A lot of business “thought leaders” and a lot of well respected business schools teach entrepreneurs to not be afraid of failure. They say: “fail early, fail often”. The premise makes a lot of sense – if you are terrified of failure you won’t take the needed risks to succeed. After all if you don’t play you can’t win. But this concept is flawed on a couple of dimensions.

Jason Fried, of 37signals, has a rebellious perspective on this topic in character with his company’s anti-establishment approach. He asks why failure has been glorified in the business context and states that people learn much more from success. Although I agree with the first part (over glorification of failure) the second part I believe can be a bit more poignant.

The fact that American society tries to round the corners on competitiveness and make everyone feel like a winner has been recognized as a major problem. No good deed goes unpunished and the desired effect of trying to make all the kids feel good actually has a strong negative effect on our society. Everyone grows up with a huge sense of entitlement regardless of whether people actually deserve the material goods or positive feedback that they think they do. Many times it is a gross mismatch but they’ve always been rewarded for mediocrity, so why stop now?

So in that context, “fail early, fail often” only perpetuates the entitlement myth. When in reality, failing is most times very very painful. Ask any small business owner if they are as casual about failure after they mortgage their house and pillage their kids college savings to start a business. It is easy to front-load this inspiration on young doe-eyed entrepreneurs and people that want to succeed so bad that they end up making crucial life decisions on emotion. Not so nice when you think of it this way, right?

So how can one distill good advice and motivation from this? Well, my opinion is that there is a crucial component missing in this discussion. It is the notion of “failing small”. This is not a new concept but I’m surprised more haven’t made the connection here. Failing small has another name: “experience”.

For example, when you are hiring someone, one of the most important things to look for is experience. It tells you what they’ve learned, how they’ve progressed and on what trajectory they are likely headed. And typically people put way too much stock into formal education. School will teach you what to do, but most times (at least in business) what NOT to do will prove to be the downfall. You can only learn that from real experience.

So why wouldn’t you apply the same logic in hiring yourself for your next business? You have to be honest with yourself no matter your amount of self-confidence. Second place is not also a winner in the real world – here’s why. If you are doing anything worth doing you can’t do it by yourself. You will need partners, investors, customers and they will all judge you. You will have opportunity costs and major expenses. You will be up against people that are smarter and more experienced than you.

“Failing small” just makes sense. You work on bigger and bigger ideas and put that experience in your back pocket. With every new venture the next one becomes easier and faster. Most importantly, your visual skills improve. You learn what to look for and can react to business killers earlier. That lets you play faster, for higher stakes and with stiffer competition next time.

Ultimately the most pragmatic business advice is to never stop. Always look for the next thing, don’t get emotional and stuck. Always keep learning and dreaming up bigger next steps.

Now calculate your risks, measure your true experience and go get em!