Mike Rundle observed that experts in the Web 2.0 industry tell others how to be successful, yet they aren’t having much success themselves.

He makes a good point.

I took a business and entrepreneurship course in college and all through the course we were told stories of entrepreneurs who were told their idea was stupid. The story always ended the same – the entrepreneur ignored the naysayers and became successful. At the end of the course, we had a competition where all of our business plans were judged by local entrepreneurs. My team won, meaning the judges thought our plan was the most likely to succeed. The funny thing is, we had been told not to believe what others say about your idea, so in retrospect, winning probably means our idea was the least likely to succeed.

I’ve witnessed the same thing in other areas too. Actors and performers get lucky and are vaulted into stardom, and are asked how they did it. The reality is they’re looking around wondering how in the heck they got there because they failed hundreds of times before and don’t know what they did differently that last time. If they lost all their money and fame and tried over again, they would continue to fail like the hundreds of others that are still failing. Much of what they say isn’t tried and true advice, it’s what they think made it work for them.

Some claim that failure is the right strategy. You make sure to fail so many times that you’re bound to succeed at least once. I read somewhere that the average person fails 9 times before a success, so you might as well plan to fail to get the failures out of the way. While that may be true, there are many people who have failed miserably hundreds of times without seeing success. It’s also not something people need any help with. We can fail quite well on our own, thank you very much.

After all, how many people want to create a web site that will make enough money to live off of? How many people have actually done that? At WordCamp 2006 I attended the session on how to make money with your blog, excited to learn new ways to earn money. At the beginning of the session they asked how much people were making, and I found I was making more than all but two or three other people in the room (many had never made more than $10/month). The presenters provided some useful advice, but I had heard most of it before.

Just because someone has been successful doesn’t mean they know how to be successful, but some people are both successful and know how to be successful. Those people have made it big, then lost it all, and then come back again. From my anecdotal observations however, that’s the exception rather than the rule.

One such person who has managed to fail spectacularly, then win it big is Steve Jobs. At a Stanford commencement speech, he talked about how others can do the same thing.

“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.”

You are the expert. You know your strengths and weaknesses better than anyone else. You know what you are good at and what you’re passionate about. If you work on do what you love and don’t make it big, at least you’ll be doing what you love. Being able to honestly say you absolutely love what you do every day makes you a success, regardless of your critical acclaim, celebrity status or wealth.