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Navigating the Holiday Season Through the Lens of the Enneagram

Date01 Dec, 2023
Type Team Optimization
Author Flipp Advertising

The holiday season is a time of joy, festivities, and celebration, but for many, it can also be a time of stress and self-reflection.

Each person experiences this time of year in their own unique way, influenced by their personality traits and perspectives. In this blog post, we will delve into the holiday season through the lens of the Enneagram, exploring how each personality type approaches and feels about this special time of year.

Type 1 – The Perfectionist

For Enneagram Type 1, the holiday season can bring a mix of excitement and anxiety. The Perfectionist is drawn to the idea of creating the perfect holiday experience, from meticulously decorating the tree to planning flawless gatherings. However, the pressure to meet their own high standards can lead to stress. Type 1s may find it challenging to relax and fully enjoy the season, as they may become preoccupied with ensuring everything goes according to plan.

To navigate the holiday season successfully, Type 1s can benefit from embracing flexibility and recognizing that perfection is not the ultimate goal. Embracing the imperfect moments can lead to a more fulfilling and joyful holiday experience.

Type 2 – The Helper

Enneagram Type 2, also known as The Helper, thrives during the holiday season. This personality type is driven by a desire to help and support others, making them natural gift-givers and party planners. Type 2s find joy in the act of giving, and the holiday season provides ample opportunities for them to express their love through thoughtful gestures.

However, The Helper should be cautious not to overextend themselves in their eagerness to assist others. It’s important for Type 2s to balance their giving nature with self-care during this busy time. Setting boundaries and ensuring they take time for personal relaxation can enhance their overall holiday experience.

Type 3 – The Achiever

For Enneagram Type 3, the holiday season is a chance to showcase their accomplishments and project an image of success. The Achiever enjoys the social aspects of the season, such as holiday parties and gatherings, where they can network and shine in the spotlight. However, the pressure to maintain an impressive facade can lead to stress and burnout.

To fully enjoy the holiday season, Type 3s should focus on genuine connections rather than the need for external validation. Embracing authenticity and allowing themselves to relax without the pressure to constantly achieve can lead to a more fulfilling holiday experience.

Type 4 – The Individualist

Enneagram Type 4, The Individualist, often has a complex relationship with the holiday season. While they appreciate the opportunity for self-expression through unique and meaningful traditions, they may also feel a sense of melancholy or nostalgia during this time. The pressure to conform to societal expectations can be challenging for Type 4s, who value their individuality.

To make the most of the holidays, The Individualist should embrace their creativity and incorporate personal touches into their celebrations. Creating new traditions that resonate with their sense of self can bring a sense of authenticity to the season.

Type 5 – The Investigator

The holiday season can be a mixed bag for Enneagram Type 5, The Investigator. On one hand, they may appreciate the opportunity to delve into new topics or explore unique cultural traditions. On the other hand, the social demands of the season may feel overwhelming, leading Type 5s to retreat and seek solitude.

To strike a balance, The Investigator should prioritize self-care and set realistic expectations for social interactions. Allocating time for solitude and engaging in activities that align with their intellectual pursuits can enhance their overall holiday experience.

Type 6 – The Loyalist

Enneagram Type 6, The Loyalist, approaches the holiday season with a mix of excitement and caution. The security and predictability of holiday traditions provide comfort to The Loyalist, but the uncertainties associated with family gatherings or the pressure to conform can trigger anxiety.

To navigate the season successfully, Type 6s should focus on building a support system and cultivating a sense of security. Open communication with loved ones and setting realistic expectations can help ease anxieties and create a more enjoyable holiday experience.

Type 7 – The Enthusiast

The holiday season is a playground for Enneagram Type 7, The Enthusiast. This personality type embraces the festive atmosphere, seeking out new experiences, and enjoying the thrill of the season. However, the fear of missing out or the avoidance of negative emotions can lead Type 7s to overcommit and burn out.

To fully savour the holiday season, The Enthusiast should practice mindfulness and be present in the moment. By slowing down and appreciating the joy in each experience, Type 7s can create lasting memories without feeling the need to constantly move on to the next exciting thing.

Type 8 – The Challenger

Enneagram Type 8, The Challenger, approaches the holiday season with a sense of determination and a desire for control. They may take charge of holiday planning, ensuring everything runs smoothly. However, the fear of vulnerability and a reluctance to show softer emotions can impact their ability to fully connect with the holiday spirit.

To embrace the joy of the season, The Challenger should allow themselves to be more vulnerable and open to the emotions that arise. Building meaningful connections with loved ones and expressing genuine emotions can lead to a more fulfilling holiday experience.

Type 9 – The Peacemaker

The holiday season is a natural fit for Enneagram Type 9, The Peacemaker. This personality type values harmony and connection, making them enjoy the sense of togetherness that the season brings. However, the tendency to avoid conflict can lead to unexpressed needs and desires.

To make the most of the holidays, The Peacemaker should prioritize clear communication and self-expression. By acknowledging their own needs and openly sharing them with others, Type 9s can create a more authentic and fulfilling holiday experience.


The Enneagram provides a fascinating framework for understanding not only how individuals experience the holiday season, but how they approach life. Each personality type brings its own strengths and challenges, and by embracing self-awareness, individuals can navigate the festivities with a deeper understanding of themselves and those around them. At Flipp, we use the Enneagram as a cornerstone of our culture in understanding the individuals on our team, and how we can optimally work together. If you are curious about the Enneagram, what your number may be, or the numbers of those you work with, please contact us to learn more about Enneagram Training for your team. Happy Holidays!