How To Stay Cool When Your Family Asks About Your Career At Thanksgiving

Like many millennials, Lily Davis, 28, gets anxious around the holidays. Working as an actress and a nanny, Davis worries about how her family will judge her career path, especially given that her father doesn’t seem to understand what exactly it is that she does.

“I feel like I have to prepare myself,” Davis said. “I have to do a meditation every morning for weeks before I go into that situation.”

Compared to previous generations, many millennials career paths that may seem "unconventional" to an older generation. According to projections in the Freelancing in America Survey, almost half of working millennials freelance in some capacity — far more than any previous generation. And, for those who do not work in traditional 9-5 jobs, who are in-between jobs, unemployed, or self-employed, the holidays can be a particularly trying time. Whether it’s a barrage of prying questions, or an inability to comprehend certain career paths, family gatherings are often ripe for scrutiny — or indifference.

Wandy Felicita Ortiz, 23, works as a freelance journalist and publicist and often finds it difficult to explain her work to her family. "My biggest stress with family around the holidays is being judged," Ortiz told Refinery29. “I try to stress that my work is just as valid as that of people who work one job full-time — it's not that people freelance because they're ‘lazy.’”

Davis and Ortiz certainly aren’t alone. Whether it’s working a side hustle to keep your dreams afloat, or working fulltime as a freelancer, it can be difficult to legitimize work that falls outside of normalized expectations.

We asked Celeste Headlee, award-winning journalist, communication expert and author of We Need to Talk: How to Have Conversations that Matter, for some tips on how to handle these uncomfortable questions.

Headlee says that one of the best ways to navigate difficult conversations with family this holiday season is to try to identify whether a comment is constructive or destructive. If the former, Headlee says to try to meet the person where they are at and, if the latter, to try very hard not to take it personally — ”it's probably not about you,” she adds.

Another tactic Headlee suggests is to practice asking questions like, "why do you say that?" Posing questions without hostility and with genuine curiosity can shift the tenor of a conversation from a debate to an exchange of ideas, Headlee said.

Headlee makes a clear distinction between a situation that is respectful and one that is abusive. A respectful conversation can serve to break down barriers and shed light on one’s motivations and underlying concerns. However, if someone is being abusive, Headlee says that, sometimes, it’s best to walk away.

For Alisha Miranda, 32, who works as a Digital Project Manager and graduated into a recession back in 2008, career has always been a contentious topic. “More years than not, I'm in-between jobs and after so many layoffs, I've stopped giving my family updates about work altogether,” Miranda said. Lately, Miranda has reached the point where she has stopped spending the holidays with family. “It can feel really embarrassing to fail at ‘adulting’ when having a job is such a big part of that expectation.”

Every family is different — and so is every career path. As such, the particular challenges faced during the holidays will vary greatly. Still, keeping in mind that, belittling commentary from family is often a reflection of the commenter — not the person whose life is in question — can help to deflect many of these unpleasant interactions.

Ultimately, each person is the expert on their own life and family, and as such must decide what is the best way to handle these scenarios. And while this may mean ultimately choosing to forego family holidays altogether, it can also mean finding opportunities to build bridges.

“At the end of the day, I’m not doing what I’m doing for my dad’s approval,” Davis continued, adding that while she sometimes dreads justifying her chosen career path to her father, she hasn’t yet given up hope. “I wish he understood that I’m an artist, that I’m willing to babysit eleven year old brats on Wall Street for $20 an hour so that I can live the life that I’ve dreamed of living.”