How to Have Better Conversations Over the Holiday

Ah, the holidays! Some people look forward to them, some people dread them. 🦃🍁🎄🎁

Regardless of your situation (and everyone has a unique situation)—it’s important to mentally prepare for getting together with friends + family, especially if it’s been a while since you’ve seen each other in person.

It can be easy to jump to topics like work, dating, politics — they seem like easy and obvious choices. 🫶🏼 But if you’re looking to level up your conversations, try keeping them open ended!

💬 What’s interesting to you?

💬 How have you been spending your time?

💬 What’s something I don’t see on social media that you spend time doing?

❤️ Lead with love.

❤️ Don’t assume ill intent.

❤️ Swap judgment for curiosity.

❤️ Prioritize JOY.

Here are some great examples to keep in your back pocket this year.

❌ Instead of: “So you’re still in the city right? I always see the crime reports on the news…How are you staying safe?”

✅ Try: “Ok, Chicago. Tell me about Chicago. What are some of your favorite things to do in the city?”

❌ Instead of: “So, how’s your job?”

✅ Try: “Walk me through a day in your life! So it’s Sunday morning, you wake up —what do you do next?”

❌ Instead of: “Well you look like you’ve lost some weight! Has somebody been hitting the gym?”
✅ Try: “So what’s been interesting to you lately? Do you have any hobbies?”

❌ Instead of: “Do you have a boyfriend yet? When are you going to bring somebody home for the holidays?”

✅ Try: “So is dating something we want to talk about? Are we living our best single life? Do you want me to change the topic?”

Every single person is living a life just as full and complex as your own. So ask them how they’re doing. Know they’re doing the best with what they have.

🫶🏼 We are all more alike than we are different. You got this! 👏

👉 Looking for a new job? Sign up for my Career Workshop Intensive, a 4-part program designed to help you get a job you love ASAP. 🌈