Lessons Learned: Why My First Business Failed

Alyssa Gregory
Alyssa Gregory

booksA number of years ago, I was working full-time as a designer and received a lot of requests to design sites on the side. At the time, I knew very little about business ownership, but always felt an entrepreneurial pull and it seemed like a good idea to start a web design company. Needless to say, I learned quite a few things from my initial venture, and thought I’d share a few of them with you.

Lesson #1: All marketing isn’t created equal.

I can’t even tell you how much money I wasted on ineffective marketing. From a massive mailing to local companies that I never qualified, to a decal on my car, to flyers that sat stacked on my desk for two years, I had my marketing focus all wrong. Not to say any of those things won’t work, but they certainly didn’t work for me, at least in the way I was executing them. I thought that by doing something, I was doing the right thing, but all I was doing was wasting time and money by floundering around with no idea of what to do next.

The lesson is not to market your services for the sake of marketing or because an idea sounds good. You need to be focused and intentional in all marketing activities. This is accomplished by defining your business and your goals, and then researching until you uncover the most effective way to market to your target audience. There is a right technique for every business, regardless of marketing budget. Take the time to figure out the right way from the beginning.

Lesson #2: Systems are necessary.

After being scattered, disorganized and stressed with the administration of my business, I learned that you need systems; you need processes; you need standards. Having a set way things are done in your business — from billing, to data management, to your work process — is necessary because it enhances productivity and allows you to take on more. Plus, if you ever want to work with subcontractors, hire employees or otherwise expand personnel, you need documented systems for everything that make your business move.

Lesson #3: Don’t let financial pressure derail you.

Shortly after starting my business, I was laid off from my job (an Internet startup who joined the ranks of failed dotcoms). Then 9/11 happened. I was plunged into full-time business ownership in a matter of weeks. I found myself starting to worry about money, and I took a series of part-time jobs. This was the exact opposite of what I should have done, which was to take my fear of financial shortcoming and turn it into the fight to make my business succeed. I lost precious time at part-time jobs that were completely unrelated to my goals and should have spent that time working on my business.

Financial pressure is tough to deal with when you’re self-employed, but if you’re serious about being successful as an entrepreneur, you can’t let that push you off course. Whether for you that means taking another job, cutting your rates or taking on work that doesn’t support your business goals, it’s a vicious cycle that can hinder your success.

Lesson #4: Be honest with yourself.

In my struggle with my first business, I learned some valuable things about my passions, my skills and my dreams. What I realized was that I wasn’t satisfied with design alone, and my desire to support small businesses in other ways lead me to change my business model. The most successful entrepreneurs regularly check-in to make sure they are staying true to themselves and their business goals as they change over time.

Over the years, I’ve collected a number of resources that have helped me with various aspects of business. Here are some that you might find useful, too:

Image credit: Sanja Gjenero