“Experience is a dear teacher, but only a fool will learn from no other.” Benjamin Franklin
Business owners learn a lot from their experiences. As a friend says, “Experience is what you get when you don’t get what you want.”
In many companies, you can trace the history of their employee issues through their handbooks. The dress code says that Fridays are casual days. Then it goes on to say that casual dress does not include ripped jeans, low-cut blouses, flip-flops, shorts, sleeveless t-shirts, pants that drag on the floor, baseball caps, piercings over a certain number, dressing in the clothing of the opposite sex (Real! I’ve seen it!), or graphics that include crude or offensive language.
You can visualize every incident, the counseling, and the subsequent managers’ meeting that added more language to the handbook.
But the experience that comes in operating a business is usually the results of making mistakes. We don’t tend to change our behavior because of our successes. If it works, we don’t want to break it.
You want to do some marketing. You decide to send postcards to prospects. If they buy, you keep sending postcards until they don’t work anymore. As long as they keep working, you keep sending them. When someone says “Where is your Facebook Fan Page?” you respond “My customers aren’t interested in that. They like postcards.”
How do you know?
We fear making mistakes, but if you do what you’ve always done, you’ll get what you always got. (attributed variously to Mark Twain, Zig Ziglar and Tony Robbins.) As an owner, it’s your job to make 
mistakes. That’s the best way to control their potential damage, and to keep your employees from making them for you.
How do you decide which mistakes to make? That seems like a foolish question. I once saw a business assessment instrument that asked “What is your system for identifying the things you haven’t thought of?” At first blush it seems idiotic, but every one of us would gladly lay out cold, hard cash for such a system.
The problem is, we don’t make the mistakes we don’t try, but we have no way of knowing whether not trying is a mistake. For those of us who founded our businesses, the leap of entrepreneurship was a huge risk. If it was a mistake we failed, but if it worked, if we were tenacious and strong-willed enough to make it work, our appetite for risk began to decline.
When your business is successful, you enjoy the financial trappings of that success. You also feel an obligation to safeguard the livelihoods of the employees who depend on you, and the customers who depend on your product or service. You won’t take a “bet the company” risk except in the most exceptional circumstances.
It’s easy to then progress down the slippery slope of risk aversion. Avoiding a “bet the company” risk progresses into avoiding a bad year, then a bad quarter, then a bad month. If you aren’t careful, it becomes an avoid-loss-at-all-costs mentality. The status quo is safe. Change is risky. Why bother?
But you have to risk some losses in order to have new wins. You have to try new things, or the risk of not changing grows to company-threatening proportions.
Set aside a mistake budget. Periodically, say once a quarter, deliberately spend some time and money on trying something you’ve never tried before. Attempt a new marketing approach. Introduce a new product. Hire for a new position to do something that no one in your company currently does.
If the new idea is a mistake, you have contained the downside risk. If it isn’t, you’ve avoided an even bigger mistake- doing nothing.
