Getting dating advice from friends and family is a part of life; but when you’re an entrepreneur, dating comes with a lot of unique challenges that friends and family members can’t always help you with. With Valentines day around the corner, love is on the mind for many of us.

Common Dating Challenges for Entrepreneurs

Being an entrepreneur already makes you pretty unique. According to the United States Census Bureau, the US population was over 328-million in 2019, and yet there were only 774,725 new businesses established in the first quarter of 2019. The number of entrepreneurs is low compared to the national population.

Entrepreneurs live a high-risk life compared to employed individuals.  When we consider that nine out of ten startups fail, we have to take into consideration how stress can affect relationships. According to, in 2017, the US had a divorce rate of approximately 30%; however, divorce lawyers speculate that divorce among entrepreneurs was approximately five to ten percent higher than the national rate. The current US divorce rate is significantly lower; however, that’s because fewer people are getting married and choosing to co-habitat instead.

As entrepreneurs, we have to be diligent in managing our relationships with the same passion and drive that we strive to manage our businesses. Therefore, we need to make sure that we are in the right place mentally, emotionally and financially to manage a relationship. 

Can your relationship handle the time needed to maintain your business? Here is what my fellow entrepreneur Adrian Gabriel Hernandez has to say about managing your time.

Dating Advice from Adrian Gabriel Hernandez of Titan Fitness


Adrian is a personal trainer and the owner of Titan Fitness. Adrian’s schedule is based on client availability. He was quick to communicate the importance of time management in personal and professional life.

“Don’t leave quality time to chance! Make the time. I live by my calendar and will literally schedule out time to spend with friends, family, and significant others just like I do business meetings, workouts, etc…”

This is brilliant advice considering that entrepreneurs are not nine-to-fivers. Anyone who calls themselves an entrepreneur, but “clocks out” at 5:00 PM is not a serious entrepreneur. Entrepreneurs listen to the call of opportunity and opportunities don’t stop coming through at 5:00 PM.

Even though you’re not a nine-to-five person, it’s necessary to have boundaries for your business. Don’t let your professional life overwhelm your personal life.  If you are ready to date, make sure that you allocate the time for dating. Focus on this person with the same focus that you give your business. Don’t check your emails or take business calls while you are on a date. If you scheduled the time with this person, commit to it.

Always be aware of the difference between needy and neglected.

Since we don’t clock out when things get hectic, it’s important to identify if the person you are dating is needy or neglected. Before dating, evaluate how many hours you average a week working for your business. Let the person you are dating know you work X many hours a week on average. This gives the person the choice to accept or decline the parameters of this possible relationship. Awareness means acceptance if the dating moves forward.

If your partner complains a lot, they are not happy with your schedule. It is time to change your schedule or end an incompatible dating relationship. It’s important to date a person you are compatible with from the beginning. Don’t avoid the red flags.

Dating Advice From Marylizbeth of MS Paint

MS Paint

Marylizbeth Green is the Co-Owner and a key painter for MS Paint in Austin, Texas.  As a former artist, her passion for art started her love affair with paint. Like all entrepreneurs, she felt a calling to quit her job and ended up starting a company with her business partner. She has been creatively painting residential and commercial interiors with her artistic skills for over four years.

“Call me?” An Instant Messenger text popped onto my phone screen after I sent Marylizbeth an email asking her a few questions. Instead of responding to her message, I immediately called her. One thing I know about entrepreneurs, time is a valuable resource. Now will always mean “now,” and certainly not “later.”

Marylizbeth answered her phone while she was driving to meet a client for a paint consultation.  Her tone was direct and blunt; just like her. She got to the point immediately answering the question I emailed her.

“What advice would you give to an entrepreneur who is interested in focusing on dating?”

“Learn to love what you physically or mentally loathe, and then you’re ready to accept someone as they are. For example, I hated to run. So I ran every day seeking a runner’s ‘high’ and found it. I fell in love with it; then I allowed myself to date after divorce.”

Marylizbeth explained to me how the running analogy fit into her theory on dating. After her seven-year marriage ended in divorce, she took time to herself to reflect and focus on her own growth. One thing she learned about dating is to stop dating people who have expectations for you that don’t align to your own values.

“Don’t take things too seriously. Find someone who knows exactly who you are and doesn’t expect you to change. I love myself too much to accept someone’s need to change me.”

I could tell that Marylizbeth was an open book. She approached dating with authenticity. She didn’t feel the need to impress anyone. She is unapologetically Marylizbeth all the way and all the time. 

She met her current girlfriend Jaclyn almost two years ago and has been happily involved since then. I asked Marylizbeth what has helped her maintain happiness in her relationship and her response was immediate.

“I learned to never hold my partner accountable for the things that bother me. I’m responsible for my own emotions. Sometimes we do things that bother each other, but what I feel has nothing to do with anyone else but myself. I know that I’m not perfect. I can be a handful with my attitude, but I found someone who doesn’t put up with my crap.”

I could hear the amused affection in her voice as she talked about her girlfriend.  

“We’re nothing alike, and that’s what I love about her. She’s sweet and amazing, but she’s no pushover. Find someone who loves you a lot and scares you a little.”

You deserve to be loved for who you are now. Not for who you imagine you are becoming. There are ups and downs to being an entrepreneur because you are a risk-taker. Maybe you’re not where you need to be financially. Maybe you work too many hours right now. Maybe you’re wealthy. It doesn’t matter. Be confident enough to be yourself while you are dating. You’re not meant to mold yourself into a role. That’s what makes you unique.

Dating Advice from Grace Gravestock of New Paradigm Transitions

Grace Gravestock is a Human Design Coach and the Owner of New Paradigm Transitions. She talks as fast as she moves through life. She is that entrepreneur who is always thinking of multiple projects simultaneously. She shares a common entrepreneur trait that many of us have; high-energy, high-intensity life-style. She has crashed and burned enough in her life. This pattern led her to monitor her awareness regarding love and self-care.

Since we kept playing phone tag, I called Grace after she finished eating dinner. She sounded hyper and excited to help. She is the quintessential coach.

“If you’re concerned about dating, try to focus on your relationship with yourself first. How do you show up for yourself? Do you exhibit the qualities within yourself that you seek within a partner? It’s important to measure how well you’re doing by checking the markers that indicate where you are with yourself.”

Grace was emphatic about her perspective on self-care. She went on to explain;

“Self-care is a measurement of your own self-worth. We can only attract the amount of love we want from another person that we give to ourselves. How do you measure your self-love? How is your health? How is your weight? Are you happy with the way you feel? You don’t have space for a partner if you don’t take care of yourself. “

I asked Grace, how she was able to come to this perspective and what her personal experience with mastering self-care was. Grace’s personal story is similar to many workaholics’s stories. She overworked until she suffered from chronic migraines for years.

“I realized that my headaches for 18 years were simply my body’s way of telling me to get off my computer and stop over-working. For many years, I felt that I was a victim of my circumstances (sole bread winner, workaholic, challenging jobs that required so much time etc). What I realized recently was that my real issue was my own boundaries around time, work and self-care!”

Grace made many lifestyle changes several years ago. She was diagnosed with a critical health condition and went through a divorce. Her life went through a complete overhaul. These painful changes led her to commit to a better life. She started to eat healthier, exercise and focus on self-care. The migraines came less frequently, and she felt optimistic about the progress she was making in her life. 

As with many entrepreneurs, business opportunities can come in waves. As a mover and a shaker, she began to over-commit to her opportunities. She started getting back into the express lane. She started staying up late too many nights in a row, working on her computer and neglecting her self-care. The headaches started coming back. 

“If you’re an obsessive workaholic, your life will reflect the results of this. You may accomplish a lot with your work for a while, but your life will be lopsided and your results will be short-sighted. To build a healthy business, requires the healthy foundation of a healthy person and life. In this New Paradigm, self-care is increasingly important. To neglect this is to set yourself on a course of eventual self-destruction. That might show up in your relationships, your health or both, but it will not be without consequence.”

I felt as if she were talking to me, since I have been guilty of this myself. Her voice was full of compassion.

“Take a break. Take time for self-care in order for you to experience the 360 degrees of abundance you were made for. If you can get this, and take care of yourself first, love will come to you. If you can’t take care of yourself, you won’t be able to take care of a relationship.”

Dating Advice from Alethea Jimison of Words Sell

All of the entrepreneurs that I interviewed shared great advice for dating. They touched upon:

  • Attention management (time-management)
  • Authenticity (values)
  • Self-care (health)

Understand what you are looking for and accept people for who they are. Identify people who are not in alignment with your values immediately. Be compassionate when you say goodbye. Love yourself enough to take care of your health and well-being so that you can give the same love and care to someone you imagine dating.

I wanted to close this out with my one bit of advice. Be compassionate to yourself and to other people while dating. Be patient. Just like you wouldn’t settle for a job to feel secure, never settle for a mediocre relationship to feel secure.

Have any more dating advice for entrepreneurs? Let us know down in the comments.

This article originally published on GREY Journal.