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The Challenges of Starting a Business in Midlife

These three entrepreneurs dealt with obstacles to launch successful firms

By Susan Lahey

At 22, you might wake up and say: “I’m quitting my job today to start a business.” But it’s a different story when you’re a first-time entrepreneur in midlife, in a down economy, with kids, aging parents or just the screaming awareness that you’ll be facing little or no income for the foreseeable future.

For many people launching businesses in their 40s, 50s and 60s, the process more closely resembles that long trip up the ladder to the high dive, where you linger, staring at the water, until one day, you jump.

But second-act entrepreneurship is huge and growing. According to the Ewing Marion Kauffman Foundation, a leading researcher on entrepreneurship, more businesses are being started by people aged 55 to 64 today than by those under 25.

(MORE: Starting a Business After 50: An Expert's Tips)

Here are stories of three people who’ve started successful businesses in their 40s and 50s, sometimes by overcoming their fears and doubts:

Getting Past Being a One-Woman Show

Kristi Curry, 49, quit her lucrative, but exhausting job in the telecommunications industry in 2001 to take time off. The former financial adviser began helping her mother and her mom’s friends plan for their futures. That’s when she knew she knew she had a viable business idea: to start a firm helping older people get their estates in order and prepare for death and the possibility of disability.

In 2006, Curry launched “Now and Then” Planning in Austin, Texas. But as Curry’s parents’ health declined and her partner began having health issues, she had months where she couldn’t run the business. That showed her she couldn’t succeed as a one-woman show. She needed to scale the business, which frightened her.

“I had a whole internal fight with that. If you scale it, that’s when you end up with the super highs and super lows,” she said.  “But it was time for me to get serious about growing the business.”

(MORE: 5 Ways to Avoid Small Business Burnout)

Ultimately, she hired her first employee in 2013, marketer Karen Robertson — who Curry had met at a local business-incubator networking event. “When you’re thinking of bringing in someone else to invest their time and get paid really minimally for future returns.... it’s very, very scary,” said Curry.

But bringing in Robertson was exactly the tonic for her fears. Over tacos and wine, Robertson proffered a clever marketing strategy far beyond what Curry had imagined.

“That day,” Curry said, “all the fears you have start going away. Now you’ve got somebody who understands it, who gets it, putting effort into this thing.”

Today, “Now and Then” Planning is thriving, with one-on-one packages, video tutorials, teleseminar courses and workshops.

Reducing Risk With a Side Job

Chris Mihm, 45, a former teacher and founder of Senior65, a Washington, D.C.-based firm helping people make smart Medicare choices has one tip for would-be midlife entrepreneurs: “Don’t quit your job until the last possible moment.”

When he launched the online health insurance marketplace Medicoverage in 2003, he also took on a part-time job as director of product development for a firm called Get Ahead Learning. He kept that part-time gig for five years. Last November, Mihm pivoted to launch Senior65.

“When I pitched my first company (investors) said: ‘That’s a good idea, but don’t quit your day job.’ It was my day job," said Mihm. "The next day I went out and got a part-time job at an educational startup.”


(MORE: 10 Tips for 'Senior' Entrepreneurs)

Mihm says that if you’re worried about your startup paying the bills you might wind up making bad decisions because you’ll be too focused on the short-term, thinking “I can’t pay for marketing because I have to pay for my family’s food.” 

Getting a Boost From a Board

Back in 2008, Suneet Paul, now 54, knew he had the experience and connections to launch his Austin-based business, which offers point-of-sale financing for retailers’ customers. But after decades at Dell, many of them as vice president and general manager of Dell Financial Services, he had to overcome the fear of prospecting for clients for a company no one had heard of. 

“It was like, if you don’t have a Dell behind you, who are you?” said Paul. Prospects would say “Who else is doing this?” and he couldn’t give them examples.

But Paul knew enough from his decades of experience to create a board of advisers, since they could help make connections that he couldn’t. After pulling together a NewComLink board, the business began to fly.

What a Psychiatrist Suggests

Fear is normal when starting a venture, especially for people who’ve been raised to be risk-averse as many midlifers have. But Dr. Michael A. Freeman, a psychiatrist and serial startup owner who researches entrepreneurship for the University of California at Berkeley, said business founders must be able to distinguish an opportunity from a threat.

“If you’re looking at something as a threat, that doesn’t mean you’re wrong,” Freeman said. “Are you worried because you don’t have enough money to get the business off the ground, don’t understand corporate taxation or haven’t done a competitive analysis? If there are real threats, you should respond to every one of them.”

But, he added, if the threats are irrational — you worry unnecessarily and expect catastrophes — you need skills to avoid being sucked in by them. “That might include cognitive behavioral therapy, mindfulness or non-attachment to your rational fears,” said Freeman.

The biggest key to dealing with fears, said Freeman and the three entrepreneurs profiled, is surrounding yourself with supportive entrepreneurs and mentors who can guide you when you’re standing on the high dive. They can be a huge help in preventing belly flops.

Susan Lahey is a veteran business reporter and magazine editor who has written books on midlife career change, employee engagement and motivation. She co-wrote Repurpose Your Career: A Practical Guide for Baby Boomers and helped launch Silicon Hills News, a digital newspaper about Austin tech startups.

Susan Lahey Read More
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