A Day in the Life of a CEO & Founder

One of the big lessons I learned in 2021 was that at the end of the day (or the end of my life), all I really want is peace.

I think that’s what most of us are after—happiness, peace, joy. I believe that finding the life hacks, the daily habits and routines, that contribute to your peace is imperative to being a successful (and calm) leader and human. If I can optimize my life (which really means optimizing my time) to adopt activities that help me maintain a state of peace, then I’m all for it! When I am able to have that foundation of peace and joy, then my decisions as a Founder and leader are clearer, more impactful, and more meaningful to me and those around me. My job is to make the best decisions possible for our organization and I strive to make sure my days reflect that by being intentional about who I spend my time with, what activities I’m engaged in, what I read, how I show up, what I do, and how present I am in each moment.

I encourage you to take a look at how you’re spending your days. Find the life hacks that will contribute to your peace, adopt them, and make them non-negotiable.

Here’s what a typical day looks like for me…

A Day in the Life of a CEO

4:30AM

Wake up and immediately drink a glass of water and go outside for a few deep breaths of fresh air (yes, even when it’s -10° and snowing or humid and 95°—the point is to shock the system and move quickly into a different state). Sometimes I even go out barefoot in the snow to really feel alive!

4:40AM

Meditate for 20 minutes. I’ve been practicing Transcendental Meditation for the past 10 years or so.

5:00AM

I grab a cup of coffee, black and usually a seltzer (Waterloo is my go-to), and get settled into my focused journaling, thinking, and planning time.

5:05AM

Journal. I have several different journals I write in each day while drinking my coffee, using the Evernote app. You can find some journal prompts in this post. My journals include:

  1. Life Journal – This is a stream of consciousness where I write about my life, my thoughts, my challenges, my successes, the good, the bad, and the ugly. I also reflect on where I focused my time the day before, where I failed, what went well, and do a quick check-in with myself about how I want to feel today and whether or not I’m being responsible for my peace today. I also write out my priorities for the day.
  2. Gratitude Journal – I write everything I am grateful for, usually 70-100 things that come to mind. I just keep it flowing.
  3. Journal for my Wife – Every day I write something different about her that I am grateful for. I also journal about what she’s doing, how she’s growing, and include photos.
  4. Journal for my Kids – Each child (I have two girls and a boy) has a separate journal and I write something about each of them—something new they learned, a milestone, a moment we shared, etc. I also pull in photos and add to the journal. This is really me recording everything they say and do (which is usually the funniest part!), so that we have a history of their life.

Future Self – I review my future self (go here to create your own), which gets delivered to my inbox every morning.

Emails – I quickly check emails and set the course for the day for my company. I usually send out a few emails touching base with my leadership team, and share any ideas or items that need attention. I also answer any questions they may have so that I don’t create a roadblock for them to get a project done.

6:00AM

Workout for about an hour. I either go for a run, bike ride, or workout via Tonal.

7:15AM

We have a long driveway, so every morning Sarah and I walk the kids to the bus stop. It’s about a 7-minute walk down our driveway, and 5 or so minutes sitting with them at the end of the road, but it’s some of the best 15 minutes of the day. It’s a great time to chat with them about the day ahead, listen to their thoughts, fears, or what they’re excited about. We talk, we’re engaged, we’re moving, we’re outside. I love this time.


Sarah and I walk home together, talking about kids, the day, life… it’s really purposeful time with her too. Typically, that conversation leads into a 10-15 minute conversation back at the house. It’s quiet and wonderful. Sarah makes me a smoothie every day for breakfast, usually some combination of greens, veggies, fruit, and a scoop of Vega protein.

8:15AM

I usually leave for office between 8 and 8:15 depending on the day. I listen to Audible (right now, The Almanack of Naval Ravikant) or sometimes rock out to music and sing loudly! I turn up the music loud enough so I don’t have to hear myself sing. My kids are obsessed with The Comeback by the Zac Brown Band right now, and they got me listening to it too!

8:30AM

Arrive at the office, grab a seltzer, and finish up any emails. I like a clean inbox. Review any meeting or presentation prep for the day ahead. Review and sign anything left on my desk from the night before that may need my signature.

9:00AM

Record an episode for The 200% Life Podcast about the 2022 trends that leaders will need to be aware of and act on in the year ahead.

10:00AM

Call with the CEO of another company to discuss organizational design and how to begin scaling.

11:00AM

Call with the Chairman of the Board and leadership team of another company to discuss moving ahead on a joint venture deal.

11:30PM

This is my free period. I have about an hour and a half most days and I spend that time making phone calls to check in on personal items (for example, finishing some projects at my house), check email, eat lunch (Ezekiel bread topped with a spicy black bean burger, tomato, avocado, and a side of seltzer water), and then meditate for 20 minutes before I jump back into another burst of work in the afternoon. I also answer random calls and texts throughout the entire day in little pockets of time between meetings.

1:00PM

Conduct a group coaching and training call for our Project | U participants.

2:00PM

Call with the CEO and Co-Founder of a PropTech company to explore potential collaborations.

2:30PM

Meeting with the head of the international real estate division was canceled. I pop out of my office for a few and go over some items with my Executive Assistant and Chief of Staff and then I grab a seltzer and answer as many emails as I can.

3:00PM

Consultation call with potential future real estate partners.

4:00PM

Call with venture capitalist to discuss the next steps to monetize and bring our SaaS to market.

4:30PM

Quick clean-up of my inbox and head home. On the 15 minute commute, I will call my mom and then my dad. I make it a point to speak with them every day because you just never know when the last day might be.

5:30PM – 6:00PM*

*Depending on the day, I may work until 5:30PM or 6:00PM finishing up calls or responding to emails. This is not the norm and I don’t think it will be long-term, but it is simply the season of business that I’m in right now. My kids are also in activities until about 5:30PM most days, so we all get home right around the same time.

5:30PM

Evening family time begins! We have dinner, play, snuggle, deal with the kids fighting, you know, all that fun stuff! I put my phone in a drawer (85% of the time) so I can be present with my family. I do this until I feel like our “present” time is over, sometimes that’s because the kids have chosen a solo activity or because they’re on their tablets (they have 1 hour a day to use them). During that time, I may jump back into my email or I may not. If we’re engaged in a game, in the hot tub, wrestling, playing hide and seek, then I may not pull back out of my time with them. But I pay attention to the energy and their needs which is the general rhythm of the night for us.

7:45PM

We start the bedtime routine for the kids, which can take anywhere from 30 minutes to 2 hours.

9:00PM

I’m usually asleep by 9. I am a big believer in the power of 7-9 hours of sleep a night and I have optimized my sleep environment to make sure that no matter how many hours I get they are quality hours. Some of my sleep “tools” include Eight Sleep, a fan, a vibrating mattress, and the Whoop app. I like to be purposeful and present when I sleep too!

If you are a Founder, what does a “typical” day look like for you?

Like this post?

Share on Facebook
Share on Twitter
Share on Linkdin
Share on Pinterest

Leave a comment

Search

Recent Posts

GET THE LATEST UPDATES

We won’t flood your inbox. Opt out anytime.