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I have contracted with my position for quite a few years. I have an opportunity to start my own full time business. I have weighed everything out: good, bad, and ugly. I was specifically asked to do this by other colleagues as a need exists. My field tends to see people branch out on their own frequently and successfully. I’ve had a side business for a long time. It does great. I’ll keep that, too. Guys, I am scared shitless but I feel like I am supposed to do this. Would you do it? How do I get the nerves to go away? I am set up fairly well to be able to afford several months until I’m actually making some money. Not to mention I could always go back to contracting with what I do now worst case. Is it crazy? When do you just do it? Like I said, I have the side business but I have always had the security of my main job.

Deena, I'm sure others with more direct experience with this will post, but meantime I just wanted to offer you some supportive thoughts.

On the Pro side:

a. You have the doors back to the contracting world pretty well-oiled? (You know exactly what to do to get back into that situation, I assume.)
b. Others you know have done this, it sounds like?
c. You seem excited by the opportunity.

On the Con side:

a. No guarantees ever, with self-employment. That's really true of every job, however.
b. Lots of 'former' self-employed, talented folks find they eventually need to cycle back into employment, so what would that look like, in your line of work?
c. We all need a cheerleader, and being one's own boss can be daunting because usually, there are no supportive voices you can count on, day-to-day.
d. Harder to budget with irregular chunks of income, but the real trick is not to let the 'post-payday' flush checking account mislead your spending decisions.

Only you can weigh and measure all these factors, but ask yourself: if you wait a few months to assess the whole situation further, will you feel like you missed the chance to do this? Is it time, in other words, for this change?

Major concerns on starting your own business that stop me are:
Health insurance
Retirement
Having a fail safe if things don't take off or if economy tanks that I know I can get a job w/ benefits again.

I have considered several options outside of healthcare, and will eventually make a jump at some point. But those are the considerations I think on, and plan with, and research on.

We did have a fairly thriving side business for several years to help make ends meet, then we had career advancements, and the time at job made us cut back on the side business.

The problem I had was that I was a tech guy, but self-employment requires selling. I was lousy at selling, and I'm an introvert, so I'm lousy at networking, too.

If your network can keep you employed or if you're good or can become good at selling yourself (and contracts), I'd say: go for it.

Thanks. I feel like I need reassurance. I have went over it 1 million times on paper, in my head, while in the hot tub, you name it. It makes sense yet I’m terrified. I am putting final details into motion and should be making the leap soon.

My business is helping start ups and small businesses.

Feel free to ask me anything. I’ve 15 years experience and can give you some strategies that can help you.