I've always wanted to be an entrepreneur

I’ve always wanted to be an entrepreneur.

Or maybe it’s just that I can’t hold a normal job. I’m too messed up.

I don’t think I can maintain a relationship with any kind of authority figure, such as a boss, without either completely subjugating myself, and then resenting, or just plain rebelling.

I’ve always dreamed of becoming this wonderfully successful entrepreneur at a young age. (And by wonderfully successful, I mean an irreverent billionaire, who becomes rich and famous by breaking all the established rules. No wonder Richard Branson is a personal hero.)

I’m close to 40 now, so I guess that didn’t happen. (Unless of course 50 is so much the new 40 that 38 is still considered young. Nah, who am I kidding?)

I remember Howard Rheingold some years back at the Reboot conference in Copenhagen saying that most big tech industry successes were made by men in their 20s, citing Apple, Microsoft, Google, and others, as examples. Seeing as I was already past 30 at the time, it set off a minor depression in me. Imagine that! I’m much like an anorexic, whose self-image says they’re really fat when everybody around them is like “dude, you’re way too skinny!” I actually, literally, in my own head, thought that I was just on the verge of creating the next Apple or Microsoft. It sounds crazy from the outside, but inside of me, I had to entertain that self-delusion in order to bear living at all.

I’ve always believed that to have any worth as a human being, creating a billion dollar entrepreneurial success was what I had to do. How did I come to that conclusion? I’m not sure, really.

But the belief was that if that didn’t happen, every breath of air I breathe, every drop of water I drink, every bite of food I eat, even the physical space I take up, could (and should) be put to better use by giving it to someone who would go and create that billion dollar success. I was taking up precious resources that could go to someone worthy of it. Me? I’m just a resource-sucking worthless piece of shit. Yes, I can see how ridiculous that is, but a part of me, deep down, still really believes it, even after years of therapy and personal development.

The other thing I was hoping to gain from being a super-successful entrepreneur was entrance into the alternate reality that I was certain existed for the super-successful where the weather would never suck and there’d never be a traffic jam and they didn’t have to deal with the laws of physics when getting from A to B and there’d always be a magnificent chef with amazing, fresh ingredients to cook them a delicious meal every time they might get a little hungry for a snack.

I have had to remind myself (repeatedly) that no matter how rich or successful you are, the feeling of the warming sun on your skin is going to be the same. The look of a magnificent sunset is going to be the same. The feeling of hot water on your skin when you shower at an outdoor shower in the sin is going to be the same.

Yes, you may have a helicopter or a private jet or a fancy car, but the roads you’re driving are going to be roughly the same I’m driving, and no amount of money is going to get you a better iPad or iPhone or MacBook Air than the ones I have. Still, my brain insists on believing that the super-rich must live in an  alternate universe. I mean, seriously, how can anyone stand living in this one?

I guess that’s the core issue here. On my good days, I feel connected, I feel love, I feel that I’m loved, supported, wanted. Some days I even manage to love myself. Some days I might even feel worthy of being here. A little bit.

But most days, I feel like I’m so unworthy, the only way to keep on living is to hope that some day in the future, when I’ve become this wonderfully successful irreverent billionaire entrepreneur, then I’m going to be okay, worthy of being here, worthy of love - perhaps even my own.

But only if I achieve all these things. And the absolute worst thing that could possibly happen is premature love. What would happen if I allowed myself to receive the love that others have to offer me all the time? What would happen if I allowed myself to - gasp! - love myself? Then surely I’d stop striving, and I’d never be worthy of love.

It’s such a weird game that my psyche plays, but it’s been playing it for quite a while, and it’s gotten real good at it.

Every time I learn more about coaching, personal development, spirituality, and whatnot, that just becomes another club for my ego to beat myself up with and keep me stuck in the same drab routine.

And sometimes, I get to the bottom of it, and I manage to love myself. To really love myself. It happened about a month ago, around my 38th birthday.

I talked to Colleen Schell, a coach I met at the Wisdom 2.0 conference, who helped me see that my whole story about being different from others, about not being able to trust people, and so on, was pretty much pure fabrication, based on a few facts that were probably misinterpreted, such as being stuck in an incubator for the first 48 hours of my life. (I’m saying “pretty much” and “probably” because a part of me is still thinking “wait a minute, this really did happen, and it was painful” … the pain was real, but the interpretation was not.)

And that helped me see how this fabrication, this story about being different, and not being loved, and not being able to trust other people, was really all about keeping my own and others’ love away from me, because I felt I wasn’t worthy of love, and that if given love prematurely, I would never become worthy of love. That was the underlying construct that held all of the other stories in place.

And that in turn helped me see that instead of denying myself love now in the hope that I’d improve to a place where I would be worthy of love in the future, I could instead choose to love myself now. And so I did. And it was absolutely awesome!!!!

For a while.

Because every time I see little signs that I’m getting closer - revenues are increasing, more signups to my newsletter, more traffic to my blog - I start getting my hopes up that I really can become this super-successful-billionaire-25-year-old (which would violate the laws of physics). And then inevitably something happens that shatters that dream again. And each time it just seems to get more painful, not less.

I haven’t quite cracked the code yet. I wish I had, but I haven’t. It’s clear that I need to discipline to remind myself to allow myself to love myself. To allow myself to just be. To force myself to not look to the future for salvation.

But looking to the future is what I’ve always done, because the now seemed so painful, so confusing.

I’m guessing that many fellow entrepreneurs share some of this tendency to look towards the future for salvation. I think it was Bob Geldof who talked about creating a business as a way of creating a place where you can exist, because existing in the “real” world is so painful. I may be more extreme than most, but at some level, we’re all misfits.

I while back I got an email from an entrepreneur in his mid-20’s who was close to a multi-million-dollar exit. All of his adult life, he’d dreamt of this. All of his adult life, he’d worked hard towards this particular goal. And now that it was finally within reach - he was depressed.

I guess you can get lucky and get really successful early on in life, to discover, like Steve Jobs, that the money and the success doesn’t really give you what you deep down hoped it would - making you feel worthy, okay, lovable, loved.

Or you can get unlucky, never get much of anywhere with your business, and that way be forced to look for the core issue.

The problem with this kind of “only after I achieve x will I be okay” pattern is that x is completely relative: It’s always 15-50% beyond what you have achieved. It’s not really about what you achieve. It’s really just a mechanism from keeping love it bay. Because deep down, love is what I fear most of all. Because the part of me that fears knows that love is the only thing that can demolish it. Love is the kryptonite of self-hate.


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