5 Reasons Why Dating An Entrepreneur is NOT for You (2022)

by Positive Hustle

I am an entrepreneur man and I want to share with you why it is incredibly hard to date a person like me.

We entrepreneurs are a very different breed.

We don’t belong in any relationship but have all the qualities you would want your partner to have.

We dress up nicely, are driven and ambitious, risk takers, a bit rough around the edges, some of the smartest people in societies, and massive amounts of potential, or pretty well paid because our potential has finally paid-off.

Yet, stay away from us if you can’t handle someone being obsessed with something that has NOTHING to do with you.

Below are 5 reasons why dating an entrepreneur is crazy:


1. We Are Always Thinking About Our Work

We are always ready to leave you and go back to our laptops and get on our cell phones. We can’t even go to bed without checking our emails because we are convinced that one night our big break will be sitting in our inboxes waiting for us to open it.

If you aren’t ready for someone like us, you will swear that we are cheating on you because we always have our phones.

Of course, there are tons of cheaters masquerading as entrepreneurs, but in truth, real entrepreneurs are not even trying to get into a relationship because we don’t have time to chase you and our dreams.

We are essentially, married to our jobs. Yes, we control our own schedules, but we control them to work our fingers into the ground. We need this work!

We don’t like where we are and we are completely convinced that where we want to go with just a few good moves away from becoming a reality. Go to lunch with us, you will have to demand that we leave our phone in the car.

Which, to an entrepreneur, is liking asking us to leave our dreams in the car while we eat some food that has nothing to do with our dreams. Oh my Lord! We hate doing anything that is taking time away from our dreams. Do you know someone like me?


2. We Don’t Like Losing

We don’t like losing anywhere. We don’t like to lose an argument or in a game of checkers! We are always in competition and this doesn’t have to be in competition with you — depending on the level of maturity of your entrepreneur.

Yet, please be advised, we don’t like to lose. Every day that we don’t wake up millionaires, or whatever our goals are, we have lost, and we hate this fact.

Therefore, every day you talk to us, kiss us, we are essentially holding in hidden anger because our plan yesterday didn’t work, or it didn’t move fast enough.

Basically, we are always on edge, you just don’t see it because we have become epic leaders and we know how to mask what we are going through so we don’t push excess pressure on our families or teams.

You will never see this tension boiling beneath our skin unless you begin to doubt us and stop believing in us. This is just about the only thing that can actually crack our perception we have mastered showing others.


Why is this the only thing that can basically make us lose it?

Because you haven’t realized that we work very hard to hear you say, “Good job baby.”

Everything we have done lately has been for you to be proud of us. We see you dealing with us and putting up with our inconsistencies, so we have dedicated our lives to working hard so it can all be worth it for you.

Therefore, when you stop believing in us, our outer shell has been cracked.


3. We Want to Do the Impossible

What we are trying to do is absolutely insane! We are not realistic and we most certainly do not have realistic goals! In fact, by everyone else’s definition, we are insane.

However, consider this, everyone who has ever changed the world or invented something new were all called insane. It is interesting to note that this world is never kind to geniuses until those geniuses have died.

When they die, they are appreciated and loved. We are not naive. We understand that when we die, the same will happen for us.


4. We Have Not Eaten Today (At least, Not Well)

We have no time to think about things like, “Did I eat today?”

In all honesty, eating is the last thing on our mind. We are too busy eating the tasks on our to-do list. In fact, the most addicted of us, literally punish ourselves and won’t eat until we finish a certain task we are trying to accomplish. We say to ourselves;

“I don’t deserve to eat yet. I will eat when I have finally finished what I said I was going to do.”


5. No, We Don’t Want to Watch Your TV Show With You

Entrepreneurs hate TV. At least the way you watch it. A book is a TV for us. Additionally, the more you watch TV is the more you stay in poverty, and we are trying to get out of poverty!

We love you very much; but to watch your television program with you is the worse form of torture you can possibly give to us.

We want to spend time with you, but you watch three programs back-to-back-to-back-to-back and all we can think of is how much work we could be getting accomplished while you are distracted watching TV.



There you have it. I can think of many other reasons, but if you are crazy enough to date us, then you are phenomenal and deserve the whole world.

Here’s a quick recap on 5 reasons why dating an entrepreneur is not for you:

  1. We are always thinking about our work
  2. We don’t like losing
  3. We want to do the impossible
  4. We have not eaten today
  5. No, we don’t want to watch your TV show with you

Are you dating an entrepreneur? Leave a comment below.

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