How to Disappoint Your Parents without Accidentally Pleasing Yourself

Like most people that have never accomplished anything of note, I like to consider myself an experiential person. Which means that I live more for experience than for stuff.

Stuff like a nice car; a big house; fancy vacations; or being out of debt. You know, the stuff most adults get once they decide to be grown ups. The kind of stuff your parents want for you.

I can’t help it. I read Walden at age 16 and I never quite got over it.

As a result, I didn’t do a great job at buying into the system, even though the system was the only thing I was ever good at—I was a good student; the kind of student that thoroughly studied Transcendental authors. (Or would that be Thoreauly studied [wink])

This convenient passion for living life to the fullest also meant that I left a lot of jobs before I got really good.

In fact, in many things in life, I’ve quit just as I hit Seth Godin’s proverbial dip.

Summed up, the dip is the point where you’re bored, but you’re still not good. And if you can get through that, you will eventually succeed. Unless the dip is actually a dead-end. But we can talk about that in a different post.

I’ve tried to be brave, but in much of my alleged bravery, it’s possible that I’ve also been stupid. Even the fact that I’m writing this blog right now is evidence of my unhealthy attraction to stupidity—I reduced my hours at work so I could, without sacrificing tv time with my new wife, have more time to write.

Who does that???

I do. This guy right here.

The impression that I’m actively trying to live life is important to me. Not so important that I risk everything to pursue my dreams, but important enough that I constantly feel restless, frustrated and dissatisfied.

Pushing through the hard, boring, tedious times when everything feels inefficient and too hard, and you think you suck, and you feel trapped, and you just want to enjoy life, that part isn’t easy to get though.

You hear the advice all the time—be bold; brave; take risk; follow your passion; your bliss; your heart. But there are mouths to feed and bad decisions to regret and to pay for…

And I know I should get out of debt. But I have this idea in my head that everybody is in debt and that it’s not that bad and that I’ll get out of it later.

I really think I will get out of it later.

Once I get a job that pays me what I’m worth. Or maybe once my business takes off.

Except, as Penelope Trunk will tell you, startups are pretty much a money suck, so the shy side of my brain tells me that I will probably have for the next 10 years the same debt I’ve been carrying for the last 10 years. But I ignore that side of my brain because he’s such a buzz kill.

So instead, I try to keep one foot in what most people consider real life and the other foot in the messy mud puddle of dreams.

I mean, at the very least, I’m writing this blog. And I already have, what, three posts? So what if I’ve started about 12 other blogs over the years, all of which never got much more than three posts.

This time I mean it.

Plus, I’m writing a book. I’ll tell you more about that some other time.

But, really, is there a blogger out there that isn’t writing a book?

I’m just a guy in a coffee shop with a computer, trying to suck the marrow out of life through a broken straw.

And my half-assed, semi-cowardly approach to living my dreams may hurt me in the end. It certainly weakens my position in the world of normal, middle-class, american adults.

But I don’t really see myself belonging with that group. Even though I’d also never be accepted by the cool, artistic kids living in their cars or in their shared, rustic, run-down hipster apartments.

Still, it feels better to write a book or a blog post than it does a TPS report.

It feels good to pretend to be a writer. Or a musician. Or just someone that doesn’t fully buy into the basic culture of the suburban wasteland.

It feels good to set some time aside and say, “I’m spending 3 hours of my life on something I may not be very good at, and I enjoy.”

And maybe I’ll find focus; traction. Maybe I’ll find my voice.

Maybe you will too, if you just get out there. If you just do 1% more than you did yesterday.

But if you’re going to split your time between your dream life and what grown ups call reality, know this:

A handful of disappointment comes from placing your imaginary future into two different models of success.

If you live a life next to Walden pond, you should probably plan on living in a small cabin (or a shack. or a trailer. an old van, maybe).

But many people want the benefits of both lifestyles. They want the freedom and satisfaction of living life deeply, of sucking the very marrow out of life, without giving up the simple pleasures of having a stable, good-paying soul-sucking job, of having a big house, a happy family, a dog and a boat.

So be the guy that has the boat. Or be the person that lives in the woods.

But maybe don’t get your heart set on wakeboarding Walden pond.