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Why Delay Your Dream Job?

Three executives who decided to start their second-act careers sooner rather than later share their stories and tips

By Matthew Solan

Yvonne Ulmer faced a dilemma. She was settled into a high-level, comfortable position as provost for St. Petersburg College in Florida. She had been with the college for more than two decades and was five years from retirement and full benefits. But the thrill of her success was gone.
She had already decided what she wanted to do for her second-act career: be a professional life coach. But Ulmer, now 59, was conflicted. “I was ready to move on, but felt I had to wait for the right time,” she says. “But I also knew that if I held off for another five years it would bring me down professionally and emotionally.”
So she made a hard choice. She followed her instinct by walking away from her job at St. Petersburg College, which meant a significant drop in income. “You won’t make the jump off the bridge unless it is burning,” she says. “So I lit the fire.”

(MORE: Encore Careers for the Rest of Us)
Not many boomers are willing to take that leap of faith while still gainfully employed. A 2011 study from Civic Ventures found that of the 9 million boomers who went on to have second-act careers, a majority had been thinking about it since before age 50.
But a growing number of midlifers, like Ulmer, are opting to bypass the thinking and waiting period. They’ve decided to grab their dream job now. 

Seeing the Obvious
What if you are ready for the leap, but not sure where to jump? If you examine where and how you spend your time, you might find that dream job in front of you.
Gary Reich, 62, a senior vice president of operations for a chain of hotels in Maryland, was always active — hiking, skiing and competing in bike races. A friend who owned a gym mentioned that he would make a great personal trainer. Reich got his certification, but never imagined it as a new career until he noticed how most personal trainers did not enjoy working with older clients and vice versa.
“It was perfect once I thought about it,” Reich says. “There was a need — plus, I really enjoyed it.” He moved to Colorado and opened 50-Plus Fitness. “I wasn’t unhappy in my old career, but now I am thrilled I no longer do it,” he says. “It turns out this is what I needed to do all along.”

When Fate Says Do It Now
The decision to pursue a second-act career earlier instead of later doesn’t always have to be a conscious one. Sometimes the do-it-now move can be made for you, one that may even lead you in a direction you never imagined.

(MORE: Career Shift: 'You're Never Too Old' Success Stories)
Elizabeth Venturini, 53, had built up a solid 30-year marketing resumé working for Fortune 500 companies when she was laid off. “I quickly realized that the jobs boomers like myself had been educated for had virtually disappeared,” she says.
Venturini feared trying to squeeze back into a crowded workforce. “I was worried that I didn’t have the connections or experience to move on, and that I’d invested so much in my career track that I could never do anything else.”
But she was mistaken. Upon noticing how parents today are so stressed out about getting their kids into the right college, Venturini saw a need that wasn’t being filled. It went beyond letters of acceptance. Parents wanted to be assured that their kids would graduate, get a decent job and never have to move back home again.
“This boomerang kid effect was a problem, so I decided to attack it head-on,” says Venturini, who gave up marketing to become a college career strategist. “I realized I had the valuable skills and experience that would be a good fit in my new chosen profession. I never thought about making this change until I had to, and then it felt so natural.”


7 Early Encore Tips
Pursuing your second-act career early can be daunting even to the most confident and prepared person. Helping make that transition feel natural does take forethought and preparation. So before you set fire to your bridge, you need to explore some options to ensure a somewhat soft landing. Here are some tips from Fulmer, Reich and Venturini.

  1. Invest in yourself. Many second careers require additional education, whether it's a second degree, job certification or simply brushing up on rusty business skills. "Do a thorough self-assessment and look for gaps — what do you lack?” Fulmer says. For her, that meant going back to the classroom for an intense, 70-hour program at the College of Executive Coaching in Santa Barbara, Calif., to round out her credentials as a life coach. But it could also include Accounting 101 and marketing strategies. Do not think you know everything. “I thought I knew a lot about business because I had my MBA and years of experience,” Venturini says. “But I never learned how little I knew about business until I started one of my own.”
  2. Prepare for tough times. The downside to "now rather than later" is that you often have less time to prepare for or predict all obstacles. So be ready and willing to endure a few rocky times. Besides the obvious income question mark, you may have to be a one-person operation. After years of relying on a fully staffed office, Yulmer was suddenly her own personal assistant, public relations firm and office manager. “I write my own newsletters, make all my appointments and answer every call — I’m the whole package and that is challenging,” she says. “I had to learn how to balance that with the actual work with my clients.”
  3. Find a mentor. It often takes two to tango: Seek out a mentor or career coach — someone you admire — who can guide you into a successful career change.
  4. Focus on the fun. Your passion needs to stay strong in good times and rocky ones. “You are building a new career, but your passion should be front and center,” Reich says. “If it isn’t fun then you should not do it.”
  5. Build a personal board of directors. Fear is always going to be present and you’re going to question your choice more than once. When that happens turn to your personal board of directors — an unofficial support team you can reach out to when doubts arise. These can be close friends or business associates who you can talk to for reassurance and get help working through issues.
  6. Accept a demotion. Odds are you were settled into a comfy corporate environment with a long title for a long time. Depending on the industry and job you may have to take a less prestigious title and/or lower salary until you establish yourself again. Do not let pride get in the way of the bigger picture.
  7. Go Hollywood. Build a strong online profile: Facebook, LinkedIn, Twitter. It should reflect who you are today — not 20 years ago. “Showcase your skills and talents that are relevant and in demand by today’s employers,” Venturini says. Remember you may be new, but you still bring a lot of skills to the table.


Matthew Solan is a health and fitness writer based in St. Petersburg, Fla. His website is Read More
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