How do you know when the time is right to take the plunge, quit your job and focus on your own business? What about family risks?

How do you know when the time is right to take the plunge, quit your job and focus on your own business? What about family risks? –@adamclay211

What is a risk? I met someone the other day who worked for 38 years at GM. He was a middle-manager so he had no golden parachute (he wasn’t a high level executive) and he had no bronze parachute (he wasn’t a union member). Net result: he lost his life savings, his job, his savings.

There is no corporate safety. The risk to your family is you becoming inbred in your corporate job. You must leave, just as I recommend in the post “10 Reasons You Have to Quit Your Job Right Now!” http://bit.ly/fpBXNZ.

That said, don’t go crazy. Make sure you are smart and jumping to something better than you are leaving.

If you are going to a startup, you are investing not cash (which comes and goes), but your entire life, your dreams, your skill sets, your soul. In other words, do your due diligence.

Here’s a sample checklist:

A)    Talk to clients. Are they happy?

B)    What are the backgrounds of the heads of sales?

C)    Has the CEO built and sold a business before and taken care of his employees in the process?

D)    Does the company have at least 1 year’s cash?

E)    What are their plans for future rounds of fundraising?

F)    Who are the current investors on the board? Do they have deep pockets to keep funding the company?

G)    Is the company squarely positioned in what you feel is a strong demographic trend?

H)    Has the company proven its flexibility (i.e. has it already had a chance to learn from its mistakes)