How 5 Guys Left Their Jobs and Found Something Better
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Money & Career

How 5 Guys Over 40 Left Their Jobs and Found Something Better

Changing careers isn’t as impossible (or risky) as it feels

Steve Silberberg
Courtesy Steve Silberberg

Todd Lamb always thought he’d be running his own business someday. But life, as they say, had other plans. He became a dad at a young age. That, along with his love for public service, led him to become a cop. 

He kept a side business, and when it looked like it could provide predictable income for his family, he decided it was now or never. 

He’d learned that philosophy in the field, during hostage rescue missions. “If there's a 70 percent chance that your plan will succeed, that's the time to go,” he explains. “You will never get that opportunity again.” 

So at the age of 45, Lamb left law enforcement to run his own wellness company, PureLife Organics. His business hit $40 million in revenue this year, so his midlife leap into entrepreneurialism has really paid off.

If you’re ready to make a career 180, either by choice or necessity, here are a few pointers from Lamb and others like him who changed course midstream.

Find what lights you up

At 58, Peter Cellarius was a tech executive making seven figures, on track for a CEO role. In his spare time he volunteered at a suicide crisis line. 

“I was at dinner with a friend,” Cellarius recalls. “He said, ‘It's so weird. When you talk about the CEO stuff, you look all somber, but when you talk about volunteering, you light up.’ ” Cellarius decided soon after to sign up for graduate school and pursue a career as a psychotherapist. 

Steve Silberberg was a 43-year-old software programmer who hated his job. “Every day, I would sit there thinking, ‘Is this all there is?’ ” he says. His father died at 54, so he was determined not to waste another year doing something he didn’t feel passionate about.

“I decided to do something really self-indulgent, which is to go backpacking,” he says. “And now I take people on backpacking trips for a living.”

Work two jobs, then dump one

Shaun Eli was a banker who took comedy classes and performed at night and on weekends for six years. 

“At some point, I said, ‘I have two jobs, and I don't want to have two jobs anymore,’ ” he explains. At age 42, “I got rid of the lucrative one in favor of the fun one.”

Danny Kofke, a 44-year-old special education teacher, took a similar approach, writing several personal finance books in his free time. Knowing he’d like to transition into financial speaking, he booked practice talks. 

“Sometimes I did a presentation with two people in the room,” he says. “Sometimes I’d drive 100 miles to do one.” Over time, he honed his skills and landed bigger gigs. “All that practice led me to being a motivational speaker,” he explains. 

Put away 12 months of expenses

Two years before making the jump from corporate to the great outdoors, Silberberg went to a financial planner and asked, “I’m thinking about doing this. What should I do?” 

He spent the next few years beefing up his savings, until he had “a year’s worth saved up.” Combined with a low-expense lifestyle, he felt confident taking the risk of leaving a steady paycheck behind.

Forget your fallback

When he decided to pursue a new career, Cellarius opted to pretend there was no backup plan. “If this wasn’t right for me, I knew I could have called my old boss,” he says. “But that needs to find a home in the back of your mind.”

The front of your mind needs to be “the moving-forward part,” says Cellarius. “If you try to keep them equally salient in your mind, it's like you're pushing the brake and the gas. The car doesn't travel well when you do that.”

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