The Day I Realized My To-Do List Was My Worst Enemy

And my best friend.

Photo by Kelly Sikkema on Unsplash

Lost in pool of tasks

I feel powerful as I write down more tasks in my Todoist app. Just like a protein does to grow my muscle, adding more tasks boosts my self-worth, as if I know what I'm doing. It also acts like a torchlight that guides me through my day, making me feel less lonely as I got more shits to do. But little did I know that instead of being guided through the unknown, having more tasks to do made me as lost as ever.

Every Sunday after lunch, I would head to a coffee shop to plan my week. As the caffeine ran through my veins, I felt alert and prepared for what lay ahead. The more tasks I added to my to-do list, the more confident I felt. However, as the week progressed, I found that I didn't have enough time to complete all my tasks. By the end of each day, I'd still have unfinished tasks, which was disheartening.

This cycle happened again and again:

Without realizing it, days turned into weeks, then into months. I felt like I was left behind and couldn't finish the project I'd always aimed for in the first place. I told myself I didn't have a priority. I blamed that new tasks kept coming in during the day, preventing me from checking them off my list. I blamed Lex Friedman's 8-hour-long podcast with Elon Musk for distracting me. And I wondered if the 24-hour long day duration was even applicable in today's fast-paced world.

But all these alleged problems wouldn't solve the real problem behind the curtain, creeping out behind me like a monster under the bed that grows larger the more I ignore it: My inability to handle hard tasks.

I came to learn it from listening to Shaan Puri's podcast:

By default, most people tend to choose a known task over an unknown one when setting task priorities, as it feels easier. Consequently, they may end up avoiding important tasks that are challenging but have the greatest impact.

"Oh, right…" I told myself this was the culprit behind every task I couldn't complete, which made me feel bad about it.

Realizing this felt like a slap to the face.

I remember I chose to reply to a bunch of emails from my clients rather than redesign a new landing page for my business. I chose to set up email sequences for my client's newsletters rather than prepare for the sales pitch that would get me new clients. I chose to listen to a podcast from a creator I've listened to for years rather than learning how to create an app using A.I. with no code that would help me launch my SaaS business.

I chose to stick to tasks I knew the most rather than pushing myself to handle tasks I was less familiar with and considered as hard. It was why I kept feeling left behind from my goals and couldn't make meaningful progress on my projects.

To ensure I wouldn't fall into the same trap twice, I made three mental game checklists to keep myself in check so I would stick to my goals and what's important.

1. What would make today great?

This question is like a word from God. This quick prompt will prevent me from being trapped on a never-ending to-do list that keeps on coming, like my family Whatsapp group notifications. It pushes me to think of one or two meaningful things that would truly make the day great. So I can make peace with other remaining tasks I couldn't finish that day.

Making 30% progress on redesigning my business landing page would make my day great, as it would have a more long-lasting impact on getting me new clients than doing cold DMs.

2. Identify high vs. least resistance tasks

Generally, most people can use the Eisenhower matrix to set priorities. Additionally, I find this 3x3 matrix post by

John Cutler

interesting.

However, identifying high vs. least resistance tasks works well for me. I think you know this very well. We resist some tasks so much as if encountering a big boss in a dungeon. As a result, we keep postponing work on that particular task that we consider as hard. Instead, subconsciously, we shift to the least resistant one as a coping mechanism. We reply to emails, attend meetings, and answer Slack chats to trick our minds into thinking we are working on important tasks. Eventually, we were left behind the target and couldn't fulfill our scheduled goals.

Analyzing and improving my sales pitch is harder than continuing to do it without making progress in getting more new clients. It requires a huge mental effort to sit down and dedicate time to understanding where I went wrong and where I could improve.

3. Do hard tasks when you feel most energized

Once I know the highest resistance task, it will be easier to tackle if I set a particular time when I feel most energized: in the morning after a workout with caffeine intake. Then I’ll be ready to face it hard on!

The most energized state can vary for everyone, so manage your energy, find when you feel most productive, and face the hard tasks right on!

Move closer to the goals

By implementing these three mental game checklists, I've found myself making more meaningful progress on my projects and feeling more aligned with my goals. It's not always easy to tackle the high-resistance tasks, but the sense of accomplishment when I do is unparalleled.

Earlier this week, I worked for 3 hours to analyze and improve my sales pitch as my "make today great" task. Knowing it as a high-resistance task, I scheduled it for my peak energy time right after my morning workout and coffee. I crafted a compelling pitch and sent it off to some career coaches I wanted to work with.

My number one rule is that every time I find myself reflexively adding tasks to my list or avoiding that big, scary project, I take a step back and ask myself:

"Am I choosing this task because it's easy or because it's important?"

In the end, true productivity isn't measured by the number of tasks I complete but by the impact of my work. By facing my resistance head-on and prioritizing what truly matters, I can make strides toward my goals and find fulfillment in my daily accomplishments.

P.S. I have made a peace with myself that a day should no longer than 24 hours.

Thanks

clare chai

, Becky Isjwara, and

Harrison Moore

for thoughtful feedbacks to make me prioritize and publish this story!

Life Update

• 🔊 Podcast binge-ing: 10 AI Business Ideas From The Queen of AI ft. Sarah Guo.

• 💎 My favorite quote of the week: “The worst thing someone can do is not even attempt the thing they wish for. The second worst is to attempt it half-heartedly."

• 📚 Books I'm reading: 40% of Genghis Khan and the Making of the Modern World. I'm super invested with the book at the moment. Real world, move away!