Counter-Intuitiveness Comes of Age

Penelope Trunk’s Brazen Careerist: The New Rules for Success is one of the rare career books that is often counter-intuitive in its guidance yet stays with you a little longer than expected. I was both amused and engaged by chapters entitled “Be a Sponge,” or “Assume the Job Description Was Wrong” or “When Writing Your Resume, Don’t Be Too Honest.”

A former professional beach volleyball player, software executive and IPO survivor, Trunk reinvented herself a few years ago as an author, blogger and career columnist for Yahoo! Finance and the Boston Globe (The Climb).

It’s not so much that Trunk advocates lying on your resume, what she preaches is closer to spin control, though she doesn’t call it that. “If you’re too honest you sound like a psychopath,” she says. After all, a resume is “not a list of every truth in your life. In my mind it’s absurd that people give advice that says ‘Don’t lie on your resume’ because it’s totally useless advice. ”

The trick she explains is “knowing how to frame your life in a way that is informative but not lying.” For instance, Trunk says she dropped out of a graduate school English program to take a job managing a website for a Fortune 500 company. “It would be ludicrous to put in my resume that I left to pursue a lot of money instead of taking out more Stafford loans,” she says. In her resume, she doesn’t claim to have graduated from the English program, just that she attended.

Trunk makes sharply observed points about changes in the workplace and what this means for job seekers and hiring managers. She is at her most salient when she contrasts and compares generational changes between what the “millennials” want versus the Gen X and Gen Y and Baby Boomers before them. “The workplace divide is no longer between men and women it’s between older and younger people,” she says. “Now it’s young people valuing time vs. older people valuing money.”

The Gen-Ys and Millennials don’t want to climb corporate ladders any more than they want to work sixty hour weeks, says Trunk. Instead they want mentors, time-off and personal development – and many of them are smart enough to negotiate for it right out of college. Seeking more responsibility doesn’t hold the same appeal to the new generations. “Getting promoted is moving along on someone else’s path,” says Trunk. “Young people are all about personalization and customization and generally it’s not going to be a step someone else has laid out for them.”

Getting ahead, says Trunk, entails more emotional intelligence than anything else. “Being likeable matters more than being competent,” she contends. She argues this is, in a way, a good thing. “The idea that we value skills first is tragic and it has lead to backstabbing, hurtfulness and workplaces that don’t care about personal lives.”

Trunk, who enjoys saying things “straight,” strongly advises budding careerists to specialize rather than become generalists. In this sense Trunk’s advice is somewhat akin to the popular concept of personal branding, which she calls typecasting. “People with power need to see you as someone who is extremely good at something, and no one is extremely good at everything, so don’t sell yourself that way to senior managers.” Good point. Although Trunk would be among the first to admit that if one career path isn’t working for you there’s always another worth taking.