrix), Pomodoro technique, and some Agile prioritization tools such as MoSCoW prioritization. I’ve also tried to stick to certain thumb rules, such as prioritizing tasks others are waiting on, whether it’s your supervisor, peer, or customer. Another principle is that a customer deliverable is more important than an internal task.

I also built a scoring model, integrating scores for all the tasks by taking different attributes from various models to view the priority score and determine which task needs to be tackled first. The frameworks I brought together are:

• CEE Matrix (Complexity, Effort, Effectiveness): Analyzes tasks based on their complexity, the effort required, and the potential impact, guiding you to allocate resources efficiently.
• Value vs Effort Framework: Score given to the perceived business value against the effort they require, nudging you towards tasks that promise the most significant benefits for the least input.
• Urgent/Important Matrix (Eisenhower Matrix): Categorizes tasks by urgency and importance, ensuring immediate attention to critical tasks while scheduling or delegating others.

Was this effective? Well, it is very effective as it puts the most important and impactful task right at the top and I keep working on it. The downside is the scoring itself becomes a chore and sometimes there are some “bothering” issues that just don’t get prioritized.

So, I started applying another technique which I mentally call “The Thorny Issues” and the “Rubber Band Effect.” The thorny issues are the small sneaky stuff that keeps popping up in your mind and asks for attention. These are tasks which if left unattended may hit back later like a rubber band, the more you pull it or in this case procrastinate while prioritizing your high-priority tasks can come back and hit. These are the dormant tasks which can suddenly explode. Our intuition keeps alerting us. These sneaky little thoughts of the tasks distract us from doing our “deep work”. Experts suggest that we do the most important work first thing in the morning, even ditching email before starting a deep work session. But for me, getting rid of the thorny issues, the small 2 min tasks, those quick callbacks, the email reply that has been waiting since yesterday are the ones that need to be addressed first. Once these are taken out of the way, getting into focused work becomes much easier.

This not only applies to knowledge work but also to physical work.

How I applied this to cleaning a bunch of skate wheels: It’s not an activity that I hate, but it’s something that I don’t love either, particularly when about 100 wheels are there to clean. So, I started by soaking them in detergent for some time before beginning to scrub them for grime. I quickly sorted out the wheels that were already relatively clean and required a quick wash and scrub, leaving me with only about 20 of the wheels that were super dirty. 80/20 in action 🙂 ? Then left with the daunting task , it was time to divide and conquer. Having the ability to delegate would have been great but I just chose to finish it off the cleaning in steps taking 5 wheels at a time and it was mentally less daunting taking it in steps and entirely focused on the outcome and results – Clean wheel.

The power of quick wins helps in motivating the task to completion as it makes us believe that the task is in fact doable and not as daunting as it was.

So, in conclusion, I start my day by putting together a to-do list and on great days, the to-do list is done the previous evening. I list down the thorny issues or tasks and get them out of the to-do list before getting to the “Priority of the day” with undivided attention. This method has been effective for me and keeps me less stressed while also getting things done and most of all, satisfied by the end of the day.

Please share your thoughts on how you approach priorities, and if this approach would work for you.