I used to teach a few classes on various aspects of web development at the University of Alberta and one of the things I would say to boost the students’ confidence was, “every mistake you make, I’ve made a dozen times.”
It’s mostly true. The number might be exaggerated in some cases but every typo, every logic flaw, every design decision that I make is based on having failed in the past.
The one thing about programming failures is that most of the time, you hit the backspace button a few times, type some different keystrokes and you’re not a failure anymore. This isn’t the case for most other businesses.
If I back the microscope out a bit and look at the business instead, I see that most web design companies are pretty good at tolerating failure. Often it means a few less dollars but because the cost of failure is relatively low, the tolerance is high. If you take on greater risk in your business, perhaps the cost is high or perhaps the tolerance is very low, how does your business handle it?
Here’s a “food for thought” article: Creative Class: Failure Essential in the Creative Workplace
Ask yourself, does my company tolerate failure? Does it encourage people to take enough risks? Is it creative?