A Unique Methodology to Better Organize The Chaotic Entrepreneurial Schedule

Creating a sense of structure in a hectic world

Jordan Gross
Apr 5, 2019 · 8 min read
Photo by Nathan McBride on Unsplash

One of the number one entrepreneurial struggles, especially first-time entrepreneurs, is maintaining order in an environment in which you create the inputs and outputs.

The courageous leap to entrepreneurship allows you to step outside the traditional norms of mundane society and do something that lights an absolute fire underneath you.

So many people venture into entrepreneurship for the ability to create their own hours and not be held down by the traditional 9–5 society has tried so hard to implement. This may be the main attraction to begin, but very quickly this freedom becomes inefficient.

My Entrepreneurial Beginnings

I made the move to entrepreneurship at the ripe age of 23. I wrote and published a book on a morning routine to overcome stress and anxiety and on how to be the most productive student in the classroom or worker in the office from the moment you walk through the door.

I did so after 4 months in a management position with a prestigious restaurant group, working 6am — 8pm running daily operations.

My first few months as an entrepreneur were glorious compared to the tiresome hours I was accustomed to. I still woke up early because I am a morning person, I messed around for a bit, hit my creative high around midday, created some good content, made some cool connections, developed some cool opportunities, and then messed around some more.

I was going through the motions, but I wasn’t truly

When an aspiring entrepreneur and writer asked me the other week, “What does a typical day in the life look like for you?” I responded with the common entrepreneurial verbiage,

Then it hit me.

This was my problem. I had no remote sense of structure. I went into each day allowing it to lead and control me, rather than me leading and controlling it.

I have never received much definitive advice on entrepreneurial schedules, or maybe I just have not searched hard enough, but because of my revelation I decided to create my own methodology.

The foundation is understanding when in your life you were most successful, most productive, and when you were experiencing peak performance. This will be different for everybody, but this is my analysis and interpretation of how and when I function best, and if you are at all similar to me, use this methodology, and this guide, or at least some variation of it.

High School Establishes Structure

Think back to those high school days. Whether you were top of the class, stud athlete, the awkward chubby kid with glasses and long hair, or a combination of all three (me), your day was predetermined for you. You were required to go to class period after period, switching from one subject to the next for a set amount of time. You had a little time to recuperate between classes, you had set breaks for recovery like lunch, and you even had mandatory physical education (my favorite).

You got in early, left pretty early, then had the rest of the day to either do an extracurricular activity like sports or a club, or you could go home to do homework, and do who knows what until the process repeated the next day.

It was repetitive, it was tedious, it was long, but it was set in stone, and looking back I see all the benefits in the way high school schedules are formulated.

I didn’t so much love it at the time, but I was extremely good at. I went in as a chubby, insecure, quiet kid with glasses and bad teeth, and left as a confident, top 20 student of 450, captain of the varsity soccer and track teams, destined for Northwestern University.

College Challenges Structure with Enhanced Freedom

Going to college tests the waters of how you can control your life with more liberties, more independence, and less formulaic routinized days.

Yes, there are classes to attend, clubs to join, and parties to enjoy, but there are no periods, no mandatory gym sessions, no set lunch time, no systematic transition from one place to the next.

In college, it is difficult to focus on a schedule with so many distractions. Some people thrive in this environment, grinding in the library, acing exams, starting businesses on the side in their dorm rooms, and nailing interviews with so much free time, but this is not for everybody.

Free time for some, me included, meant more time for friends, more time for experiences away from the classroom, and more time for partying, which certainly was not always beneficial.

I did well in college, made a lot of friends, started and worked with some cool companies and organizations, and got decent grades, but I never .

I didn’t finish toward the top of my class, I was no longer one of the best athletes, and I never landed my “dream job” or anything like that.

The Traditional “9–5” Reestablishes Some Sort of Rigidity

Upon entering a job after school, things start to look more like high school. You are expected to clock in at a certain time, leave at a certain time, and work on tasks throughout the day, dictated to you by a teacher, but a teacher who has less apples and less gold stickers on his or her desk.

There is logic and there is a controlled environment which is nice, but often this first job is entirely based on accomplishing menial tasks for somebody else who then accomplishes a little bit less menial tasks for somebody else, who then uses these tasks and information to have a meeting which often leads to nothing.

I am not knocking the corporate world, everybody has their niche, but for those who would like to see their impact made from the moment they begin something, and especially if you want that impact to change the world, this may not be the route for you.

For me, I finally realized that counting leftover burger patties at 6am wasn’t exactly the fulfilling restaurant career I was looking for, so although the day had its set standards, it lacked the creative freedom I desired in building and growing something from the ground up and adding value to others.

Entrepreneurship Is A Totally Different Ballgame

Quitting a stable job and becoming an entrepreneur takes everything you have ever known or heard about being independent and completely throws it out of the top window of a 30-story building.

It can be painstakingly lonely, but worst of all, it can be painstakingly difficult to garner motivation and push forward.

This can lead to a lack of organization, each day feeling like a mess, time flying by without really feeling like you have achieved anything, and constant doubt and fear of failure.

After experiencing all of these emotions simultaneously when that aspiring entrepreneur asked me what my day looked like, I decided to make a change.

I reassessed all of my experiences in which I was craving success, motivated to be the best. Whether it was high school, college, sports, jobs, clubs, entrepreneurship, I had to choose a time in my life when whether I enjoyed it at the time or not, I was most productive, and I was thriving.

This led me back to that chubby kid who turned into a high school success story. I devised a plan to use my high school schedule as a model for how I could become more structured as an entrepreneur and schedule my day in a way that provided both systematic organization and creative autonomy.

This is what I came up with.

Your Schedule Should Emulate A Time You Achieved Optimal Performance

Entrepreneurial Controlled Chaos

My day is split into 19 “periods” with 19 different “subjects” ranging anywhere from 25 to 90 minutes. I allow myself 5 minutes in between each category to allow my mind recovery time, which is paramount in not becoming overworked or overstressed.

I have devoted time to physical fitness, personal growth and development, eating while learning, relaxation, rest, relationships, and entertainment. These are all characteristics of when I thrived most during my days in high school. I set aside personal time for creativity and thought creation, providing me with the right combination of control and freedom.

I use 12 hours a day for “work” related tasks and have been doing this 6 days a week, so 72 hours a week working.

The 3 most important attributes I will share with you in building your day, no matter what it entails or what it looks like, are intensity, consistency and flexibility.


These are short bursts or sprints in 19 different categories. Whether you have 5 minutes allotted to a task or 500 minutes, you better make sure it is uninterrupted, focused dedication to the subject at hand.

Schedule chunks of time for distractions like TV or video games, but do not deviate from the time you have to work on what you have to work on and to get done what you have to get done.

This is your livelihood, so let’s make the time count.


This is not a one and done kind of thing. This is going to take days and weeks to get used to, to feel comfortable with, and to form into a habit. This will require discipline, commitment, and repetition that will allow you to memorize this within a few weeks.

Sticking to the plan is what will allow for the success you desire and deserve. Play with it to begin and feel out what is right for you, but once the experimentation period is over, cement this schedule into your brain.

Flexibility (Light Flexibility)

With that being said, the old adage is true and there is no particular day as an entrepreneur. But, we can get close, and this is the way to do so.

Calls may come up at different times, meetings may be scheduled, and opportunities may surface outside of their allotted zones, but make sure to adjust accordingly.

Understand that your optimal schedule is not set and stone.

But the further you deviate, the closer you get to that unorganized, overworked, and overstressed entrepreneur who cannot explain the inner workings of a day in the life of you.

For more beautiful stories of love and happiness, head to https://www.journeytocloudnine.com/

This story is published in The Startup, Medium’s largest entrepreneurship publication followed by +440,678 people.

Subscribe to receive our top stories here.

The Startup

Get smarter at building your thing. Join The Startup’s +787K followers.

Sign up for Top 10 Stories

By The Startup

Get smarter at building your thing. Subscribe to receive The Startup's top 10 most read stories — delivered straight into your inbox, once a week. Take a look.

By signing up, you will create a Medium account if you don’t already have one. Review our Privacy Policy for more information about our privacy practices.

Check your inbox
Medium sent you an email at to complete your subscription.

Jordan Gross

Written by

Son, Grandson | Reimagining Personal Development | “What Happens in Tomorrow World?” Publishing Spring 2021, BenBella Books, Matt Holt Books

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +787K followers.

Jordan Gross

Written by

Son, Grandson | Reimagining Personal Development | “What Happens in Tomorrow World?” Publishing Spring 2021, BenBella Books, Matt Holt Books

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +787K followers.

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store