What online dating taught me about business

What online dating taught me about business – Paper + Oats

You guys. A note in Evernote has been sitting, unwritten in, with this title for a good 6 months. I’ve been unsure about writing it. Unsure about sharing things. Unsure about people reading these things. But here we are, and we’re talking about dating. Oh boy.

Before I talk about what online dating has taught me about business, I feel like I need to talk about my experience with dating in general. My ex-husband was my first boyfriend. We dated for four years, and then we were married. And then we weren't. I tried online dating for a few months upon moving to Nashville and I went on one single date with a guy that I met on an app that shall remain nameless and rhymes with hinder. He was very nice, but nothing there. I messaged with a few other guys on other online dating sites, but that whole world was just not my thing. Then I started seeing an old friend long-distance, and though the relationship only lasted a few months, I have a very hard time summing it up right here in one sentence. As much as we both wanted it to work, it didn’t, and in some ways, it’s been harder to get over than my divorce.

And that’s it. That’s my short-lived, minimal dating experience. It doesn’t take a thousand dates to know that dating is not easy. Yeah, there’s the fun outings, getting dressed up, washing your hair (I should probably do that more anyway). But a lot of people don’t talk about the ugly side – the uncertainty and the unknown, the difficult conversations, the fear of it all ending in an instant, and then the heartbreak when it does.

Dating is one thing, but online dating? It’s so weird, you guys. Like weird weird. I totally understand that people meet + marry that way all the time, I have close friends to prove it! But for me, I just couldn’t handle it. (I watch too much Dateline, and was convinced they were all going to murder me.)

After wading through these waters (and the popularity of this post), I couldn’t help but notice the similarities between the online dating world and the online business world. When you’re an entrepreneur, you’re kind of like a single-something looking for a new, exciting relationship. You’re sharing all your best qualities, and hoping the people like you. You’re trying different approaches, but trying to stay true to yourself at the same time. You don’t know what’s around the corner, but you’re hoping for the best.


So online dating + online business? Not all the different. Here’s a few similarities to note...


vulnerability is risky business

Those first dates are rough. Wondering if you’re sharing too much or not enough. You’re putting yourself out there, and being all kinds of vulnerable with this total stranger that you hope doesn’t think you’re crazy. The same feelings creep up when you’re starting an online business – you worry about what to share, when to share it, and hoping the people who see it will like you. But the cool part about being vulnerable in your business or on a date – or really any relationship at all – is that connection is made in our weaknesses. In those vulnerable places when we’re not quite sure if we should chime in, those are the places where relationships are formed beyond small talk. In your business, this is the connection you make with your audience where they feel camaraderie with you and the purpose behind your work. Vulnerability is risky business – but it pays off in connections, conversation, and new relationships.  


the unknown is scary

Maybe this is just me, but once you get a few dates in and connections are being made, a relationship is forming, this fear comes creeping in reminding you that the ending is unknown. It could all end tomorrow or it could go on for years. You’re heading out on a road trip, but you’re not quite sure where you’re going. And that’s scary. At least I think so. When you start your business or you shift your focus or you make a big decision that effects your work – all of these turning points have unknown outcomes and it can scare the crap out of you. One time, I ditched all my clients, took my business in a new direction, and I had no idea how it would all turn out. Another time I thought I knew exactly how a relationship would turn out, but it ended up blowing up in my face – actually, make that two times. And each time you start again or shift another direction, the unknown becomes bigger and scarier and… unknownier? Yeah, it’s a thing.


be yourself

But as scary as that unknown outcome can be, it’s more scary to end up being someone you’re not. So be yourself. In your communications online, in your meeting with that one person you’re super nervous to meet with, in your first dates and your last dates and all your dates in between — just be yourself, for goodness sake. There’s already so many copycats out there — both personal and professional — so stick out from the rest, and be original. There’s nothing worse than getting deep into a relationship or a business idea, only to realize you’ve lost yourself somewhere along the way.


it’s okay to quit

And when it’s all said and done, it’s okay to quit. When you’ve given it every last shot you have, you’ve put all your cards on the table, and it’s just not working — the other person isn’t who you thought they were, working on that new project is like beating a dead horse — you can quit. You can walk away and start over. It sucks, it’s hard, there will most likely be crying, but it’s allowed. And you might just be stronger for it.

Your turn

Any other ladies (or gentlemen!) in the trenches of dating and noticing some similarities? Am I the only one that thinks online dating is super weird, but also kind of intriguing? 


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Kelsey Baldwin

Graphic designer + blogger providing design resources to help creative entrepreneurs navigate the world of design + branding for digital products so they can share what they know.

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