How One Entrepreneur Is Hacking Sleep for Success

I get made fun of a lot, because I constantly use the term “Let’s kill two birds with one stone.”

I’m obsessed with efficiency.

One day my watch broke, on the way to get lunch I happened to walk right by a watch repair shop. I stopped in and he said it would be ready in 10 minutes.

I continued my walk to get food and by the time I walked back to my office the watch was fixed and back on my wrist.

For some reason that made me happy.

So yeah…i’m that kind of weird.

What’s this have to do with sleep? Well at the time of writing this article it’s 1:45am Wednesday morning.

I’ve always worked well late at night. All of our bodies are wired a bit different and for me i’ve always performed well late at night. I would say 10pm-2am is my sweet spot. Which has always been tough in a 9–5pm society.

Here’s the thing: You have to find ways to hack your daily routine to best maximize your efficiency.

One of my non-business goals is to workout four to five times per week. However, i’ve never been able to set my alarm 90 minutes early to get a workout in. I’ve tried so many times. Sleep drunkenness (yes thats a term) gets the best of me every single time.

One option would be for me to workout in the middle of the day. It’s something I may try in the future, but currently doesn’t work well with my schedule.

Here is a sample of my daily routine:

7AM: Wake up/Check Emails

It’s something i’ve always done since starting my company. It used to be 6am. Sometimes a major thing happens and you have to pop up right away and handle it. If nothing is pressing, I can hit the snooze for another 20 minutes.

8AM: Shower

I do this every morning. It wakes me up and a lot of great ideas come in the shower. Seriously.

9AM-6PM: Office

Grind & Collab.

7PM-9PM: Nap (Yup, a two-hour nap)

The 7pm-9pm window is reserved for a long…long nap. All kinds of resources will tell you that all you need is a 20 minute cat nap and that if you don’t fall into REM sleep that it doesn’t….blah blah blah.

I’ve done multiple “tests” and the long nap works for me and my unique innate rhythm.

Why is this needed? A) I want to workout most evenings B) I want to be alert during my peak hours.

Why not workout right after I get home? Because I feel mentally and physically spent. I have tried to workout immediately after work, but the workout always seems like its at 60%. I am groggy and not at my best.

So again, I have tested these options and have found a sweet spot of what works for me.

10PM-11PM: Workout

I usually take some pre-workout or drink a sugar-free Red Bull. This will 100% not work for most people as they’d be up until 4–5am. Caffeine effects everybody different. For me, it does its job for the workout and doesn’t linger. I’ve literally went straight to sleep after a Red Bull + workout no problem.

11:30PM-1:30AM: Work

My business partner and employees can back me up here. They get emails in their inboxes at these odd hours. They wake up to their inbox having 3–4 emails from David with time stamps of midnight, 1:10am, 2am, etc. It has become the norm.

But i’m firing at all cylinders! I’m at my peak. Some of my best ideas and long detailed plans/goals for the future have happened in this window.

2AM: Fall asleep


So lets breakdown this odd schedule a bit. First, I live alone and don’t have a wife or kids. This schedule would be near impossible for a family man or woman, or probably even un-reasonable if you live with a significant other.

However, lets get back to my overall point, you have to hack your daily routine around what works for you. This happens a lot with people who work a night-shift. If they want to spend time with family or enjoy the day-time they have to hack their day to make those things possible.

This also isn’t everyday. I adjust when I have plans or a dinner meeting in the evening. Also, this changes quite a bit on the weekends.

You’ve always been told that work is done Monday-Friday 9pm-5pm. You’ve been told that the average daily calorie consumption is 2,000. You’ve heard that you must get 8+ hours of continuous sleep.

We all are so different that its impossible to fit into a one-size-fits all approach.

You’ve never read any article that has said nap 2-hours in the evening on weekdays and crank out some work in the 10pm-2am window. Until now. I thought it was important to stand up for all my fellow night owls.

List your priorities, understand when you are at your peak and hack around that. To use sports as an analogy, if you have an amazing offensive line and one of the best running backs of all-time, don’t throw the ball 90% of the time.

Play to your strengths!

David Brickley is the co-founder and President of STN Digital ( STN Digital is a full-service digital agency with a passion for pushing the limits of creative content.