Navigating Holiday Expectations When You Feel Behind in Life

Key Takeaways

• There is no universal timeline for life. The feeling of being "behind" is based on arbitrary expectations, not reality. Your worth isn't determined by hitting certain milestones by a certain age, and comparing your journey to others' only fuels anxiety and depression.

• Boundaries are essential during the holidays. You don't owe anyone detailed explanations about your career, relationship status, or life choices. Prepare simple responses in advance and redirect conversations to topics that feel comfortable for you.

• Therapy can help you navigate these feelings. If anxiety or depression around life expectations is impacting your wellbeing, working with a therapist can help you challenge unhelpful beliefs, develop coping strategies, and build a more compassionate relationship with yourself.

Navigating Holiday Expectations When You Feel Behind in Life

The holidays are supposed to be a time of joy, connection, and celebration. But for many young professionals, the season brings something else entirely: a heightened sense of anxiety about where they are in life compared to where they thought they'd be by now.

As a therapist, I see this pattern intensify every year between Thanksgiving and New Year's. The combination of family gatherings, social media highlight reels, and end-of-year reflection creates a perfect storm for feelings of inadequacy. If you're dreading questions about your job, relationship status, or life plans, you're far from alone.

The "Behind in Life" Narrative

Many of my clients in their twenties and thirties arrive at therapy sessions in December carrying a heavy story: they're behind. Behind on career milestones. Behind because they're still single while siblings are married with kids. Behind on buying a home, behind on savings, behind on having it all figured out.

This narrative of being behind is often rooted in invisible timelines we've internalized, sometimes without even realizing it. These timelines come from family expectations, cultural messages, social media comparisons, and the life plans we sketched out for ourselves years ago when we had far less information about how life actually unfolds.

The truth? These timelines are arbitrary. There is no universal schedule for a meaningful life. But during the holidays, when you're sitting at the dinner table fielding questions about your job or love life, this truth can feel very far away.

Understanding the Psychological Impact

The pressure to meet unspoken expectations doesn't just create passing discomfort; it can have real psychological consequences. In therapy, I work with young professionals who experience significant anxiety in the weeks leading up to holiday gatherings. This anxiety manifests in various ways: ruminating about potential conversations, losing sleep over anticipated judgment, or even considering skipping family events altogether to avoid the discomfort.

Depression often accompanies this anxiety, particularly as the year draws to a close. End-of-year reflection, which is meant to be a time of gratitude and goal-setting, can instead become a painful inventory of perceived failures. When you're measuring yourself against expectations you haven't met, it's easy to overlook the growth, resilience, and progress you have made.

When Anxiety and Depression Intensify During the Holidays

The pressure to meet unspoken expectations can trigger or worsen anxiety and depression. Anxiety might show up as racing thoughts before family events, catastrophizing about awkward conversations, or physical symptoms like tension and insomnia. Depression might manifest as a sense of heaviness, withdrawal from holiday activities you used to enjoy, or persistent negative self-talk about your perceived failures.

In therapy, we talk about how these feelings aren't character flaws; they're understandable responses to very real pressure. The holiday season asks us to be "on" and celebratory at a time when many people are actually struggling. This disconnect between external expectations and internal reality can be exhausting.

What makes holiday anxiety particularly challenging is that it often comes wrapped in guilt. You might feel you "should" be grateful, happy, and present with family, which only adds another layer of self-criticism when you're actually feeling anxious or depressed. This guilt about your feelings can create a vicious cycle that intensifies the original distress.

The Career Pressure Cooker

For young professionals, career-related questions can be especially triggering during holiday gatherings. "How's work going?" seems like an innocent question, but when you're struggling in your job, recently laid off, or questioning your entire career path, it can feel like an interrogation.

In therapy sessions, clients often express anxiety about explaining why they're not where they thought they'd be professionally. Maybe you're still in an entry-level position while college friends have been promoted. Perhaps you changed careers and feel like you're "starting over." Or maybe you're in the job you thought you wanted, only to discover it's making you miserable.

The depression that accompanies career dissatisfaction or setbacks can be profound. Your career is often intertwined with your identity, especially in your twenties and thirties. When work isn't going well, it can feel like you're not going well. Add holiday family gatherings where everyone seems to have exciting updates about promotions, projects, or career moves, and the sense of being behind can become overwhelming.

What I emphasize in therapy is that career paths are rarely linear anymore. The traditional trajectory of steady advancement in one field is increasingly rare. Most people experience setbacks, pivots, periods of uncertainty, and even complete career changes. The person who appears to have it all figured out at the holiday table may be struggling in ways you can't see.

Relationship Status and the Single During the Holidays

Being single during the holidays can amplify feelings of being behind in life, particularly when family members ask pointed questions about your dating life or make comments about "settling down." The anxiety around these interactions often starts weeks before the actual gatherings, as single young professionals anticipate the inevitable questions and awkward conversations.

In therapy, I hear about the unique depression that can emerge from feeling like everyone else is partnered while you're still searching. Social media intensifies this feeling, as feeds fill with engagement announcements, couple photos, and relationship milestones. The message seems clear: you should be further along in your romantic life than you are.

What makes this particularly painful is that relationship status isn't entirely within your control. Unlike a career where you can take specific actions, finding a compatible partner involves timing, luck, and factors beyond your individual efforts. The anxiety that comes from this lack of control can be significant, especially when well-meaning relatives offer unsolicited advice or question your standards.

Depression related to relationship status often includes a fear that something is fundamentally wrong with you. Why hasn't it happened yet? What are you doing wrong? These questions can become obsessive during the holidays when you're surrounded by coupled family members. In therapy, we work on separating your worth from your relationship status and recognizing that being single doesn't mean being deficient.

It's also worth noting that many people in relationships struggle during the holidays too. The pressure to bring a partner home, questions about marriage or children, or tensions within relationships can create their own forms of anxiety and stress. The grass isn't always greener; it's just different grass.

The Comparison Trap and Social Media

Social media has fundamentally changed how we experience the holidays and how we measure our lives against others. The anxiety and depression fueled by social comparison have become central topics in therapy, particularly during the holiday season when everyone is posting their best moments.

What you see online is a carefully curated highlight reel. The friend posting about their promotion isn't sharing the anxiety attacks they've had about the new responsibilities. The couple with the perfect holiday photos isn't posting about their arguments or relationship struggles. The person who seems to have it all together isn't revealing their depression or the therapy they're attending to manage it.

In therapy, we work on recognizing when social media use is contributing to your distress. If scrolling through feeds leaves you feeling worse about your life, that's valuable information. The comparison trap is particularly insidious because it's often unconscious; you might not realize how much it's affecting your mood until you take a break and notice the difference.

The anxiety that comes from constant comparison can manifest as a sense that everyone is moving forward while you're standing still. Depression can follow as you internalize the message that you're not enough. Both of these responses are natural given how our brains are wired to compare ourselves to others, but they're based on incomplete and misleading information.

Practical Strategies for Navigating Holiday Gatherings

If you're feeling anxious about upcoming holiday interactions, here are some approaches I discuss with clients in therapy:

Prepare your boundaries. You don't owe anyone a detailed explanation of your life choices or timeline. Practice phrases like "I'm taking things one step at a time" or "I'm figuring it out as I go." You can redirect conversations to topics you're actually excited about or turn questions back to the asker. Boundaries aren't about being rude; they're about protecting your mental health and managing anxiety in social situations.

Challenge comparison thinking. When you notice yourself comparing your chapter 3 to someone else's chapter 20, pause. Everyone's path has invisible struggles and setbacks. The polished version people present at holiday gatherings rarely reflects the full complexity of their lives. In therapy, we practice catching these comparison thoughts and questioning their validity.

Find your people. Seek out family members or friends who make you feel accepted as you are, not as who you "should" be. Sometimes that's a cousin who also feels out of step, or a friend who understands the pressure you're under. These connections can be lifelines during gatherings that otherwise feel overwhelming. Having even one person who gets it can significantly reduce anxiety and help you feel less alone.

Limit social media. The anxiety and depression that come from comparing your real life to others' curated feeds are well-documented. Consider taking breaks from apps that make you feel worse about where you are in life. This doesn't have to be permanent; even a temporary break during the most intense holiday weeks can provide relief and perspective.

Ground yourself in your actual values. What matters to you, independent of external timelines? Maybe it's creativity, learning, relationships, service, or adventure. When you feel lost in comparison, reconnecting with your authentic values can provide direction. In therapy, we often explore the difference between values that truly resonate with you and expectations you've absorbed from others.

Plan self-care before and after events. Managing anxiety isn't just about what happens during holiday gatherings; it's also about how you prepare and recover. Schedule activities that help you regulate your nervous system, whether that's exercise, time in nature, creative pursuits, or simply quiet time alone. Treating potentially stressful events as something to bookend with self-care can make them more manageable.

Practice self-compassion. When you notice harsh self-criticism arising, try speaking to yourself as you would to a good friend in the same situation. Depression often includes a relentless inner critic that tells you you're not good enough. In therapy, we work on developing a more compassionate inner voice that acknowledges difficulty without piling on judgment.

Reframing Success and Timeline Anxiety

In therapy, we often work on separating your worth from your achievements or relationship status. This is deep work that doesn't happen overnight, especially when you're surrounded by messages suggesting otherwise. But it starts with noticing when you're measuring yourself against arbitrary standards.

Consider: What would it mean to define this period of your life by what you're learning rather than what you're lacking? Many young professionals I work with are building resilience, developing self-awareness, and clarifying their values during times they initially labeled as "being behind." These are the foundations of a life lived with intention rather than just checking boxes on someone else's list.

The anxiety about timelines often stems from a fear of missing out or making irreversible mistakes. But most life decisions are not as permanent as they feel in the moment. Career paths can change. Relationships can develop at different times. Financial situations can improve. The rigidity of thinking "I should be here by now" creates unnecessary suffering. In therapy, we work on developing flexibility in how you think about your life trajectory.

Depression often includes a sense of hopelessness about the future, a feeling that if you haven't achieved certain things by now, you never will. This is a cognitive distortion that therapy can help address. The reality is that people's lives unfold in countless different ways, and late bloomers often build deeply meaningful lives precisely because they took the time to figure out what actually matters to them.

The Role of Family Dynamics

Holiday anxiety isn't just about internal pressure; it's also about the actual dynamics in your family system. Some families are more critical or judgmental than others. Some have a culture of achievement where worth is measured by accomplishments. Some have members who ask invasive questions without respect for boundaries.

In therapy, we explore your specific family dynamics and how they contribute to your holiday anxiety and depression. Understanding these patterns can help you develop strategies tailored to your situation. It can also help you recognize that the discomfort you feel isn't entirely about your own inadequacy; it's at least partly about the environment you're navigating.

For some young professionals, the holidays bring up old family roles and patterns. You might find yourself regressing to a younger version of yourself, feeling small or criticized in ways that trigger childhood experiences. This can intensify feelings of being behind or not measuring up. Therapy can help you maintain your adult sense of self even when family dynamics pull you backward.

It's also important to recognize that you can't control how family members behave, but you can control how much you expose yourself to situations that harm your mental health. If family gatherings consistently leave you feeling worse, it's okay to limit your time, arrive late, leave early, or even skip events that feel too damaging. Protecting your mental health is not selfish; it's necessary.

When to Seek Professional Support

If anxiety or depression around these issues is significantly impacting your daily functioning, relationships, or overall wellbeing, therapy can provide valuable support. A therapist can help you work through the underlying beliefs driving your distress, develop coping strategies specific to your situation, and create a more compassionate relationship with yourself.

Holiday-related anxiety and the feeling of being behind often point to deeper questions about identity, belonging, and purpose. These are exactly the kinds of questions therapy is designed to help you explore. Working with a therapist provides a space where you can be honest about your struggles without judgment, where your timeline is respected, and where your worth isn't tied to external achievements.

Therapy isn't just for crisis moments. Many young professionals benefit from working with a therapist during transitional periods of life, even when things are generally okay. If the holidays consistently bring up difficult feelings, that's reason enough to seek support. If you notice that anxiety or depression is affecting your work performance, relationships, sleep, or daily functioning, that's also a clear sign that professional help could be beneficial.

The stigma around mental health treatment has decreased significantly, but many people still hesitate to reach out. If you're unsure whether therapy is right for you, consider that you don't have to be in crisis to benefit from support. Therapy can help you navigate normal life transitions and challenges more effectively, develop better coping strategies, and build the resilience you need for whatever comes next.

Moving Through the Season

The holidays will come and go. The conversations you're dreading will happen and then be over. What remains is your relationship with yourself and the life you're actually building, not the one you think you should have by now.

You are not behind. You are exactly where you are, dealing with your unique circumstances, making decisions with the information you have. That's not failure; that's being human. The anxiety about timelines and the depression about perceived inadequacy are understandable responses to real pressure, but they don't reflect the truth about your worth or your future.

If you find yourself struggling with anxiety, depression, or feelings of inadequacy this holiday season, remember that reaching out for support through therapy or trusted relationships is a sign of strength, not weakness. You don't have to navigate this alone. Many young professionals are experiencing the exact same struggles, even if they look like they have it all together at the holiday table.

The path forward isn't about suddenly meeting all the expectations you haven't met. It's about building a life that aligns with your values, developing compassion for yourself during difficult periods, and recognizing that there are many ways to live a meaningful life. Therapy can help you discover what that looks like for you, independent of anyone else's timeline or definition of success.

 Lauren Donohue specializes in helping high-achieving young professionals redefine success beyond external validation and develop meaningful connections. Lauren is trained in ACT, CBT, and EMDR.