The Five Questions You Most Dread at the Thanksgiving Table, and How to Answer Them

Thanksgiving is this week and while the prospect of gathering around a table with family can be warm and cozy, it can also be a lot.

Because getting together means catching up, and catching up means answering questions about our lives.

The people closest to us may have the best intentions when peppering us with questions about work, but they're far from objective when it comes to the answers.

Family members have too much skin in the game—opinions on what moves we should make, hopes and dreams about what they’d like to see us doing, and fears about keeping us safe from risks. (👈 This is one reason why working with a coach in an objective, nonjudgmental space can be so transformative!)

I asked the Penney Leadership community about the questions that you’re most worried about.

Here are the five questions you're dreading, and some comebacks to answer them with confidence:

➡️ 1. What do you actually do?

A) If you want the conversation to stay surface level or you'd rather move on to a different topic, oversimplify. Say something general like: "I'm in marketing."

B) If you’re open to having a deeper conversation, get more specific by offering more detail. You could say: “I work with a small marketing team at Acme Co., where we focus on telling the stories of how people are using our product in innovative ways. We actually just finished a really interesting project on...” That kind of detail invites follow up questions that will help keep the conversation going.

➡️ 2. What's your five year plan?

Use this as an opportunity to share how career expectations are shifting: “The way that career paths work now is pretty different from past generations—it's unlikely that I'll climb the ladder in one career or field over the course of my lifetime. That means that I'm navigating a lot of possible paths, growing my experience while staying flexible. The best way I can prepare for that is by thoughtfully building my skills and relationships in broader ways.”

➡️ 3. Why did you quit your job/change your career when your job was so great/you’ve invested so much in this path?

This question is really one about success. It's a great time to help others understand that the one-size-fits-all narrative of success doesn't really exist: “One thing that I’ve learned is that there’s no such thing as the ‘best job.’ I’ve seen too many people climb the ladder to reach what looks like success on paper, but they’re actually miserable. There’s the traditional version of ‘success’—moving up, making more money, landing an important job title—and then there’s what’s actually fulfilling and meaningful for me. I’m writing my own definition of success. And I’m making career choices that align with that definition.”

➡️ 4. Any job prospects?

If you're a student or unemployed, this one will make you shake in your boots. It implies that you're not of value unless you are productively employed. No matter your job title, you are still you—and you hold all of your skills and experience right in your hands. “I’m creating my own custom path. That means being thoughtful and engaged in charting my own course—getting really clear on who I am, what I stand for, and what I bring to the table, and finding opportunities that align with that. I’m mission-driven, which means I want more from my work than a paycheck. I don’t want to just find something, I want to find the right thing where I can really make an impact.”

➡️ 5. Why haven’t you gotten that promotion/pay raise/new job yet?

In American culture, we have an obsession with career progression. So many questions center around the idea of "What's next?" which implies that where you are isn't ever good enough. You can gently push back on this idea by saying: “Linear career paths used to be the norm, but times have changed. There are so many interesting ways to develop your career now beyond just climbing the ladder—through developing broader skills, taking on interesting projects, and building relationships. I’m always looking for opportunities to grow, but for me it’s not just about moving up—it’s about contributing meaningful work and learning.”

Three better questions and what I love about them:

Why not get in the driver's seat of the conversation? Instead of falling back on the tired questions above, try these out:

What’s shakin' in your world these days?
I love how this language doesn't imply that something has to be "new" to be good. We don't all need to be progressing all the time. Sometimes people are content right where they are. Let's make space for that.

What are you enjoying in your life right now?
​A friend recently asked me this question at lunch and we had a wonderful and unexpected conversation about things much more interesting than work—like washi tape and mocktails.

What's something you're excited about right now?
​Work is an expression of who we are, but it's not the whole of who we are. This question leaves room for talking about exciting things at work, but also welcomes sharing hobbies, obsessions, pop culture, and more.

Be gentle with yourself

Actively figuring out how to forge your own professional path is deep and worthwhile work. If you feel vulnerable when Uncle Bob's questions start coming at you, that makes perfect sense.

Go gentle on yourself. Slide out of the room and take a beat in the guest room. Take a piece of pie out to the quiet back porch. Hug your sweet nephew and talk about trucks. Find the softer spots in the room.

Maybe even pull up this email to remind you: you're living these questions, and living your way into the answers.

Gobble gobble! 🥧