I've been running my own business for over 12 years and can't really think of any major problems. Probably the main things were trying to wear every hat. Having to invoice, collect money, make the sales, create proposals, and all that other stuff -- when all I really wanted to do was help people make their websites better.
But you learn, and you outsource and it's all good. For me, what made it go smoothly was that I was never attached to the outcome. I hadn't really set out to be an entrepeneur and business owner, I just sort of fell into it. I was literally prepared to give it up at any time if it was no longer fun. Amazingly enough, that's a perfect attitude to have with your business because it gives you the freedom to do whatever you want.
Recently, I decided to grow my business and I have an office and employees. I can't really continue to have that same attitude as others depend on me and I have to meet payroll and all that fun stuff. I am trying hard to not worry about that stuff as I know it will only hinder my progress rather than help, but it's difficult not to think about!
I know for a fact that the less you worry about making money, the more you will make. I just need to try to keep that attitude as I sometimes watch the bank account dwindle while I'm building up my infrastructure and investing in the future of the company.
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