“Dear Remy”: Hollywood Career Coach’s Special Thanksgiving Advice for Family Harmony

I Won An Oscar. My Family Couldn’t Be Less Impressed

Dear Remy,

I’ve been a working in Hollywood for more than a quarter of a century, and a few years ago, I finally won an Oscar. I’d been nominated four times before, and this was supposed to be my moment. But my family, gathering this year in Sheboygan, Wisconsin, couldn’t care less.

Every Thanksgiving, I’m still the youngest sibling who once got her head stuck in the banister during Thanksgiving ’94. My mom calls my Oscar “that shiny Ken doll,” my cousin asked if it’s heavy enough to use as a meat tenderizer, and my dad thinks I should bring it to dinner so he can put a MAGA cap on it.

I’ve won the most prestigious award in all of show business, so why does it bug me that these nine people — including my 87-year-old grandma, who has themed her entire home around her love of country music star Conway Twitty — don’t seem engaged with my success? I even sometimes wish that my Uncle Don, a silent type who is an amateur taxidermist, would watch one of my movies.

Last year, I went so far as hiring a projector so we could all watch my latest picture — and they switched over to a rerun of Maury halfway through. Sometimes I find myself longing to be a nepo baby, just to be in a family who might find some way to connect with my work.

Remy, I’m thinking of bringing my own stuffing, just for something to scream into.

Sincerely,

Oscar-Winning Black Sheep

***

Dear Black Sheep,

Winning an Oscar is an extraordinary achievement. Few professions give you that kind of public recognition, so it’s natural to want your family to bask in your success. But Thanksgiving, as you’ve discovered, doesn’t run on meritocracy.

The jokes and jabs you’re enduring might stem from something deeper. Your dad’s dismissal might mask discomfort about feeling overlooked in a rapidly changing world. Let me ask you this: Do you ever acknowledge your family members’ achievements in the way you wish they would yours? What might happen if you approached these conversations as an anthropologist, observing an ancient, possibly endangered tribe?

What stories light them up? What do they need to feel seen? Acknowledging their lives and accomplishments could be the unexpected gift you bring to the table this year. After all, you’ve already dazzled the world. Now’s your chance to dazzle Sheboygan.

Out of the millions of people around the globe, the reason you want the recognition of these nine people most of all is because you care for them most. Show them that. And — trust me on this — you don’t want to be a nepo baby. They come with their own set of problems.

Wishing you familial fellowship (and no more Maury reruns),

Remy

I Turned My Family Into Cartoons — Should I Tell Them?

Dear Remy,

I just directed my first indie feature, and I’m dreading heading home to Poughkeepsie for Thanksgiving. My mom insists, but I’d rather stay in L.A. and avoid getting in trouble with her.

“Why is a grown man worried about being in trouble with his mother?” you might ask. Well, the movie I’ve been picking up loads of cool awards for on the indie scene … is all about my family.

It’s an art piece, featuring animation and mixed media … but I still don’t think the characters’ similarities to my nearest and dearest will be obfuscated by that. The solid old oak tree, who doesn’t budge an inch even in the strongest of winds — staying in the same position as the world changes around him — is clearly my dad. The wisp who floats around aimlessly and sometimes drops into a faux English accent when trying to impress people is my mom. And the talking petunias who babble away incessantly are undoubtedly my nieces and nephews. I can’t help it that I don’t like children.

My mom has hinted a few times that she would like to sit down and watch my latest work after the desserts, and I don’t think I can hold her off. She’s already ordered three different flavors of popcorn.

Remy—should I tell my family ahead of time that they are the true source material for my film, or hope that they just play dumb?

Sincerely,

The “Artsy One”

***

Dear Artsy One,

I can see why you feel in a bind. Often people who make art find their inspiration “close to home,” and it can come with feelings of tension and guilt.

But Thanksgiving isn’t time for your annual review; it’s a surreal performance art piece where you play “adult child returning home.” Treat it as such. They almost certainly won’t notice the similarities between themselves and the movie. Human beings have an innate ability not to truly know themselves, and I feel like this blind spot in all of us might play in your favor.

And another truism is that most families deal with the same disputes and dynamics—I’m sure your storyline could ring true for many households. The quiet, brooding dad who stays stuck in his ways is a trope in many families.

Let the movie play, and enjoy the popcorn smorgasbord your mom is providing. Thanksgiving isn’t about deep analytical scrutiny — it’s about surviving awkward moments, dodging political arguments, and secretly taking notes for future scripts.

And maybe on your next project, choose a muse that’s a bit further from Poughkeepsie.

Crossing my fingers for a drama-free viewing,

Remy

How Do I Convince My Family I’m Not Cruella de Thanksgiving?

Dear Remy,

I’m a senior VP at one of the biggest studios in Hollywood, but this Thanksgiving in Lubbock, Texas, I’m Cruella de Thanksgiving. Last year, I brought vegan stuffing, and my brother said, “She’s here to save the planet one joyless recipe at a time.”

This year, I’m bringing pies, but I overcompensated. They’re gluten-free, dairy-free, and refined sugar-free, and my family will probably accuse me of poisoning Thanksgiving with kale. Meanwhile, my niece Emma keeps calling me “the Hollywood lady,” and I know she’s heard her dad (who thinks the phrase “cancel culture” was invented for him) say, “She ruins everything with her woke nonsense.”

Should I lean into being the villain or try to rebrand myself as a festive exec with a heart? Either way, it feels like I’m in a Hallmark movie.

Yours in chaos,

Not Actually Cruella

***

Dear Not Actually Cruella,

Families have a remarkable ability to reduce even the most accomplished among us to archetypes: the hero, the villain, the one who brings weird pies. In your family’s narrative, you’re the Hollywood Lady — a character who disrupts tradition with kale and opinions.

Rather than fight this role, why not embrace it? Ask if the children’s cute decorations are made from recycled paper. Suggest a minute’s silence around the table for the turkey and everything he/she/they wanted from their turkey life before it was cut short. Bring your pies and say, “You’re welcome for saving Thanksgiving and your arteries.” Humor is your secret weapon here.

At the same time, don’t let their labels define you. Could you approach the day with genuine curiosity? Ask your niece what she’s excited about, or your brother what he’s been building in his garage. Reframe the day as an opportunity to connect, not convince.

And if they keep poking fun, remember: villains always get the best lines — and the best pies.

Yours in good humor,

Remy

Remy Blumenfeld is a veteran TV producer and founder of Vitality Guru, which offers business and career coaching to high performers in media. Send queries to: guru@vitality.guru.

Questions edited by Sarah Mills.