For myself, I've got another kid on the way. That makes two. You would think that under the circumstances I would want to stay in my so far stable e-commerce job.

Maybe so but that doesn't keep me from thinking of other options. One option would be to go off on my own and build something. I've had enough experience and formal training to theoretically build a product and a business model around it. Realistically, I've got enough cash savings to let me do something like this for maybe 4 months. I've tried to come up with something in my spare time but I've not pushed to get it to the next level.

Another option is to hook up with a friend like Bill Dagan who started his own boutique consulting firm. With a bit of hard work and imagination, I might be able to get somewhere in a small bootstrapped company. Less risk, less potential reward.

What should lead you is that inner voice that tells you if you are happy or not with the situation you are in. Does your work fulfill you creatively? If not, do you see a way as they say in boxing to "punch to get out" that is make a niche for your self that fulfills you financially and creatively.

If money is not the end all for you, and you can afford to live, I advocate listening to you heart. If your heart says to take a risk, take a risk. Whatever doesn't kill you will make you very strong.

I've taken a few risks but nothing too ballsy. I know that my stint as a sales engineer opened up a new set of possibilities for me. It also gave me a view into dealing with C-level execs. Sales experience is a big piece of the puzzle you need.