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How to Survive Awkward Holiday Conversations About Your Career

Emily Lamia profile image

Emily Lamia

A Christmas themed dining table setting.

Now that it's the holiday season, you might have a few dreaded, awkward conversations to survive. Maybe you don't know how you'll make it through Thanksgiving with that one uncle who thinks it's a great idea to talk about politics, or perhaps you're preparing to field questions about your job ( "Yes, I really do like working in the social-impact sector!").

I’ve been there.

I spent the first five years out of college working on political campaigns, which pretty much meant I was unemployed during the holidays because it was after the campaign had wrapped up. I dreaded having family and friends asking, “So, what are you doing next?” not just because I wasn’t really sure how to answer it, but because I honestly didn’t know! It felt sorta embarrassing to seem like I was constantly trying to “figure it out.”

Over time, I’ve come to realize a few things about these conversations and encounters. Below are my solutions for surviving them!

1. People’s reactions to your life and career often say more about them than they do about you.

Some people might fixate on a particular aspect of your life - your lack of a serious romantic relationship or your non-traditional career path, for example. And while part of that focus might be out of love for you- because they want to see you succeed and be happy- it often suggests that they place a lot of significance on that part of their own life. They might be trying to wrap their heads around your life as if it was made up of the same hopes, dreams, and challenges that theirs are.

People bring their own baggage to these sorts of conversations. Try and remember that their hang-ups on some part of your life could actually be speaking to their own issues rather than yours.

2. Give yourself permission to avoid certain people and skip out on various gatherings if you know that it’s just going to upset you.

Maybe you have this one friend who is going to bring up some subject that’s just going to stress you out or upset you. Do you really have to go to their holiday party? You probably don’t.

I’m not suggesting you blow everyone off, but take a moment to check in with yourself and really think about the effect some of these encounters are going to have on you.

Plan your calendar thoughtfully. Prioritize the happy hours and gatherings in December that are going to make you happy and give you the opportunity to see people who don’t stress you out. And when you do encounter those that are particularly grating, try this:

3. Take the pressure off conversations about you by asking others about themselves.

One of the things I do if I really don’t feel like talking about myself or my professional life is to plan on being the one to ask lots of questions. Remember, people love talking about themselves! If you act super excited and interested in what’s going on with them, they probably won’t even notice that they don’t know what’s going on with you.

And there are so many questions you can ask! Ask about their family, job, house, where they've traveled this year, or if they’ve got any New Year’s resolutions. If they have pets, ask about them... this will probably give you at least five minutes of photos and stories about their cat or dog.

People bring their own baggage to these sorts of conversations. Remember that their hang-ups on some part of your life could actually be speaking to their own issues rather than yours.

4. It’s helpful to have a few short answers lined up so you’re ready for any dreaded questions.

The “what are you looking to do after your internship/graduate program/fellowship?” question might be inevitable. Practice a short, to-the-point answer that tells them you’re thoughtful and polished.

You don’t need to go on and on… and you don’t have to tell them all the internal debates you’re having about what the right path for you is (unless you actually think they might be helpful in you figuring it out!).

If you’re not sure you’ll be able to deliver a good answer, try writing it out first. When we write things down, it helps us get to the point and allows us to edit until we’ve got a succinct, well-poised response.

Need some ideas for framing? Try these:

If you’ve been at the same organization for a while but are trying to pivot into a different field:

“I’m still at X organization, and it’s been great, though I am exploring what it would be like to work in X industry/or pivot into X type of role. I’m excited to see what the new year has in store for me.”

If you’re unemployed:

“You know, there’s a reason that a lot of people call being unemployed ‘funemployment’ — because it actually can be fun! Yes, I’m looking for what my next job could be, but I’m also taking this opportunity to do a lot of things you get too busy to do when you’re working full-time. Did you know there’s a great exhibit at X museum?”

Often, it’s all about your attitude and how you deliver it.

5. Identify one “Bright Spot” from the last year you’re proud of or feel excited by and work it into an answer.

I talk a lot about “bright spots” with my clients; these are moments at work where you really liked what you were working on and felt kinda jazzed by a project. meeting, event, or conference.

Take five minutes to sit with your thoughts and reflect over the last year. Was there something you were really proud of that you can incorporate into your conversations? Also use it to frame the potential for more of these “bright spots” in the future.

Not only will you feel more confident talking about yourself when you’re sharing a positive moment, but it’s likely people will remember that about you weeks after the conversation-- more than they may remember some of the other updates you shared!

This “bright spot” is a weapon in your arsenal that you can pull out when you want to show others that you’ve had a good year and are excited about what the future holds (even if you don’t feel that way all the time).

Prepare, then enjoy the cocktail!

The holidays can be a rough time for a lot of people, for a number of different reasons. Give yourself some time to prepare and think about how you want to spend your time, and how you want to approach conversations when you might not be feeling your best.

I can pretty much guarantee you that everyone struggles with these conversations and gatherings multiple times over the course of their life. Use these suggestions to make them easier throughout the season of cheer, and remember the added bonus of these events: the holiday cocktail.

Emily Lamia profile image

Emily Lamia

Emily Lamia is the Founder of Pivot Journeys, which offers career coaching, group programs, and organizational consulting to teams that want to build strengths-based cultures that increase engagement, collaboration, and productivity.

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