That is a good point that I didn't think of - "What if"
Better to have loved and lost than to have never loved at all I suppose. You are very right that I would always be wondering.
I've never thought of myself as someone who was afraid to take risks. That being said, I've had some shots that I've taken over the years backfire rather nicely in my face. I had actually been trying to convince 3 other coworkers to start our own company. One guy was completely on board, the third was interested but he wanted others to fund it (nice try) and the 4'th was downright scared like a little girl. The two of us could not have made a successful go at it and so the guy who was on board recently quit in disgust and moved to another better opportunity. (He was one of my good friends at work.)
I'm not actually that worried about it not working out between the two of us (knock on wood) as I've worked for him as a consultant for 9 years. He knows me, and I know him. The beauty for him is that I am already part of his organization. I know it inside and out (obviously). There will be no time spent training, or getting to know, or figuring out. (That's a huge bennefit for him.) Other than setting up an office in Toronto, I hit the ground running. Neither is there any recruitment cost for him (which can be substantial).
The risk is complete failure of the company due to the economy in which case, there will be no severence because there will be none to be had. I will do my damndest to ensure that that does not happen. He runs a good company. In my line of work I've seen several companies like his and his is without a doubt one of the best run, and most professional. He's grown from a company of 1 (him) to a company of 50. His problem is that he's working himself into the ground because other than me, he's not got anyone to help him out.
Where I work now I am secure because I am working for several clients. If any of them slow down, or close, it doesn't really impact me because there are other clients to take up the gap. Unless there is a complete failure of the Canadian economy my current employer is not going to close shop.