"You can only leave Morgan Stanley once."
That's what my former boss said when I told her I was leaving the bank in 1999. I wonder if CFO Ruth Porat heard the same thing when she announced she was heading to Google?
Would she even care?
That kind of Wall Street scare tactic used to send a ripple of fear through anyone thinking of leaving the high-pressure, high-paying job. But recently, we've seen more and more finance people chasing their entrepreneurial spirit — and you never hear about them going back.
I know I've never had any regrets about walking away from Wall Street. But I decided to check in with a few former colleagues to see what they were up to now — and if they ever regretted leaving.
A few of the people I spoke to headed west to Silicon Valley. But it ran the gamut of new careers and endeavors. They were on their way to Quantico, Va., to join the FBI, running for mayor, teaching high school, selling luxury cars, working in marketing, writing books and starting new businesses.
The one thing they all had in common?
They are all much happier now.
So, how did they do it?
If you ask any Wall Street professional how they make million-dollar decisions every day, they'll say it's a combination of research, analysis and instincts. But when it came time to leave, there was one driving force: Their gut.
Some left to pursue a passion. Others were tired of the grind and wanted a new challenge. Some just wanted a better quality of life.
"I don't miss the hours, that's for sure!" said Jonah, a former buy-side analysis. "I work smarter now — not harder."
"I left in pursuit of happiness. As the business changed, when the seat became more important than the individual … I couldn't be part of a Whack-A-Mole game," said Nelly D. She's now four years removed from a 15-year career as an equity-sales trader and tapping into her entrepreneurial spirit. She's been building a seasonal-fish market in the Hamptons for the past few years and has joined a lifelong friend's jewelry company focusing on sales and marketing.
Erin Duffy left her 12-year career as an interest-rate sales person to pursue a career as an author. Her first book, "Bond Girl," has been described as "The Devil Wears Prada"-meets-Wall Street."
"I got to a point in my life where I felt like if I didn't make a change, I was going to be doing that job for another 20 years and I didn't want that for myself," Duffy said. "I wanted balance. I wanted more flexibility. And I wanted to wake up in the morning and look forward to going to work."
No one I spoke with regretted their time on Wall Street — like me, they're grateful. They feel like their experience has given them a competitive advantage in their new professions.
"I learned how to work under pressure, get sh-- done and not make excuses," said Michael a former bond salesman who now sells luxury cars in Philadelphia. "Wall Street was the best training in the world." When asked why he chose selling cars he simply said, "I like it. It's sort of a family business."
My friend who is headed off to the FBI said he has just always wanted to do it. He wanted to stop threatening to do it – and actually do it.
What about the money — don't they miss the giant Wall Street paychecks and annual bonus? Did they ever feel, to quote a common Wall Street phrase, that they got out of the trade too soon and were leaving money on the table?
Everyone I spoke with sounded content about their finances despite their fears upon leaving.
"The best thing about having money is not having to worry about money," said Nathaniel, a former money manager. "Things are a bit tighter now, but I manage okay without the security of a big pay day."
Of course, just about everyone missed some things from their time on Wall Street.
"I miss the constant, but exhausting action. It wasn't for me, but I like to consistently be learning and Wall Street taught me how to think like an opportunist. And I now apply that thought process to my work currently," said Max Kabat a former buy-side trader, who's now running the goodDog marketing agency.
Personally I loved working on Wall Street, but I don't miss it. There was endless action and a need to always be focused. It was hard, but it made me a better employee. Which, on some levels, also made me a better person. I felt a need to compete every day. I liked most of the people, too. They were great, fun, witty, smart and talented.
So if you find yourself sitting across from a managing director in a conference room trying to resign. Don't shift in your seat and doubt your decision when they tell you that you can only leave that company once in your career; because once may just be enough.
Commentary by Turney Duff, a former trader at the hedge fund Galleon Group. Duff chronicled the spectacular rise and fall of his career on Wall Street in the book, "The Buy Side," and is currently working on his second book, a Wall Street novel. He is also featured on the CNBC show, "The Filthy Rich Guide." Follow him on Twitter @turneyduff.