How To Use Dating Rules in Business (Don’t)

I’m not quite sure when it happens, but there’s a certain moment in our teenage lives when our minds become clouded with dating rules. 

Maybe some of us cling onto those “rules” after reading them in a book or seeing someone say them out loud on a TV show.

I remember, years ago,  I was on the phone with a friend when a guy, who made my chest feel like tiny rockets were launching every time his name popped up on the screen, texted me. My friend told me to wait 30 minutes before texting him back.

“But he just texted me, right now, and I saw it,” I said, thinking it was weird to not reply back to something that made me feel like bouncing Jello. “Isn’t that just rude?”

“Jenny,” she said, and i listened closely because she was in a long-term relationship and i was in a long term phase of being always the single one. “It’s all a game, this love thing, that one must play according to the rules.”

“Maybe you’re right,” I said, though i stopped paying full attention after the part she said about the game and instead opened up the text from my crush and wrote back, immediately. 

I was never any good at following rules.

I was sent to the principals office in Pre-K for counting out loud when the teacher told us to count in our heads. I was benched for 3 games on my middle school softball team when the coach told me not to run home from third base and i did anyway, knowing i’d probably not make it safely to home base, but life is about the journey, not the final destination….Right?

So when I started dating, I did everything wrong.

Everything the books, the shows, and the friends taught me to do, I forgot. Wait for the guy to ask you for a second date? Not talk about the itchy topics of politics, religion, or ex’s? Not offer to pay when the bill came? No. I did what I wanted.

I’m 27 now. I’ve probably been on 342 dates. Maybe not that many. I don’t go on dates very often. But when I do go on one, it feels like i’ve been on a thousand bad ones. I’m being dramatic.

I’m 27 now and run my own business, full-time. A couple of weeks ago, when I was trying to score a meeting with a fancy person, a friend of mine said this to me:

“Stop emailing them.”

“I’m not just emailing, i’m calling too.”

“Jen,” she said, and I listened, because I make too many mistakes sometimes. “It’s just like dating, you have to play hard to get.”

No it’s not? I thought to myself. If anything, starting a business is the opposite of dating. Every rule they teach you in dating you can not do when running a business, or else you’ll find yourself out a couple thousand dollars and sitting in a pile of useless business cards for a company that’s as extinct as the dinosaurs.

Here’s what I mean: 

1. Don’t Say I LOVE you too soon

In newborn relationships, people get all jittery and shy when it comes to saying “I Love You”. Nobody ever wants to be the first one to spit those words out and nobody wants to be the only one who has those feelings. In business, you need to be madly in love with your “idea” and your business – or else, when you get a blahh-worthy email at 3am and you’re running on zero hours of sleep and your 6th cup of coffee of the day, you’ll think about shutting down the whole operation. You have to be crazy to fall in love. But that love-drunk crazy is the only reason you’ll stick around when things get absurdly tough. And they will.

2. Play Hard to Get and Seem Unavailable

It’s all about the “chase” – right? Not in business. When opportunities knock in your inbox or leave you a voicemail, you have to drop everything and wrap your arms around them. That sometimes means canceling plans with friends or giving up a mid-day gym session to sit down for a  last-minute business meeting.

3. Only Put in 30% Effort

This is a dating rule I came across when I was research dating rules for this article – and I find it insanely awful. Apparently, you need to put in little effort at first to keep the other person on their toes. With dating, you’re supposed to act nonchalant and blase. This would never work in business. If you’re not putting in every inch of effort, time, and heart into what you’re doing, it will take you 75 years to get moving with your plan or your sales goals.

4. You Have to Be Monogamous.

Start five businesses at once. Start one yourself and then join in on another one with your friends.

5. Expect “Him” to Always Pay

No one’s going to pick up the tab for your monthly business credit card bills or the legal fees you’ll tally up along the way.

6. If it’s Not Love at First Sight, It’s Not Worth Your Time

First impressions don’t mean a thing in business. It’s all about evolving and changing as you go. You don’t need to be “the best version of yourself” when you first launch a business. Your business plan can have holes in it. You can start it without knowing what the heck you’re doing. It’s all about fixing the mistakes and the errors along the way.

7. Enjoy the Honeymoon Phase

I’ve been running a business for two years – I have yet to enjoy more than 5 minutes of “free time”. I have yet to kick my feet up on the IKEA coffee table and watch as the business functions on it’s own. My to-do list has a to-do list.

8.  Don’t Give the Milk Away for Free

“Cause if you do, nobody will buy the milk.” When you first start a business, it’s all about giving out free products and services to people you know and people you don’t know. Test out what you’re selling to see if it works before you scale or expand it to the masses.

9. Don’t Talk About Your Ex-Loves

Always talk about your failures, your ex-businesses, the “ones that got away”. It’ll remind you of what worked and what was an epic mistake.

10. Be Mysterious

Put it all out there. If people read your marketing materials and have no idea what your business is or what you’re selling, then you’ll have zero customers.

11. Keep Your Options Open

Don’t. Go all in. Tell yourself that this business is THE business. Put all your eggs in one basket. Risk everything. There’s no other way you’ll be able to do it – even if in the end it turns out to be a giant failure

12. Avoid Being a Stage Five Clinger

Cling on tight, baby. This is yours and only yours. Tug onto the edges of it like a toddler onto his mom’s yoga pants.

PS. Don’t follow these rules in dating either (except the one about being monogamous – cheating is gross). It’s a gigantic waste of time. Be your own crazy self. Say how you feel and say how you don’t feel. Hug them tightly, if you like them. If that scares them, good. Let them run away like a scaredy cat. You’ll soar into the arms of someone whose eyes don’t bulge over who you are. I promise you that.