What Are Some Pros and Cons of Dating an Entrepreneur?

BY: - 16 May '18 | Single

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Dr. Buckingham, I have been single for some time because I am very picky when it comes to selecting and dating men. I have done extremely well for myself as an attorney, but I get tired of the long hours and days. Nevertheless, I love the security that I have on my job. Here is my dilemma. I recently met this guy who I like a lot and he appears to be a good fit for me. However, I am concerned because he is an entrepreneur. I have never dated an entrepreneur so I do not know much about the lifestyle. I like the fact that he works for himself, makes a seven-figure salary and controls his schedule. However, I do not like the fact that he is always busy. I like him a lot, but I am not sure about his lifestyle. What Are Some Pros and Cons of Dating an Entrepreneur?


Ms. Attorney

Ask Dr. Buckingham

Dear Ms. Attorney,

I love the fact that you are taking the time to find out if you are compatible with your friend. Some women will hear the title entrepreneur and jump all in. While the title sounds enticing, there are definitely some pros and cons depending on an individual’s perspective.

Generally speaking, entrepreneurs are driven individuals who can at times appear to be self-centered. This is mainly because they spend a lot of time thinking about how they can compete and succeed in the land of entrepreneurship. The entrepreneurial drive can be very attractive, but the grind can be very ugly at times. Also, as an entrepreneur, I have learned that no two entrepreneurs have the same personality or operate exactly the same. Given this, the pros and cons listed below are not all-inclusive nor are they applicable to every entrepreneur.

Here are the pros and cons of dating an entrepreneur.


#1 Boss Status – The entrepreneurial lifestyle is very attractive because working for oneself is the American dream. Who does not want to call the shots? As an entrepreneur, your guy friend has the distinct title of “Boss.” Being a boss is a positive in that he gets to establish his own vision and set the tempo for his business. Also, as a boss, he has the honor and privilege of influencing and helping employees, family members, and friends achieve their dreams. You get to date a man who has the ability to control his destiny and influence others’ destiny.

#2 Freedom – He creates his own schedule and workload. Not too many people have the freedom to go where they like when they like. Being an entrepreneur affords him the opportunity to live the lifestyle that most people dream of.

#3 Money – His earning capacity is determined by his creativity and ability to run his business effectively and efficiently. Unlike a conventional job where salaries are capped, entrepreneurs have the capacity to earn substantial profits.

#4 Driven – Most entrepreneurs that I know are go-getters and are always looking for ways to enhance their lifestyle. They typically display energy that keeps others motivated and excited about what they are doing. Based on the fact that he has developed a seven-figure business, I would probably argue that he is a pretty good goal setter and achiever. Both are outstanding qualities to have in a partner.

After reading the pros outlined above you are probably asking yourself, “Why Am I tripping?” Well, you are not tripping. You should be mindful of the cons as well. See, the entrepreneurial lifestyle comes with benefits, but there can be some cons as well.


#1 Boss Status – Being the boss means being busy. Your guy friend probably will spend a significant amount of time responding to company-related issues. It is not uncommon for heads of big companies to be tied to their cell phones and email. Sometimes the next big deal is a phone call away and he might not want to spend too much time away from his lines of communication. At times, you might feel like you are sharing him with the world. Unfortunately, you might feel lonely on occasion.

#2 Money – Although entrepreneurs are somewhat in control of their financial destiny, they are also vulnerable to financial losses. Taking a risk to make money is commonplace in entrepreneurship. Poor money management decisions can cause his business to fail. You have to be comfortable with the fact that his financial stability is based on his ability to manage his business effectively and make sound decisions.

#3 Driven – Some driven individuals struggle with relaxing and sleeping because they spend so much time thinking about their next big money-making idea. Their dreams and ambition can prevent them from learning the importance of balancing work and play. Being driven can be good unless it keeps your mind working up all the time and creates a great deal of anxiety. The fear of not succeeding can dominate one’s life.

#4 Stress – I have provided counseling to a lot of entrepreneurs and have learned that running a business is not joyful all the time. Firing and hiring employees, making the final decision and ensuring growth can be stressors.

Dating an entrepreneur can be tricky because the lifestyle has both pros and cons. The best thing that you can do is to develop an interest in his business and take some time to learn about his lifestyle. Try to figure out how you will fit best in his life. Just know that at times you might feel second to his business. In my experience, this is not deal breaker, but a conversation starter. Communicate your needs and work with him to develop a plan on how both of you can enjoy the entrepreneurship lifestyle.

Best regards,

Dr. Buckingham

If you have questions for Dr. Dwayne Buckingham regarding relationships (married, single, etc), parenting, or personal growth and development, please send an email to askdrbuckingham@gmail.com

Disclaimer: The ideas, opinions, and recommendations contained in this post are not intended as a substitute for seeking professional counseling or guidance. Any concerns or questions that you have about relationships or any other source of potential distress should be discussed with a professional, in person. The author is not liable or responsible for any personal or relational distress, loss or damage allegedly arising from any information or recommendations in this post.

About the author

Dwayne Buckingham wrote 216 articles on this blog.

Dr. Dwayne L. Buckingham, author of Qualified, yet Single: Why Good Men Remain Single and Unconditional Love: What Every Woman and Man Desires in a Relationship, is a highly acclaimed international clinical psychotherapist, life coach, relationship and resiliency expert, motivational speaker and corporate consultant. He is also the President and Chief Executive Officer of R.E.A.L. Horizons Consulting Service, located in Silver Spring, Maryland. To learn more about Dr. Dwayne L. Buckingham visit his website at www.DrBuckingham.com.


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Finally Boo’d Up: Are You Scared of Messing It Up?

BY: - 21 May '18 | Single

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You’re finally boo’d up and you’re singing that new Ella Mai song:

“Feelings, so deep in my feelings
No, this ain’t really like me
Can’t control my anxiety
Feeling, like I’m touching the ceiling
When I’m with you I can’t breathe
Boy, you do something to me.”

This man could be The One! He takes your breath away with his kindness, thoughtfulness and sincerity. This could be the real deal! But instead of enjoying your new relationship, you’re stuck worrying about messing it up. Thoughts like…

What if I’ve given him my whole heart and tell him I love him, he’ll leave.

What if I can’t keep him interested and he hurts me by rejecting me?

What if I become miserable and bored in this relationship?

What if I have to change who I am just to make him happy?

What if, what if, what if….

Stop. Breathe, girl.

While it’s normal to feel anxious thoughts in a new relationship, there’s a difference between wondering if you chose the right partner and being so afraid you’ll lose him that you hold your breath, waiting for the shoe to drop!

Bracing yourself for the worst will rob you of the joy of experiencing one of the best times of your life.

So to help you calm down and get those “what if” thoughts under control right now let me share with you three coaching tips to help you enjoy your new boo instead of worrying the relationship won’t last.

Tell Yourself You’re Excited Instead of Scared

Anxiety and excitement are similar emotions. In fact, it helps to think of them as two cousins who were born on the same day. It’s possible to experience the same physical and emotional response when you’re anxious as when you’re excited. Bubble guts, racing heart, shortness of breath, sweaty palms, are all signs of both anxiety and excitement. According to researchers, they’re both arousal emotions designed to help you take action.

The difference is in whether you take actions that sabotage your new relationships or actions that strengthen your connection all depends on what you tell yourself about what you’re experiencing.

Anxiety = “What if it doesn’t work out?”

Excitement = “What are all the great things I would feel and experience if it DOES work out?”

You have the power to flip the script on the gremlin of anxiety lurking in the back of your mind, simply by focusing on all the good what ifs that could happen as a result of your new partnership.

Take It One Date at a Time

So much of your anxiety is coming in through the doorway marked “The Future.” No one can predict what’s going to happen tomorrow, much less next year, so why worry about it. When you’re daydreaming about your destination wedding to someone who hasn’t even met your crazy Auntie yet, or you’re obsessing over who should say “I love you” first, you rob yourself of the greatest gift of all: the present moment!

Pay more attention to what’s happening right now in your relationship and you’ll settle your nerves (and create a stronger connection with him as a result).

Tell Him You’re Scared and Let Him Take Care of You

Focusing on how you feel and wearing your heart on your sleeve is the pathway to deeper intimacy in a relationship. So why not practice that skill right now and tell him that your feelings for him make you excited and scared at the same time.

It’s a risk, I know, to let him in on your secret thoughts. But this powerful and courageous act of vulnerability will help you break through the tendency to try to be what you think he wants instead of being true to yourself.

This point is powerful because when you spend time and energy trying to prove that you’re good enough to be with him, you can come across as needy or desperate. Plus, you’ll look to him to validate your worth and you’ll obsess and overthink every little thing he does, looking for a sign that he’s changing his mind about you.

You are already good enough and you have nothing to prove (neither does he). So open up and tell him how you feel. You’ll create the opportunity for him to take care of your needs which could bring you closer together.

Give yourself permission to get your hopes up about your new relationship by embracing your excitement, taking one date at a time, and opening up with your new boo about your feelings.

BMWK, tell me the #1 challenge that comes up when you meet someone you’re excited about below!

About the author

Aesha Adams Roberts wrote 178 articles on this blog.

Dr. Aesha is a matchmaker, dating coach, speaker and author of the book, Can I Help A Sister Out: How To Meet & Marry The Man of Your Dreams. After years of making painful dating mistakes, she met & married her husband in 11 short months and has made it her mission to help women and men find and keep the love of their lives.


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