Handling the Holidays When You’re in Transition: 7 Steps to Take Care of Yourself

No doubt about it—the winter holidays can be particularly poignant when you’re in transition.

This time of year is a common “taking-stock” time. As you go to festive parties or head home for the holidays, you can’t help but think about what your life was like this time last year, and the year before, and the year before.

If things were better last year—you had a job you loved, or you were in a great relationship, or you were happily single instead of dealing with the fresh heartbreak upon you now—the comparison can feel really sad, frustrating, or overwhelming.

On the other hand, holidays can be a time of deep awareness of what hasn’t changed.

If last year you vowed that this would be the year you finally (fill in the blank), the realization that it wasn’t can hit hard.

If you were stuck last year, and you’re still stuck now, still feeling in transition, you can get sucked into a defeatist mentality. “I’ll never figure it out.” “I haven’t made any progress.” “I guess I’m just the messed up sister.”

If you’re returning to your childhood home, being in that familiar environment can make you uber-aware of how things have changed and how things have stayed the same through the years.

As you go to sleep in your childhood bedroom, you may remember the plans you made for yourself as a kid, and think of all the things you were sure you would do, be, or have by now.

I was recently having coffee with a friend who is getting ready to go home for Christmas. “It’s always so weird to sleep in my room,” she said. “I thought I was going to be working for SNL or the BBC by the time I was an adult.” We can’t help but be struck by the gap between who we expected to be and who we are.

Add all the other elements of family dynamics to this bubbling cauldron of self-doubt and stir!

When already feeling insecure, many people tend to snap into defensiveness most easily around their families, leading you to scream “GET OFF MY CASE, MOM!” when the poor woman is only offering you a glass of wine.

It can be hard when everyone around you seems to know who they are. What’s more, you may be called on to talk about who you are, as you see people you haven’t seen in a long time and it’s time to fill them in. You may find yourself dreading the “update conversations.”

“So, what are you doing these days?” your aunt asks.

When you’ve spent the last several weeks, months, or years asking yourself the same question, it can be overwhelming coming from someone else!

If you have siblings, you are likely comparing yourself to them—playing the “when she was my age she had already been married for two years OH MY GOD!!!” game, or wishing you could afford to give gifts in the same way they can with their more lucrative careers.

All of this can lead you to feel abashed at your own thoughts—and all of it is totally normal. If your trip home fills you with this kind of anxiety, you are not alone.

Here are seven steps to take care of yourself when you head home for the holidays in a perfect winter storm of transitions.


1. Be aware of what you’re feeling.

Before you head to your family gathering, set aside some time to check in with yourself about how you’re feeling.

The more aware you are of your feelings ahead of time, the more able you’ll be to choose supportive thoughts and actions for yourself in the moment. Proactively considering your feelings makes you less likely to snap into defensive mode or feel triggered by the comments or actions of others.

Get curious: what are you feeling, and why? What negative stories are you telling yourself about your transition? What are you worried others will think about you?

On top of your own stress about being in transition, you may be feeling some embarrassment or even shame when you think about sharing your status with your family.

We compare ourselves to our more “together” siblings or other family members, married with children, or advancing in a great career they feel passionate about.

We worry that we’re disappointing our parents, or, just as bad, fulfilling an expectation they had that we would flounder. In one way or another, we feel not good enough. We want our families to see us thriving and succeeding by whatever terms we think they would define success.

It’s worrisome when we feel we don’t measure up.

2. Own your own feelings and projections.

Now that you’re clear on what you’re feeling, it’s important to be aware that many of your perceptions of how your family is thinking about you are no more than just that—your own perceptions (and perhaps projections).

It’s possible your family feels much differently about you than you do about yourself. Few people have more power to bring out our defensiveness than our families—in part because we do care so much what they think.

Give your family the benefit of the doubt; assume that they believe in you and want the best for you. You might not share their ideas about what that means, but don’t assume you’ve disappointed them just because you’re feeling insecure yourself.

3. Be proactive by creating your own story.

How will you tell the story of the transition you’re in?

Having to answer the question, “So, what are you doing now?” can be daunting when you’re really not sure yourself!

Oftentimes, family members and friends ask about work because that is a go-to subject in our society. If you define what you’re up to in terms of your career, and you’re in career transition, it can feel like you don’t have anything to proudly offer to the conversation.

Before you go, find a way to tell your story that feels good to you. You get to decide which version of “What are you doing?” to tell.

To gear up for holiday update conversations, think of two or three things that you’re excited and positive about. When your aunt asks “What’s new?” you can share about the pottery class you’re taking, or the inspiring volunteer event you participated in, or the interesting people you’ve been meeting on your job search.


4. Take good care of yourself and be self-compassionate.

Your blizzarding snowglobe of emotions is totally understandable, given that you are in transition! Now that you are aware of your feelings, you can actively choose to think supportive thoughts and bring yourself back to the present moment.

When you start to feel stressed, practice mindfulness. Here are two ways you can do that without anyone being the wiser:

  • Play a quick round of “Five Things.” Whatever you’re doing, just stop and notice. Notice 5 things you hear. Then notice 5 things you see. Then feel. Then smell. And, especially since it’s the holidays, then taste! This will bring you out of your head and into your body, and back to the present moment.
  • Find 5 minutes of silence. No devices, no book. Just sit and focus your attention on your breath. If thoughts come, say “thank you for sharing” and let them go. Give yourself the gift of quiet.

If a flurry of overwhelming thoughts starts filling your head, redirect your attention by asking yourself what hasn’t changed. It may feel like everything is up in the air; look around and take note of all the things that are the same.

5. If you’re traveling for the holidays, take advantage of your change in environment.

The holidays offer many of us the opportunity to take some time off and recharge physically—and being out of town can put much-needed distance between you and your to-do list back home.

Take advantage of the time and space to honor your basic needs.

Get extra sleep. Feed your mind by reading a book or watching a great movie. Write in your journal. Eat good food.

This time away can also be an opportunity to move you forward in your transition. We have different thoughts and ideas when we’re not in our usual environments. You may get some insights that wouldn’t have shown up back at home.

If you are in your childhood home, look around. Several of my clients have had epiphanies when they looked at their old artwork, yearbooks, writing, toys, books, and so forth—these things can be portal objects that carry you back to your childhood and help you reconnect with some important dream that may still be relevant now.

6. Be vulnerable enough to let the people who love you support you.

Instead of assuming judgment, invite your family and friends to be your champions.

Be vulnerable; share what you’re going through and ask them, what do you see in me? What do you see as my standout qualities? What advice or encouragement do you have for me?

(Remember, take in advice as a data-collection exercise. You don’t have to take all, or any, of the advice, opinions, or beliefs that someone else offers you. Listen first, and later you can separate the wheat from the chaff. Take what works for you and leave the rest.)

The year I started my business, I learned so much by talking to my cousin, who had just finished business school, my aunt, who is an editor for a business magazine, and my brother-in-law, who had just undergone a major career change himself.

When I was vulnerable enough to share my fears and dreams with family and friends, I heard many expressions of belief in me that buoyed me throughout the next year.

7. Get out of your own story and into someone else’s.

Family gatherings are amazing opportunities to ask people who love you to share their own perspectives!

Chances are, members of your family have gone through transitions that you aren’t even aware of.

Share that you are exploring new career options, getting over a bad breakup, or adjusting to your big move, and that you’re excited to get some perspective. Ask,

  • When have you made a job change?
  • What was the worst breakup you ever suffered?
  • What was the hardest change you ever made? What helped you make it?
  • How did you meet people when you moved to a new city?
  • What do you love about your job?
  • What change in your life would you like to make if you had the time, courage, money, etc.?

Ask a variety of people, or choose just one or two people you feel most comfortable opening up to.

You are bound to leave the conversation feeling less alone in your overwhelm, and you’re likely to get a new idea or two.

What’s more, when you share your journey with your family, you may learn about opportunities to find mentors or helpful contacts in your family network.


The holidays can be a tricky time to be in transition. It takes courage to lean into this unique moment in your life, and to make the most of the opportunities in front of you. Take good care of yourself this holiday season, and remember that you get to choose how you look at, and share, your story.

And in that spirit, share with us in the comments below. What transition are you embarking on this year?

9 thoughts on “Handling the Holidays When You’re in Transition: 7 Steps to Take Care of Yourself”

  1. The (somewhat) bad news: one can still worry about all these issues at an advanced age, when there are children to please rather than parents and when there are still transitions under way that aren’t a bit easy. The good news: this post is just as useful for those in later life as for those just starting out. These are solid, easy steps to take. Thanks, Carrie.

    1. Such a great point, Julesbeth. Being in transition is a challenge whether you’re 8 or 88! So glad you found the post useful.

  2. What’s also powerful about #6 is that when you are vulnerable, you allow someone else to be of service. I firmly believe that – whether we are conscious of it or not – most of us glean our greatest joy from being helpful. Why? Because being helpful is light-speed to connection and we ALL want connection. The particular Christmas exchange you describe was the highlight of MY Christmas experience.

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