A day in the life of an entrepreneur: A look at my typical day


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I tend to spend a lot of time on this blog offering small business advice. But I rarely spend time talking about my own personal day-to-day routine.

How entrepreneurs spend their day seems to be a topic of curiosity and fascination for a lot of people.

It’s that fascination that inspired me to write this blog post.

While I can’t speak for all entrepreneurs, to satisfy ye curious Googlers, I can at least give you a look into this entrepreneur’s life with a glimpse of my daily routine.

Before we begin, I want to note that my typical day is an ever-evolving thing. I am always pivoting. And I’m always coming up with new ways to make my life less stressful while improving my bottom line.

To me, that’s really the best thing about entrepreneurial life – OK maybe aside from the money – it’s never boring!

My “normal” day-to-day looks nothing like my “normal” from five years ago. Or even two years ago, for that matter.

What is an “entrepreneur”?

Let’s start with the basics, what makes one an entrepreneur? 

By definition, an entrepreneur is someone who operates a business and generally takes on a considerable amount of risk and responsibility in doing so.

I don’t always like to call myself an entrepreneur. This is largely due to the fact that the word is often misused on social media. 

But as someone who owns and operates two LLCs – a graphic design agency and a media company that serves as an umbrella for our blogs – that is, by definition, exactly what I am.

Morgan Overholt types
I make most of my money through graphic design, freelancing and blogging

How do entrepreneurs make money?

Successful entrepreneurs make money in a variety of ways. And gross earnings vary wildly from one entrepreneur to another depending on the size of the business(es) and the types of products and services they offer.

Some entrepreneurs barely make any money at all. Others make thousands. Some are fortunate enough to make millions or even billions.

Some of the most common ways entrepreneurs make money include offering services or products for sale to consumers (B2C), offering services or products for sale to other businesses (B2B), creating content for ads, subscriptions or lead generation and investing.  

How I make money

As I mentioned earlier, I own two small businesses. 

My now-biggest source of revenue is content creation. My largest blog is TheSmokies.com which I own and operate with my two business partners, my second-biggest blog – MorganOverholt.com is sole-owned by yours truly. And my partners and I are launching a third blog this year – HeyOrlando.com.

Read Also: Is it worth it to start a blog? How we made $100k in less than 2 years

My second biggest source of income is the freelance and graphic design business, of which I am the sole owner. The design business used to be my primary source of income before I made the conscious decision to pivot to a more passive income model in 2021.

And while these numbers may vary dramatically from year-to-year or even day-to-day, my monthly revenue stream normally looks something like this:*

*Editor’s note: The following figures were taken from my December 2021 earnings report. They represent gross income from both companies. All have been rounded to the nearest hundred.

  • Freelance/Design Agency: $14,300
  • Blogs: $37,500

That’s a total of about $52,000 in gross revenue per month. Which will likely equate to roughly $600,000 by the end of the year (in 2022).

And all of that equates to anywhere from $130,000-$200,000 in personal income depending on how much I decide to pay myself, and how much I decide to invest or put back into the businesses.

Morgan Overholt by the pool in Miami
Owning your own business also means you mostly get to dictate how and where you spend your time.

What do entrepreneurs do all day?

Every entrepreneur’s day-to-day routine looks different from the next. Some are early birds, some are night owls, some work from home and some maintain a strict corporate-like schedule.

Some barely make ends meet, others are Jeff Bezos or Richard Branson rich and many fall somewhere in between.

In the early days of launching my businesses, I used to hustle 10-12 hours a day, six days a week. Long days, back then, were the norm.

Today, I’ve strategically reduced my workload to improve both my mental and physical health.

Here’s a closer look at my typical day now:

  • 9:00 am: Wake up
  • 10:00 am: Check email, Trello and Slack to review my daily tasks
  • 10:30 am: Update the project queue
  • 11:00 am: Go to the gym or take a walk (if it’s a sunny day)
  • 11:30 am: Shower
  • 12:00 pm: Meetings and phone calls (if applicable)
  • 1:00 pm: Lunch
  • 2:00 pm-6:00 pm: Work on the blogs/design projects
  • 6:30 pm: Check e-mail one last time
  • 7:00 pm: Update project queue for the next day
  • 7:30 pm: Dinner
  • 8:00 pm: Relax and unwind
  • Midnight: Get ready for bed

Read Also: Best tools for freelancers 2022: 14 essential resources for your business

I usually work anywhere between 5 and 10 hours per day.

I think it’s a common misbelief that all entrepreneurs have to get up early and start their day with some sort of aspirational morning routine.

I’m not a morning person. I’ve always been a night owl and find that I do my best creative work in the late afternoons. It’s also the best time to sneak in a bit of deep work as the late afternoons tend to be fairly distraction-free.

I used to walk to an office every day. But in late 2021 I transitioned into working from home (and am happy I did).

I sometimes return to work after dinner if I am feeling inspired. But I try not to make a habit of it. Instead, I try to spend the rest of the day relaxing with my husband or spending time with friends.

Going to the gym somewhat regularly is a new habit that I’ve been trying to adopt since I began working from home.

I also used to spend a large portion of my workday pitching to potential clients. But today, that need for pitching has diminished significantly due to a steady stream of work and reoccurring semi-passive income.

I don’t eat breakfast. And if it wasn’t already obvious enough – I don’t have kids.

Morgan Overholt's Home Office
A candid glimpse of me on a normal workday, in my home office.

What do entrepreneurs wear?

What an entrepreneur wears during the day is going to depend on the type of work they are required to do, who they have to see and where they have to be.

Because I mostly work from home and am only seen from the waist up on Zoom calls during the day, I tend to take the professional yet comfortable route.

I normally wear jeans, shorts or leggings with a form-fitting top that pairs nicely with a blazer should I need to throw one on for a meeting.

I do my hair and makeup every day and do not allow myself to wear sweatpants. Feeling slouchy just doesn’t put me in a productive mindset. 

Can entrepreneurship be learned?

I’d like to end this article by answering another frequently asked question that often pops up in my research: Can entrepreneurship be learned?

I’m here to emphatically state that yes, entrepreneurship can be learned.

I didn’t set out in this world to be a business owner.

While I’ve always had big dreams, I used to think I’d find success working for someone else.

But after rage quitting my job in 2017, I knew that true success would only be achievable if I became my own boss.

Fortunately, my husband comes from a family of entrepreneurs. It is with his help and encouragement that I eventually made the leap.

I don’t consider myself to be a person of above-average intelligence or skill, I just figure things out as I go.

At the end of the day, I’m just a regular human being like anyone else, albeit, perhaps, with a slightly higher energy level.

Sure, it took a long time, and a lot of hard work to get where I am today. I am no overnight success. It’s been a steady climb, and I’m still making my way to the summit.

But growth excites me. I tend to treat entrepreneur life like a video game. I’m always trying to get to the next level.

I read books, listen to podcasts, constantly hone my skill set, constantly strive for personal growth and am always on the lookout for new opportunities and ways to improve my bottom line. I’m always coming up with new business ideas.

I cannot tell you what a great feeling it is to be in control of your own life and career.

And trust me, if I can figure out a way to become a successful entrepreneur, anyone can.

“The secret of getting ahead is getting started.”

Mark Twain

Did you enjoy this glimpse into the life of an entrepreneur? Are you thinking about becoming an entrepreneur? Let me know in the comments below. And don’t forget to connect with me on social media.

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