Honesty When Dating as an Entrepreneur

When we think of entrepreneurs, we think of Disney’s Brave Little Toaster and his (or her) quest to be a success. Being an entrepreneur is a brave undertaking. It takes guts to step out of the normal 9-5 and take a chance on a dream that is bigger than yourself. But, what a lot of people don’t tell you before you take that leap is that it’s going to make a lot of other areas of your life challenging.

Honesty When Dating as an Entrepreneur

One of these areas where being an entrepreneur can cause issues is the world of dating. You see, unless you’re planning on exclusively dating only other entrepreneurs, you’re going to have to make some special considerations. People that haven’t been business owners or haven’t tried starting their own company are going to struggle to understand what you’re doing, why you’re doing it, and what the struggles are you’re going to face.

Luckily, we said that being an entrepreneur “can” cause issues in your dating life. It’s not an absolute that happens just because you’re an entrepreneur. With effective communication and some proactive steps, you can have a wildly successful relationship with a non-preneur (okay, maybe that’s not a real word). You are not doomed to struggling with dating just because you’re trying to start your own company.

The key to this success comes down to one word – honesty.

In this article, we’re going to talk about the importance of honesty when dating as an entrepreneur. If you can learn to be honest with a new potential mate, you’re going to find things work out a lot easier. For those of you that are entrepreneurs or are setting out on the road to start your own business, we highly recommend you take a few minutes and read what we have to share with you today.

You can’t be mad at someone else or blame them for not understanding your life choices if you aren’t willing to honestly explain them to them.

The three things you don’t talk about on a first date – money, politics, and religion. You’ve probably heard someone over the age of 65 say this on at least one or two occasions. The problem is that this cliché is outdated and not something that people really abide by anymore. Frankly, we don’t mind, though. We’re big proponents of open communication even if it breaks grandma’s rules.

Even if you want to follow grandma’s rules, you’re still most likely going to go on a second date with someone, and grammy never talked about keeping away from these topics then. Basically, it’s going to come up. Your date is going to ask you what you do for a living. This is not because they’re some closet gold digger (hopefully). They’re going to want to get to know you and what you do for a living is probably a decent portion of who you are.

When they ask you what you do for a living, what are you going to say? Well, if you’re like a lot of entrepreneurs we talked to, they doctor and doll up what they do to try and make it sound a little better. Why? Well, there’s something a little less appealing about saying, “Oh yeah, I work 16 hours a day, 6 days a week, and make zero dollars trying to make this crazy idea work.”

While that might seem like the right thing to do, it’s going to create issues for you in the long run. Here’s the “bottom line up front.” The more honest you are in the first conversation you have with a  new date, the easier things are going to be in the future of your relationship. Remember, “bad” news does not get better with time.

Is the truth really that bad, though? Yes, you might not be making much money right now, and there may be a chance you fail. But, the positive or negative of that all comes down to how you frame it. Let’s look at a scenario and show you the right and the wrong way to frame what you do.

Let’s say you are starting a new t-shirt business that you are passionate about. You sold a few shirts and realized that you could possibly make a lot more money if you took things to the internet and to trade shows. But, you had to buy a bunch of product up front, pay for marketing, a website, SEO, etc. You also have to spend a lot of time at trade shows, packaging, and shipping products, designing new shirts, etc.

Basically, you have a cool new business idea, you’re not making any money, and you’re spending a lot of time with “not a lot to show for it.” Now, let’s look at the right way and the wrong way to share this with a new date.

The Wrong Way

“Yea, I’m an up and coming clothing design mogul. I’ve got product moving to four different countries, designers in the middle east, and my production team is in southern Asia. We’re making a big move now hoping to position ourselves strongly to compete with the major players in the industry. What do you do for a living?”

We get it. Yes, you design clothes and are up and coming. But, just because you shipped a couple shirts to people in Mexico, Canada, the US, and one to Europe does not make you an international businessman or woman. And your production team in Asia? You meant the company you found on Fiverr in India?

If this is how you’re presenting your business, you’re not doing yourself any favors. Here’s how you should be presenting this to a new date.

The Right Way

“Well, I decided to take a chance and pursue my passion of designing t-shirts. It’s a new company, so I’m not exactly crushing it yet, but we have some really strong leads, and I work my butt off every single day to try and make my dream happen. People think I’m crazy for taking the leap, but I’m a big proponent of chasing your dreams and going after what you want even if everybody else thinks it’s nuts.”

Bravo! If this is how you’re sharing your business endeavors with a new date, then you’re doing it right. We can see all of you that aren’t doing this sitting there in fear right now. How on Earth could you ever dream about being this honest with someone?

Here’s why this is important. The truth is always going to come out. We repeat, the truth is always going to come out. Why? Well, the world of starting a business is not an easy road, and it comes with a handful of struggles that will humble the most proud.

The struggle is real. The struggles with being an entrepreneur are real. And when these struggles show up, you’re going to be humbled pretty hard. If your mate that your dating isn’t prepared for this or gets blindsided, it’s not going to be pretty. You see, in the second example of how to share what you do, we accomplished a lot of things.

First, we positively let them know that we are passionate, driven, hard-working, and willing to take chances to get what we want in life. All sexy traits. What we also told them was that we were not successful yet, and they shouldn’t think they’re with some super rich clothing design mogul who bathes in $100 bills for fun.

What happens when times get tough, and we can’t afford to go out on a date? Or what happens when we’re so busy that we need to work when we had a date planned? Well, if you framed yourself as this superstar who had already made it, they aren’t going to understand. Why would a big design mogul be out of money or need to work late on a Friday night? Couldn’t they just pay someone else to work for them?

This is why you should never give a false impression of who you are or where you are in your success pipeline. How great would it be if during these tough times you could lean on the person you are dating for support? Well, if you frame things properly from the beginning and they’re on board, they will be there to support you.

Here’s what you need to realize. An entrepreneur is who you are. You are that second way of explaining what you do. You’re going to have ups and downs as you chase your dreams. Two things are going to happen when you use the second way of explaining your job/position.

1 – The person you explain it to is going to get turned off and leave. Here’s a news flash. This is NOT a bad thing. If they aren’t able to support the idea of you taking a chance to make it big and chase your dream, then you don’t want to be with that person anyways. We do not care how hot or cute they are. This is not someone you want to be with.

You want to be with someone who is going to support you and likes who you are. This includes your business endeavors and choice to take the road less traveled. It’s MUCH better to find out that someone isn’t going to support you from the start instead of months into the relationship when you really need the support. Can you imagine if things are going bad with the business and then your significant other gets mad or leaves too?

And, you can’t really blame them. You deceived them, and they don’t want to be with someone who isn’t completely honest with them.

2 – They’ll love the fact that you’re passionate about something. You’ll learn they aren’t all about money, but are excited that you’re willing to take a chance to go out and get what makes you happy. They’ll realize you’re trying to make a life for you and your future family. They’ll see that you like to work hard and you aren’t scared to stare fear in the face.

The honesty will most likely be much better received than you think.

There is one thing that even the most supportive of potential dates is going to need to hear. They’re going to be concerned that you don’t have a plan to support yourself (and way down the road support them). As an entrepreneur, part of being successful is having a plan in place to keep you and your family afloat while you chase your dreams.

Make sure that you have a plan in place for this and make sure that you share it with your new potential mate. It’s important, though, that you do it in a way that doesn’t sound like you need to make an excuse for what you’re doing. Basically, don’t say something like,” This is my passion, etc, etc. But I swear I still have money and a plan to make it while I wait. I promise I am not a bum.”

If you come across like that, they’re probably going to assume you’re a bum. Just add something on to your description from earlier in the article like this.

“I know it’s a long shot that the business works out, but I’m going to give it my all. In the meantime, I’m also _________ to keep the food on the table and the wheels turning at the house.”

That might not be the best example of how to frame it, but you get the idea. Just make sure that you demonstrate that you understand the importance of having a plan to well, keep food on the table. At a later date, you could also let them know you have an exit strategy and a backup plan if the idea doesn’t work. That’s probably a little heavy for the first few dates, but if things start to get serious, it will be something you’ll want to share.

If you don’t have a backup plan, you need to get one. If you don’t have a plan to keep food on the table now, you need to get one. It does not make you a “superstar” who is “super driven and dedicated.” It makes you reckless. And, being reckless is not an attractive quality.

  1. Be honest about who you are, what you do, and where you are in your entrepreneurial journey.
  2. Don’t be scared to tell the truth that you aren’t a success yet. Most successful entrepreneurs go through several failed ventures before they find the idea that helps them make it big.
  3. Share that you’re passionate, driven, hard-working, and willing to chase your dreams.
  4. Make sure that you initially share you have a short-term plan to keep food on the table. In due time, share that you have a longer-term exit plan in case the business dream doesn’t work out.
  5. Remember that an entrepreneur is part of who you are. Don’t be ashamed of it, and don’t feel the need to hide the struggles that come along with it. In the long run, you’ll be happy to have someone by your side who is ready to support you in any way possible. That way, when you are successful, you’ll have someone worth sharing the spoils with.