Why I Love and Hate Being Friends with Entrepreneurs

Most of the entrepreneurs I know are workaholics.

Workaholism is an addiction to being busy. It’s a constant need for more — more growth, more revenue, more scaling, and like any addiction, there is never enough.

Over time it becomes an obsession, and we are driven mindlessly by the idea that somewhere in the not-so-distant future there will be a haven, a reprieve, a time when we can “not work so much” because we’ll have accomplished what we set out to do.

For many entrepreneurs like me the choice to be self-employed or start our own business was a reaction to our parents’ generation. It was our own “4-Hour-Workweek” revolution, and we vowed to not be a slave to the man and not to postpone our happiness until retirement.

So how is that going?

I know many business owners, some incredibly “successful” — but they aren’t free. In fact, they are just as trapped in their job as anyone working in corporate America — maybe even more so because they are now responsible for the lives of their employees as well. If they were some corporate stooge, they could just give 2-weeks notice and roll the fuck out. Peace bitches! I’m off to backpack Europe.

We’ve fallen into the same trap as our parents’ generation — the “I’ll be happy when…” trap. Instead of “I’ll be happy when I retire” we now say “I’ll be happy when I make 10K/month in passive income” or “I’ll be happy when my company sells for millions of dollars”.

It’s the same lie, repackaged for a different generation.

It’s a lot like the heaven myth. If you walked up to the average spiritual seeker today and said to them “you should work hard now so one day you can enter the gates of heaven” they would laugh at you. Spin that story into “you should work hard now so one day you’ll be enlightened” and they’ll say “where do I sign up”?

We love to tell ourselves we’ve evolved, but the truth is we’re still human — and part of the human condition is being addicted to a better future. It’s the pot of gold at the end of the rainbow, and instead of looking up and marveling at how beautiful this rainbow is, we start searching for gold — all the while missing this brilliant display of colors that’s happening right now, in this moment.

That’s our life. More, more, more — never satisfied with what’s in front of us.

“We Should Hang Out More”

This brings me to the reason I love and hate being friends with entrepreneurs. I love them for their their willingness to think outside the box, their creativity and fresh ideas — and I hate the fact that it’s so hard to have a real friendship with them.

We have to play calendar karate to set aside time, then when we finally do it’s a relief to just be hanging out, walking on the beach or shooting hoops together. Then we part ways and I always hear the same line — “we should hang out more”.

Yeah motherfucker, we should — but not “after you finish this project” or “after you launch your book”, because that’s like an alcoholic saying “just one more drink”. It’s never one more drink, and for the workaholic entrepreneur being busy is not a temporary state, it’s a permanent fixture.

I live in a sleepy surf town north of San Diego called Encinitas, and even here it often feels like my friends keep a calendar that’s analogous to the Mayor of New York. We are workaholics, and we justify it by telling ourselves we are “changing the world” or “making an impact” when the reality is we’re just as neurotic as the next over-worked asshole who posts pictures of himself with his laptop at the beach.

How ridiculous is it for people to post pictures of themselves working at the beach? Why does everyone think that has anything to do with happiness?

Here’s what that picture means to me.

They aren’t enjoying the beach because they are working — and if that wasn’t bad enough, they can’t even work because they are too busy snapping pics for Instagram. On a scale of 1 to 10, how much do you want to be that person’s friend? Exactly.

And yet, these are people I love and am close to, because on a deeper level we share the same values. Freedom, creativity, sticking it to the man, we love all these things — but somewhere along the way we started compromising and strayed from the reasons we got into entrepreneurship in the first place.

I’m not saying we shouldn’t “follow our passion”, start businesses and live the life of our dreams, but I am saying that while all that’s happening let’s not forget the simple things that actually make us happy, and let’s keep our friends close, because we need them to keep us honest.

Deep conversations, long walks for no good reason and quality time are things that I want more of, and when my friends tell me how they are scaling their company to triple their business over the next year they might as well be saying to me “we won’t be hanging out much”.

And that sucks. I know it sucks for me, but I also imagine it sucks for them, because underneath that workaholic shell is a person who gets sick of staring at their computer screen all day.

Underneath that façade of busyness is a person who would really just love to spend a weekend in the woods, or take off to Asia for a month and live on twenty bucks a day.

And underneath my shell of pissed-off, blogger-ranter guy — is just someone who misses his friends.

The sentiment in this article represents one of the reasons I started IntimacyFest. I wanted to create an event where people just focused on connection, not all the things we do to get connection.

This year IntimacyFest will be June 15-18 on my favorite piece of land in Southern California. For more info visit intimacyfest.com or the Facebook event.


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