Originally posted at Cirillo Hooper & Company

As a small business owner you have to wear many hats. The operations hat, the marketing hat, the HR hat, the accounting hat, the IT hat, the legal hat and many more. This is done out of necessity rather than enjoyment or strategy.

You only have a limited amount of capital and you didn’t want to spend it on web developers, bookkeepers and lawyers, so you bootstrapped and did it yourself. You built your own website, you kept your books on a spreadsheet and you downloaded template contracts and changed a few words. This was done out of necessity, not enjoyment and probably saved thousands. My concern is you also might have a website that scares away customers, a spreadsheet that makes your accountant cringe and contracts as water tight as a sieve.

So when is a good time to stop wearing all the hats? It comes down to cash and opportunity cost. If you believe it is reasonable that you will get more business by having a professional website, then the investment was worth it. If you are spending all weekend doing your books, when you could pay someone a couple hundred to make the problem disappear, then it’s worth it. If the cost of getting a lawyer to review your contracts is cheaper than the potential lawsuit, then it’s worth it.

Sometimes an entrepreneurs biggest enemy can be themself. Know when to take a hat off and start focussing more energy on growing your business.

Photo: http://www.flickr.com/photos/staipale/3963327366/