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Naomi Zirkind had five degrees from MIT and eight children at home in Morristown, NJ, when, one day in 2004, she realized she needed help. After 11 years out of the full-time workforce, she was under financial pressure to restart her career. And she had no idea where to start.

“I felt like I didn’t know anything about anything because I had been out of it for so long,” says Zirkind ‘83, SM ‘83, Eng ‘85, EE ‘85, PhD ‘89. “I needed guidance on how to make a plan and get back into it. I needed some advice.”

That afternoon at her home computer, Zirkind pulled up MIT’s Institute Career Assistance Network (ICAN) and began searching for an alumni advisor. Someone in biomedical engineering, preferably in New Jersey, would be best. Five names came up; Rick Lufkin ‘68 was nearby.

“My first impression of Naomi was–here is this very smart lady, but she has been operating in a career vacuum for many years,” Lufkin says. “She contacted me directly, and we started exploring.”

As a student at the Institute, Zirkind worked diligently, dutifully, and often alone. Ask her about it today and she’s quick to praise her colleagues and her advisors, who she says were brilliant and an inspiration to work with. But, says Zirkind, “feeling like I was part of a huge crowd was discouraging to me … and while I was at MIT, I felt that it wasn’t acceptable to ask for help.”

When she reached out to Lufkin, she simultaneously capitalized on MIT’s broad network and retreated from the idea that seeking help was somehow foolish. Lufkin thinks things are different now: in the last few years, he says, undergraduate education at the Institute “has developed very much around group processes, simulating the professional working environment of the professional working engineer, which by definition is more collaborative.”

But other ICAN advisors say some alumni may still be missing out on the useful MIT connections that they might find through either ICAN or the Online Alumni Directory.

Mike Koss ‘83, SM ‘83, has been an advisor in the Seattle area for several years. “MIT students and alums tend to be more independent minded and less used to networking or asking for help and advice,” he recently wrote. “I see that in my own behavior as well, where I tend to tough out a problem on my own rather than ‘bothering’ someone else.”

The ICAN tool takes at least some of the edge off “bothering” someone or soliciting advice, because it’s online. Indeed, ­Zirkind and Lufkin’s mentoring relationship unfolded almost exclusively online, and Zirkind says that made things simpler for her. Lufkin agrees that there were times when he needed to be brutally honest with ­Zirkind, and sending those messages through e-mail was probably easier than delivering them face to face.

And Lufkin could be very tough. “You have reached a stage in your professional career which many/most engineers … reach after a few years–technical/skill-set obsolescence,” he wrote in one e-mail to her. But in addition to offering frank feedback, Lufkin also suggested areas where Zirkind could grow, challenged her assumptions, and constantly combed his own network for contacts. Along the way, they developed a mutual trust.

“We went through many blind alleys and a lot of exploration of possible career development strategies and suggestions,” he says. “I wasn’t there to speak ex cathedra about how to do things. But I could listen and suggest avenues that I thought she’d be comfortable exploring.”

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