How to fix your relationship with time?

During my preparation for the two career design workshops, I took some time to review my ten categories of life:

I started with the areas that I’ve been resisting.

Why go to resistance? It’s because resistance often points to critical issues that need attention yet lack attendance. The sooner you can acknowledge the problem and accept your past behaviors, the easier it is to move forward.

With this awareness, I took a hard look and identified the area I had been avoiding for a long time: my relationship with time.

Even though I love optimizing and have a decent throughput, I have a love-hate relationship with time. My relationship with time is manifested in my struggle with the calendar. Sometimes I would miss a meeting because I “forgot” to check the calendar.

It took me a while to pinpoint my resistance against the calendar. Initially, I couldn’t understand why logging things on the calendar would make me anxious. After a deeper reflection, I was able to trace this resistance back to my senior year of high school — the dark age of my life.

During my senior year of high school, I was cluelessly putting together the college admission materials and trying to stay afloat of my local school work. I didn’t have a counselor or much guidance, so I was experimenting with all kinds of random tips on the Internet. To find more time, I logged everything on my calendar. Being a PM certainly did not help.

As a result, I developed an extremely stressful relationship with the calendar subconsciously. The calendar was a living proof of my constant anxiety and fear. And I resisted putting everything in my calendar again.


Working on my relationship with time

Now that I identified the root of my anxiety, I was able to tell myself a different story. Since there are only 24 hours in a day, I told myself to collect data on how I spent time, rather than relying on my biased estimation:

RescueTime Tracker
  1. First, I began to track my time with RescueTime. In addition to the digital tracker, I tracked my workout, meditation, and sleep schedule on paper.
  2. Second, I began to plan my schedule with more buffer. For example, after running the workshop, I would have a 30-min lie-down time to recover from the 60-min dopamine rush.
  3. Third, I began to schedule creativity time to do topic deep dives, create guides, and write my book. In addition to my creative work, I made sure that I would spend quality time with Chris every day.
  4. Last but not least, I began to put positive events in my calendar to fight the negative association.

Life experiment: 1000 creative hours

One of the experiments I’m running this year is 1,000 creative hours. Over 261 workdays in a year, 1,000 hours come down to 4 hours of creative work every day. In an eight-hour workday, this essentially means that 50% of my work has to be creative. I have managed to reach this threshold, and I’m excited to share more lessons from this experiment with you after I hit the milestone.


If you want to improve your relationship with time, start today by spending two weeks tracking everything. Then, you can find the plan that best fits your lifestyle.