Your Brilliant Second Career

Your work experience makes you a valuable commodity. Figure out how you want to parlay it into a new career for yourself

I have always wondered how a kid in his second year of college is supposed to pick a major and then, a couple of years later, dive into a career. At that stage in life, most folks know almost nothing about the range of careers that are available and have so little life experience. It's no wonder that, in survey after survey, midcareer professionals report that they "fell into" their areas of specialization. Few, if any, of us, after all, have childhood dreams of becoming a procurement manager, a process engineer, or a human resources information systems analyst. And yet, here we are.

What's exciting these days is that, with average job tenures getting shorter and shorter and big-company lifetime jobs already a thing of the past, more and more midcareer professionals are finding job happiness in Chapter Two careers—sometimes in radically different areas from the gigs they've held for the first 15 or 20 years out of college. Still, sitting in your cubicle at XYZ Corp., it can be hard to imagine yourself taking the necessary steps onto a wildly different career path. Here are some ideas for getting started.

Your first step, as you contemplate a midcareer shift, is to identify what you do well and what you enjoy doing at work. If you're looking at an entrepreneurial endeavor, you'll also need to know what things people and/or businesses will pay for. And if you're planning on paid employment with a different focus, you'd be wise to look into the five- or 10-year hiring outlook for the field you're considering.

Making Your List

Planning your second career is a very different exercise from your first career choice. This time, you have the benefit of your work experience and life experience, and free Internet research to help you on your way. You are looking for a field that will not only provide an income, but will exercise muscles you may not have flexed in a while (or maybe, ever).

Write down the elements you'd like to find in your second career: More flexibility? Less administrative burden? More creativity, less travel, more analytical work, less writing? After 10 or 20 years in the workforce, you should have a good sense of what you're good at and what you enjoy.

But if you are struggling, ask your friends. Send a group e-mail to 20 business and personal friends and ask them for their advice. Or gather a group of folks together and enjoy a roundtable conversation over lunch. You may learn about professional areas that you didn't know existed. One friend of mine, Sherry, was a technical writer for 20 years. She's very skilled, but she was completely burned out on technical writing. "I feel as though I have written every manual in the world," she said. She couldn't do it anymore. She did her research, and made the transition into a new career as a product trainer.

The World Outside

For starters, she conducted a hefty number of hours of online research, focusing on career-oriented sites like, and read job descriptions on to see how a range of working people spend their time. She realized that one thing she badly needed was face-to-face interaction, and eventually she found the Web site, the online home of the American Society of Training and Development. At that point, she began attending local ASTD meetings and talking with training people—and realized that corporate training was her best next-career destination.

Sherry was able to take her expertise in making complex language simpler, and use it in a new role training salespeople on product features and benefits. No writing—but lots of instruction, conversation, and humor—and the person-to-person interaction she had missed while writing manuals in a cube for two decades.

If Sherry's second career took her three or four steps down a logical path from "my current career" to "my next one," plenty of folks have journeyed much further. My friend Jennifer was a consultant for Accenture (ACN), traveling around the country and advising energy companies on their IT strategies. When that became too much of the same, she took a job managing an Aveda store and salon. That led her to an assignment leading the marketing efforts for a high-end retail complex.

A Coach's Insight

Likewise, my brother Dave is a talented software engineer, but he has always loved rock-climbing, even growing up in less-than-mountainous northern New Jersey. So, Dave left a steady job in the Bay Area to join a prestigious guiding company in Jackson Hole, Wyo. He still designs software architecture, but he does it around his climbing-guide schedule now.

If you know that you need a change, but are otherwise completely stuck, you might find it worthwhile to invest in a series of sessions with a career coach. Find a competent coach through a coaching Web site like CoachU, or via referrals from friends. Ask for references. Ask each coach to share his or her approach (there are wildly different philosophies and methods used in career coaching, and each coach has a slightly different style) and schedule a trial session before you commit to an ongoing program. A coach's insights may be just what you need to zero in on the second career that will get you excited about work again.

Once you have a direction, start talking to people. Look at your current résumé and see what skills and experiences can translate to the field you're moving toward. If there's education or certification involved, begin collecting data from schools and looking at schedules, fees, and requirements. A major second-career shift can take a year or two to accomplish, but that's a drop in the bucket to someone who has already been working for 20 years or more.

A Foot in the Door

If you're ready to plunge into a second-career job search without additional training, it's time to pull out the networking stops. Major career changes almost never happen through or any other job site. Employers have to hear from a trusted employee, vendor, or customer: "I've got a friend who would be perfect for that job opening. You have to meet her. She comes from a different field so she's not an obvious candidate, but I know you'll be impressed when you speak with her."

You will find that some companies are dead-set on specific, nearly identical experience in their job candidates, while others are open to job applicants from different backgrounds. Don't waste your time on the first group. Now that you know what kind of work you want to do in Chapter Two, there's no sense mucking around with companies who have no appetite for career-changers. Every week, commit to making two new contacts at likely companies, and don't stop until you've got a foot in the door.

Will you have to take a pay cut to make your big move? It's not certain, but you should plan on it. You may have to change your spending habits for a while or even move to a less fabulous residence to get the work situation where you want it. And working your way back up to your old income level may take a few years. But after all, isn't that scenario preferable to toiling away at work you don't love?

Time to Get Going

There's an old story about a man who heard a neighbor playing the clarinet. "Boy, you're a good clarinet player," he said. "Could you teach me to play?" The clarinetist said, "If you want to make that commitment, of course I could. It takes time to get good." "How long?" asked the prospective student. "In seven years you'd be quite good," replied the musician. "Seven years! I'll be 46 years old in seven years!" Said the clarinet player: "How old will you be if you don't study clarinet?"

How old will you be in five years if you don't pursue your dream? Get started now.