Career
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How NOT to Find a Mentor

I had just gotten off the phone with a friend telling me how her mentor recommended her to a new job that she was thrilled about. Just the same week, another pal described her amazing lunch with her mentor who gave her feedback on her business plan and introduced her to potential investors. Another friend was going to a book party for her world-famous mentor. The idea of a mentor sounded great! How could I get one?

These same friends told me varied acquisition stories, from being assigned a mentor during their stints at big corporations to reaching out to industry leaders cold (and then somehow magically transforming the acquaintanceship into a mentor/mentee arrangement). No place where I had worked offered those programs, and, if they did, they weren’t geared for those of us in editorial. And as for the reaching out cold, I just didn’t see how that was going to work.

I considered my job history. Maybe I had a mentor and didn’t realize it? Thinking over my early years in the job force, I had worked with some powerful women — one of whom in particular was synonymous with investigative business journalism — but I just knew that my choice to go from fearless Wall Street columnist to writer of The Fabulous Life, a TV show chronicling J.Lo’s Crème de la Mer purchases, was a ticket off that mentee train.

I had always wanted a real mentor, but my friends’ great experiences had given me an especially acute case of mentor fever. Plus, I had recently started working a new job at a big media company that I quickly realized was incredibly political — something I’m not. I desperately needed a friendly face who could offer some guidance. To my knowledge, the company didn’t have a program to encourage editorial employees to find mentors. It was time to take matters into my own hands.

Around that time, I started hearing about a woman who just joined the company to run a division. Several mutual acquaintances who knew I was feeling isolated suggested that I reach out to meet her. They figured it could be good for networking and maybe I could transfer to work for her. After a few weeks, I finally got up the nerve to send her an email inviting her to lunch in the company’s fancy cafeteria. I couldn’t wait.

It did not go as planned.

I just knew that my choice to go from fearless Wall Street columnist to writer of The Fabulous Life, a TV show chronicling J.Lo’s Crème de la Mer purchases, was a ticket off that mentee train.

From the moment we got off the buffet line to sit down, it felt like the most awkward first date you’d never want to go on. I had no clue how to attain a mentor, and I had just assumed it was as easy as getting someone to want to be invested in your life. Not a problem at all! I would just find a way for us to bond, I thought, embarking on an embarrassingly ham-fisted plan. But she wasn’t too thrilled about any of the personal details that I hyperactively kept trying to share. When she realized, early on in our meal, that I had only been there for a few months I could feel her disappointment. I can only imagine that she was likely only interested in learning more about the company, figuring that I knew the lay of the land. She was not at this lunch to find a mentee.

I did not give up. I asked her to lunch again. Hey, I figured, if this mentor thing was meant to be we should be meeting regularly, right? Not sure she saw it that way. She replied faintly enthusiastically about getting together again, but there were always natty scheduling problems.

That got me thinking: Why would anyone want to be a free advisor? What was in it for her? Could I even pay for a personal advisor?

A few years later, my mentor acquisition project basically abandoned by then, I ended up running into my would-be mentor. We were both guests at a dinner thrown by an acquaintance who had left the same big media company a few years earlier. I didn’t know her well but was touched at the invitation. (I had left by then as well, so she probably felt some kinship.) Seated across the dining room table from each other, she was fairly blasé towards me. I’m pretty positive that either she had no clue who I was or, if so, did that thing people do when they run into a bad date. It dawned on me then that not only did she probably not have a clue about my mentor hunt, she may have even thought I was hitting on her. Sigh…at this point in my 40s, the likelihood that she (or anybody else) would be a mentor to me was not looking promising.

As I was settling into my acceptance of never finding a mentor (and burying my jealousies of friends carrying on about their fantastical mentor get-togethers), a younger woman whom I had once hired emailed me for work advice and to ask if I would mind serving as a job reference. Of course! I routinely did this for about half a dozen women a year and thoroughly enjoyed the process. I would take them each to lunch every few months and serve as a sounding board to help solve thorny office and career challenges. She landed the job easily — no surprise because she is brilliant, hardworking, and very talented. When she wrote me to let me know, she thanked me—for being her mentor.

I had no idea.

(Photo: Shuttershock)

Filed under: Career

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Caroline Waxler

Caroline Waxler is a journalist, editor, author, and the founder of Harkness Hall, which programs content for talks, conferences, and festivals. She has curated summits for organizations including: Advertising Age, Autism Speaks, Condé Nast, Forbes, Google, Lucky magazine, Razorfish, and WWD. Waxler has written for television, print, and digital platforms, including Fortune, Glamour, “Good Morning America,” MTV, Wall Street Journal, and the New York Times. Barron’s and Amazon named her investing book, “Stocking Up On Sin,” a top book of the year. She has also helped to report and write books about the deputy director of the FBI, and the rise and fall of Bernie Madoff. A University of Pennsylvania graduate, with a major in Latin, Waxler resides in New York with her husband, Michael. You can find her on Twitter at @cwaxler.

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