The Entrepreneur’s Dating Game Part 3: It’s Complicated

When I hear the word “entrepreneur”, I can’t help but think of the show Shark Tank. You know, the show where all these different entrepreneurs pitch their businesses to a bunch of wealthy investors (the sharks), hoping for some moola so they can make it big.  Some of the businesses are genius, and the sharks get into bidding wars over who will invest.  Other businesses just aren’t the right fit for the sharks.  But, one thing all of these businesses have in common, are extremely ambitious entrepreneurs, with really great ideas and big dreams.

I’ve never pitched an idea to a room full of millionaires, hoping for some of their money.  But, I am a doer.  I’m determined to a fault.  I have a need to make things happen.  And I’ve had several businesses of my own!  I am an entrepreneur. 

Here’s the thing about being an entrepreneur…it’s like dating. From start to finish, entrepreneurs play the dating game.  And the entrepreneur’s dating game is just as confusing and complicated as the regular dating game. But, the end goal is the same, to find your true love.  The yin to your yang.  Your better half.  The one.  And, when you’ve found the one, it’s magical.

Now, let me tell you all about how I found “The One” that made my entrepreneur heart sing.

Part 1: First Love
Part 2: The Rebound

Part 3: It’s Complicated

The Entrepreneur's Dating Game

Man, the dating game is rough.  So many ups and downs.  So many emotions.  Tears.  Drama.  And it all comes to a head when you find yourself in an “it’s complicated” relationship.

We’ve all been there.  That relationship that has so much going on under the surface, it’s just too hard to explain to people, so you just tell them “it’s complicated”.  Let me introduce you to Emmie Designs.

It’s so complicated, I don’t even know where to start.

I still hadn’t found “The One”

I needed some creativity in my life.  I still hadn’t found “the one”.  But, I wasn’t ready to give up.  I was starting to get a feel for what I liked and didn’t like, and what I needed out of a relationship.  But I just wasn’t sure where to look.

At this point in my life, I had a really solid friendship with Photoshop.  We did everything together.  I met Photoshop around the same time I met my first love.  And when my first love was over, Photoshop stuck with me.  And was there for me through my rebound, and was ready to help me through whatever came next.

I started to have feelings for Photoshop.  Like, we could really be something.  And everyone knows a good relationship is built on a really solid friendship, right? I started thinking Photoshop was exactly what I needed in my life, and it had been there the whole time!

We both really liked digital scrapbooking, and started spending SO much time together.  Photoshop helped me find my creative side.  And together, we designed digital scrapbook pages and digital scrapbook elements.  

The Entrepreneur’s Dating Game

So, of course, my old business partner/sister-in-law and I decided to open an Etsy shop.  Emmie Designs became home to all things digital.  And we really thought we had a good thing going.  Until there were no sales.  Etsy just wasn’t the right place for digital scrapbooking.  It was too complicated.

Ok, so I know one thing for absolute certain.  I like making money.  That is a must have quality in my next relationship (and, in case you haven’t caught on, I really mean business).  No compromising.

Photoshop and I needed to break up.  We were really better off as just friends.  Plus, I’d just been introduced to Photoshop’s cousin, The Silhouette.  You know, to make things even MORE complicated.

I warned you!  Complicated.

This time I moved on from creating all things digital, to creating things with my hands.  My sister-in-law and I were still business partners.  And we kept our business name, Emmie Designs.  We just started using The Silhouette Cameo to create our signs and banners.  Then we even ventured into sewing pillow covers.  We were a mess.  But it was different this time.  At least that what we kept telling ourselves.

The Entrepreneur’s Dating Game

Unfortunately, this relationship with The Silhouette was just too much work.  And we kept doing the same things over and over again.  Until we eventually just couldn’t anymore.  Every now and then we made some money, but I couldn’t rely on it. It was too much.  We weren’t in love.  We were just trying to make something work.

The Entrepreneur’s Dating Game

So we ended things.  Goodbye Emmie Designs! And all your complications.

But, don’t worry, I was getting close to finding “the one”.  And next week I’ll tell you all about how I started my journey to falling in love. Or, catch up with Part 1 and Part 2.

And if you like love stories, check out my real life love story HERE!

comments +

Leave a Reply

Your email address will not be published. Required fields are marked *

get to know me!

about emily


love sweet love



wedded bliss



It's about more than hiring someone to hold a camera and snap a few pics. Wedding photography is about capturing the joyful, bright, authentic moments of your big day in a way that beautifully tells the story of your love.

Your moments matter.

St. Louis, Missouri

privacy policy


st. louis wedding photographer


© 2023 EB photography, LLC

Emily Broadbent Photography