I've forwarded this to a friend. After 10 years in a job, things finally fell out and he walked. He hated the job but it paid the bills and kept his family comfortable.

All this time he's been talking how he has been going to work on a startup, do something for himself. After his job finished I said to take a couple of months and get his head clear before launching into anything. It's now a couple of months later, and instead of coming back to me with a plan and some ideas, he's instead going to an interview with someone who rang him up out of the blue.

I'm not sure at this point whether to help overcome his fear or just write him off as a possibility to do something with. I had a couple of good things we could have collaborated on, but I think he is drifting back towards a job he will end up (start out?) hating. In the past this individual has built some tools and sold them on the side, has good networking skills and some good ideas. Personally I just feel he's too frightened to step out, even though they (as a family) are pretty secure financially.

So I guess what I'm asking is should I offer encouragement to step out, or just let him choose to walk back into another corporate job? Should all choices to follow an entrepreneur dream be self motivated, or does it sometime help if a friend gives you the 'it's now or never' speech?