Why My First Foray Into Deep Work Failed

Toward the end of 2020 I watched a Lex Friedman video on YouTube where he went over his daily routine. I found it fascinating for some reason and was especially interested in what he was calling Deep Work.

The concept seemed like something that would work for me given the need for more focused work time. I was finding myself constantly jumping between screens handling each task in the moment while at the end the week wondering what the hell I actually accomplished.

I took the concepts of dedicated work periods in the video and did a bit of research into this notion of deep work. I discovered that Cal Newport crafted this work methodology back in 2016 in his book aptly called, Deep Work.

We were in the midst of the pandemic, I was parked in front of my computer all day, I had a growing list of to-do items, and I constantly felt like accomplishment and productivity were laughing at me. So, I decided to implement some of these practices.

Keep in mind, I had not read the book at this point so in effect I was just winging it.

What my schedule looked like

I created a new work schedule and established a couple of periods for deep work sessions—one in the morning and one in the afternoon. Here is how I structured my day.

Great! I was ready to go. I set out to adhere to this schedule come hell or high water. I would have significant dedicated time in the morning and afternoon to work on relevant and meaningful tasks.

I reserved the middle of the day for shallow work such as meetings, email, and other tasks that didn’t require significant cognitive commitments. I even implemented a 15 minute Power Nap (PN) at 2pm to serve as a jolt to my productivity for my afternoon deep work session.

What were the results

Unfortunately, this schedule was doomed to fail. I was too prescriptive with my scheduling and used deep work as the sole guiding principle for how my day was structured. While I gained significant benefit from these deep work sessions I also realized that I had set aside too much time during my day for it.

Additionally, my job as CTO requires a high number of meetings and other dynamic commitments. These are the exact opposite of deep work but are necessary at the same time. I continued to shrink or delete deep work time blocks due to these unpredictable conflicts.

After a month or so I was deleting so many deep work blocks that I ended up abandoning the strategy all together.

Lessons learned

There were a number of reasons why this experiment failed but these were probably the biggest.

  • I didn’t read the book
  • I was too prescriptive in my schedule
  • I carved out too much time in my day, especially for a deep work newbie

I found myself drifting back into old habits after my failed experiment. I was scattered across multiple computer screens, spending too much time in email, and not making any sort of headway into large and meaningful work.

After getting a taste of the benefits of deep work, I decided to give it another go with some changes to my approach. The first step was to actually read the book. Seems logical but when you are excited about something that could be beneficial to your daily routine, you tend to jump right in.

I highly recommend taking the time to read the book. If you are like me you won’t be able to put it down and you’ll knock it out in a few days. With knowledge in hand I was in position to effectively implement a new deep work framework.

In future posts I will keep you updated on my journey toward deep work mastery. At the time of this writing it has been less than a month since putting these new techniques into practice, but I’m already seeing much better results.


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