Woes of an Overscheduler

I am an overscheduler.

Since I discovered the default calendar app on my first smartphone in 2011, inputting planned events into time slots has become a favorite pastime. If you ever wanted to know where I was going and when, all you had to do was peek at my phone. The obsession only escalated as productivity apps became more powerful and back-to-back work meetings became commonplace in my life. "I have meetings from 9 am to 11 am, then 12 pm to 3 pm, so I'll work on this project from 11 am to 12 pm after I catch up on emails in the morning. Then I'll finish writing meeting minutes at 3 pm, send it out, and go home." But now that I'm not planning life around meetings, I plan every half-hour increment of my free time with something on my to-do list. In a single day, ambition would have me believe I could wake up at 5 am, get ready, go to the gym, write, rewatch lectures, complete assignments, meal prep, complete a hive inspection, read, practice piano, eat dinner, clean up, shower, and go to sleep by 10:30 pm.

I never stood a chance.

Lately, I've seen the same mistake unfold differently week after week. It's exhausting. I'm neither achieving the work I've planned out nor feeling satisfied with what I've completed. Then, at the end of the day, unhappy with my progress and yearning to turn back time, I soothe my soul by scrolling through Webtoons, Instagram, and Reddit—anything to avoid facing the disappointment in my inability to accomplish what I'd set out to do.

I wonder. How can I intentionally set a productive yet reasonable schedule? What are the barriers between me and success?

Unrealistic Expectations

As much as it displeases me, there are only 24 hours a day, and humans need rest. Back in middle school, I remember reading Twilight by Stephanie Meyer and feeling envious of the vampire Edward Cullen. He didn't need sleep and could spend the quiet hours of the night endlessly reading. I would've traded my humanity for that ability in a heartbeat.

In my reflections, I've noticed two trends in my scheduling pattern. I do not schedule breaks or buffer time between activities, and my estimation of how long it will take to complete a new task is exceptionally poor. What does this look like? Imagine a day planned out from 5 am to 10:30 pm with 1 hour, maybe 1.5 hour, events back-to-back. The night before, I would feel ambitious about tackling the mountain of to-do's looming over me. But by the end of the day, I deleted 75% of the planned events and re-arranged my entire schedule because something inevitably took more time than anticipated. As I reflect on the day and prepare for the next, my overwhelming disappointment drives me to bite off more than I can chew… again.

The cycle I keep repeating stems from my ignorance of the reality of life. Is it possible to work continuously without breaks day after day? Yes. Is it sustainable? No.

Ali Abdaal once shared a story from his time as a doctor. The clinic was busy, and no matter how quickly he worked, the patients in the waiting room remained stubbornly full. Anxious about the never-dwindling line, he sought advice from his mentor, who simply stated:

"The waiting room is always full."

As a metaphor for life, I realize the list of tasks, to-dos, and projects is endless. But time is finite. By trying to fit as much as possible into a single day, I set myself up for failure and disappointment.

So, what is the daily limit for scheduling tasks? It sounds obvious, but it should be primarily driven by the time necessary to allot each task. By default, calendar apps set timed events for an hour, and meetings are usually scheduled for an hour. So, who says an hour isn't enough time to complete a task? The world seems to operate by the hour!

This thought process and the planning fallacy, a human tendency to underestimate the time needed to complete a task, are key contributors to my overpacked schedule. There are many potential techniques to overcome this mistake that I won't get into. Personally, I plan to start tracking time spent completing specific tasks to use as estimates for the future.

Prioritizing Unimportant Tasks

Without clear prioritization, it's easy to fall into the soothing lull of false productivity. Not sure what project to work on? Clear your inbox! Get that sweet dopamine hit from checking something off. Plus, it was quick! You feel great about achieving Inbox Zero. The rest of the day looks similar - you tackle small tasks as they pop up. A colleague needs your input on something - you immediately jump on it. Another email comes through from someone flagging an issue that should be addressed - you start troubleshooting as soon as the notification pings. You're invited to a meeting, but it's unclear what your role is - you attend anyway. You are so busy and productive! But as you lay your head down for the night, you wonder, "What have I accomplished today?"

The answer is nothing.

What you have essentially done is appear to be busy. But in reality, you haven't made meaningful progress towards your projects. How did this happen?

For me, it's a combination of factors. I am congenitally ambitious and believe I'm superhuman. The result is that I perpetually have an overwhelming number of projects I try to tackle simultaneously alongside my day-to-day duties, all of which need to be done. Understandably, my meager attempts to juggle it all result in less than meaningful progress. While I am doing work, I'm not working on anything of substance.

As they say, "If everything is a priority, nothing's a priority." The problem here is focus. Despite living in a world of infinite opportunities, the reality is that you can only choose to pursue some. People have come up with many different rules to live by to manage this. The Eisenhower Matrix is a time management tool that helps you avoid the urgency trap and prioritize non-urgent but important tasks that are often neglected. In the Most Important Task (MIT) method, you simply choose one to three tasks related to your goals to commit to that day. The Agile prioritization method considers priority and sequence to drive task order. The right rule to use varies depending on the scenario. For me, the more difficult decision is deciding on my priorities. The most helpful tool I've used to tackle this is conducting a Commitment Inventory, a method to determine what should and should not be on your to-do list. I recommend reviewing this article by Jackie Ashton for a detailed step-by-step if this also sounds like you.

However, the most crucial part of staying true to the course in your heart is routinely reflecting on how you truly feel about a topic. After some time of pursuit, you may realize certain goals are less important to you than you initially thought. Your perspective may have changed. Your life circumstances may have shifted. Regardless of the reason, if you feel some discourse between your feelings and actions, don't be afraid to say, "This is no longer something I want," and change course accordingly.

Procrastination Station

Have you ever put off a task day after day, which turns into weeks, then months, even years? In school and work, procrastination leads to last-minute scrambling and subpar performance. In personal projects, procrastination can last for an eternity without a system of accountability. Why do we procrastinate? For me, it's a combination of perfectionism, fear, and anxiety.

I am most frequently struck by the grips of procrastination when facing a project or task I've never done before. The fear of the unknown that lies ahead sometimes makes the challenge feel insurmountable. Imagine staring up a snowcapped mountain from the very bottom, only to see shrouds of clouds masking the trail to your final destination. Where does the journey end? What trials and tribulations lie in between? What if I don't make it? Where do I even start?

The thing about procrastination is that it's a double-edged sword. It hurts you in both the short term and the long term. Your long-term goals come screeching to a halt as you procrastinate every day. In the short term, your self-esteem takes a hit as you beat yourself up over your chronic procrastination. So how do you overcome it?

First, recognize your signs of procrastination and return your focus. Second, do it. If there's anything I've learned over the years, it's that you'll never be 100% ready for anything. The perfect plan doesn't exist. Mistakes are an inevitable part of life. The only surefire path to progress is taking that first step. Whatever the challenge that lies ahead, just do it. Two steps forward and one step back is still one step forward. By slowly chipping away at the challenge, the fog starts to clear, and the mountaintop becomes visible. The next thing you know, your momentum and confidence begin to snowball, and when you look back, you find you're much closer to the peak than when you started.

Anything is possible with a combination of mindfulness and embodying an action-oriented attitude.

As Shia LaBeouf eloquently stated in 2015, "JUST DO IT!!!"

References

1. Planning fallacy. Wikipedia. Updated July 18, 2024. Accessed August 7, 2024. https://en.m.wikipedia.org/wiki/Planning_fallacy
2. Greene J. Why we're bad at estimating time (and what to do about it). Zapier. Published February 25, 2019. Accessed August 7, 2024. https://zapier.com/blog/how-to-estimate-time/
3. Greene J. How to prioritize tasks: 10 task prioritization techniques. Zapier. Published October 2, 2023. Accessed August 7, 2024. https://zapier.com/blog/how-to-prioritize/
4. Ashton J. The commitment inventory. Todoist. Accessed August 7, 2024. https://todoist.com/productivity-methods/commitment-inventory
5. Why you put things off until the last minute. Mass General Brigham McLean Hospital. Updated August 5, 2024. Accessed August 7, 2024. https://www.mcleanhospital.org/essential/procrastination
6. Snowball method: a productivity booster. Lark. Published December 16, 2023. Accessed August 7, 2024. https://www.larksuite.com/en_us/topics/productivity-glossary/snowball-method
7. MotivaShian. Shia LaBeouf "just do it" motivational speech (original video by LaBeouf, Ronkko & Turner). YouTube. Published August 31, 2015. Accessed August 8, 2024. https://www.youtube.com/watch?v=ZXsQAXx_ao0