Sleep and Productivity Habits of a Startup CEO

Question: “How do CEOs who sleep for only 4-5 hours daily manage to function and run multi-million dollar companies?”

I am currently on my 37th hour of being awake and my ability to function on 4-5 hours of sleep is (perhaps ironically) attributable to meticulous understanding of my body’s rhythm. More specifically, my brain’s rhythm. People tend to categorize themselves as “morning people” or “night people,” but when you only sleep 4 hours a night, the two categories lose meaning. Every night eventually becomes morning, and every morning eventually becomes night. And I’m working all the while.

  • Categorize Tasks

Early on, I discovered that the types of tasks I do on a daily basis could be grouped by category.

  • There are tasks that involve correspondence: email and phone calls.
  • There are administrative and operational tasks: reviewing financials and forecasts, putting together board decks, drafting and negotiating contracts.
  • There are collaborative tasks: team meetings, team-building exercises, strategy sessions, providing feedback.
  • There are also solitary creative tasks: drafting blog entries, coming up with new ideas and concepts, exploring some inspiration that may have struck, crafting plans for the future.
  • Finally, and just as important as anything, there are tasks that I do simply because I want to and, in my mind, deserve to do. I call this “Robbie Time.” This is when I sit on the couch and binge-watch NOVA. Or Ted talks. Or turn off the lights and listen to This American Life … you get the point.

Once you have grouped and categorized your own task-types, the question becomes two-fold: (a) how much time should you spend on each category, and (b) when will you brain best perform each type of task?

  • Create Your Schedule

There are people who exercise first thing in the morning and can’t fathom exercising at any other time. What I’m suggesting is really no different.

I wake up each day between 8:00am – 8:30am and, like many, I’m not sharp until about 11:00am. Rather than waste those hours, I can be productive on mindless tasks: emails and phone calls. On the other hand, after midnight, I am my sharpest and can spend the midnight+ hours on solitary tasks that require creativity. Here is the schedule that I have developed:

8:30 – 11:00am (“Daily Correspondence”): I think of these hours as my morning rush. I typically go straight from bed to my computer and handle phone calls, emails and, in general, time-sensitive but low-level items. It’s a hectic few hours (and the worst of my day), but this period of time allows me to “clear my plate” of timely housekeeping items and ensure that everyone in the Company is able to move forward that particular day.

In order to stay focused on “clearing my plate,” I typically perform my Daily Correspondence from home.

11:30am – 2:30pm (“Team Collaboration”): By this point, our employees have had their coffees and are hitting their groove. So am I. I head into the office and hold meetings, strategy sessions.. etc. My focus is good, having dealt with all emails earlier. During these hours, I am able to turn my phone off and collaborate with 100% attention.

2:30pm – 5:00pm (“Administrative/Operational Time”): While the rest of the team is working on further developing whatever we talked about from 11:30am-2:30pm, I use the lull to handle contracts, board correspondence — the painful-but-important tasks where every detail counts. My brain is still sharp at this time — able to focus on the task at hand — but not sharp enough that it is coming up with any new or exciting ideas. It’s the perfect time for me to focus on administrative things.

5pm – 8pm (“Creativity Lite”) or (“Daily Correspondence Pt. 2”): Having survived the day, I can usually turn to light, enjoyable creative thought for a few hours. I can write a blog post (or this book-like Quora answer, for e.g.), allow my mind to wander and explore the surface of some ideas I may have…I whet my appetite and plan for the activities that lie ahead later that evening.

Depending on the day, I may, instead, need these three hours to catch up on correspondence from the day.

8:00pm – 11:00pm: ROBBIE TIME!!!!

11:00pm – ?? (“Creative Exploration”): With the rest of the world sleeps, I begin to get my second wind. Starting around 11:00pm, I become serious about creativity. It may seem purely self-indulgent, but our business grows the most during these hours. Most people look forward to sleep; I look forward to these hours when I am overcome by new ideas, the desire to explore, to learn, to investigate. I am also free to send emails without the stress of immediate, poorly-thought-out responses. Eventually, I go to sleep, feeling satisfied and excited to share my ideas the following day.

The Weekend: During the weekend, I avoid checking my email and spend all my time split between “Creative Exploration,” “Robbie Time” and sleep. I relax, I sleep a lot, I indulge … I pretend to be a normal human being.

  • Caveats

Email: Due to the way I group my activities, I will miss some emails or be slow to respond to some. I am okay with that. If you couldn’t tell already, I am of the firm opinion that email is a horrible way to communicate.

Exercise: You may notice I don’t have time allotted in my schedule to go to the gym (and I’m not currently motivated to make the time for it), but I do conduct about 50% of my one-on-one meetings while walking out and about the neighborhood where our office is located, and that will just have to do for now.

Robbie Friedman
About the author: 

Robbie Friedman is the Chief Executive Officer of ViewABill, a cloud-based web- and mobile-application that provides real-time data on service providers’ billable activity. Prior to his CEO role, Mr. Friedman held several leadership roles in private practice and corporate law, and he has his JD from University of Michigan Law School.  Follow Robbie on Twitter.