3 Reasons Entrepreneurship is Like Dating, But Harder

Entrepreneurship is Tougher Than Dating

Whether it's online dating, friends setting you up and everything else in-between, the dating world is a jungle. Not many of us get it right the first go around.

I've met a few of those high school sweethearts who are still happily married into their retired years...so so rare! Yet, the life of an entrepreneur is not for the faint of heart either. Speaking from experience, entrepreneurship is a lot like dating, but much harder.

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Recently, I tried online dating for the first time. It was an interesting experience. More frustrating than fun. Lots of creeps, lots of humble braggers, and lots of blocking profiles required.

Online dating wasn't too different than meeting someone at the work or through friends either. My past relationships have mainly been through work, and boy did I dodge some bullets.

Despite my rocky dating history, the entrepreneurial emotional roller coaster is much tougher. Here's why...

1. Kissing a Lot of Frogs

Frogs are alive and kicking in the gig economy. In the world of startups and freelancing, there are are lot of "froggy" leads. You know, the ones that want to "pick your brain" indefinitely and don't have any intention of paying for your services. Ever.

Sometimes leads become clients, which is great. However, sometimes those clients become high maintenance too. You know, the ones that have no boundaries when it comes to texting, calling, emailing, and basically respecting your time.

So should we all just stay at home and never attend another networking event? Of course not. It's all about managing expectations.

Each time I attend a Meetup or some sort of networking event, I don't expect Prince Charming to be waiting for me as soon as I step in the room.

I expect there will be many frogs among a few potential clients. And that's ok if there are more frogs than potential clients. After all, I don't have the bandwidth to serve every person in the room.

Over time, I've gotten better at reading people so the "dating" period is shorter when I can sense whether it would be a good fit. Bottom line: Keep on dating and kissing frogs!

3 Reasons Entrepreneurship is Like Dating, But Harder

2. Broken Engagement

What's worse than frogs? Tigers what hide their stripes.

My last relationship lasted three years. We talked about getting married and almost made it to the alter.

Towards the end of the relationship, we were doing long distance and going through a really rough patch. I was dealing with tough family issues and he had his own set of work challenges overseas.

After ghosting me for a few weeks, he ended things over text. That was the last I ever heard from him.

This was a guy who would go out of his way, drive across the city to take me home so I didn't have to wait 20-minutes for the next train. Someone who would buy me flowers, just because. Someone who flew across the world to spend time with me even if it was just for a few days.

So back to Tigers. In entrepreneurship, some people show their stripes only when the going gets rough. Other times they are showing their stripes but we might not be willing to see it.

A local marketing agency once asked me to help with one of their biggest accounts. After submitting a strategy plan and doing a lot of work upfront for over a month, they decided to go in a different direction right before signing the contract.

It felt similar to a sudden breakup. We had several emails where it was a green light. Until it wasn't.

But at the same time, I chose not to see the stripes too. Initially, the Digital Director was very excited and responsive to all emails. Then the communication became less responsive and practically ghosting happened all over again. Had I seen those stripes two weeks sooner, it would have saved a ton of time!

3 Reasons Entrepreneurship is Like Dating, But Harder

3. Some People Just Don't Like Peaches

You can be the ripest peach in the world, but there's going to be people that hate peaches. It's not personal.

I learned this the hard way when dealing with the local marketing agency mentioned earlier. Sometimes you just have to give it your all and your all isn't always what the lead wants at the moment.

All that time and effort put into the account felt like a waste. But it wasn't. The lessons were priceless though. Bottom line: It's never personal.

Feeling burned out from entrepreneurship? Thinking of getting off the emotional roller coaster ride?

Before your throw in the towel, we might be able to help make things easier. Be sure to check out these free resources we use to build our business!

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