A few days ago, I talked about what gave me the confidence to start my own business, as part of a series going on over at Small Business Trends. Up next, I answer the question, “Have you ever taken a “bet the farm” risk in your business?”:

While I think that there are many things we have done in our business that can be seen by different people as a “bet the farm” move, I can think of two instances where I knowingly knew that I was putting everything on the line.

The first was when I decided to take the side-blog business that I had going on, and turn it into a full-fledged, full-time business. The risk that was that it was either sink or swim. Either it would thrive, or it would die. Luckily, we enjoyed almost immediate success. If things didn’t work out so well, everything that I was doing would have had to have shut down so that I could return to the traditional workforce.

Secondly, and this may be getting a bit technical, but changing the entire underlying infrastructure that we use to publish our websites was a very risky move. Considering that a very large percentage of our traffic comes by way of search engines, and considering how finicky those search engines can be when you make major changes to the structure of any website, it was a real cross-your-fingers moment in our history. We made sure to make the transition as easy as possible by using a carefully crafted .htaccess file to make sure that everything got carried over and that nothing got lost. That was another highly successful move that paid off, resulting in a lot more flexibility as it pertains to publishing our data.

What about you? Have you ever “bet the farm” with a risky business decision that you hoped would pay off?