Career Risk: What if you could view the future of two possible career paths?

“I wish I could see the future of both paths.” Sherry said.  She had the chance to go into a small company run by her friend’s father in East Lyme, CT.  This path would put her in eventual partnership with her friend doing work that she really enjoyed.  Her other option was to stay put in her “safe cubicle” as Sherry put it in Hartford, Connecticut. 
I want to clear that despite my general encouragement to take risk I fully understand the benefits – even if exaggerated and somewhat illusory – of the safe cubicle. From a pure economic perspective, I know that most people will take an $80,000 job over a job that “could” pay $160,000 one year and $60,000 the next, even if the numbers indicate that the risk makes sense. The thought of possibly making $20,000 less will freeze most people even if they have an equal chance of making a great deal more.
That was basically the situation Sherry faced. Sherry believed she would enjoy working in the new company “10 times” more. But she was stuck because of worry about making less money.
So I told her my story. I have a credentials doppelganger. “Ted” and I went to the same law school. We were from the same general area in New Jersey. Our colleges were roughly of the same prestige. Our early legal paths were roughly equivalent in the resume building years of our career. And in 2000 we both found ourselves unhappy at different law firms. 
I took the leap to start an education business which, at the time, was considered crazy, particularly given my academic background. It was a huge financial risk. Ted stayed the course to prevent financial risk. 
As my education companies grew, I find myself in position to being very close to never needing to work for money again – 3 children heading to private colleges will be the one reason to keep generating income! Ted told me that he is having trouble paying his bills. 
I should add that Ted makes a lot of money compared to most people. But – and he said it before I thought it – he’s spent a lot of money to cover up unhappiness.  Had he taken a leap of any sort to happier work, he wouldn’t find himself in his current position: 20 years of unhappy work in order to be financially set and now discovering that all that unhappy work was for nothing.