Scary Conversations, Part I

On this Substack, I write a fair bit about how to have “courageous conversations” with your twentysomethings, or how to talk to your young adult kids when you’re afraid of how the conversation will go.

Last week, I gave a workshop on a similar topic for the summer interns at a global corporation. It was about how to help young adults have “courageous conversations” of their own.

For context, we talked about how fear throws people into fight-or-flight—and how fight-or-flight makes people feel angry-or-anxious—and how, when we’re feeling angry-or-anxious, we tend to argue-or-avoid.

When I asked the interns how many of them, in the past week, had either avoided a conversation with someone or had an argument they wished they hadn’t, almost everyone raised a hand.

Here are the topics they said were currently having trouble talking about:

Asking a boss for time off for a family vacation or a wedding

Telling parents you want to go abroad for school

Talking to roommates about chores and bills

Compromising after an argument

Talking to landlords about maintenance problems

Rescheduling a 1x1 with a senior employee at work

Talking to parents about something they don’t want you to do

Holding friends accountable if they’re going in a questionable direction

Talking to a partner about bad choices they’re making that affect you

Sending back food or coffee when someone gets your order wrong

Going to a professor’s office hours to talk about a bad grade or missing class

Telling your mom you have plans when she wants to hang out with you

Doing performance reviews with peers in a business fraternity

Telling someone what you want or don’t want in from a situationship or hook-up

Negotiating money, such as rent or salary

Talking to a boss about transferring to another team or another role

Talking to your parents about switching your major

Telling someone you don’t feel like hanging out

Ending a relationship or telling someone you’re not interested in dating

Asking if an internship will be paid or unpaid

Telling an internship you may want to work for someone else next summer

Admitting you’re wrong to your parents especially when they’re usually right

Talking to fellow students about their behavior when you’re in a leadership position

Talking to your partner about what you need in a relationship

Talking to your advisor about forgetting to drop or register for a class

Telling a manager or professor they have been pronouncing your name wrong

Asking parents for help because you don’t want them to think you’re screwing up

Telling a friend when they’re in a bad relationship

Saying you’re sorry about something you’ve done wrong

Talking to a manager about being late and having ADHD

Telling a roommate they need to make some of their own friends

Telling parents you’re having a hard time because you don’t want them to worry

If you’re a parent reading this Substack, you may forget how scary it is to have difficult conversations—even with your friends and family—when you’re young. That’s why, when we go about town with our kids, they’re mortified when we send back food we don’t like or when we walk up to a salesperson and tell them what we’re looking for. It’s tough to imagine simply telling someone what you want or need.

Instead, most twentysomethings avoid having difficult conversations—and, when they finally do have them, they may come in swinging. Next week, I’ll share the advice I gave them for what to do instead.

In the meantime, ask yourself: Is there something your twentysomething is avoiding talking to you about?