8 Brutal Truths You MUST Know About Loving An Entrepreneur

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It's intense, but it's worth it.

Dating an entrepreneur can feel like dating an alien species. Men are from Mars, Women are from Venus, and Entrepreneurs are ... from Saturn? It can sure seem like it sometimes.

If you're an entrepreneur, then you get it. Our lives can look pretty foreign from the outside. This article will help you explain your lifestyle, your work, and your why to those who may not fully understand you. And, maybe even more importantly, reaffirm that you are not alone.

If you're not an entrepreneur yourself, but you want to date—or are dating—an entrepreneur, this article will help you understand why we do what we do. Because let's face it, the dating lives of entrepreneurs is confusing and challenging. There's a totally different set of mindsets and circumstances that shift the way we look at all aspects of our lives —including dating.

But, it doesn't have to confuse anyone on either side of the dating process. In this article, I'm going to share with you the eight things you should know about dating an entrepreneur. These come from our personal experiences, our client stories and from the many conversations we've had with fellow entrepreneurs.

Now before I tell you about these eight things, I have to tell you this first. As entrepreneurs, our values, our drive and our interests set us apart from many others, but let none of this mean that we're anything but human. We all eat, sleep, and put our pants on one leg at a time.

Despite our work, and our drive to change this planet for the better, we have the same core needs as those around us: sustenance, shelter, love and connection.

Let's dive in.

1. We Believe We Can Have It All

This is both our source of greatness and our biggest challenge. Let me back up a bit so you can get a fuller picture of what I'm talking about. Our story goes something like this.

At some point along the way, we decided that we weren't interested in writing the story of our parents, grandparents and great-great-great-grandparents. We realized that we're the sole creators of our lives. So, we set off to have the densest, most fun, and happiest lives possible.

With our new-found inspiration, we found a way to quit everything that didn't bring us joy. Leaving our jobs, and even a few friends behind, we quickly realized that this was a lot harder than we first imagined.

When we left that job, we started our passion project. But since then, we made little progress towards turning it into an actual business.

With our savings depleting at a quicker rate than we imagined, we started devouring business books, and learning to play the business game became our new 9-5.

Our businesses grew, as did our knowledge of ourselves and the inner workings of the world around us. We came to realize it was all a game, and we started playing to win.

Somewhere along the line came the thought that changed everything: "I can have it all. I can really have it all." All it'd take was a rewiring of our childhood programming and the right mindset, both of which we knew were fully available to us.

We dove head-first into our business, but the rest of our life began to suffer as a result. That just wouldn't do. "I can have it all." So, we started to take better care of our general well-being, but quickly realized that we'd done a complete 180. Now, our businesses were suffering! That wouldn't do, either. 

We began swinging back and forth and still do today (granted, on a smaller scale). We can have it all. We really can. But, the balance needed to make it truly work is tough to pinpoint. We spend a lot of time pushing to the extremes, and missing the mark. Motivation, burst of perfect action, slip up, guilt, spiral, spiral, spiral, motivation ... it never seems to end for us.

Balance. Balance. Balance. We're, well, working on it. If we have to, we'll work until the day we die to figure it out. But, we can and will have it all. 

2. This Is The Deepest Relationship Of Your Life

When we start something, we go all in. We explore the deepest depths in every aspect of our lives. And, that includes our relationships too.

We'll want to share a lot, and learn a lot about you too. And, with that sharing, comes depth. Don't be surprised if you feel unusually close to us early on. We definitely won't be your typical partner.

We've done our research. We've studied people. Maybe we're a bit eccentric sometimes, but we have a really good understanding of humans.

If you're willing to dive deep, we're willing to take you there. Prepare yourself for some tough questions, some big shares, and some serious depth.

3. We'll Fall Off The Face Of The Planet ... Again

We're really good at diving head-first into new things. But, sometimes (more like usually), as we dive into those things, the other aspects of our lives begin to suffer.

It feels really good for us to spend a lot of time with our partners, especially after jumping straight into the deep end together. It's the missing puzzle piece we've been searching for all this time: love.

But somewhere in there is the nagging feeling that our work is beginning to suffer. We'll try to micro-calibrate, and do something practical like setting hours-of-operation, but this whole balance thing? It just doesn’t give us the "hit" we're looking for. We want to feel great. We want productivity in our lives, and, for us, that means going balls-to-the-wall.

We'll dive back into our work, slowly at first, but then, almost out of nowhere, we'll seem to fall off the face of the planet. Our minds will be totally consumed with our work.

We understand how you feel. It must have to do with you, right? Well, really, it has nothing to do with you. We absolutely LOVE you! But, even while we're deep in our work, we're not totally blind to the world around us. We know our relationship is slipping, and we actually feel really guilty about it.

But, we know that if we don't maintain at least a certain threshold of productivity, we'll feel guilty about our business too.

We'll come around soon. Just bear with us. Soon, the guilt of not spending more time with you will consume us. We just won't be able to help but pour our everything back into you.

4. It's Not Just "Work"

You see, when we started this work, it was more about our freedom than the impact. But, when we got serious about it, we realized the impact we could have on real-life human beings.

What once was a crazy idea, has since become a LOT more. It's our way of improving the Universe in some small way. We're adding real value to the world.

We can have it all, and we truly believe that. But, our work just has to come first. And shouldn't it? It's not even just about us anymore. It's the well-being of the entire planet!

And, sure, maybe we've only directly impacted a few hundred people so far. But, our dreams are WAY bigger than where we are today.

Unlike our old job where we were a cog in the machine, we ARE the machine now. We've never been so proud of something in our lives.

Here's the problem, the output is growing every day. We know at some point we need to hire more people to help us, but we've been bootstrapping from the beginning. This is our baby. And, it's just really hard to let a piece of that baby go.

Depending on where we are in the pendulum swing of our continual search for balance, we're either "not working enough" or totally consumed. Catch us in the latter and it may feel like you're dating a zombie.

We know that in times like these, it's probably easy for you to resent our work. After all, last week, we were spending that time with you! But, asking us to "leave our work at the office" is like asking us to leave our legs at the office. It's a piece of us. When we're working on a project, it means a heck of a lot more than what it looks like from the outside.

Our work isn't something we can just set down or shut off. At least, not very easily. Because, in many ways, it IS us. That's why even eluding to the fact that our work isn't important is bound to spark some resentment.

Look, we're not even 100% sure that our work is going to have the level of impact we're envisioning. To have someone so close to us reaffirm the doubts in our minds is worse than a sucker-punch to the face. It's a sucker-punch to our dreams.

Instead, try giving us a gentle reminder that we're a bit off-balance, and we'll come swinging back in no time.

5. We'll Beat Ourselves Up—A Lot

Balance. Balance. Balance. Yeah, we're still working on it.

And, until we get there, there's a lot of spiraling. Remember the cycle? "Motivation, Burst of Perfect Action, Slip Up, Guilt, Spiral, Spiral, Spiral, Motivation."

"Spiral" is in there three times for a reason. It's the nasty side effect of the "I can have it all" mindset.

Deep down, we know we need to find balance, but settling for anything less than perfection isn't high on our to-do list. We became entrepreneurs so we could write our own stories and craft our lives how we wanted it.

We spend a lot of time working with computers, and sometimes we forget that we aren't one ourselves. We only have 100% to give, and it rarely feels like enough.

More than anything,

  • We want a thriving business.
  • We want a loving relationship.
  • We want the epitome of health.

We want it all, and when one or more of those things suffers, it's easy for us to feel like we're not enough, especially when our other high-performing friends seem to have it all figured out.

We don't want to feel bad about ourselves. It just happens sometimes. Bear with us. Give us a pat on the back. Tell us how much you love us and believe in us. Encourage balance. We'll snap out of it.

6. We'll Push You.

We want greatness, and we'll try just about anything to get there. We push ourselves because we believe in ourselves. It's one of our greatest forms of self-love.

And, when we love someone, it's just natural that we'd love them the same way. We believe YOU can have it all, as much as we believe that for ourselves.

We've gone deep and grown some serious feelings for you by this point. Pushing you to your best is our way of showing you how much we care about you. But, the last thing we want to do is make you feel inadequate or lesser.

But, at some point, we're bound to slip up. You'll feel like we want you to change because we don't like who you are. At its worst, you may even feel like you'll never be enough for us.

But, that's far from the truth. We don't want to fix you. We craft every aspect of our lives. Do you really think we'd consciously choose someone we thought was sub-par? No way. You're already so much more than we could have ever imagined.

When we push you, it's because we love you. Seeing any bit of suffering in your life, is a reminder to us of our own struggle. And, you know what we do with struggle? Be proactive about it!

We're pushing you because we want you to love growth as much as we do. Growth has become our life. Seeing our progress gives us the fulfillment we've been looking for, and we want the same for you!

7. We Want To Share Our Freedom With You

As you know, our lives are a bit hectic. But, overall, we're pretty damn happy. We have so much more freedom than we did before.

And, now that you're a part of our life, we want to share that freedom with you. Travel to Thailand for a month? Why not?! Two-week backpacking trip in the Alps? Um, yes! Mid-day walk on the beach? How about every day?!

Our freedom would be empty if we didn't get to share it with those we love. 

8. We're Weird. I Mean, Really Weird

Growth has become our life. And, a part of that is in exploring to and past the "weird" line.

We'll do anything at least once. We take "YOLO" (you only live once) to a whole new level. Chocolate Beetles? "Sure, why not?" Tantric Sex? "Let's give it a try." Polar Plunges? "Of course. I heard they're great for productivity!"

When we're not working on our businesses, we're learning about all the awesome things this world has to offer.

We're modern explorers. We're information and experience addicts. We push the edges of existence. And, over time, our views and interests can start to look a bit weird.

We're not typical in any sense, but we love that about ourselves.

The Takeaway

Maybe you're an entrepreneur yourself. Maybe you're considering dating, or just started dating, an entrepreneur recently. Or, maybe you're in a long-term committed relationship with one of us goofballs.

Regardless, my only hope is that you find some clarity or comfort in these words.

In the end, it all boils down to this: Despite what we say and do, we're human beings. We crave love, touch, and connection, even when we're locked away for a week working on our latest project.

That being said, we're likely to put our businesses before much of anything in our lives. At one extreme, we forget to eat, sleep, shower and even socialize. At the other, we take better care of ourselves and our relationships than 99.9% of the general population.

You have to understand: this comes in waves. As much as we're chasing a perfect balance of the extremes, we rarely find it. And, once we do, we often pop back one way or the other out of a desire to improve even more.

We truly believe we can hack our lives into perfection, but the journey is a bit rocky.

If you can handle our sometimes fleeting heart, we're glad to give you our everything.

We'll dive deep. And, I mean deeper than the depths of the ocean deep. Deeper than you've ever gone with another partner deep. Because that's how we live our lives.

But, sometimes we go a bit too deep too fast. Balance, remember? It's something we're still trying to get a hang of.

We'll chase the perfect life, crafted to our exact specifications, until the day we die. But, to us, the chase is often more exciting than the destination.

If you want to get somewhere and stay there, we may, at some point, have to go our separate ways. But, if you love the chase as much as we do, if you love uncertainty, and pushing to the furthest edges of humanity and possibility, then you're everything we could have ever imagined in a partner.

We'll disappear, reappear, dive deep and run away all within a moment's notice. But in the end, that's just our way of saying, "I love you."

This article was originally published at Dating for Entrepreneurs. Reprinted with permission from the author.