Failing Like a Boss

I failed a lot in the past two months since leaving my cushy corporate job in Alaska.

What’s funny? That’s not even a hard thing for me to admit. Quite the opposite. I’m proud of it.

I used to avoid failure like the plague, only coloring “within the lines,” in order to get all of the gold stars and accolades that were deemed worthy of pursuit by my parents, peers, media and society as a whole.

I managed to “win” at a lot of those things too, by listening to the well-meaning advice of others. I managed to game the system from within — think of the honor roll, dean’s lists, varsity sports teams, scholarships and name brand schools and affiliations you could think of. And you know what?

Most of it fucking sucked. Hard.

Why did it take me over 30 years to figure this out, if it seems so simple to many out there that have courageously walked their own path and beat their own drum since childhood?

Well, as it turns out, walking your own path isn’t as simple as some of the advice-givers and self-help writers would have you believe.

There are a few common, and thorny obstacles to confront:

Social Conditioning — The way we’ve basically been trained to behave. Complete carrot and stick dynamic at play, since our first kiss from our mom.
Acceptance within a tribe / Sense of Belonging — Human’s (shout out to Americans!) love to call themselves independent — when the reality is we’re INTER-dependent at our best, and co-dependent at our worst. No man is an island.
Vanity, Ego & Pride — which take a lot of internal work to truly master, and it’s never truly “done,” it’s an ongoing process.
Hope — we have to have some evidence, whether external or some internal belief that things are going to improve and get better in our lives, in order to keep forging forward on our current path.

Becoming aware of these potential obstacles can go a long way from turning them from a hindrance to an accelerant forward on your path.

What have you been failing at recently, and how has it been instrumental to your bigger picture growth?

Most of my recent failures and cock-ups (love that term) have come via website and other tech related hassles to my business getting off the ground with initial traction, traffic and compelling content. As much as I love the Internet and all that it is capable of for my generation, I am just now realizing the depth of my ignorance of all the inner workings.

That’s tough to admit, as I like to consider myself a fairly tech—savvy person.

You’d think, in the year 2014 with all of the amazing tech and communications advancements in just the last 5 years, getting a good-looking website (that does what I fucking want it to!) off the ground wouldn’t be as challenging as it seems to be. Can’t I just drag and drop things to be where I want them to be, and have the website know exactly what I want it to do?

No? Crap.

Turns out, I needed a big ole slice of humble pie, so I could just sit back, shut up and learn from others. Noted.

For a moment there, I even thought the way forward for me was to become a programmer, in order to build my own sandbox from the ground up.

FAIL.

I lost interest in that pretty quickly, and remembered one of the best rules of top-notch entrepreneurs.

Seek out the best talent and PAY THEM. Don’t try to specialize at everything just to save a buck. Time is worth more than money.

Fortunately, I wised up.

I know myself well enough to know that my strengths lie in long-term strategy, bringing talent together & project execution — so I’m sticking with that. I’m pumped my own hubris was able to subside long enough for me to hire people whose strengths lie in coding, design and other aspects of web development.

The thing is, even though I am hiring people to help me with the tech stuff behind the scenes, I couldn’t help myself and had to start tinkering with the code and other tricked out things behind the scenes in WordPress.

Why I Can’t Just Leave Well Enough Alone

This part is simple. I learn by fucking things up and putting them back together again — hopefully a bit better than they were, and me a little wiser for having the stones to risk breaking something. This applies to many areas of my life, not limited to:

Experimental (and controversial) Dating & Relationship Strategies
Failing a Graduate School Class — And nearly losing a $50,000 scholarship in the process
Getting into amazing physical shape,letting it all go to shit — Just to get it back again by getting disgusted enough with myself.

You could say that I have a whacky passion for blowing certain aspects of my life to smithereens, just to see what the fundamental building blocks are, when I’m forced to put it all back together.

I believe most people just accept things at face value, that certain things just “are,” and we have to go along and accept them as is.

The unconscious script we tend to run says something like “who are we to try to tinker with things as they are, improve them, challenge them, or…GASP, perhaps jettison them from our lives altogether!

This can apply to jobs, relationships, body types, intelligence, and other “accepted” institutions.

Hogwash. (I’ll never say hogwash again)

Steve Jobs said it better than I can:

Life can be much broader once you discover one simple fact: Everything around you that you call life was made up by people that were no smarter than you and you can change it, you can influence it, you can build your own things that other people can use.

BOOM

Ole’ Jobs is giving us carte fucking blanche to get out there and start breaking shit. If we want to have an exceptional life, it means we need to start doing less accepting and more tinkering. Ahem, blowing shit up on purpose.

Tinker. Fail. Re-build. Make it better.

Is there really any better teacher than getting your own hands dirty in the sandbox?

I’ve yet to find one.

Get dirty.