"Fail your way to success." Really, self-help section?

You’ve probably heard this trite crap rebranded six ways from Sunday, so I won’t join the legions who abstractly proselytize it. Instead, I'll just tell you how I really feel about failing.

Knowing right from not being wrong

It’s not totally your fault that you don’t want to fail at things. The negative perception of failure was woven into your spirit from the moment you were barely old enough to fail.

Your parents probably used some set of negative reinforcements to keep you in line. Granted, this is necessary stuff. Serving up a diet of no's is a parent's duty.

The no’s echo far beyond your childhood doorstep, though.

Failure aversion truly becomes a way of life when you go to school, an environment where failure is anything but right. The modern American school system demonizes failure.

Failure is an F. Failing in school means you don’t move forward. Failing in school also happens when you speak up, stand up, look different, or dare to ask a question that’s anything other than an instruction clarification. School rewards failure with embarrassment.

By the time you reach the senior years of grade school, you've learned that the system rewards you for being on time, sitting still, following rules, and staying in line. You learn that average earns an A.

Then, after being normalized and infantilized for nearly a fifth of a century, something magical happens: You go to college.

Suddenly there are fewer rules, fewer authorities, fewer consequences for abnormality. It’s a huge shock, but for most, it’s a helluva fun one. Many people refer to their college years as the best of their life. I think the bliss of college life has little to do with kegs, hormones, and favorable metabolism, though.

College is a golden age of self discovery because you’re allowed to be a self for the first time in your life. If you want to skip a class, fine. If you want to schedule your first class at 3:00 PM, that’s okay too. You have choices. You’re free to make them, enjoy their rewards, and suffer their consequences. It’s an education in experimentation.

And it will never happen again.

College is just a momentary departure from the real world—a spring break in the grand scheme of your life. You need a paycheck, after all, and the only way to get one is to go back to school.

So, you enroll in corporate America, school for adults.

Like grade school, you’re told where to be, when to be there, and for how long. You learn that school was right: life really is just an alternating series of five- and two-day segments.

Instead of being picked up by a bus, you take a train, or maybe a car pool. You’re then dropped in your cubicle – a vial of ingredients: one part human, one part computer, trace amounts of other inanimate inputs, and no parts originality. A steady drip of electronic instructions are fed into this three-walled box, and if you’re the normal human ingredient, output happens on the factory floor—a landscape that looks eerily similar to a classroom when the cubicle walls are removed.

The school mentality quickly sets back in in the corporate school house. There are cliques, often cafeterias, and always the unspoken rule of not failing through the unwavering observance of instruction. Whatever you do, don’t do things wrong. Be the same as everyone around you, and you’ll be sure to get the same raise as everyone around you.

Clarify at all costs. Don’t—not even for a second—wonder if you’re doing the right thing. Know it.

A late life commencement address

As someone who has managed people, been managed by people, and seen people managed by people, I’ve come to a simple conclusion.

People who move forward—by any definition—must fail out of normality. And the simplest way to fail more in the corporate school house is to ask fewer questions. A great way to ensure that you’ll never ever graduate from school is to constantly ask your boss for clarification like you learned to do in school.

The need for explicit instruction may be so deeply ingrained that you crave it, and you sit fidgeting until it arrives. If unclear instructions land in your inbox, does it breed angst until you vanquish all opportunity for misinterpretation?

Vague orders shouldn't trigger nausea. They should be seen as an exit sign in the corporate school house.

Instead of groaning when your boss gives you a vague directive, look at it as an opportunity to be yourself.  Use judgement. Assume things. Make decisions, even bad ones. Get in the habit of replying with answers, not questions.

Don’t be afraid that you’ll give your boss the wrong output to a vague instruction. You will sometimes. And you will fail on occasion. But in this chapter of your life, failure is a bargain. It's a negligible expense for discovery and self-improvement.

Over time, your boss will likely realize that you don’t need instruction because you’re really good at solving problems on your own. Not only that, by walking without one hand held, you'll be more agile. You'll get better at fending for yourself. You'll learn things about your business that no one else knows.

Instead of being another human ingredient to production, you'll become an indispensable asset. Instead of being an employee, you'll become a brand. Your boss and your company will become your client. Everything will be negotiable.

And all of this can happen without ever physically leaving the corporate school house.


Step one is to mentally graduate from school. Where you go after giving yourself this diploma is entirely up to you. Just know that the best years of your life never have to end. Contentment results from having a sense of identity; being appreciated for it is bliss.

What have you failed at lately?