How to conquer dating and business: 5 contrarian rules for both…

I recently made a few small changes to my professional and personal life and it had profound consequences, what’s weird is that the rules I followed were interchangeable…

A lot of people make this common refrain: treat your business like you treat your dating. The only problem is, what if you suck at dating? Well then that advice kind of sucks. But here’s what’s pretty amazing, if you get good at dating you’ll get good at business too!

So after experiencing an entire year of trying and failing in many (hilarious) ways, and sometimes a lot of genuine pain, here are 5 guidelines that I’ve found work magically which will hopefully save you the trouble.

NOTE: These guidelines apply only when you’re starting out. Once you get established the rules change considerably, but these rules apply to anything from starting a business, to getting a new job, to finding that special someone.

1. Don’t hump his/her leg

This is commonly referred to as “college guy syndrome,” but I think everyone is guilty of it. If you went to college (or watched the movie Van Wilder) you know the college frat party scenario. Guy walks into a party and says to his buddy, “sweet party! let’s get wasted! There are so many chicks here! Let’s get some chicks!” then proceeds to embarrass himself by trying to hook up with everyone and anyone at the party, all on the same night, all within 10 minutes of conversation.

I think the most common mistake is going in for the “close” (or the “clothes”) too soon. It’s an unspoken rule that you shouldn’t have sex with someone until AT LEAST the 3rd date. It’s a good rule, trust me.

It’s the same in business, don’t write a cold email to a potential client or your boss asking for something big until you’ve had at least 3 good interactions back and forth. If you don’t believe me, go ahead keep cold-emailing and cold-calling and trying to hook-up with everyone. Chances are you’ve already tried this approach and have gotten frustrated.

But don’t worry, this advice doesn’t require you to be celibate for 3 years before making a move. Here’s how…

2. Date more than one person at a time

Here’s how to guarantee frustration: trying to date one person at a time, or trying to get one client at a time, or trying to get one job at a time.

If you put all your feelings, hopes, and desires into one person you’re inevitably signing up for a rollercoaster ride. You’re letting that one person’s whims decide whether you’re elated or terrified. If they call you back, joy of joys! But if they don’t call you for 2 weeks, oh no!

Here’s how to avoid getting scared of the rollercoaster: go on more than one ride. If you’re going to apply for a new job, apply for 25 new jobs. If you’re going to start dating, start dating at least 3 people at a time. Of course you’re not going to get all 25 jobs, and of course you’re not going to be a douche and have relationships with all 3 girls/guys. But it’ll give you a much smoother ride and much more options to choose from. Plus it’ll also shorten the process of finding that special job or true love. And, having more options will naturally eliminate college-guy syndrome because you won’t be so desperate. Speaking of desperate…

3. Don’t let them know you love them (too soon)

This one might be controversial, but again this is for when you’re first starting out. Guys make this mistake all the time. They go on a date with a girl they think is gorgeous and proceed with a barrage of, “you’re so beautiful, you’re amazing, you’re gorgeous,” then almost drop to one knee and propose.

Saying things like, “I think we’d make the perfect team!” to a client is not going to get them to like you, it’s going to make them ask questions why you’re so desperate. Just the same, saying “I think you’re perfect” is going to freak your date out. Take it easy, be a little mysterious.

BUT, and this is a big BUT, don’t hide everything either. A lot of guys and girls are guilty of this and it’s the worst thing to lose someone because they didn’t think you were interested in them. Even if you don’t show them you love them, show them you like them. It’s all about keeping them intrigued, so you could say something like, “you’re funny I like you,” or to a client, “your website looks awesome by the way.” Everyone likes to be complimented, but not too often and not too much or it raises questions. (It’s like that saying “if it’s to good to be true, it’s probably too good to be true”)

4. It’s okay to be friends

This is for those A-type achiever personalities who don’t like to give up. Maybe the person you were dating/working with turned out not to be the one. That doesn’t mean you should pursue them even harder. Learn to move on quickly so you don’t fall into the sunk-cost fallacy. You invested time into building a relationship and maybe you only got to date #2, but that doesn’t mean you should be an asshole. It’s okay to be friends.

Some of my best friends came from dates that never went anywhere, and some of my best clients came from people I worked with long ago. Maintain a friendly relationship because people grow and move and change, and you never know if that C+ date is going to become an A+ in the future, or if that small startup is going to become the next AirBnB.

5. BECOME interesting

This is probably the most important rule because it will take you the farthest. Everyone, and I mean EVERYONE, is attracted to interesting people. While it’s obvious how this works in dating, it surprisingly carries over into business. Would you rather fly on United, with its spartan seats and drab lounge area, or would you rather fly on Virgin, with its built-in live TV and quirky safety videos? Both will get you where you need to go but one is far more attractive than the other.

It’s the same for business. Nobody wants to go to a workplace with boring employees who just do their jobs. People want to be around interesting people who keep them entertained. While it’s important to do your job, it’s even more important to put a smile on people’s faces. So if the next time your boss/client asks you “how was your weekend?” and your best answer is, “o I just watched netflix,” you need to change something. Add life to your life and you’ll go a long way I promise.


As always I hope this was helpful and although some of these seem like simple no-brainers, I know I still have to fight to keep myself in check.

Feel free to tweet at me on the twitters if you have any other tips @bogdanyz

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