Leaping Into New Waters

You may have lots of experience in your old field, but it won't necessarily help you make a break. What you need: focus, preparation, and chutzpah

Will 2007 be the year you finally make good on your resolution to give up the daily grind and find work you love? Perhaps you're a lawyer who's painfully aware that being in a courtroom isn't as much fun as it looks on TV. Or maybe you're a baby boomer, whose concept of retirement is an opportunity to do meaningful work rather than join the golf crowd. Unfortunately, changing your career or downshifting is easier said than done, even when you have a lifetime of experience in a wide variety of positions. To be successful, you will need to jettison some old assumptions about how to find jobs.

When you've applied for positions in the past, you've proudly listed your accomplishments, figuring they would help you climb the corporate ladder. And in your old life, that was true. But when you're applying for work in a completely different field or at a lower level, your stellar résumé may be treated with suspicion.

A potential employer, who hasn't been privy to your soul searching, is likely to see multiple red flags in your application. The hiring manager can't understand why, for example, you would want a job that pays perhaps a quarter of what you're currently making. She may doubt your sincerity, commitment, or understanding of the work environment. Worse, you may be perceived as not having the basic skills for the lower-level work. So you're not only overqualified but underqualified as well, and your application is likely to be consigned to the circular file.

This means you're going to have to employ a totally different job-search strategy. You have to find a way to tell your story. And you can't do that with a standard application or a laid-back "come and find me" approach. The key to getting your application to the top of the pile is focus, preparation, and a fair dose of chutzpah.


It pays to know exactly where you want to work, why you want to work there, and what you have to offer. Don't waste your time applying online to hundreds of jobs or going through headhunters. Replying to job ads is another recipe for disappointment, because your application by itself will raise the dreaded red flags. Preparing careful approaches to 20 employers will get you much further.

Always do online, in-depth research on your targeted employers and their personnel. The more you discover, the better you'll be able to identify where you might fit within the organization. And advance information about the background of your future boss or interviewer can be invaluable.


Throw out your old approach to résumés and cover letters. When an employer reads your application, he doesn't want to know about your 10 years of progressively responsible experience in a different industry. He wants the answers to "red flag" questions. Your new résumé should demonstrate that you have the knowledge, skills, and abilities for the open position—not one several levels up. And your new cover letter should provide a compelling argument for why you want the position for which you're applying and why you're the right person.

A good way to reinvent yourself on paper is to do a combination functional and chronological résumé. In the functional part, you can easily zoom in on the experience and characteristics your new employer needs, highlighting accomplishments in each area. Don't forget your volunteer work—it may be the most relevant experience you have. And remember that when you list the positions you've held, you get to decide how far back in your work chronology to go. You don't have to include that first job out of school—or even your first few positions. Nor do you have to state the date of your degree.

I once avoided being viewed as overqualified by not sending a résumé at all for a position that was significantly lower than the one I'd left when I moved from Washington, D.C., to Rhode Island. I simply wrote the hiring manager a three-page letter describing how I thought I could be helpful in the open position. The letter got me in the door for an interview, and only after I was hired was I asked for my résumé.


However compelling your application, you have to find a way to reinforce your value through a face-to-face meeting. There's no substitute for personal connections, so cultivate relationships with friends and fellow alumni who work in your chosen field. Find like-minded people through CivicVentures.org, or for women, thetransitionnetwork.org.

Any time a trusted person puts in a good word for you with an influential person in your desired field, you have a major advantage. Ultimately, of course, your goal is to get an interview for an open position, but with a little chutzpah, you can often get your foot in the back door, even if an opportunity doesn't officially exist.

Dan was a seasoned international business executive who wanted to transition to a lower-level position in academia for his final working decade. He focused on North Carolina, moved to the area, researched target institutions and departments, read job descriptions of open positions, and prepared his résumé. Then he got to work making calls requesting informational interviews. With his foot in the door, and a good story, Dan was referred to many other department heads. He started by asking for information. But after several "informational" interviews, he ended up with a job in the international-studies department.

Overqualified doesn't mean unemployable. Your background and experience provides much material with which to work. But recasting yourself in a new light requires a different mindset. With focus, preparation, and chutzpah, you will soon be on your way to a more fulfilling life.

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