Do You Run Your Business Like a Dating App?

“You can’t just say that to him,” my brother-in-law scolded me. “Tell her Jess.”

My sister, looking regretful, “Yeah… you can’t say that to a guy.”

“Why not?” I asked indignantly, honestly perplexed by their responses.

What was my verbal transgression?

I had gone out on a date with a guy and… gulp… told him that I liked him and I wanted to see him again.

Like a scene out of a bad rom-com, they proceeded to school me on the rules of dating.

I was 36, a year past divorce and starting to play the field. It had been 12 years since I’d dated. I wasn’t looking for the man of my dreams. I was looking to have fun, go out, meet people and make up for too many sexless seasons.

In the weeks prior they had set me up on all sorts of dating apps. How they knew about these things I have no idea – they’ve been married with kids for years. For sure they were living vicariously through me, looking over my shoulder as I swiped left, then left again, and the occasional right.

“Not that guy,” my bro-in-law would say. “You can do better.”
“He’s cute,” my sister would chime in. “You should give it a shot.”
Go team!

“That’s dumb,” I responded to their “rules of dating” diatribe.
“Why would I want to date someone who’s intimidated by me saying what I want?”

They looked at me with expressions of utter hopelessness.

Flash forward a year. New city. A plethora of dates under my belt. Pretty sure I’m ready for a real deal relationship. I meet a promising prospect. I roll just like I do – straight up, shoot from the hip, real and raw. He ends it after 5 dates.

I’m ragingly pissed off. I haven’t been dumped since high school. This stings. Big time.

Do I even like this guy? I wonder. Or is my ego just bruised?

I realize it’s all ego and decide I need to get over myself.

I run away to the beach for a weekend and through 48 hours of sunshine, sand, saltwater and the better part of a bottle of tequila I determine that I’d rather be alone the rest of my life than have to pretend I’m something I’m not in order to have a relationship. If me being me freaks a guy out, then he’s not the guy for me. Period.

I make a list of what I want in a relationship, in a partnership, the non-negotiables. It’s a long, long list. It reads like an entrepreneur / personal development junkie’s 10 commandments (except that there were about 30 of them):

Thou shalt be happy with thine own life
Thou shalt not be needy
Thou shalt respect the opinions of others
Thou shalt be invested in thine own self care
Thou shalt get that my work is important to me and that I’m never gonna be a 9-5er
Thou shalt not be made uncomfortable by my emotional, intuitive, woo-woo-ness

You get the picture.

I was looking for a partner who would fit into my life, complement it, honor & respect who I am and what I bring to the table.

I wrote the list and then I went back to the real world.
And 6 days later I met him.

Here’s how it happened: I showed up fully myself.

I told him that I work a lot of hours and sometimes I work at night, and I love it. I told him that I absolutely must go to yoga, write in my journal, and meditate on a frequent basis… like almost every day. I told him I was training for a marathon and that meant very few late nights and Saturdays monopolized by long runs. I told him that I dance this thing called Qoya that’s about connecting with the divine feminine, that we use crystals and angel cards and that all my friends are super woo. I told him that I travel a lot and in fact, I was going out of town for 10 days and I fully expected he’d be seeing someone else when I got back. I told him I was hard to date.

“Okay,” he said. And smiled through it all.

Months later he told me that he’d had the same revelation not long before we met — that if he couldn’t just show up and be 100% himself, if he had to try to make someone else happy, then he wasn’t interested.

Years later, we’re both still showing up 100% ourselves in what feels like a true partnership.

Now, I’m not naive. I realize that relationships are challenging and they evolve over years and decades.

I also know this:

Starting with authenticity and alignment is a way, way (way) stronger foundation than anything you could build following “the rules”, showing up the way you think you’re supposed to, trying to meet someone else’s expectations, trying to make them happy.

My question for you is this:

When it comes to your business, are you showing up fully, authentically, 100% yourself, in a way that feels aligned with who you are and what you value?

Or are you showing up like a Cosmo reading, rule following, people pleaser, swiping right for everyone who seems even vaguely promising, like you’re trying to win them all over, whatever it costs you — integrity, dignity, freedom? 

Are you looking for clients/customers whatever the cost or are you willing to hold out for true partnerships that are built on a foundation of aligned authenticity and sustainability?

Are you building partnerships or chasing one night stands?

Don’t get me wrong… a one night stand can be a lot of fun, and a business one night stand might just be what you need to pay the bills. Today.

BUT it’s not a sustainable way to run your business.

If you’re slapping on lipstick and laughing at someone’s bad jokes week after week after week just to fill up your calendar, that shit’s gonna get old after a while. Before long you’ll be hiding out at home in your pjs with a pint of Ben & Jerry’s on Friday night.

And the same will happen to your business. I’ve seen it more times than I can count.

Hell, I’ve done it myself.

Hustling without alignment is EXHAUSTING.

You can only do it for so long before you burn out and want to hide out.

If you want to build a sustainable business, you have to do the alignment work first.

Build a foundation of authenticity. Show up and shine in all your imperfect glory. And trust that you’re awesomeness will attract the perfect clients to you.

If you’re playing the short game – quick cash and out – then by all means, hustle it up.

But if you’re in this for the long haul, then authenticity matters more than anything. It might require more patience, more trust, more conviction, more risk.

But do the work. It’s worth it. I promise.