The soon-to-be entrepreneur

I had the opportunity to speak to a soon-to-be entrepreneur today. He was (probably still is) struggling with the what some might consider the ultimate decision in the entrepreneur’s life, and that is, when to make the jump.

He’s got a sweet job at a Fortune 100 company and is staring at a nice promotion that’s already been offered to him. One of the C-Suite execs actually encouraged him to stay.
But he’s also been offered the keys to a shiny new startup.  Decisions, decisions, decisions.
I explained to him about my experience in making the jump. I had a sweet, cushy job at FirstData in Denver, CO. I lived 1 mile from the office, so I was usually home by 5:15, which, in Denver, that’s a really big deal between April and September. I was making great money. I was taking an old (really old) brand into the 21st century (literally…this was 1999-2000). But my side business was ready for a permanent pilot, and I had a choice to make.
After a lot of thought and careful consideration, I had decided that I wanted to leave FirstData and make the jump, take the plunge, be my own boss, etc., etc. Lots of people encouraged me both ways, but the final kicker was when I presented the whole deal to my wife. I said, “we have 18 months of money, and I want to leave my job and work full time on CWNP.” Her response was epic, and is a huge part of the reason that I’ve been able to carry on as an entrepreneur. She said,

“Go for it.”

So I told this soon-to-be entrepreneur to go through all the positives, negatives, nuts and bolts, ask the investor every conceivable question he could think of, and then present the entire thing to his wife, and see what she says.
Many times, we just need the right person to encourage us to chase our dreams. Everyone else may be screaming “YES!” but they don’t matter.
Ultimately for me, it came down to my wife’s gut feeling and response, and the quote from Michael Jordan above. I may fail completely and lose everything, but I do not want to look back on my life and regret not trying.
What is your “make the jump” story?

What do you think about that?