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You Can Learn A Lot About Business From A Few Dates…

If you know me, or read this site on a fairly regular basis, you’ll know that I’ve been single for a little over a year. Since then, I’ve been pretty much avoiding anything remotely related to dating. I was like a deep sea diver who needed to spend some time in a decompression tank before starting that process again.

At the same time, I am one of those people who realizes that they need to do whatever is scaring the hell out of them to actually grow and become a better person. And so, I bit the bullet and went out on some dates. The results have been somewhat horrifying in a comical sort of way…

But they have also provided a lot of lessons. Some that I can even apply to business. Here goes:

Listen To Your Instincts

I knew that things were doomed with the second guy I went out with before the date even happened. I was thisclose to canceling, but my sister said to give him a chance. I don’t think I’m going to be taking too much advice from her in the future… To say that it was the most horrible date ever would be almost giving it a compliment.

I knew that it was not going to fly, but I still went. I should have listened to my instincts. I definitely trust them in business – and you should, too. The next time you are trying to make a decision, listen to yourself first. What do you think? After all, it’s your business – and your life!

Some Things Are Just Not A Good Fit

Okay – back to the dude from date #2. It really wasn’t a good fit. We had zero in common.  I want to go see bands, go to the museum, or discuss books… That guy had never heard of any bands I liked, and I find it really hard to believe he has ever stepped foot in a museum or read a decent book.

To be honest, the first guy I went out with wasn’t half bad. He had read a lot of  the books I had, and it was cool to hear someone else’s take on them. He had a good sense of humor and we could make each other laugh pretty easily. But there were lots of awkward moments.

His idea of a good time was having a Dance Party USA in someone’s living room, while my idea of fun is going to watch a band. He was into fashion and wore scarves as accessories. I think if a guy wore an ensemble like that to some of the places I go, he’d get his ass kicked. So, yes, there was some stuff in common… but at the end of the day, it would just be more work than it was worth. We’d both be making too many compromises.

In business, some things are just not a good fit. I enjoy  business and marketing. Indie Biz Chicks is the perfect fit for me.  When people ask me if I like what I do, my face lights up and I say “YES! I absolutely love it. It’s who I am and I could not imagine not doing it.” If your business doesn’t make you happy, it’s probably just not a good fit. Find the one that is. You may have to try a few different things, but once you find the one that fits, you’ll be glad you spent all the extra time and energy looking for it.

You Need To Follow Up, Promptly!

There are a lot of “rules” out there about dating. Unfortunately, I have always had a strong dislike of rules and authority. Apparently, the girl is supposed to casually wait a few days after a date for the guy to contact her. Meanwhile, the guy can be out there, thinking about calling, but not calling because he doesn’t want to appear too eager.  At the end of three days, he’s supposed to call. And if he doesn’t call, you should just think “well, he’s just not that into me’ and move on.

I think this is a bunch of bullshit.

Seriously, if you like someone, just call them the next day. What’s the big deal? You went out on a date, right? If they like you back, they’ll be glad to hear from you. And if they aren’t happy to hear from you, there really is no point on going out for a second time, now is there?

The same thing applies in business. Follow up with your customers and clients in a reasonable time frame. If you let them sit around too long, they’re going to find someone else to do business with.

Be Clear And Direct…

Near the end of the date with dude #2, he asked if there was a possibility for a second date. Now, remember, to me, this was the most horrible date, ever. Apparently, he had no clue.  I was honest. I said “no.” My sister, and some of my friends, are a bit astonished that I said that. But why lie? I wasn’t feeling it. I’m not going to lead the dude on.

When you are talking with a client or potential business partner, be clear and direct. Let them know what you are willing to do, what you expect them to do, what you want to be paid, etc. Get everything out in the open so that there  is no miscommunication or hurt feelings later on down the road.

And Most Importantly, Don’t Give Up

Now, when it comes to dating, this is something that I have to remind myself to do. Dating is not exactly the big bag of fun some people claim it is. Honestly, it would be a lot easier to just give up. But how will I ever find the cool dude I’m looking for if I just give up?

Now, in business, I have no problem with this lesson! When I started Indie Biz Chicks, I knew it wasn’t going to be easy to start a website, get traffic, etc. There is a lot of work that goes into a content site. There were a lot of nights where I was staying up till 2 or 3 in the morning, trying to get the site built. I originally created everything in HTML and a few months later, I learned about the advantages of WordPress, so I switched everything over.

I’ve had a major corporation copy my work, I’ve had a hacker try to get into my server and hold my site hostage for money (did he really think this site was making me that wealthy?), I’ve moved across the country, went through a huge break-up, my computer totally crashed and died, I spent months  not feeling good  to find out I had a B12 deficiency and spent some time in the hospital getting blood transfusions… and that is just the tip of the iceberg. This is just stuff that’s happened in the past 16 months. A lot more stuff has happened since I started this site in 2007…

The point is, stuff happens to everyone. The vast majority of us never get anything handed to us on a silver platter. If your business is really important to you, you’ll go out there and do whatever it takes to be sucessful. You’ll hit a lot of roadblocks along the way and there will be days where you feel totally discouraged and want to cry.  But if you really give a damn about what you’re doing, you’ll pick yourself up and do it all again the next day.

There will also be those days when everything just falls into place and you can just feel that you are in the right place at the right time and this is truly what is meant to be. And going through a little ‘business hell’ is worth the days of ‘business heaven’. Trust me.

P.S. If you know any cute single guys in Michigan who like tattooed girls that are into music, museums, and the DIY scene, let me know.

Crissy Herron


Crissy Herron is the founder of Indie Biz Chicks. She is the self-described "World's Best Aunt," loves Motion City Soundtrack, is awesome in the kitchen, and is a proud resident of The Mitten State. (that's Michigan, by the way.) And, oh yeah, she used to live in Alaska. (she likes the cold.)

  • Great article Crissy. I like the correlation between dating and business although sometimes with dating I believe you need to stop the search and trrust that the dude will enter your life no matter what.

    Easier said than done, but it could be the guy who walks past your letter box at the same time as you’re collecting the post, so if the dating gets too tiresome that’s something you could think about.

    After having said that, keep dating so you get more content for your great posts. lol

    Good luck 🙂

  • I like this particularly:

    “If your business is really important to you, you’ll go out there and do whatever it takes to be sucessful. You’ll hit a lot of roadblocks along the way and there will be days where you feel totally discouraged and want to cry. But if you really give a damn about what you’re doing, you’ll pick yourself up and do it all again the next day.”

    Everyone I know who has ever started a business (and I know many) has felt this way… and I have felt this way about dating. The road will be difficult, but if you have it in you to go the whole distance it’s totally worth it.

  • I love this post! It’s excellent!

    A note on dating: I met the love of my life when I was going through a bunch of really horrible stuff and NOT wanting anything to do with relationships. When we met, he was pretty much in the same boat. It’s been almost three years now, and I love him more every day. 😉

    This strategy, of course, does not work when applied to business; however, I have found that if you TRY TOO HARD, people will notice, and that can turn away potential clients.

    Love the blog!
    Jennifer Moore
    JenniferLynn Productions, LLC

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