My Mini Experiment on Hacking Productivity

by using Pomodoro and the Productivity Planner

Chip Dong Lim
5 min readJul 26, 2016
The two tools I used to keep myself to be more efficient and productive over the past week.

When I left my office around 7:30pm one day a few months back, I had a different feeling—it was one of the few rare occasions I saw the sunset. I realized something was wrong.

I am a true believer that in order to get great design work done, I need to continuously push myself and work long hours, to the extreme that there was this one time I was sleeping on the couch in school, only to wake up to a class of design juniors the next morning. I was still a design student at the University of Washington back then.

Fast forward to a year later since I graduated, my working pattern did not seem to change much. Until about a week ago after I finished reading Rework by Jason Fried, I know this way of working is unsustainable and unhealthy in the long term, and I need to do something to balance it out.

“Our culture celebrates the idea of the workaholic. We hear about people burning the midnight oil. They pull all-nighters and sleep at the office. It’s considered a badge of honor to kill yourself over a project. No amount of work is too much work.

Not only is this workaholism unnecessary, it’s stupid. Working more doesn’t mean you care more or get more done. It just means you work more.”

—Jason Fried, founder & CEO of Basecamp

Jason James from We Are Mammoth also wrote this awesome article. Here’s a similar statement he put out:

“LONG HOURS ≠ MORE PRODUCTIVITY OR BETTER WORK.”

My Attempt to Be More Productive

I came across the Pomodoro Technique via my colleague Vipul, and The Five Minute Journal via Alex’s Youtube video The Truth about the 4-Hour Work Week. I combined both techniques together. The result? I got more work done in the office and stay motivated over the past week.

In short,

  • Pomodoro: Uses a timer to break down work into intervals (thus smaller chunks), traditionally 25 minutes in length, each separated by a 5-minute break.
  • Productivity Planner: Limits a maximum of three to five tasks on a daily basis. The most critical, important task of the day has to be accomplished first, with secondary and additional tasks later.

1.

For the Pomodoro technique, I am using this iOS app called Pomodoro One. It’s a simple application that serves as a 25-minute count-down timer and allows you to customise the default Pomodoro time and break time.

The Productivity Planner helps me to beat procrastination and get more productive.

2.

I am using the Productivity Planner to plan out my day, starting with the most important task to be done and additional tasks, followed by recording my target and an actual number of sprints, and evaluating how productive I am by the end of the day before I leave work.

You can grab the Productivity Planner here, or get the Quick Start guide PDF here for free.

Tim Ferriss, the author of The 4-Hour Workweek recently had a public chat at Googleplex, and shared about his morning journal ritual in the latest podcast #175: How to Cage the Monkey Mind:

“The Five Minute Journal is created by a reader of The 4-Hour Workweek. The concept of the lifestyle design is that you take two and a half minute or so in the morning and then again at night: One is effectively focusing and planning exercises, and there’s also a gratitude component — which I think it’s very critical for those of us who are driven type of achievers. It’s very easy to be constantly focused on the future instead of pausing for a second.

Depression is an obsession of the past and anxiety is the obsession of the future. If you look at achievers, they tend to be very future focus. And as soon as they hit their goal, they don’t have time to celebrate — it’s a small win, this isn’t good enough, it needs to be bigger and better.

That could be very self-destructive, even if you rack up a lot of wins at the same time, the gratitude component is extremely critical. That takes about two and a half minute each day. It also helps to identify your focal point, your priorities so that when it inevitably that 10% of the monkey mind pops up to dance in front of you and distracts you, you can return to that. At the end of the day, I find it incredibly helpful.”

What I Learned

  1. The Pomodoro One app and the Productivity Planner have helped me to be more disciplined and gave me an overview of my work before I start the day. By checking in with my manager, copywriter and other stakeholders, I manage to prioritise, pick up the work where I left of the day before and realign the goals of the day.
  2. I have to admit that I often use up the time I am supposed to take a short break to finish the task, try to run against time, and cut into another Pomodoro cycle. I guess there’s a point when you’re really in the working mode and just couldn’t stop! Perhaps a subtle audio reminder such as “Five minutes left before taking a short break” would really help me in this situation.
  3. I observe that my productivity decreases over time, especially towards the evening — to a point when more coffee also couldn’t be much help.
  4. I feel a bit frustrated when there are interruption of plans and constant back-and-worth revisions happening, which I understand it’s unavoidable and part of the design process. But I think when your mind is framed in this Pomodoro + Planner mode, it happens.

P/S: I managed to finish writing this article in 5 Pomodoro cycles (around 2.5hours). I haven’t been writing for a while so please forgive my grammatical mistakes here and there :)

What are your productivity hacks?

I really appreciate it if you would share your experience by commenting below ⇣ or sending me a tweet on Twitter 🐦. Thanks for hitting the 💚 if you enjoyed this article!

Chip Dong Lim is a designer currently working at KFit. (What is KFit?)
View more of his past design work at
madebychip.com.

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Chip Dong Lim

Design @GrabSG · Interaction Design Alum @UW Seattle · Passionate about #Healthcare · Winner of @AIGAdesign & @UXAwards · http://madebychip.com