The Way We Work
January 28, 2013 by Amy Sept

“I’m not a spring chicken!” admits Hiland Doolittle, a serial entrepreneur and recovered heart transplant patient who turned to online work when his health forced him to slow down.

Now in his 60s, Doolittle isn’t necessarily what comes to mind when you think of the future of work, but he’s one of a growing number of experienced professionals leaving the traditional office life behind.

A report last year by MBO Partners found more than 40 percent of independent workers are over the age of 50. Many of them are turning to online work.

“Not that many years ago, the idea of working online meant you had to be a young geek — I don’t think that’s true anymore” echoed Denise Loubert, a long-time corporate writer who has also started four businesses during her career.

“The Internet opened up the world for anybody,” she added. “There are all kinds of people of different experience levels, it’s not just young whippersnappers.”

Jim Nayor

Jim Nayor, who spent his career working for major ad agencies in New York City, thinks it’s that deep experience that enables the freedom of online work. “Once you’ve established your career, you can afford to go on [online platforms]; once you have your credentials and you’re confident of those credentials, you can make a go of it.”

Nayor noticed that those who find greater success online often have significant offline experience — something supported by oDesk’s own statistics.

When we looked at earnings growth among contractors, there was a clear relationship between higher education and greater experience — a 2.6 percent increase in rates for every year of experience listed.

Bending Work Around Higher Priorities

By its very name, the “future of work” points to a destination, a path experts estimate will have 1.3 billion people working virtually within a few years. It speaks to a new generation of workers who define work on their own terms, connected via an office that moves whenever — and wherever — they do.

However, mature workers like Doolittle, Loubert and Nayor often have a different set of priorities than newer freelancers.

“We live for our grandchildren,” Nayor said of himself and his wife. “They are the loves of our lives; anything and everything we can do for them, we do.”

Nayor says he turned to freelancing because of a lack planning. “I did a poor job planning for our future; I retired, and I needed to do something.” Initially, he travelled and did work for different marketing agencies; then he learned about oDesk and moved his business online.

Now, he says, he can work whenever he needs to. “My time is my own.”

Denise Loubert

Loubert appreciates the flexibility of online work, but also likes the efficiency of it. She briefly considered pairing with a graphic design company but eventually decided against it. “I was going to all these meetings and dealing with issues around payments,” she said, calling such use of time “unnecessary.”

“I make a living through oDesk,” she explained, adding that if she worked in the offline world, “I’d spend my time going to networking events and trying to convince people to pay me; I’d only work half the time I do now.”

Loubert thinks an entrepreneurial spirit like hers is perfect for online work. “I have to keep reminding myself I want to retire,” she said. “It’s a worldwide market; you can work with anybody.”

A Change of Pace

After a career of running his own businesses, heart issues caused Doolittle to step back. He says he was pretty sick when he started working online.

Hiland Doolittle

“In many ways, it saved my life,” he explained. “I couldn’t do much more than write, but [online work] kept me abreast of what was going on in the real world.”

Managing his own online business is more or less second nature for Doolittle anyway. “I’ve always had a lot of entrepreneurial endeavors; some were successful, and some were not,” he said. “It’s just a way of life for me.”

Online work lets Doolittle pursue a wide variety of interests at whatever pace suits him at the moment. “I love to work and I love to learn — my present career lets me do both.”

The Future of Work — For You

Loubert schedules her work around her social life, but she avoids getting distracted by it. “I have daily and weekly goals — you have to be disciplined for this kind of work.”

She also says it’s easier once you figure out how to focus your energy. “This time last year I was struggling, but now I turn work down every week. I learned that if you home in on what you actually want to be doing, people eventually just come to you.”

Doolittle has had the same experience, explaining that when he first started working online he wasn’t sure it would work out. “It took me a while to figure out that I really needed to establish a niche in a few things.”

When it comes to building good relationships with clients, Nayor says mutual respect is important. “I use Skype or call people directly,” he said. “Once you connect in other ways than just email, you start to develop a rapport with them.”

He advises giving clients more than they expect or pay for. “It’s the old adage: Promise them anything and deliver more.”

In their 2012 State of Independence report, MBO Partners found that 58 percent of baby boomers chose to become independent — and rarely turn back. While it’s a path that has its ups and downs, these three professionals have found a way to make it work for them.

Are you a mature professional who turned to online work for more flexibility or a change of pace? Leave your stories — and your advice — in the comments section below.

Amy Sept

Managing Editor

As the managing editor of the Upwork blog, Amy Sept works with regular and guest writers to share information that helps freelancers and businesses navigate the future of work. She owns Nimbyist Communications and helps non-profits, startups, and small business owners get their content marketing on track.