Dating an Entrepreneur (from the Entrepreneur’s Perspective)

The season of summer lovin’ is in full swing. Cuffing season is on the way. But before you get too excited, you’d better think twice: You’ve got a business to run.

Some folks can’t cope with dating a business owner. Others will happily adapt to your lifestyle and support your professional growth. Knowing the difference can make or break your ability to maintain a self-sustaining brand and your mental health as a self-employed person. 

The key? Finding someone who understands—and supports—the time you put into your business. 

Ten to twelve hours a day, six days a week, is not uncommon for people growing their brands. And even though you may have come to accept this, it doesn’t mean your partner will. Here’s how to maintain a healthy relationship as an entrepreneur (and sus out someone who might not be a great fit for your lifestyle).

An entrepreneur is intrigued by a future thriving business more than their current relationship.
Dating an entrepreneur can feel like they’re more concerned with the prospect of a thriving business than the possibility of a healthy relationship.

Blurring the lines between work and life

“It’s my birthday, candles are lit, friends are singing, my phone buzzes,” Branson Knowles, head of Top Mobile Banks, recalls. “It’s work; we’ve got a problem that needs immediate attention. I sigh, excuse myself, and spend the next two hours on the phone, pacing around the yard, my slice of birthday cake left unattended and my partner’s amused yet resigned smile etched in my memory.” 

It’s a scenario that many self-employed professionals know. It can be tough to draw the line between your work life and personal time. But if you’re serious about your relationships—be they familial, friendly, or romantic—you’ll have to find that boundary sooner or later.

There’s a dichotomy in being an entrepreneur: you’re a half business entity and half an average human. Starting a business is like having a baby. It needs your constant attention, care, time, and even sleepless nights. But it doesn’t grow up—it just keeps growing and demanding more of you. That is, unless you learn to set boundaries and strike a balance.”

—Branson Knowles

Knowles notes that achieving a healthy business-relationship balance isn’t about striking that perfect 50-50 split. Instead, it’s about clearly identifying your priorities and knowing how to adjust on the fly.


Tips from experience

I can attest to Knowles’ lessons from my own life experience. In a previous relationship, I kept my schedule relatively fluid to accommodate time with my partner. 

I saved low-effort tasks for when he was home during my workday. This way, I could follow along with a video game he was playing while I worked. When I could block off days to relax, we got the time to hike, visit a museum, or go on a dinner date. 

Thanks to the somewhat adaptive nature of my workflow, I often matched his days off, which supported my own weekend work-life balance

Knowles reminds us workaholics: “Starting a business doesn’t mean you have to renounce your personal desires, just like being in love doesn’t mean giving up your entrepreneurial dreams.” Here are three ways you can make it work for both your business and your love life.

1. Find a hobby that you and your partner both love. 

It’s best to identify something low-effort. This way, it’s easy to integrate into both hectic and laid-back work weeks.

2. Take your partner’s schedule into account when building your own.

If you control your schedule, try to accommodate your partner by matching up your days off whenever possible. 

3. Resist after-hours correspondence.

Muscle memory will have you opening up your email app almost every time your phone is in your hand. Do your best to resist it. Being mentally absent from one-on-one time with your partner is just as bad as not spending time with them at all.

Just because I wasn’t at my laptop, it didn’t mean that I was disconnected. My free time was being eaten up by thinking about work, leaving my mind and heart only half dedicated to everything else and leaving me feeling exhausted.

My partner was right: I wasn’t going to achieve anything by worrying about it. But, I was going to achieve a lot by NOT worrying about it. So, I pushed work out of my head and continue to do so when I’m not at my laptop. 

It allows me to be fully present with my partner and others around me, and allows me to disconnect. I find that when I do return to work, I often feel more rested and ready for whatever the day has in store for me.

—Ray Slater Berry, Founder & Manager of DSLX Ltd


Placing boundaries on your workday

Sometimes, making that first step into a relationship is the hardest part, especially as an entrepreneur. Michael Donovan of Niche Twins remembers a time when he fumbled the dating phase: 

I was on a dinner date, sitting across from this wonderful woman, but I was so caught up with checking my website traffic stats that I barely paid any attention to her. She left before dessert, understandably upset, and it hit me hard. That was a wake-up call to get my priorities straight and start setting boundaries.

—Michael Donovan

The truth is, such a mistake can creep up on you at any point in a romantic connection. However, it can become a much bigger issue when you’re established in your relationship, particularly after the honeymoon phase. 

Once you’re more comfortable with your partner, you might start reverting back to the habits you had as a single entrepreneur. Suddenly, you just want 30 more minutes on the clock… then another hour or two… until finally, you’re back to working those 12-hour days you once  shortened to spend time with your once-crush, now-lover. 

It’s not the worst thing in the world to work a full 10 or 12 hours as a business owner. But it can be hard on your partner. The key to making it easier is being open and consistent in your communication so they know what to expect.

A business owner keeps busy during the week and relaxes with their partner on weekends.
As an entrepreneur, healthy dating can be a stress-reliever.

Tips from experience

You’ve got to know when to snap out of work mode. It’s easier said than done. Donovan suggests that you reassure your partner that they’re a priority in your life while also making your commitment to your business clear. 

If you’ve got to work long hours, be upfront about that. And if your workload frequently shifts from heavy to light and back again, be clear about that, too. The last thing your relationship needs is last-minute cancellations and broken promises of quality time. 

My work tends to be pretty open-ended. I never know exactly how long an article will take to draft, edit, or revise. Depending on the complexity of the assignment and the deadline, I could be working for several hours or stretching the task over multiple days. 

My partner would try to wait up for me, but there were plenty of times where I’d stay up working into the early hours of the morning. It broke my heart every time he went to bed without me. 

In hopes of saving you (and your partner) the heartache, here are my top tips for self-employed professionals with slightly unpredictable schedules. 

1. Take as many breaks as you can throughout the day. 

If your partner works part-time or from home, take several 10-15-minute breaks to spend time with them. That way, you don’t completely neglect them if a task demands an indefinite amount of time. 

2. Don’t give false hope. 

One of my biggest pet peeves during work is the question, “When will you be done?” I can’t always answer it, and I won’t lie or give a false estimate. 

Be honest with yourself and your partner—if you don’t know, you don’t know. (But that’s not an excuse to stay up all night working.) 

3. “You are not your business.”

Remember David Mason’s, founder of Barbells Abroad, mantra. Don’t make your business your whole identity. Develop a sense of self apart from your profession. Otherwise, you’ll get lost in it and lose your ability—and possibly, even your will—to end the workday, making yourself completely unavailable to a partner or a date. 

An infographic showing the advantages and drawbacks of dating an entrepreneur.
Dating a business owner—yes, even being self-employed, yourself—has many pros and cons.

Keeping up mutual support

Remember, your partner has professional ambitions, too. You should be just as supportive of their achievements and aspirations as they are of yours.

But despite over half of “American daters” being interested in co-owning a business, it may be best to keep your work and love life separate. Integrating your business and relationship can make it difficult to not only spend time alone but also break up, if that ever becomes necessary.

Ryan McKenzie, co-founder and CMO of Tru Earth, suggests that entrepreneurs find ways to encourage and support their partners outside of their businesses. In other words, don’t make your brand the center of all the milestones you celebrate together. Leave room for your partner, too. 

At the same time, McKenzie says that you can afford some time away from work, too. Give yourself enough time off the clock and, if need be, away from your partner. 

“Don’t forget to nurture your personal well-being. Setting aside time for yourself and engaging in activities you enjoy can benefit both your mental health and your relationships.”


Tips from experience

I once considered blurring the line between my work and love lives by offering my partner my services to build up his brand. Thankfully, I didn’t, as it would have made the relationship too transactional and introduced tension unnecessarily. 

This doesn’t mean it’ll never work for anyone. It just means that you need to know yourself and your partner well enough to determine your boundaries. 

My boyfriend and I kept our jobs separate. Whenever he got a promotion or joined a new company, I always congratulated him and told him how proud I was. He did the same for me when I completed new projects and publications. 

McKenzie and I have a few pointers on how you can achieve the same balance while upholding self-care in your own entrepreneurial and romantic endeavors. 

1. Be careful mixing business and personal life. 

According to Mckenzie, it can be tempting to involve your partner in your business. But separating the two realms is important to maintain a healthy balance. 

Working for or with your partner can (and probably will) confuse your interpersonal dynamics. 

2. Don’t get a big head. 

It’s easy to become a bit big-headed about the importance of your work as a self-employed professional, especially when you’re the main breadwinner of the household. 

Tame the ego. Your partner’s work is just as important as yours. 

3. Communicate openly with your partner. 

Let each other know when you’re going through hard times at work. Listen to each other’s needs and be ready to support each other when the going gets tough. 


I knew you were trouble when you walked in

Sometimes, even when you do things “right,” your partner simply refuses to accept the realities of dating an entrepreneur. 

For example, before my previous boyfriend and I were ever in a relationship, I was abundantly clear that I regularly worked long hours and that this would not change in the foreseeable future. He seemed to accept it. But as time passed, he demanded more of my time, to the point of toxicity

Adjusting my schedule to enjoy video games with him during the workday or hiking in the evenings/on weekends was never enough. Our quality time didn’t count for him because it wasn’t scheduled in advance, but rather it became available as I continuously adapted my workload. 

To him, my rare need to reschedule a family event became an attempt to get out of the gathering, despite my attendance at the new time and date. When it came down to unwinding alone, he accused me of not wanting him around. In short, he was a major jerk, always centering his needs above my own and those of my business. 

These types of people will degrade your mental health and, ultimately, the stability of your business before you know it. Be discerning and recognize the signs of someone who says they understand and support your lifestyle before they prove to you that they never did to begin with.

When dating an entrepreneur (or dating as an entrepreneur), it's important to recognize healthy vs. toxic qualities in a partner; this graphic compares the 2

Possible impacts of an unhealthy partner on your business

Putting up with a partner who relentlessly complains about and undermines you can have serious consequences for your business. 

There were countless days where I had to cancel my entire workday because my toxic boyfriend would make me feel so horrible or put me in such a heightened state of emotion that I simply couldn’t focus anymore. Other times, he’d make me feel so guilty for talking about work that I began to bottle up my feelings and thoughts about clients and projects. 

It got to the point where the only person I could consistently talk to was my therapist or my journal. And the pressure of being the main breadwinner, with a partner who demanded I spend less time at work and less time discussing it, made it all 10x worse. Such mental and emotional isolation can make you bitter and unpleasant to work with. 

You must be discerning about who you do and do not allow into your life as an entrepreneur. If not for the sake of your business, then at the very least, for the sake of your own mental health.


Love your business and your partner

Maintaining a business and a relationship is harder than it seems. You’ve got to manage your own work-life balance and well-being while also being attentive to your partner’s. All the while, you’ve got a brand to grow and clients to serve! 

It’s a tough deal. But it’s not impossible. 

Being upfront about your job and what it takes to run a business is critical when dating as an entrepreneur. As long as you’re honest about both your own needs and your partner’s needs, you’ll see your business and love life flourish.