Working as an Independent Contractor

A generation ago, you were expected to find a career and stick with it until retirement. But today’s experienced professionals in a variety of fields–from IT to PR to HR–are finding their second wind as self-employed, independent contractors. Dissatisfied with the confines, limitations, or politics of the corporate jungle, many highly accomplished workers are forging their own paths.

Freedom, Independence, and All That Jazz

Sherman Green is an independent contractor for a radio station in Florida. Green had been an employee with the station for over 25 years, holding several top executive positions before deciding to “retire” into independent consulting. He now oversees two major fundraising events, working as a consultant for the station’s Jazz Festival and producer for its Wine Festival Weekend.

Overseeing both projects requires a lot of time and effort. Planning for the jazz festival alone begins six months in advance of the actual event. It can be a challenge to manage the myriad details required to bring an event together without a structured work environment and cadre of co-workers, says Green. On the other hand, he says, living outside the confines of a corporate structure gives you the chance to work how and when you want–without being shackled to someone else’s idea of how to do your job. “It gives you the independence to do what you want,” he adds, “to do it on your own time, when you want to do it. You’re not bound by any structure.”

But there are drawbacks. Green warns against the “forbidding health insurance and benefits issues. You lose those benefits you would normally get from a job: health insurance, payroll deductions, vacation. All that becomes your responsibility to supply.” Yet the biggest challenge for most contractors, he admits, is time management. Can you stick to a schedule and meet deadlines without ever tuning in to see who’s on Oprah? “You must have enough discipline to meet goals without being supervised,” Green says, “setting deadlines for yourself. But, if you can work without a lot of structure, it can be a great way to go.”

Doing It Yourself

Victoria Nielson runs an HR consulting company in Northern Virginia. She, for one, doesn’t mind facing the challenges of independent contracting. Nielson turned her back on an 18-year career in corporate HR because there were no challenges left. It was time to try something new. “But I’d already been involved in two start-ups,” she says. “If I was going to do that again, it was going to be for myself. I decided it was time to make a change.”

Acquiring clients was one of the first challenges she faced as an independent contractor. “I think that we’re all challenged by that,” she notes. Then, when the clients and jobs eventually roll in, it’s tough to function without the systems and procedures you left behind in the corporate world. “One big challenge was just getting my systems set up,” Nielson remembers. “In the beginning, you don’t have any resources to pull from. You haven’t had to use them. It took some time to develop my own templates.”

Despite those challenges, Nielson knows why so many professionals become independent contractors. “That’s because many times the corporate world does not walk the talk. In other words,” according to Nielson, “they’ll say they can give you the flexibility that you want, yet are unable to do so. And they’ll tell you they can compensate you accordingly, yet when the time comes, the resources typically are not there. If you want to be in control of your own destiny, which a lot of people want to be, they’ll decide it’s time to take charge and move on.”

Escaping Merger Madness

Bob Gorman, an independent contractor since 2008, fled the corporate world after one too many brushes with merger madness. Formerly a top executive in the healthcare industry, Gorman watched companies absorb other companies on a regular basis. He left to form his own Massachusetts-based communications firm. “I’d worked nearly 30 years in various public relations positions,” he says, “and I’d finished 13 years [on the last] job. I’d just finished going through my third merger and had decided that wasn’t an ordeal I wanted to go through again.”

Gorman managed to leave with a “very comfortable package” and, still in his mid-50s, explored several employment options. “I also have a Ph.D. in Mass Communications,” he says, “and had been teaching part-time in an adjunct position.” Neither Gorman nor his wife wanted to relocate, which is often required of senior corporate executives. “So I decided to go into consulting and combine that with teaching,” he explains.

Gorman, like Green and Nielson, is happy with his decision to be an independent contractor. But, also like his counterparts, he found the lack of corporate resources and support took some getting used to. “What you do lack is the usual support structure. That’s a problem when you’re working to produce something like a brochure or an annual report. You’d normally have co-workers to help coordinate the production of those things.”

Yet Gorman’s experience has been very rewarding, despite the occasional lack of corporate resources. He’s happy to be steering his own ship. “Like anything,” he confides, “there are advantages and disadvantages, but for me, this is really the way to go.”