Tagged: Entrepreneurs

10 Things I've Learned While Dating an Entrepreneur

- by Alyson Shane

"Everyone says that they want to date someone driven" John said to me last night "but most people can't actually date someone with drive and ambition because they feel threatened by it."

He made this comment as a result of a conversation we were having about the kinds of things that we talk about with one another. 

Mostly, we talk about work, projects we're working on (freelance or otherwise), ideas we're brainstorming, and articles that we've read online. Most of our conversations are purpose-driven, go very deep, and circle around a few key topics such as Virtual Reality, product development, writing, content creation, and our views about life and our place in it. 

While, admittedly, John is slightly more "on" 24/7 than I am (I'm more like 23/7, sometimes I need to switch on the Wii and play Twilight Princess for the zillionth time) we're both pretty much talking, thinking, and working on stuff constantly. 

Dating someone who is this "on" all the time has been an adjustment. I've never dated an entrepreneur before, and making the switch from dating guys with regular 9-5 jobs that get forgotten once 5pm Friday rolls around has taken some real getting used to.

Below are 10 things that I've learned in this crazy almost-year of being together:

1. Get ready to have a lot of free time

Personally, this works well for me because I also have a ton of stuff on the go and we can optimize our time together, but for a lot of people this would be a real challenge -it's hard to be with someone who is constantly thinking about or talking about work. 

However, this is a good opportunity to make sure that you don't get too caught up in the relationship and become one of those couples who goes into complete hibernation mode once you get together.

2. Passions don't count as "work talk"

I still struggle with this, honestly. Sometimes I just don't want to talk about VR anymore -I don't want to bounce ideas about virtual experiences all night, and because so much of what my partner's work does involves VR sometimes I have a hard disentangling talking about VR the passion from talking about work. 

But it's important to make, and remember, this distinction.

3. Take an active interest in their work or you will go crazy

This relates to the previous point. I learn by seeing and doing, and if I'm just looking at a screen and saying "mm-hmm" my eyes glaze over pretty fast. 

By asking questions, giving feedback and trying to be involved in whatever they're working on, it not only keeps you from going crazy, but also makes them feel validated, important, and can provide them with feedback or ideas that they may not have received otherwise.

4. Kiss your bender days goodbye

When you work for yourself every day lost to a hangover is a day where you could have been improving your service or replying to clients. 

So the days of partying from dusk until dawn and depleting all of your brain waters to the point where going on Facebook is a challenge quickly become a thing of the past.

5. They will forget things. All the time.

At least, things that aren't work-related. John can recite minute details about code he's written or the intricacies of a project he's working on, but he needs constant refreshers on what we have planned this weekend, the grocery list, or phone calls that he needs to return. 

It's not that they don't care -far from it, in fact- but the space in their mind is at a premium and if something isn't an immediate, pressing need (like work) then it gets filed away somewhere, likely to never be seen again.

6. You aren't their only priority

Let me be clear: a good partner will always make you feel special and like you are a major priority in their life, but you shouldn't be their only priority and you might not even be their top priority all the time. 

There are definitely days (a lot, in fact) when I know that John's company is taking precedence in his head over our relationship, and that's okay, because I know he will make "us" a priority if it needs to be.

7. You don't have to be like them

While being with someone who is motivated 24/7 can do wonders for your own motivation and productivity, when you just want to spend the day vegging out eating an entire can of Pringles while marathon-watching BoJack Horseman and they'd rather work on, well, work, it can be hard not to feel like you're just wasting your time in comparison.

But it is totally okay and healthy to take breaks, which leads me to my next point...

8. They need help "turning off"

If left to their own devices they will just work and work and work. That's it. So sometimes they need some gentle (and sometimes not-so-gentle) prodding to actually relax and not just focus 100% on work-related stuff. 

9. Forget having a regular schedule

Traditionally-employed people tend to have pretty predictable schedules; even people working shift-based work, like a server or a nurse, generally have a pretty firm grasp on when they are and aren't available. 

When you're dating an entrepreneur every available hour of the day can (and likely will) be put towards working on something. This is in addition to the meetings, meetups, Skype calls, conferences, hackathons, and other hustle-type activities that come with the entrepreneurial lifestyle. That's just how things are.

10. You will have doubts early on, and that's okay

Dating someone who is constantly focused on other things can be taxing, and I have definitely had moments where I feel lonely, annoyed, or frustrated -and I'm a pretty driven person, myself! 

But the longer we've been together the more I've tried to adjust my expectations around what are and aren't reasonable demands to make of my partner, and when it's okay to make those demands (spoiler alert: I'm not always the greatest at identifying those times...) 

There have been difficult moments, sure, but more often than not this crazy roller-coaster ride has been filled with moments of exhilaration, excitement, pride and, most importantly, fun. I wouldn't trade it for the world.

Have you dated an entrepreneur? What was it like for you? Did I miss anything? Tell me!


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