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3 Signs that You’d Make a Better Entrepreneur than Employee

I remember being highly offended when my husband accused me of being a terrible employee.

We had been enjoying a glass of wine on the balcony of our high-rise apartment and reminiscing about how we’d gotten so far in such a small amount of time.

Three years prior, I had chosen to quit my job in the corporate world to work for myself.

Since that time, I had more than doubled my salary and moved to an apartment that I never would have dreamed possible in an affluent neighborhood in Miami, Florida.

Looking out into the Miami skyline, my former life felt a million miles away — that is until I was snapped out of my indulgent state of self-congratulatory bliss by my husband’s brutal honesty.

“Not a good employee — what are you talking about? I was an excellent employee!” I retorted.

“No,” he replied. “You turned out to be a great entrepreneur, but you were a horrible employee — and that’s okay, because entrepreneurs don’t always make for the best employees.”

Curious to see if there was any weight to this theory, I did a bit of googling and, as it turns out, he might be right.

There are many traits that successful entrepreneurs share that are not always coveted by employers in a large corporate setting.

And I was personally guilty of quite a few. Here are three signs that you might make a better entrepreneur than employee.

You don’t blindly follow orders or seek permission

When we think about an employee who isn’t obeying orders we often think about someone who is lazy.

But that’s not the kind of rule-breaker we are talking about here.

We’re talking about a rule breaker like billionaire Mark Cuban, an entrepreneur, television personality and investor.

According to an article in Forbes, Cuban was once fired from a job for breaking the rules in an effort to land a large sale.

The sale was worth about $15,000 at the time, which meant a handsome $1,500 commission for then-young Cuban.

However, it required getting his boss’s permission to leave the office to pick up the check, which his boss wasn’t happy about. He told Cuban not to do it, but Cuban did it anyway, and he was fired on the spot despite having just landed a large sale.

I too have been guilty of disobeying orders at work when I assumed the genius of my idea would result in high-praise and forgiveness.

When I was just 20 years old, I worked a brief stint as a sales clerk at Rack Room Shoes at the local strip mall. It was a brand-new store at the time, and the warehouse was a mess.

Every time a customer would ask about a particular size or color that wasn’t on the shelf, most of us would walk back into the warehouse, poke around through a disorganized pile of random boxes long enough to make the customer think we were being productive. Usually we would return empty handed.

One day, when sales were slow, I got the bright idea to organize the inventory.

At the end of my 8-hour shift, the miscellaneous shoe mountain had been transformed into a clearly labeled, brand-alphabetized mini warehouse.

But when I told my boss what I had done, accolades did not follow. Instead, I was met with a look of confusion and asked why I had done such a thing.

I could share many stories of taking initiatives and doing things my own way that either went directly against my employer’s wishes or at the very least was a “ask forgiveness instead of permission” type of scenario.

I was never trying to be a bad employee. In my mind, I was making the company better by improving sales and taking initiative.

But the truth is, working in a corporate environment isn’t about going rogue, it’s about being a team player. And if you want to take an initiative, it’s advised you go through the proper channels and receive permission to do so.

Inversely, in the world of self-employment, those who take initiative and go the extra mile are frequently rewarded by the direct impacts of those efforts.

Good entrepreneurs know how to turn ideas into action and hate the idea of having to cut through layers of corporate formalities and approvals to get it done.

You’re too emotionally invested in your job

Being too emotionally invested can be a double-edged sword for both employees and entrepreneurs alike.

On one hand, caring deeply about your work might push you to constantly work harder and seek out areas of improvement.

But it can also wreak havoc on your personal life, and often go unnoticed, or even looked down upon, by your superiors.

If you want an incredible example of unchanneled passion, look no further than billionaire and TV personality Oprah Winfrey. Oprah was fired from a local news station after a producer told her she was “unfit for television news” and too “emotionally invested” in the stories she was covering.

As an employee, I’ve shed an incredible amount of tears over my work.

I wanted nothing more than to be noticed and appreciated by my superiors. I often took my work home with me. I studied and honed my craft. I put effort into working as hard as I could, and I put in the extra hours whenever necessary.

I never shied away from an opportunity. My career, albeit working for someone else and toward someone else’s goals and prosperity, was my life.

Perhaps that’s how I found myself in tears laying on the concrete floor of my apartment in my 20s after being temporarily demoted because a high-end customer had complained that they “didn’t like” me.

I couldn’t wrap my head around how the off-handed comment of a single person could instantly negate years of hard work.

Despite being reinstated just a few weeks later, I honestly think something changed from that point on.

I realized that I had been killing myself for someone who clearly didn’t fully appreciate the effort or the emotional investment I was making. It was at that point that I began to question why I cared so deeply in the first place.

Even today, I continue to struggle with the tendency to become overly emotionally invested in my own business. At least now I can safely say that my emotional investment will at least usually produce some sort of direct, usually financial, benefit.

And that’s the difference.

If you’re a passionate career-driven person, you might as well focus that passion on something that will actually provide a direct benefit, versus something that risks getting ignored.

Oprah didn’t lose her passion. She just learned to channel it correctly for an audience who would appreciate it.

You have a high risk-tolerance and like to challenge the status quo

Are you someone that likes to try new things, push the boundaries of what’s possible and take risks?

A young Anna Wintour, now Editor in Chief at Vogue, proved herself to be a risk taker when she made waves as a junior fashion editor at Harper’s Bazaar for innovative photo shoots. But her editor thought they were too edgy and she was fired after just nine months on the job.

A study once asked more than 1,000 employees from a variety of industries across the nation whether or not they had seen leaders challenge the status quo or encourage their employees to think outside of the box.

Of those polled, 42% said never or almost never, 32% said sometimes, 26% said fairly often or very often and mere 3% said always.

There’s little incentive for an employee to challenge the system or take a risk when innovation is so rarely encouraged in the workplace.

And yet, there are still plenty of individuals like myself who feel trapped when we are stifled and stagnant.

But it’s not surprising that we continue to persist. Afterall, studies have shown that risk takers and innovative thinkers tend to be more intelligent and happier in life.

Which is why, for some, roadblocks in the workplace can be frustrating over time.

When I worked for other people, I constantly saw flaws in the system and areas for improvement. But when raising those concerns to superiors, I was often told: “That is just the way we do things around here.”

I used to have a recurring dream where I would find myself in a burning building, screaming at everyone to get out while people around me remained still and unwavering as the room became engulfed in flame.

When I decided to take the ultimate risk to work for myself and launch my own business, I stopped having that dream.

I had finally realized screaming at people who refuse to listen was a fruitless task. I needed to be in an environment that would allow me to explore the limits of what’s possible in life, and in my career.

As the old saying goes: Nothing ventured, nothing gained.

I often wish I could go back in time and tell my former self that it’s okay to be passionate and rebellious when it comes to my career. While these attributes were not always looked upon favorably by my employers, they’ve certainly come in handy in my new-found role as a small business owner.

If you’re not cut out for the life of an employee, it might be time to consider the life of an entrepreneur.

Morgan Overholt

Tennessee native Morgan Overholt is a freelance graphic designer, owner of Morgan Media LLC and co-founder of Morgan and her team have worked with nationally recognized clientele from all over the world, including the Centers for Disease Control Foundation (CDCF), Kimberly-Clark, and Stanley Black & Decker.

Morgan transitioned into the role of freelancer and small business owner after spending nearly a decade in the traditional corporate world left her feeling unsatisfied and unfulfilled. Today, Morgan is passionate about sharing her story with other hopeful entrepreneurs who hope to follow in her footsteps. She has been featured on, Refinery29, and Business Insider.

Originally published at on November 30, 2020.



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Morgan Overholt

Morgan Overholt is a freelance graphic designer and owner of Morgan Media LLC. She is also a contributor for Business Insider and Collective.