30-Day Challenge: How to Build a Morning Routine

Dudefluencer: Build a morning routine

I insisted 2020 was the year of the 30-day challenge because I knew that I needed that extra motivation to grow as a person. I wrote out my list; I planned ahead. Each new habit was going to build itself into the next I told myself. So in January, I passed the 30-day meditation challenge, and my goal for February was to build a morning routine.

In my head, everything was laid out: meditation when I first woke up, then a round of exercise, and maybe some reading or writing for 30 minutes.

And I failed.

I didn’t even complete one morning routine for the entire month of February.

So instead of getting back into the groove of waking up early and exercising, my 30-day challenge turned into something more: a way for me to accept failure and use that as motivation for future success. Here are three lessons from building a morning routine that I learned along the way.

Early mornings

Dudefluencer: Morning Coffee

My childhood Saturday morning routine began at 5:30 A.M. I’d be awake before anyone else in the house, so I needed to be sneaky. I turned my television on, muted the sound, and drifted away to whatever channel played morning cartoons.

As I grew older, I woke up two hours early for high school, did all of my weekend chores at the crack of dawn, and never got out of bed later than 7 A.M. on the weekends. For all intents and purposes, I was a morning person.

So it made sense that I chose a career that forced me to wake up at 5:15 A.M. every day and teach my first class before 7:30. Those early mornings were one of the better perks of being a teacher, I always felt like I accomplished so much in those two hours between my alarm clock chirping and first class bell dinging. There was no reason for me to build a morning routine because one was pre-designed for me.

Once I left education, something changed. I slept in later. I stopped being productive in the morning. Technically, it was impossible to start a morning routine because I didn’t wake up until the afternoon.

That’s why I was so excited for February to get back into a rhythm. Besides, if I wanted to be a successful entrepreneur, I knew that I should get up early. Starbucks president Michelle Gaas wakes up at 4:30 A.M.; Apple CEO Tim Cook starts even earlier at 3:45 A.M. 

Author Thomas Corley studied 177 self-made millionaires, and “found that nearly 50% of them woke up at least three hours before their workday actually began.” This allows successful people to work through their sleep inertia and be in their groove by the time they start work.

Knowing this, I went into February confident that I could take the success of January and continue onwards. But sometimes your 30-day challenges don’t go according to plan.

Lesson 1: The Importance of Structure

I’m a structure kind-of guy. I need to know what’s going to happen throughout the day, so having a set schedule helps a lot. Research tells us that routines provide a wide variety of benefits, including helping alleviate the symptoms of ADHD, bipolar disorder, and insomnia. For me, routine and structure aided with my anxiety.

I never made the correlation between structure and my anxiety until I read an article from Mariana Plata. Her career transition was similar to mine: Plata moved from a traditional 9-5 gig to the life of a freelancer. She found joy in binge-watching television shows and setting her own schedule until she fell into what she describes the “Procrastination Vortex.” Plata says that after a few weeks, she noticed changes in her behavior: “One in which I was quickly losing contact with myself, my passions, and motivations.” I’ve been feeling the same way lately.

What I hoped to achieve by building a morning routine was re-introduce the structure that served me so well as an educator.

There was one issue: I wasn’t ready to get into a morning routine.

On February 1st, still lagging and sick after our trip to Buffalo, I slept in until 9:30 A.M. Not a great start to the month. As I continued to feel ill, I couldn’t muster the strength to get up early. Rachel eventually poked me in the middle of the week. “Garrett, aren’t you supposed to be starting your morning routine?” I still hadn’t made any progress.

Calculating my scorecard, in the first week of February, I had gotten up before 9 A.M. twice, meditated three times, and exercised once. And by exercise, I mean I did a 45-second plank.


The rest of the month wasn’t much better. Part of that was because I never gave myself a formal structure. I assumed I’d be able to get out of bed, get right into my routine. I learned too late that for me to be successful in building a morning routine, I needed to formalize it and stick with it. That meant setting my alarm for the same time every morning, getting everything I needed for the day ready the night before, and actually holding myself accountable with others.

As I take a look back through February, I recognize that I didn’t formally succeed in building the morning routine I planned out in my head, I did start to unknowingly build patterns into my mornings. For example, in the past couple of weeks, I started waking up at 7:00 A.M. every morning to have breakfast with Rachel. It’s one of the highlights of my day knowing that I get to start off next to my wife.

Because I am a child.

On days that we go into work together, I’ve taken up reading in the car. I started because I couldn’t find the willpower to finish Willpower (#irony). Still, I quickly realized that those 45 minutes in the morning were the perfect time for me to put my phone away and read. Rachel listened to her Oprah podcast, and I focused on my book.

Dudefluencer: Cat's and Writing

For non-workdays, I’d finish breakfast and write for a couple of hours until it was time to take our dog out for her morning walk around 10 A.M.

I didn’t realize it at the time, but I started building a morning routine again. Not the one I planned on, but the one I needed.

Advice for structuring a morning routine:

  1. Keep it simple: If getting up early is going to be difficult for you, then don’t add a new exercise routine to the schedule. Focus on one new task, and repeat it the morning after morning until it becomes second-nature for you to do it. Then add something new to your morning routine.
  2. Write it down: By not formalizing my morning routine, it required me to make a choice every single morning. As I found out from Willpower, making those decisions affected how much energy I had available for other tasks. If I were to have scheduled my morning routine, that would have been one less choice to make in the morning, making it easier for me to wake up and get right into it.
  3. Find an accountability partner: Sometimes, when building a morning routine, scheduling your activities isn’t enough. That’s why if you have roommates or friends, it’s essential to ask them to help you get started in those first few weeks. This way, you have someone else to motivate you until your body begins to learn healthier habits.

Lesson Two: Make Your Mornings Feel Special

After I quit my job and struggled to find a new one, there was a part of me that felt let down. Like I had become a failure, or that I wasn’t as good as I thought I was. What I didn’t comprehend was how those feelings manifested into a cycle of depression and loneliness that led me to struggle to build a morning routine.

A 2017 study explored the relationship between loneliness and depression, and identified that “feelings of loneliness predicted the development of MDD (Major Depressive Disorder).” No longer have a group of peers, or even students around me caused a collapse of my social circle, thus leading me into a depression. Said depression then left me lethargic, melancholy and struggling to wake up in the morning.

As I said above, I arrived to work a few hours early every day and accomplished most of my work while the halls were quiet and the classrooms empty. During one of my earliest therapy appointments, the doctor gave me a Myers-Briggs test because we were going to try and analyze some of my behaviors. After grading my test, my therapist looked at me, confused.

“Garrett, you scored really high on the extrovert scale. Based on how you describe yourself, I didn’t think you’d be such an extrovert.” It was true, though. I love being around people; I gain energy from being around people. That’s why teaching worked for me. For eight hours a day, I’d be surrounded by people and get to release all of that “entertainer extrovert energy.” Of course, it’s much harder to get work done while you’re trying to socialize all of the time.

But what happens when you’re an extrovert, and you spend too much time by yourself? Well, you become understimulated and are left alone with your thoughts. There’s nothing wrong with that in small bursts. In fact, it’s necessary for growth as described by Kathryn Rose: “It can be very easy to lose touch with your inner self when you’re constantly surrounded by people.” But for those of us who are energized by other people, situations like Plata’s where you find yourself not taking care of yourself like you should because there’s no schedule to attend to.

Because I started Dudefluencer by myself, my work-life didn’t revolve around me being around other people. In fact, all of my time became introvert time. While I tried to focus on my work, I couldn’t help but feel alone and lost. I’d continuously flip through the tabs on my browser, avoiding typing my next sentence. Why would I want to develop a morning routine based on taking introvert time for myself if all day, I was already alone?

Dudefluencer: Lonely Mornings

Too much extrovert time can cause you to burnout by spending too many mental and emotional resources on pleasing others. Too much introvert time can cause feelings of loneliness and depression. While teaching, too much extrovert time caused me to build a successful morning routine. As a new business owner, I tried keeping the same routine while not rebuilding my extrovert time.

That’s why if you’re going to build a morning routine, you should also think about it will affect the rest of your day. One of my big mistakes for February was not creating some extrovert time later into my day so that the introvert time I desired in the morning felt special (and needed). Because of that, my morning routine became no different than the rest of the time I spent all day.

I noticed that once I scheduled time with friends or co-workers, my energy in the morning grew. I made introvert time for myself because I needed it. It’s weird to say that being lonely was one of the reasons why I struggled to build a morning routine, but it was.

Lesson Three: Accept Failure

Standing on the top turnbuckle, professional wrestler Drew McIntyre (real name Andrew Galloway) points his fingers at the massive WrestleMania sign atop Minute Maid Park. McIntyre had just won the Royal Rumble, which means in a couple of weeks, he will main event World Wrestling Entertainment’s biggest show of the year against Heavyweight Champion Brock Lesnar.

After years of hard work, McIntyre has reached the top of professional wrestling. But he wouldn’t be in this spot if not for his failure.

Signed at 21 years of age in 200, McIntyre was chosen by WWE owner Vince McMahon as the chosen one, only to flop in front of live crowds and be out of the company by 2014 saddled with the gimmick of a failed Scottish rockstar. After his release, McIntyre faced a dilemma. “This is the one thing I know, I genuinely believe I can make something in this business, make myself something in this business. I believe I can make a difference. It’s time to put up or shut up.”

For the next three years, McIntyre rumbled through the independent wrestling scene, re-inventing himself as the Scottish Psychopath and running roughshod against all opponents. Then in 2017, the Chosen One returned to the WWE, a bit older and far wiser. McIntyre returned as almost a new man, and armed with the lessons from his failure, climbed back to the top of the mountain where he’s a beloved babyface for millions of professional wrestling fans.

McIntyre never gave up on his dream and willed himself back to the main event of the grandest stage of them all.

I can’t write a piece about building a morning routine without writing about failure. By all statistical categories, I failed my 30-day morning routine challenge. Even today, the second to last day of February, I still haven’t nailed down a reliable schedule.

And February was one of my easier 30-day challenges.

So if I’m going to be successful through the rest of the year, I must learn to accept failure. So instead of beating myself up over not building a morning routine, I’ve instead focused on where I’ve succeeded.

I have found a couple of morning activities that are really important to me: breakfast with my wife, and reading in the car. Those two combined make for an excellent start to building a new morning routine. I’ve also made it a point to reach out to friends more often that way, my introvert time feels special (and sometimes needed). And most importantly, I’ve begun to formalize my 30-day challenge plans for March.

Fitness instructor Amanda Vogel writes in Fitness Journal, “Give them (clients) a heads-up that it’s one glitch in the fitness journey, not the stop point. When we address the possibility of a significant setback with new and existing clients, we can help them leverage failure to eventually excel.” Vogel continues to argue that failure is critical to our success, and for me, not completing my second 30-day challenge might be the push I need to work even harder throughout 2020.


Building the perfect morning routine was far more complicated than I thought it would be. But by not succeeding this month, I formulated a plan for me to be successful throughout the rest of the year. Onto day number two of March’s 30-day challenge.

To follow my 30-day challenge journey, make sure to follow us on Facebook and Twitter!

If you enjoyed this, be sure to check out some of my other pieces here on Dudefluencer:

Why 2020 Will Be The Year Of The 30-Day Challenge
5 Steps To Building Healthy Habits
3 Lessons From My 30-Day Meditation Challenge

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7 Responses

  1. This is great. I definitely struggle with getting out of bed early. I’ve been trying to do the Morning Pages, but it’s hard. I have depression and, even though I’m being treated for it, I still struggle with being tired all the time. So I’m accepting that I can’t get myself up every single day, but if I can do it some of the time that’s a plus.

    1. I’m sorry to hear about your depression. I suffer from depression as well and completely empathize with the difficulty of waking up in the morning. Taking small steps is always a better way to build a habit than trying to go all-in right away. I wish you the best of luck and you can always reach out if you’re in need of a pick-me-up.

  2. I attempted and keep trying to attempt the waking up 3 hours early. It has yet to work for me. I’m sure working from home where my office is only a few feet away from my bed is not helping. I took the Meyers Briggs test too and got Extrovert which was a surprise to most since I do spend quite a bit of time alone.

  3. I keep trying to get up 3 hours early in the mornings because of an article I read in December, and it still hasn’t happened. I’m sure working from home with my desk only a few feet away from my bed is not exactly helping either. I took the Meyers Briggs test too and it was surprising to some that I got extrovert also.

    1. I totally get it. I think part of my struggle to wake up early in the morning is because I work from home, so I don’t need to spend time in the morning getting ready to meet people or drive anywhere. Maybe find an activity that you really love and schedule it for the morning?