How to Date an Entrepreneur | Tips for a Successful Relationship

Dating an entrepreneur

As the only child of two writers, I often joke that I didn’t have a choice in the career I chose. I went to sleep to the sound of my parents typing at their keyboards as they worked late at night, I came home from school and listened to their story ideas and told them mine, and I started writing stories as soon as I could spell.

Being a writer is in my blood and is woven into my identity, but it’s not my only passion. I actually went to school for art and decided I wanted to be a dolphin trainer. After school, I worked with dolphins for about six months before I realized that I really didn’t want to work for other people. Like my parents, I wanted to be fully self-employed. Unlike them, I had published no novels and didn’t have a name for myself in the writing world, so I had to figure out how to pursue a career that allowed me to write when I wanted. 


My dad suggested I start a dog-walking business, so at 21, I did precisely that. Now at 33, I’ve been an entrepreneur for most of my adult life. I own a doggy daycare business, get commissions to paint pet portraits, and work full-time as a writer, both in fiction and non-fiction. It wasn’t an easy path to get here, and I definitely couldn’t have done it without my parents, but sometimes I wonder… Other than just the fact that I’m weird, I’ve wondered if being an entrepreneur is one reason I’m still single.
dog walker graphic

Okay, I don’t really think that, but I have recognized that whoever I bring into my life is going to have to be a pretty flexible and understanding individual. Like my parents, I am pretty much always working, and when I’m not working, I usually feel like I should be. I have had to learn how to shut that part of my brain off, and yet when I’m really tapping into a story idea, I want to talk about it to all of my friends even when I’m not by my computer.


career woman graphic
In some ways, I think there’s a correlation between being an entrepreneur and being single—mainly in that when I’m not with my friends or family, I’m focusing on how to expand one of my three businesses. Because I don’t work for other people in an office or corporate environment, I’ve developed a sense of independence that has made me feel like I don’t really need a guy. And yet the few relationships I’ve had, I’ve learned a lot of the difficulties that come with being an entrepreneur and dating someone who isn’t.

So maybe you’re the entrepreneur looking for a way to express your concerns to your partner, or maybe you are the partner realizing you’re falling in love with your partner and wanting to figure out how to walk this line of dating an entrepreneur. Either way, read along to learn some tips and tricks for how to have a successful relationship with an entrepreneur.


Respect Their Time

Dating an entrepreneur or professional can be an exciting and unique experience, full of opportunities for growth, learning, and adventure. Entrepreneurs are often driven, ambitious, and passionate about their work, which can be both inspiring, intimidating, and confusing when you’re used to dating someone who follows the normal 9 to 5 like you.

Entrepreneurs are often incredibly busy individuals, running their own businesses and trying to grow their companies. This means that their time is extremely valuable, and they have little of it to spare.

Be patient and understanding, but make sure you communicate your needs and expectations clearly. Especially in the early days of your relationship, it’s important to be honest–not just about your needs with your partner, but with yourself. Their businesses were here before you, and although entrepreneurs can learn to compromise and practice turning off their work minds, you, as their partner, may not always come first in this relationship.

If you live the 9 to 5 life, dating an entrepreneur can be incredibly rewarding. Entrepreneurs are often very creative and innovative and may have a unique perspective on life and business. People who live more of a static scheduled life may find this attractive as it allows them to open in a way they normally wouldn’t with their job.

Woman running her own business
Entrepreneurs also have a lot of drive and ambition, which can be contagious. Being around someone who is constantly striving for success can inspire you to pursue your own goals and dreams. Maybe you’ve always wanted to sing but never felt compelled to try because everyone in your life told you, “this will never be an actual career.” Do you know who will not say that to you? Your entrepreneur friend.
couple on a coffee date

So, how can you respect an entrepreneur’s time while still having fun in your relationship? Try to plan ahead. Instead of calling them up last minute and asking if they want to go out, try to plan your dates and outings in advance. This gives them time to prepare and make sure that they’re not neglecting their work in favor of spending time with you. Just because they may work from home or have more flexible than you doesn’t mean they can just drop everything when you say, “hey, let’s go.”

Unless I’m feeling it, I can speak for other entrepreneurs—because every profession is different—but when I’ve worked four thirteen-hour days in a row and haven’t seen another human being other than my UberEATS delivery man, then I’m probably going to have a different reaction to that invite. And when that happens, when I say yes and accept the call to adventure, I’m going to go all out in my spontaneity. Because if there’s one thing I love about being an entrepreneur, it’s that my time is my own to do with it as I please. Every day is different, and every day I’m free to choose what I want to do.

However, it’s important to remember that dating an entrepreneur is not for everyone. If you prefer a more stable and predictable lifestyle, dating an entrepreneur may not be the best fit for you. It can be challenging and demanding and requires a lot of flexibility and adaptability.


Understand They’re a Little Different

They are often incredibly passionate about their work and have a drive to succeed that is unmatched by others. They eat, sleep, and breathe their business, and it’s difficult to tear them away from their work. You may not understand their business, but if you’re going to be part of their life and date an entrepreneur, it’s important to embrace their passion and support them in their endeavors. It’s likely there’s going to be a lot of ups and downs, hits and misses, and the person they’re closest to is the person they’re going to vent to.

And don’t forget to have fun! Just because your partner is passionate about their work doesn’t mean that every conversation has to revolve around it. Make time to do things that you both enjoy, whether it’s going out to eat, seeing a movie, or taking a weekend trip. You can support them by still having a life separate from their business, just like you have a life other than the one at your 9 to 5. By understanding this, you two can build a strong and fulfilling relationship.

Woman being supportive of her partner

Man spending time alone at restuarant on his phone

Cultivate Your Independence

It’s likely your entrepreneur partner may not be free every day after 5 when you get off. If this is new to you, it’s important to understand that not every single moment of your relationship is going to be spent together. Even if you guys live together, there’s probably a huge chance that your partner will still work even if you’re sitting next to them. While dating an entrepreneur, it’s important to maintain your own hobbies, interests, and friendships. Don’t rely on your partner to be your sole source of social interaction and entertainment. Instead, find activities you enjoy and pursue them on your own. Whether it’s joining a sports team, taking a class, or volunteering in your community, find something that brings you joy and fulfillment.

Don’t rely on your partner to solve all your problems or make all your decisions for you. Take responsibility for your own life and decide based on what’s best for you. This not only shows your partner that you’re a strong and independent person, but it also helps you build confidence and self-esteem.


Adaptability and Flexibility

Entrepreneurs are known for their ability to thrive in environments that are constantly changing. They are always looking for ways to improve their business and are not afraid to take risks. It’s part of the fun and challenge of the job. Everything can grow and blossom, but it can just as easily collapse and sink. As a result, their lifestyles are often unpredictable. One month they could hit a new high in income, and the next, they’re barely making enough to pay rent. They’ve had to learn to adapt to changing times and new circumstances. 

My parents, for example, have published over a hundred novels through traditional publishing companies, and now, later in their careers, have adapted to the digital age by self-publishing their books as well. 

While dating an entrepreneur, it’s important to be open-minded and willing to try new things. Entrepreneurs are often excited about new ideas and experiences and may want to share them with you. Embrace their enthusiasm and be willing to explore new things together. This not only shows them that you’re supportive of their work and interests, but it also helps you build a stronger and more dynamic relationship—and they’re going to know that you’re someone they can trust to come with when they have new ideas.

In the same sense, be prepared for last-minute changes or cancellations. Entrepreneurs often have busy schedules, and unexpected events can arise. Try not to take these changes personally, and be understanding of their situation. Instead, find ways to be supportive and flexible. Maybe you can reschedule your plans for another day or connect virtually if they can’t make it in person. 

couple on picnic date

However, this will only work if you, the partner, communicate your needs to the entrepreneur you’re dating, and they respect your desires.


Chat it Up!

Effective communication is crucial for any successful relationship, but this is especially true when dating an entrepreneur. Entrepreneurs often have crazy schedules and juggle multiple responsibilities, so clear and open communication is essential for maintaining a healthy and happy relationship. 

Don’t be afraid to communicate your own needs and expectations clearly. If you have a 9 to 5, you probably only get a certain amount of time off a year. If you plan a vacation during these weeks, and your entrepreneur partner wants to join, make it clear to them that these are plans and commitments that you can’t change. One of the most important aspects of effective communication is honesty and transparency.
couple talking at dining room table

By talking about and discussing your desires, you both can build healthy boundaries that can lead to a healthy compromise of habits. If you get off at five and your entrepreneur partner needs to work until midnight, ask if they can take a one-hour break to watch a movie with you or go on a walk. It may stress them out at first, especially if they’re in the groove of things, but if you put emphasis on your desire for quality time and you make that clear, then your partner should accommodate that. And if they can’t, then maybe they can take a day off and spend it completely with you.

Of course, this conversation is geared at you, the person dating the entrepreneur, and how you can learn strategies and tips to incorporate your life with an entrepreneur. But there’s a whole other side to this conversation, and that’s how the entrepreneur opens up their time for you. If your entrepreneur partner isn’t respecting your wishes and desires or making the same compromises you are, then entrepreneur or not, this isn’t a suitable partner and not someone you should sacrifice your time for.

Effective communication is essential when dating an entrepreneur. By being honest and transparent, avoiding assumptions, staying connected, and being patient and understanding, you can build a strong and successful relationship with your entrepreneurial partner. Don’t be afraid to speak your mind and express your feelings.


Final Thoughts

Dating an entrepreneur can be exciting, but it can also be challenging. Be patient with your partner as they navigate the ups and downs of their business, and be understanding when they need time and space to focus on their work. And with any relationship, don’t sacrifice your time to someone who isn’t giving you the same respect.