Listen Live
Praise 100.9 Featured Video

One of the most attractive qualities about dating an entrepreneur is the flexibility of their schedule. However, on the flip side, entrepreneur schedules can be completely unconventional. Some employees who punch the clock may be able to leave work at work and box out the typical 8 to 10 hour day for their employer with nothing to complete or bring home with them after 6pm. Yet, entrepreneurs, who are often times responsible for everything associated with their businesses, are constantly working around the clock. While some of you are winding down to watch all three Shonda shows on Thursday with several glasses of wine, other are working.

MUST READ: Pay The Cost To Be The Boss: Top 10 Qualities You’ll Need To Be An Entrepreneur

When I met my husband, I had just been let go from one of my legal positions as of counsel due to the recession. I had already started my practice and had it incorporated in New York. I had a couple of clients here and there, but my end desire, at that time, was to obtain another full-time job. Yes, when we met I told him that I was a business owner. Despite my confidence in announcing to him when we met that I had my own practice, I still pined for and wanted a steady pay check.

Years passed, and we continued to date. I obtained another full time job, and got let go from that one as well. Throughout our years of dating, my now husband made it clear that he was not comfortable with my entrepreneurial life. He was, and still is, a 9-to-5’er who swears by a W2. The “life and times” of an entrepreneur just does not make sense to him. Why would anybody want to subject themselves to sporadic paychecks, crazy clients and shady health insurance? (Pre-Obama Care, of course)

I often times asked myself the same thing until I realized and totally accepted that my lot in life was to pursue entrepreneurship, whether I liked it or not. My soul simply would not rest if I did not go for it, and that is just what I did despite the numerous disagreements we had while dating about my pursuits as a business owner.

The good news is he decided to marry me anyway despite his trepidation with entrepreneurship. In the end, if he wanted me he had to accept my goals and dreams of successfully owning my own business and having the freedom I so desperately needed. Though my husband is still learning to accept what comes along with dating and ultimately marrying an entrepreneur, happy beginnings and endings may not always happen for the dating entrepreneur.

If we decide we want to meet someone for lunch or coffee in the middle of day, without any fears of being away from the office for too long, we can. If we have parental duties that require immediate attention, it is nothing to hop in the car or on the subway to go tend to them.

I have attempted, on many occasions to fashion my work time around “normal” business hours. I figure if I stay at my desk the same hours and time of day that full time employees do, then everything will work out just fine. This is not the case. Being the owner of a business requires being available to your clients and customers at any time. This is especially the case when you are building at the start-up phase. So, as our time may be flexible, it also may be limited, which can prove difficult when carving out special time for a special someone, or even to peruse the social scene or internet for companionship.

As timing may prove difficult in developing a successful dating pattern and practice, the number one issue with dating an entrepreneur will be money. What do you mean you don’t get paid every two weeks? What do you mean that client did not pay you even though they received your invoice two months ago? Entrepreneurs, and their significant others, have to be realistic in understanding and accepting that cash flow is not as consistent as it would be working as a full-time employee. Additionally, those who choose to date an entrepreneur have to realize that the most important thing that risk taker needs from their significant other is support. Plain and simple, to date an entrepreneur, support has to be present and abundant.

I recently spoke with a fellow attorney who desires to start her own practice, but has not taken that leap to do so because her boyfriend is not supportive. She makes the most money between the both of them, and they are parents to an 8 month old. Despite her guilt of working crazy attorney hours and not being with her daughter as much as she would like, she stated that she has to present a plan to her boyfriend to get him to support her vision. She recognizes that the cost of childcare almost makes it not worth going to work, and working for herself from home may yield them the same net pay as if she was still going in to an office for someone else. But her mate does not see it the way she does, and she desperately desires his support in order to take the first step to starting her own practice.

As entrepreneurs are consistently in pursuit of the two most precious resources known to mankind (i.e. – money and more time), seeking a mate while in the midst of all of the craziness and uncertainty that already exists is daunting. However, in the end, if you can find someone who not only shows interest in you, but also shows interest in and supports your entrepreneurial vision, and the crap that comes along with it, then you have a keeper!

Rashida Maples, Esq. is Founder and Managing Partner of J. Maples & Associates ( . She has practiced Entertainment, Real Estate and Small Business Law for 10 years, handling both transactional and litigation matters. Her clients include R&B Artists Bilal and Olivia, NFL Superstar Ray Lewis, Fashion Powerhouse Harlem’s Fashion Row and Hirschfeld Properties, LLC.

MUST WATCH: Tika Sumpter Gives Her Relationship Deal Breakers


Boss Lady Problems: The Most Common Barriers To Women’s Entrepreneurship

Fact Check: Black Entrepreneurship Pushing Growth & Development In Detroit Is Nothing New

On Your Own: Here’s Why Entrepreneurs Will Never Make ‘Enough’ Money

Lonely At The Top: Is Dating Harder For Entrepreneurs?  was originally published on