Deep Work is Hard

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energy refocus

I recently took a one-month sabbatical to refocus my energy both professionally and personally on the heels of closing our Fund II. I had a calendar built of projects to tackle during the 4-week period and was ready to launch into a productive cycle of deep work that day to day schedules rarely allowed time for. However, I quickly realized that my deep work muscles had atrophied significantly in the typically monkey minded environment of emails, meetings, phone calls, and constant information flow. Even without the burden of day to day work biting at my heels, if there were any interruptions such as a lunch with a friend, or a doctors appointment, or a critical board meeting, deep work would be largely destroyed with the travel to, event, and travel from.


“I quickly realized that my deep work muscles had atrophied significantly in the typically monkey minded environment of emails, meetings, phone calls, and constant information flow.


Deep work time would be reduced from 3 hour blocks to maybe 1.5 hours. On days that were pleasantly uninterruped, when I would sit down in the morning to start working through fund strategy, portfolio construction opportunities, or communication planning, my mind would quickly wonder back to my inbox, or to the coffee shop next door, or to a quick phone call I had forgotten to make. It was hard to stay on-task for longer than 1 hour.

In retrospect, this should have been expected. Deep work, as defined by Cal Newport in Deep Work: Rules for Focused Success in a Distracted World is “cognitively demanding” work. It takes thought without strict guidance or prescription. From the book: “Deep work is hard and shallow work is easier and in the absence of clear goals for your job, the visible busyness that surrounds shallow work becomes self-preserving.” Not only this, but deep work has to become a priority and a habit in order to really develop strength. Just the sheer amount of time it takes to conduct deep work makes it a challenge to fit into normal workflows.


“The key to deep work is to define mini-goals so they can be accomplished within the limited period of time blocked out for the work.”


The key to deep work is to define mini-goals so they can be accomplished within the limited period of time blocked out for the work. One of my key challenges was not defining the goal narrowly enough. The goal of develop a communication plan is too ambiguous to make progress on in a few hours. Instead, a goal of “outline quarterly, monthly, and weekly communication needs” is easily accomplishable. Making the task and goals smaller also makes them easier to digest and accomplish. More on this below.


Time Blocks

I scheduled blocks of time to work on my inbox. Since my mind seemed to always go to my inbox, I tried to tackle it before starting projects so it wouldn’t eat up minutes of deep work. My inbox is regularly my worst distraction as I see pop-ups come in and feel compelled to respond. Setting up blocks helped relieve the pressure. For me, this was usually 9am-10am (once I get into the office, get organized and prioritize my checklist), again around 2pm-3pm (during a deep work break), and finally at 8pm+ after the kids go to bed (note: I don’t like this last one as it usually keeps me up too late to get good rest, but is usually necessary to get through all the emails)

Detailed Outlines

I created a more detailed outline of deep work projects. As mentioned above, this was the biggest key to being productive. “Developing a Communication Plan” was too ambiguous. Starting with a blank canvas and a clock on the wall, I wasn’t able to get into a rhythm. As I outlined the process in more detail, smaller steps came in to focus that allowed me to work in smaller time blocks as I marched toward my goals.

smaller time blocks helped me march toward my goals.

mini-tasks

By using a a stopwatch, I was able to create a greater sense of urgency around the deep work projects. If I knew I had to accomplish 3 mini-tasks in 1.5 hours, I knew I had about 30 min per task and would set a stopwatch to notify me that it was time to move to the next step or stop deep work and take a break.

If there was something that was outside of my core skillset, but would take a good deal of time such as formatting a PPT or running data on venture studios, I would outsource. For me this is usually a freelancer from Upwork or an intern that understands the project and goals. This would often supercharge the timeline for the project at hand. Doing this for deep work, unfortunately, is often limited, but when there is a task that fits, it really helps to bring in reinforcements.

Start Writing

For me, writing is the best conduit to go from shallow-work to deep-work. Outlining, adding to it, getting organized and then picking a place to dive deep. It was like a good warm up and is slowly becoming a stronger muscle. It’s getting easier to pick up the pen and start writing.


This really helped me get my deep work muscles going again, and while it will always be easier to shift back into shallow work, my mind has developed a fondness for deep work again that has been missing for a long time. Its akin to being addicted to sugar and then tasting a perfectly cooked beef tenderloin; it takes more time, but is well-worth the effort.


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