Career-hopping may be a millennial's game. But for 56-year-old Richard Silver, it's never too late to quit your job in pursuit of happiness and fulfillment.
Silver was making six figures as a real estate broker for the Corcoran Group in New York City in 2011 when he decided to quit and follow his passion as a travel photographer full-time. While many people his age might have been saving for retirement, Silver entered his 50s by selling his Manhattan apartment, storing his belongings with friends and seeing the world. He's visited 72 countries since then (favorites include Myanmar, Bolivia, Russia, Spain and Thailand).
"I know I'm an anomaly. There's not many people changing careers at this age," Silver tells CNBC Make It. "I'm young at heart and spirit…. My energy level is that of a teenager."
Silver isn't a stranger to taking risks with his career. He's been a stockbroker, a family beer business owner and a real estate broker. He says he took a big pay cut when he left real estate for photography — earning on average 80 to 90 percent less — but his happiness, lifestyle and health outweigh a large salary.
In October 2016, Silver signed up for Remote Year, a 12-month program that supports professionals who wish to work while traveling.
For $27,000, the program provides accommodations, transportation and co-working spaces in the cities on the itinerary. Most of the other 77 participants in the program were in their 20s and 30s. But that didn't stop Silver, who has visited over 40 countries in the last year and a half.
To make his dream of being a travel photographer a reality, Silver says careful planning was a must. Here is Silver's best advice for quitting your past life to pursue your passion.
Test out your new idea before quitting
Do your homework on the new industry before you leave your current job. Using the security of a steady paycheck allows you to to build out your side hustle and take risks you wouldn't normally take.
Silver began to seriously pursue photography during his last couple of years working in real estate. His job as a broker allowed him time to travel, so he began building a photography portfolio and gauging whether he could make a living off his photographs.
He connected with a few galleries and eventually caught a break with Lumas, a German-based art company with galleries around the world.
"It gave me the confidence to see that I can make some money with photography," Silver says.
Have some money in the bank
Before quitting and embarking on a new career path, make sure you have some money saved up. Your new venture may take some time to turn a profit, or it may not pay as much as your current job, as Silver experienced.
A good rule of thumb is to save three to six months' worth of your fixed living expenses before making the leap, says Megan Lathrop, a Capital One money coach and career workshops co-lead. Some financial experts advise having even more set aside for the unexpected. Suze Orman, financial expert and former CNBC television host, recommends having at least eight to 12 months' worth of living expenses saved.
Honestly assess your expenses and lifestyle and weigh that against how much you estimate your new gig will pay. For Silver, he knew his income would be much lower as a photographer than it was as a real estate broker, so he knew he would need to dip into his savings to finance his lifestyle.
"I'm at the mindset where I don't mind going through my savings to live my life," Silver says.
Asked about his retirement plans, Silver says he hasn't given much thought to it. "I've been a 'wing and a prayer' person for many years now and that's my game plan for my future too," he writes in an email.
"I know not so smart especially since I come from a financial background…. If I had to I could easily live in Southeast Asia on the cheap for many years and it's beautiful there too."
Don't leave your other career in turmoil so you can't go back
Even if you're leaving a job you despise, it's important that you exit on good terms with your boss and colleagues. While it may be tempting to make like the flight attendant who announced he quit over a plane's PA system and escaped down the inflatable emergency slide, a professional, thoughtful resignation will go a long way toward planning for your future.
You may need to return to your old career if the new one doesn't work out. Maybe you'll need a reference from your boss somewhere down the line. Bestselling management author and CNBC contributor Suzy Welch says it's important to never quit a job in a way that could "haunt your career for years to come."
"It's good manners to leave gracefully," she says. "It's smart business to leave generously."
When Silver left real estate, he says he wanted to keep the door open in case he ever decided to return. That meant keeping his broker license active by taking continuing education every two years.
And while you're at it, Silver recommends a polite, responsible exit from the other parts of your life as well.
"Don't say to your landlord, 'I'm leaving tomorrow…. The heck with you,'" he says. "Don't do it like that."
Have a support system
Silver is single, has never married and has no kids — "No obligation to any other human beings except myself," he says — which has allowed him to live his nomadic lifestyle. But he still believes in building a network for yourself.
"Make sure you have good friends and family who can help you out just in case," Silver says.
When he packed up and left his life behind in New York, he stored his furniture with friends in Manhattan and the Hamptons, and he left his clothes in a friend's basement.
As he wraps up his current trip abroad, Silver says he plans to spend the summer at his mom's in Florida before he takes off on his next adventure and continues traveling "till the day I die."
Making the leap to change up your career and lifestyle can be daunting, but with some thoughtful planning and preparation, Silver asks, "What's the worst that can happen?"
"If I can do it at my age, anybody can do it," he says. "Just do it. If you don't like it, guess what? Go home. Go back. What's the big deal? And do not, do not look at it as a failure."
—Video by Mary Stevens
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