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February 4, 2020

How To Tell a Date You’re an Entrepreneur that Quit His Job

In 2016 my online business did well enough that I decided to quit my job and pursue it full-time. I finally had some free time without the job, so I decided to check out the dating world. I had this notion that women would be super into me now because of the successful business.

“So wait, you don’t have a job?”Confused Girl

Crap. I’d forgotten that women are very pro-job. I also forgot that entrepreneurs sometimes get negative reactions from success.

With Valentine’s day coming up, I thought I’d indulge myself and take my first stab at dating advice on this blog. Here’s my advice on how to explain to your first date that you’re an entrepreneur without a job.

Wait, Women Don’t Get Riled Up About This. Do They?

Women respond poorly to telling them you run a business and don’t work a job. When I tell other people this happens, I usually get one of these reactions.

  1. There’s no way women react this way to you being an entrepreneur. Women love successful men. Ergo you must be a terrible date/person, and you’re explaining this wrong.
  2. I’m an entrepreneur who has been through this, and I know exactly what you mean.

I used to be the former. I thought I’d have to beat women off with a stick when I quit my job. At that point, it was becoming obvious how well the business was doing.

It’s a natural thing to think, but it’s wrong. If you’re telling a woman what you do, she will usually not react well to finding out you don’t work a job. Let’s explore why that is.

Your Profession is Unfamiliar (AKA You’re Weird)

Just like actors in Hollywood, we all get typecast into specific roles. For instance, you probably feel like you know what every Will Ferrell movie is about. Even when given no other information.

The same thing happens with jobs. If I told you I was a nurse, policeman, accountant, or janitor. You immediately feel like you know something about me.

But, when you tell your date, “Money comes out of the Internet,” no-one knows what to make of that. In a way, that’s good, but in a way that makes you “the other.” It’s difficult to form an emotional connection with somebody you feel that way about. Emotional connections are the primary purpose of the date. Strike 1.

You Come Off as Lazy

In this society, we think of people who don’t work as lesser people. Don’t believe me? Go talk to any stay-at-home Mom about stay-at-home mom-shaming.” These are Mothers raising children for Christ’s sake! If we turn on Moms, we’ll literally turn on anyone without a job.

For most entrepreneurs, people assuming you’re lazy is pretty rich. I built my business while working a full-time job. I spent years working every waking moment to get it to this level. It’s infuriating for someone to assert that I’m lazy because the company I built from nothing pays my bills now.

But, you can’t take the bait. The person you’re talking to will make an offhanded remark like this, and you just have to let it go. Sure, you’ve got the chops to win the argument, but on a date, there is no “winning an argument.” By winning, you lose. Strike 2.

You Think You’re Better Than Me?

You will get the comment, “So wait, you don’t work a job?”

Your instinct is going to be to explain that you have a business that makes lots of money, so you don’t need to work a job. You don’t want the woman to think you’re a complete dead-beat.

However, money is a sensitive subject. Remember, the point of a date is to connect. You’re not going to be doing a lot of connecting if you’re sitting around talking about how you make all this money and don’t have to work. While you explain that, she’s going to be sitting there thinking about her shitty job and how she has to go back tomorrow.

Rather than being a reason to connect with you, it becomes a pretty great reason to hate you. Strike 3.

You Come Off as Full of Crap or Overcompensating

Women have the same type of typecasting done to them that we do to people with jobs or Will Ferrell movies. We all think that women are very into super successful affluent men.

This stereotyping causes men to shout how affluent and successful they are at women even when they’re not. Ironically, even though you actually are affluent and successful, by talking about it directly, you don’t come off that way.

You come off like all the other guys trying to shout how great they are. You come off as less-confident by trying to quantify your success. It starts to feel like a plea for the other person to like you. Strike 4.

So how do you fix this problem? How can you tell a woman what you do without running into these pitfalls?

Well, you’re in luck because I have painstakingly failed my way into the solution. Here we go!

1) Avoid Interview Style Dates

When you go for food or drinks with your date, there’s not much to do besides talk. If the woman doesn’t know what you do for a living, it will be the first question she asks you 100% of the time.

Good luck recovering the date if you fall into any of the above traps within 5 minutes of sitting down. You might as well get up and leave at this point.

The solution? Go do something where small-talk isn’t the first thing that happens. Go for a walk. Go to the zoo. Go on a hot air balloon, it doesn’t really matter what you do. Just do something active where the focus isn’t entirely on the interview portion of the date.

After you’ve been walking around looking at giraffes for a while, the dates going well. Now you can screw up the above things, and it won’t be as big of a deal.

2) Come Prepared With Other Interesting Things To Talk About

You’re going to get asked what you do for a living, no matter what. Your goal is to have already set a positive tone before you get to that conversation. Once your date likes you, you have more leeway with screwing up this conversation.

But, this subject will eventually come up, so let’s go over how to deal with it.

3) Tactfully Brand What You Do

You’re going to get asked what you do and how you phrase it is vital. Luckily, there’s a quick and dirty way to brand it that works wonders. Let’s see what that looks like.

“What do you do for a living”Girl

“I work for a local media company that sells x, y, and z online.” -Me

“Oh, that’s cool, what do you do there?” Girl

“Well, it’s my company, so technically I do everything”Me

How is that Any Different than Saying you Own a Business?

You’re probably saying, “Shaun, that’s no different than saying I own my own company.” And you would be very wrong. Here is how it’s different and why it works.

Step 1: You Establish Company Legitimacy

When you say, “I started my own business,” it comes off as sketchy to a stranger. You’re clearly a person and not a company. They’re going to be very skeptical.

Instead, you need to carefully introduce the brand to establish its legitimacy. This way you won’t have to convince the girl of this later when she’d have otherwise become skeptical. The thought that it’s sketchy never enters her brain because you established that it was cool before she had any reason to suspect otherwise.

Step 2: Tell Her You Work There Because You Do

I work more hours on my business than most people work at their jobs. It’s also not a lie to say I work for this company as it pays me a salary. So I go with that.

If you said, “I run a business and don’t work a job.” You’re inviting a nasty discussion about how you don’t work a job. By phrasing it this way, you’ve snuck into the bank without triggering the alarm. Congratulations!

Step 3: Tell the Person You Own the Company

Twist ending, you do tell her that you own the business.

Since she had to dig this fact out of you, it doesn’t come off as bragging. Because you phrased everything the way you did, you didn’t trigger the “sketchy company / he doesn’t have a job / is this guy poor” alarm.

However, there is always a chance she’ll react poorly to this info no matter what. And in that case.

Conclusion: Don’t Date Women Who Can’t Handle You Being an Entrepreneur

Some people just aren’t compatible, and that’s OK. I love my business. It’s a big part of my life that isn’t going away any time soon. If somebody can’t appreciate that about me, I’d much rather get them out of my life ASAP than pretend that it could work out.

Shaun Poore went out on a few dates after leaving his job thinking women would be extremely impressed with the whole starting a business thing. They weren't. They were more scared at the social implications of me not having a job than they were impressed by what I'd built. It's something I found strange, but to each their own.