Seth Woolard is currently underemployed and has been looking for work. He says: “I keep telling myself tomorrow is a better day, and picking myself up, but it would be nice to get some results.”
Seth Woolard is currently underemployed and has been looking for work. He says: “I keep telling myself tomorrow is a better day, and picking myself up, but it would be nice to get some results.”
Michele McDonald for The Boston Globe

When the housing market tanks, a large percentage of real estate agents seek new careers. But after more than 17 years in the business, real estate broker Seth Woolard wasn’t ready to give up when the recent housing boom went bust.

When he lost his job as an agent in a corporate real estate office, he went back to running his own real estate business in Worcester. He got his auctioneer’s license to try to capitalize on the flood of foreclosed homes that came on the market and learned to navigate the complex hurdles of short sales, when owners sell for less than they owe on the mortgage.

But eventually, despite a tireless work ethic, Woolard became discouraged. The Spencer resident says he’s been out of work — or underemployed — for two years, despite applying for 300 to 400 jobs. His dream: breaking into local government as an assessor.

Advertisement - Continue Reading Below

“I keep telling myself tomorrow is a better day, and picking myself up, but it would be nice to get some results,” said Woolard.

When he met with career and workplace expert Elizabeth Freedman, author of “Work 101: Learning the Ropes of the Workplace without Hanging Yourself,” he asked, “Can you help me make the most of my time? I’m feeling really crunched for time.”

Freedman had the following tips:

Pick a lane. Although a job search doesn’t have to take hours upon hours to be effective, the time spent has to be one of the “best activities” that have the greatest likelihood of paying off, said Freedman, who is also an executive coach at Bates Communication.

These include planning a job search strategy and trying to make valuable contacts. Freedman suggested developing a targeted list of towns and their assessors — reaching out with a crisp, audience-focused e-mail. “Time management is huge when it comes to job search success,” said Freedman. “This means keeping your ‘eye on the prize’ and not allowing yourself to get distracted by other activities — like selling insurance or applying for jobs that don’t fall under the assessor umbrella.”

Develop a “drip campaign” for staying on the radar. Woolard needs to focus on building relationships and having conversations with people who have the potential to hire him. “Get used to asking the question, ‘Who else should I speak with?’ and being very clear about what you’re looking for,” said Freedman. People in his network should know what he is looking for and how they can help.

For example: “I’m excited about taking my 20 plus years in real estate and applying that to an assessor’s role. Do you know anyone currently working as an assessor or data collector that I could reach out to?”

A “drip campaign” means reaching out on a consistent basis. “Even if they don’t have something for you today, that doesn’t mean they won’t six months from now, so you want to stay in front of your target audience with valuable ideas and insights on a regular basis,” said Freedman.

Rehearse the interview process. Woolard has had a few interviews, which Freedman applauded, but that handful was probably not giving him enough practice. “Think about anticipating the questions you’re likely to be asked, whether in an interview or informal phone conversation, and write down answers,” said Freedman, who also recommended getting recorded, ideally by a professional, or even just a family member on a smartphone.

She encouraged him to use free or low-fee resources for career coaching, such as state-sponsored One-Stop career centers or career centers at his alma mater, Framingham State. “When you do sit down for a conversation, you want to be at your best.”

In a challenging economy, Woolard was competing against high odds, so it’s no wonder that he felt he was swimming upstream, said Freedman. But if he remained true to the traits he listed on his resume, “proactive self-starter and friendly team player with excellent communication skills,” the talent he showed in real estate sales were bound to translate to other industries. “Put yourself out there, and be systematic in your search, and your efforts will be rewarded,” said Freedman.