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Dustin Hodgson | MyCreativeShop

What choosing where to park says about entrepreneurs

As I pulled into a Subway parking lot near our office, I realized that the closest parking spots were actually the worst spots to back out of. However, people consistently chose to park there. Why is that?

For whatever reason, I found it to be an interesting observation and one worth analyzing a little more.

Since there are already enough people talking about the psychology of parking, I decided to take a different approach to this.

I wanted to know – is there a connection between where you choose to park and the type of entrepreneur you are?

In order to answer this question, I needed a list of the different types of entrepreneurs. Luckily for me, Kimanzi Constable made a great list back in 2015 that still seems relevant today. However, I felt like adding one more type to the list.

Types of entrepreneurs

Let’s dive right into the list Kamanzi made and put some high-level detail on each type.

  1. Skeptical Entrepreneur
  2. Copycat Entrepreneur
  3. Research Entrepreneur – hmmm…I wonder which one I am?
  4. Determined Entrepreneur
  5. Accomplished Entrepreneur – oooo, nevermind I pick this one!

Here is the one type I’m going to add:

  1. Neverprenuer – This will make sense later.

Before I go into detail, can you guess which one you are?

Skeptical Entrepreneur

The Skeptical Entrepreneur sees the success of others and believes those people are getting to the top by skipping the stairs and taking the elevator. When adversity hits, these entrepreneurs struggle to dig in and grind to achieve success.

Skeptical Entrepreneur

“This is the scariest type of entrepreneur.”
– Kimanzi Constable

Copycat Entrepreneur

The Copycat Entrepreneur sees the success of others and hits the real-life copy/paste button. They lack originality in their approach to entrepreneurship & have no shame in doing exactly the same thing as a leader in their industry.

This may sound like a bad entrepreneur, but like Tim Soulo said, “…many of our favorite things bear a strong resemblance to the earlier work of others.”

Copycat Entrepreneur

“You can’t copy anybody and end with anything. If you copy, it means you’re working without any real feeling.”
-Billie Holiday

Research Entrepreneur

The Research Entrepreneur loves to analyze different strategies and soak up as much knowledge as they can. They struggle with taking action due to their need to continue to arm themselves with all the information they can gather.

Research Entrepreneur

“Information overload is a symptom of our desire to not focus on what’s important. It is a choice.”
-Brian Solis

Determined Entrepreneur

The Determined Entrepreneur is the Rocky Balboa of entrepreneurs. They know that success is possible if they battle and never give up. They’ll take some punches, but in the end, they’ll stand victorious alongside all accomplished entrepreneurs.

“It ain’t how hard you hit…It’s how hard you can get hit and keep moving forward.”
-Sylvester Stallone, Rocky Balboa

Accomplished Entrepreneur

The Accomplished Entrepreneur has gone through the battle of building a business and reached some level of success. They’re now experiencing the freedom all entrepreneurs long for, but they’ll continue to push forward & seek out more challenges in life as well as business.

Accomplished Entrepreneur

“My biggest motivation? Just to keep challenging myself. I see life almost like one long University education that I never had — every day I’m learning something new.”
-Richard Branson


The Neverpreneur is too afraid to fail. They’ll get close to taking a leap, but ultimately they will let fear consume them. This person, unfortunately, doesn’t get to experience the journey every entrepreneur embarks on. They’re the ones that say things like, “I thought of the iPod years ago!”


“Fear is the disease. Hustle is the antidote.”
-Travis Kalanick

Now that I have my list of entrepreneurs, I need to build a list of the different types of parking lots…

Types of parking lots

In an effort to try and put some organization into how I could ever answer this question, I decided to create two categories of parking lots based on my endless amounts of parking experience (impressed?).

  1. The Big Lots – Think Walmart, Target, etc.
  2. The Small Lots – Think restaurants, hair salons, gyms, etc.

Fun fact: Did you know that a mathematician solved the puzzle of the perfect parking lot? Cue the slow clap for David!

Anyway, on to the meat and potatoes of this post!

What does the Skeptical Entrepreneur do?

Hello, Skeptical Entrepreneur! If you remember, this is the “scariest type of entrepreneur.” Let’s see how they handle each parking lot…

The Big Lot
Since you don’t believe success is possible, you’re going to park at the first spot that matches your standards. You won’t even drive to the front to see if there is a spot closer because you believe someone else has already taken it.

If you see another car pull into the spot you could’ve gotten, you’ll complain and say life is unfair.

The Small Lot
You handle a small lot completely different than a big lot. You believe in shortcuts, and a small lot is filled with a bunch of quick wins. You take whatever is closest to the entrance, but since you’re not used to success, you park awkwardly and stick out like a sore thumb.

What does the Copycat Entrepreneur do?

Nice to see you again, Copycat Entrepreneur! Remember, this person loves seeing the success of others so they can copy it…

The Big Lot
Since you struggle with having original thoughts & enjoy watching the successful succeed, you’ll willingly drive around the parking lot waiting for a front row spot to open up, so that you can taste the success others have had.

Out of every entrepreneur, you will take the most attempts at trying to find an open spot in the front. When a front row spot does open up, you won’t be able to feel the same level of joy the others who parked there felt because your passengers now hate you, and deep down you’re not a fan of yourself either.

The Small Lot
Just like the big lot, you long to get as close to the front as possible; however, in a small lot this means you may choose the instant gratification of a front row spot and neglect to recognize how difficult it will be to back out.

What does the Research Entrepreneur do?

How very, Research Entrepreneur! I feel like I’m talking to myself and everyone knows it, but here goes nothing…

The Big Lot
You’ve learned from the past and have realized that driving by the front row once may just pay off. However, if there isn’t an open spot up front, you’ll likely take the first available one you see after that.

Contrary to what you might think of this entrepreneur, their process won’t drag on as long as the copycat. However, they will think about their decision outside of the car more than any other group. They’ll notice things that the other entrepreneurs won’t, like how they forgot to park by a cart corral or how another vehicle close by didn’t park between the lines. They observe and analyze more than others.

The Small Lot
You look at a small lot and start to see the problem areas. You avoid those areas and settle on a spot that’s easiest to get out of. You likely point out the problems others will have backing out as though describing how to solve a Rubik’s Cube (Crap, this is me!).

What does the Determined Entrepreneur do?

Yo, Determined Entrepreneur! There’s something about you that tells me you’re going to figure this out…

The Big Lot
You believe there is a front row spot with your name on it, and you just have it have it! You head right up to the front and take at least two passes by to see if there is an available spot. However, unlike the other entrepreneurs, you notice the open spots you saw on your way to the front and circle back to get them, creating your own imaginary front row victory.

The Small Lot
Hello, Moses! The Red Sea has parted and this determined entrepreneur is coming in hot! You’re a shark in a pool of minnows, and you have no shame in claiming the best spot in the entire parking lot. It doesn’t matter if you park in a spot that’s hard to back out of, because you’re the best driver in that lot, and it won’t be a problem for you.

What does the Accomplished Entrepreneur do?

Take a chance, Accomplished Entrepreneur! We’re honored to have you here, and we look forward to seeing where you choose to park…

The Big Lot
You float into the parking lot riding a wave of success and park wherever the heck you want to. The last thing on your mind is where you’ll park your car (or jet), because you’re on your own schedule and the walk to the door is filled with time to brainstorm your next great idea.

The Small Lot
You pull into the small lot and let everyone else get the best spots. You enjoy letting others eat first because you learned along the journey that in order to climb to the top you have to take care of those around you.

What does the Neverpreneur do?

Whatever the parking lot, the Neverpreneur does things like this and the web says thank you!


It might be time to change where you park…

I want you to ask yourself these three things when you park your car today:

  1. What type of entrepreneur am I today?
  2. What type of entrepreneur do I want to be tomorrow?
  3. How far away would I need to park to come up with at least one great idea before I reach the front door?

Enjoy the journey!