Gen Y was born for entrepreneurship. They are confident risk-takers, distrust institutions, crave individualism, are impatient to rise to the top, and want to do something that changes the world.

It should come as no surprise that young people are skipping the corporate world and hanging out their own shingles at an unprecedented rate. However, as a business owner of over six years, there is one thing that I think Gen Y is unprepared for - failure. It happens every day, all the time. It sucks, and it’s embarrassing, but it’s only dangerous if you let it get on top of you.

Here are my top five tips for Gen Y entrepreneurs who want to learn the single most important lesson of business ownership - how to fail:

1. Get Knocked Down

Cool Hand Luke and Chumbawamba (pick your favorite pop cultural reference) both famously, and repeatedly, got knocked down. But we remember them because they got back up again. How you are defined as a business owner will not depend on what you do wrong – trust me, there will be plenty of that – but on how you respond. Conventional wisdom (meaning what old people believe) holds that Gen Y only feels confident because they have never experienced failure.

Honestly, there is some truth in this, overprotective parents being the chief culprit. But, that doesn’t matter; everyone will fail spectacularly at some point. When that happens, there is only one thing that will shut the haters up. Never make excuses or place blame; instead, get up, dust yourself off, and say, “Again!”

2. Listen to the Man

The economic crisis has exposed the corrupt practices of a number of banks and corporations, demolishing the trust of many young people. On top of that, even when not evil, Corporate America can be head-poundingly dull. I certainly never want to go back to the land of fluorescents and cubicles, so I can’t fault Gen Y for wanting to avoid it altogether.

But, if you want to get paid, you are probably going to have to deal with some corporate clients. Watch them, observe their habits, learn their customs and language. At least be able to mimic them when necessary. Eventually, you will find people in those organizations that you bond with on a genuinely human level. But, first you have to learn to…

3. Follow the Rules

One time in a college English class, I wrote an essay that was moody, poignant, insightful, and nearly-Joycean in its exquisite subtlety. It also received a big, fat “F.” When I questioned the professor about it, he said, “It’s a fantastic piece of writing, but you broke nearly every rule of grammar, and that’s just page one.” I tried to argue that I use punctuation more like music notes – to set tempo and flow (still do) – and he said something that I will never forget: “That’s fine, but show me you know the rules first, before you break them.”

I know, you are an outlaw, a cutting-edge, forward-thinking, one-of-a-kind business ninja who is only slowed down by the rules. So is everyone else. Clients want to see that you know the basics first. Establish that, then you can impress them with how different you are.

4. Treat Your Boss like an Idiot

You started your own business, and you got shiny new cards that proclaim you the President/CEO/Emperor, or some other fancy title. Congratulations, you made it to the top! First order of business: figure out how to pay for those shiny new business cards. Being an entrepreneur is a shortcut to the boss’ chair, but it’s also a shortcut to the boss’ responsibilities. The Corporate Ladder came about because people realized that there were lessons that needed to be learned at every step, before you were ready for the top. Now, somewhere along the line, a few rungs fell off, making it harder to get there. But, the lessons are no less important.

Recognize that taking the Corporate Elevator means that you just have way more to learn once you hit that top floor. Be humble, be open to feedback, and be ready to acknowledge your mistakes.

5. Be Selfish

When you start a business, changing the world should never be your goal. Making money should be your goal. Look, I’m all for saving the Spotted Booby, or bringing irony to Arkansas, or whatever noble goal you are passionate about. But, being an entrepreneur in a capitalist society means hustling every day for that cheddar. Not because of the awesome stuff that money can buy, but because if you don’t make money, you will go broke. And, if you go broke, you will never change the world. It doesn’t mean you have to be a jerk, but it does mean that you have to work day in and day out, just to keep your head above water. Most importantly, be prepared to go under, again and again, before you are able to float in the sun. And never, ever, stop paddling.

Companies fail for all kinds of reasons, but people only fail when they quit trying. You got this. Now, go out there and make it happen!

AuthorChad J. Barker