The CEO Morning Routine That Carried Me Through My Hardest Year

Why I Needed a Morning Routine

In 2014, I found myself going through a time of tremendous change and stress. I was the CEO of a company that had recently raised our Series A. We had ambitious plans for the year, and I needed to show up with a clear head for the work at hand.

But at home, I was facing the loss of a child, a complicated divorce, and my first few months as a single-parent.

Life was overwhelming to say the least.

Up until that point, I was not particularly intentional about my mornings. I might wake up, check email, hit the gym (maybe), then head to the office.

With the challenges I was facing that year, I realized I was going to need to get a lot more intentional about preparing myself for the day.

The CEO morning routine I crafted that year has served me well ever since.

In my coaching work, I have been surprised to find how few leaders have an intentional approach to their morning. We often explore this in coaching sessions as part of a broader effort to bring support around the leader in her role and life.

I decided to share my own routine here, along with the logic behind each step and the results I have experienced over the years.

My 5-Step CEO Morning Routine

Total time: roughly 1 to 1.5 hours.

Let me walk through each step.

Step 1: Meditation (10 Minutes)

Meditation has been big for me. I have struggled with depression since my teenage years, and I have found meditation to be the single most powerful antidote to allowing depression to drag my whole day down.

When I first started meditating, I assumed like most people that it was about quieting my brain and finding some elusive state of bliss.

Over time, I have learned that meditation is more about:

1. Separating my sense of self from my thoughts and feelings
2. Finding some space between stimuli and response

Both of these results are gifts on the hard days.

Knowing there is a me here who is not my thoughts and feelings allows me to witness my moods like I might witness the weather.

I do not get mad at myself when it is raining outside. Why then would I get frustrated with myself when I am having a depressive or anxious day?

That is just the way my internal weather is showing up that day.

Meditation helps me note the mood or thought I am having and see that I am ok apart from it.

This noting creates the separation between stimulus and response.

As children, we have no separation. Something happens and we immediately react. As adults, our brains are more developed, and we have the opportunity to create space between an event and our chosen response.

As a coach, I often see leaders enslaved to their moods and the swings of their companies. When they feel motivated, they judge themselves as good. When they feel anxious or sad, they believe they must fix the mood or they are failing.

Their sense of well-being is deeply tied to the recent performance of the business, quickly damaged by unexpected bad news.

Meditation offers some space here. And such space is a prerequisite of great leadership.

I have found guided meditation from services like Headspace and Waking Up to be helpful, but sitting in silence for 10-minutes and simply paying attention to the feeling of your breath is a great place to start.

Step 2: The Worry Board, a Simple Worry Management Technique

After I have completed a short meditation, I open up what I call my Worry Board. This is goofy but I promise extremely helpful.

There is quite a bit of data out there that shows if we schedule time to worry then our brain will actually be less anxious the remainder of the day. It is almost as if our brain thinks "Oh, I don't need to worry about this now; there's time on the calendar to worry later."

A 2006 study found that participants who were encouraged to postpone their worry to a certain window in the day experienced less worry and fewer psychosomatic symptoms of worry.

I read that study in 2014 and began setting aside a few minutes each morning to worry. I would simply write down in my journal the things that were causing me anxiety that morning.

What I quickly realized was that big worries and small worries were taking up the same kind of space in my head.

Whether a parent had a health scare or I had a minor issue at the office, I simply felt worried.

That observation led me to start categorizing my worries each morning. It proved extremely helpful.

How to Set Up Your Own Worry Board

I use a Trello board (you can do this on paper if you prefer) to bucket my worries into these categories, from most minor to most severe:

• Quick fix: things annoying me that I know will be quickly resolved with a bit of effort
• Everyday work: stuff that is just part of the job (most of my worries land here)
• Personal financial issue: money stuff, intentionally placed toward the minor end to remind myself the items below are a much bigger deal
• Relationships: worries about my connection with the people in my life, because if life is about connection and love these deserve real attention
• Health of self or loved one: the big stuff
• Significant loss or death: the biggest stuff

I also added two resolution columns:

• Resolved: items I have fixed
• Deemed not important: items that turned out not to matter after all

Categorizing my worries really helped me. It allowed me to put small worries in their place.

When I have big worries on the board, like when a loved one has a health issue, it allows me to actually note for myself:

Wow, I have something really big going on right now.

That noting allows me to provide myself some space and grace on the hard days.

As I add items, I often write a brief note to myself ('You got this, you have been through this before.') Or a note on how I plan to resolve the issue.

Moving items to Resolved or Deemed not important has served me enormously over time.

Seeing a long list of resolved items reminds me I have faced many challenges since starting this practice.

This knowledge bolsters me on the hard days.

Seeing the long list of items deemed not important reminds me that most daily anxieties end up being not all that important in the long run.

Step 3: The Gratitude Board

With some dedicated worry time out of the way, I find it helpful to turn next to gratitude.

I use a second Trello board for this, but use whatever medium works for you.

I divide the major areas of my life into columns. Right now, mine read:

• Adventurer
• Learner
• Husband
• Papa
• Friend
• Athlete
• Artist
• Coach
• Entrepreneur

Under each column, I add a card for something in that area that I am really grateful for.

Just seeing the columns reminds me each morning of the many parts of myself and my life.

When I was going through my darkest days in 2014, I found it helpful to ground myself in the knowledge that the loss I was feeling around my child, impacted a part of my life.

The Papa part of my life was in tatters.

But there were other parts of my life, even then, that were healthy and thriving.

That realization was life-giving.

I was not hiding the hard parts. I was acknowledging those and holding space for them. But I was also inviting myself to hold them in context of my broader life.

Reading through the items each morning broadens my awareness to my full life experience.

I may be facing difficulty at work, but if I zoom out I can put that difficulty in the context of my life's bigger story.

For me, that has been a big fucking deal.

This practice also helps me pick my head up and make sure each area of my life is getting attention.

I am reminded that I am not only a father and an entrepreneur. I am also an artist.

This reminder encourages me to hold some space in my day to write or to pick up my guitar.

Holding space for each of the major areas of my life is buoying when one of the areas feels like it is burning to the ground.

Step 4: Journaling for Entrepreneurs (10 Minutes)

After grounding myself in a broader view of my life through a review of my gratitude board, I open my journal.

In my teenage years, I was prone to long, wandering journal entries. Part of me wishes I had a practice like that now, but I do not.

What has been most effective for me as a working adult is the Five Minute Journal format:

• 3 things I am grateful for this morning
• 3 things that would make today a great day
• 1 'I Am' statement, something I would like to embody (such as 'I am grounded and present' or 'I am closely connected to the people I love')

In the evening, or the following morning, I add:

• 3 things that made today great
• 1 thing that would have made today better

Why journaling for entrepreneurs matters: Each of these prompts trains your mind to look for and celebrate the positive, building the resilience that founders need most.

As entrepreneurs, we are prone to ride the positive and negative waves of our companies. But that wave riding inhibits the quality we need most to succeed in our leadership roles: resiliency.

Retraining our brains to notice the positive helps build resiliency and keeps us buoyant on the hard days.

One of my superpowers as a founder is my ability to drive a product and company toward excellence. I can do this because I can zoom in quickly on any area of imperfection. Sometimes I can even see around corners to the improvements that will be needed next. That is a superpower, and one that I see often in founders I coach.

It can also be my kryptonite.

Spending my days steeped in what needs improving can eviscerate my inspiration.

Leaders and teams run on inspiration.

Holding space in the morning and evening to plan for and celebrate the positive has been a powerful counterbalance to my natural perfectionist tendencies.

Journaling also keeps me honest. It allows me to look back over years and realize how far I have come.

I tend to be my own harshest critic. Terribly mean in fact.

Journaling allows me to zoom out, look back, and see the growth that has taken place in my life.

Step 5: Exercise (30-60 Minutes)

The last critical piece of my CEO morning routine is exercise.

A lot has been written about the benefits of morning exercise so I will be brief here. And specific.

In my early twenties, I ran. Running cleared my head but left me weak.

Then came 8 years of Crossfit. Crossfit made me strong and was a brilliant outlet for my anxieties. You must be in the present moment when lifting big weights to exhaustion. But Crossfit beat up my body and proved unsustainable.

I now practice Olympic weightlifting and the Happy Body regimen. I love this practice because it makes my body both strong and flexible. It also builds over time. The focus is not on getting into perfect shape in 90 days. The focus is on being better this month than last for the rest of life.

I now train my body in the same way that I desire to build my businesses and my life.

When I build a business, I want to build a business that is better, stronger, more capable, and more resilient this year than it was last year.

I want to build a life for myself that is richer, fuller, healthier, more impactful, and more me this year than it was last year.

And I want to help my clients do the same.

How to Build Your Own CEO Morning Routine

This practice does not take away all my worries. Nor does it make every day blissful. But it does help to ground me on the hardest days.

It creates space.

It makes me 20% clearer. And that 20% is a big deal.

The specifics of your morning will be unique to you. Most of the power is in the intention and the repetition.

The change comes from training our minds and our bodies that there will be a predictable time in our day when we will receive attention from ourselves, where we can share our worries and hopes openly, and where we can find a buffer from the imposition of the busy, consuming world.

I would invite you to play with whatever routine works for you. And I would love to hear what you discover along the way.

If you are looking for support in building a sustainable leadership practice, coaching can be a helpful place to explore what is working and what is not.

Wherever you are in your life today, wishing you peace and support.

-Matt

Frequently Asked Questions

How long should a CEO morning routine take?

A realistic range is 60 to 90 minutes. The key is not the length but the consistency. Even a 30-minute routine that you do every day will produce more results than a two-hour routine you only manage once a week. Start with one or two practices and build from there.

What if I am not a morning person?

These practices do not have to happen at dawn. The important thing is that they happen before your workday starts, before emails and Slack take over your attention. Some founders do a version of this routine over a long lunch or in the late evening. Find the window that works for your schedule and protect it.

Can journaling really help with founder anxiety?

Yes. Structured journaling, like the Five Minute Journal format, helps train your brain to notice positive patterns instead of fixating on threats. Combined with a worry board practice, it gives your anxieties a designated time and place, which reduces the background noise of anxiety throughout the rest of the day.

Do I need to follow this exact routine?

No. This is a framework, not a prescription. Some founders skip meditation and add breathwork. Others replace the Trello boards with a paper journal. The power is in choosing practices that address your mental, emotional, and physical health, and then doing them consistently.