For me, the consistent point of failure in running my own business is never being able to wear all of the hats. I simply can’t be the salesman, the legal assistant, the project manager, the engineer, the art director, the visual designer, the developer, the quality assurance tester, the accountant, and ultimately the deadbeat bill collector. What’s worse is trying to handle more than one client simultaneously! I’ve let four freelance businesses go by the wayside because I can’t maintain all of these roles. Somebody with more capital might hire people to pick up some of the responsibility, but how can an entrepreneur start a business solo?
There is no simple answer to this other than WORK MORE. Being the boss means you wear all the hats until you can afford to hire people. It means you say no to parties because you are busy. It means you sacrifice A LOT so that in 3,4 or 5 years you can be the guy leaving early and taking vacations. Most people that start businesses, myself included, can not see long term because they are just trying to make it to next month. Work hard and sacrifice and sooner than you think you can afford people to take some of that load off. At some point you have to jump off the cliff and quit the job that supports you so that you can spend more time on it. SCARY time but remember, you can always get another job. That is way easier than spending your entire life wondering “What if”.