Taking the plunge from corporate hack to entrepreneur

The first time I worked at a start-up was by accident. I was the executive editor at IDG’s Publish magazine, and they decided to close the publication.

The president of my business unit made me an offer — I could lose my job with IDG, or I could lose my job with IDG and take a job working with him and three other people on a new start-up.

I took the job.

Two years later, that little start-up was acquired by Ziff Davis Media, along with the whole staff. There I was, back in a corporate environment.

I stayed for almost three years before leaving to found my current start-up.

Working in a corporate environment had its perks. I enjoyed hiring a staff, for example.

It was nice to have money to spend on servers and security to make sure that our sites were not going to go down in the middle of the night. I had the chance to work with and learn from a large group of people. And the 401k program and comprehensive health and dental insurance sure were nice.

But ultimately, I couldn’t stay. I finally figured this out on a trip to Arizona after stopping at Frank Lloyd Wright’s school, Taliesin West. After the tour, after an hour of hearing all of the creative ideas that came out of the school, I wanted to cry. All I could think about was going back to my corporate job, where I did just about the same thing, day after day.

That was my breaking point. And most entrepreneurs I talk with who left a corporate environment to start a company had a similar experience. They reached a point where all the positive aspects of working for a big company just didn’t matter anymore — they had to get out.

But what happens after the I-have-to-get-out moment, when the practicalities set in? How does anyone actually leave the corporate world for a start-up?

For me, there were five major things that I had to deal with before I could make the leap.

Other people have a different list. But discovering your list of objections and coming up with solutions (or a compromise that you can live with) is how you will ultimately be able to leave the corporate environment to start your company.

Here’s my list:

A good idea — This may seem obvious, but once I decided to leave, I had to come up with a business idea. Some people already have the idea, but that wasn’t how it worked for me. So I spent a couple of months brainstorming possible ideas and came up with a number that I thought were good enough to start businesses around.

Money — This is the one universal issue that every start-up founder deals with. There are a lot of ways to get start-up money, but figuring out which is right for you and your business — and actually securing the cash — are hurdles to cross before the business starts.

Fear — It’s scary to leave a comfortable job with a steady paycheck for the uncertainties of a start-up. For me, it was even more frightening to realize that I would be ultimately responsible for whether the company succeeds or fails. This feeling doesn’t ever totally go away. But I have decided to just live with a certain, manageable level of anxiety. And I do a lot of praying.

Insurance — This may sound like a petty detail, but it’s really not. Health insurance costs are astronomical, and everyone knows a story about that guy who didn’t have health insurance and got into a car accident. I was able to get health insurance through my husband’s company, but I realize that this solution is not available to everyone.

Support — I admit that I could not have made this decision without the support of three key people — my husband, my best friend and my business mentor. I actually hate to admit this need for approval, but without the support of the people whose opinions I respect the most and who know me the best (all my strengths and weaknesses), I wouldn’t have moved forward. Thankfully, they were all encouraging.

At the end of the day, I know that being an entrepreneur requires a great deal of flexibility, adaptability and perseverance. But I also know that to become an entrepreneur, you just have to take the leap, jump into the fray and start something.

Melissa Chang is the founder of Pure Incubation, an Internet incubator based in the Boston area. She blogs at 16th Letter.

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