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  • Writer's pictureAnna

Enneagram Artist Dates Idea: The Head Triad

Welcome back to the third and final part of my Enneagram Artist Date blog post series. If you missed part one on the Gut Triad (8, 9, and 1) you can find it here and part two on the Heart Triad (2, 3, and 4) here. The premise for this series in a nutshell is that I’ve created artist date ideas based off each enneagram number!

Again, I am not an expert or “master” at the enneagram, because my expertise started with a counseling session and has continued into every enneagram dank meme account I can get my hands on. If you want to learn more about the enneagram, I’d highly recommend reading The Road Back to You! If you don’t know your enneagram number, I recommend that you avoid taking tests, and instead read or listen to an enneagram book or podcast to get a better idea of what number you could be. Or even have a conversation with a friend you trust who knows the enneagram about what number you could be, but make sure that friend is loving enough to not type you outright but instead help you on your journey of typing yourself. People react to learning their number differently, but the core motivation and fear should resonate with you in a meaningful way.

The enneagram is made up of nine numbers: each number represents a vice and passion. The enneagram is broken into three triads: the Gut Triad made up of 8, 9, and 1, the Heart Triad made up of 2, 3 and 4, and the Head Triad made up of 5, 6, and 7. This blog post is all about the Head Triad, also known as the Fear Triad. Below are my interpretations of what may be blocking each Head Triad creative and some artist date ideas that could aid in their quest to be creatively inspired!

Artist Dates for a Five: Get Involved

Enneagram Fives are known as the “Investigator or Observer.” They value transparency and are very smart: known for their research skills, being well-read and full of interesting facts. They are knowledge-focused and fall into the temptation of replacing firsthand experience with concepts. For Fives, my advice is to get involved! Fives can become so preoccupied inside their minds, books and research that they lose the value in gaining insight and knowledge from others. Fives tend to hit a dead end in their creativity when they do not seek understanding from a firsthand experience or from another; but by getting involved with others, collaborating and learning from others, their skills can become mastered and they can be fulfilled and finally move forward.


  • New Hobby. Join a group, club, or team of a hobby which you know nothing about, and try to immerse yourself in this new hobby or skill by learning through others and first-hand experience. It’s okay to not know everything about it, and you don’t have to know it all to start. Figure it out along the way and have fun!

  • TedTalk. Let others in on the story, the winning combination, the “secret sauce,” of your achievements. Share what you know! Invite friends over to teach them a new game, record a video of yourself explaining the details behind a creative project, teach a friend, family member or mentee something new!

  • Plan a Prank. Fives are extremely creative, witty and smart. Here is your chance to combine what you know and have a little fun! Consider this your April Fools from the past and make sure to keep the prank safe and light-hearted.

  • Game Night Think Tank. Just as the French had their literary salon, this think tank is all about creating amusement and transferring knowledge through conversation. Consider a theme like ‘What would you do if you were stranded on an island?’, ‘How would you survive the Zombie Apocalypse,’ or even ‘Real life pandemic, what do you think is the best way forward?’

  • Write to Your Past Self. Write a letter to your past self during a season of struggle or a year of childhood bliss. Think of a specific memory, something profound that shaped you (either in a good or bad way), and write to yourself how much you will grow, where you have gone, and who you have become now. Reflect on who you were and who you have become, where you were and where you are. Remember growth isn’t linear, and it took many winding roads to get to where you are now.

Artist Dates for a Six: Get Grounded

Enneagram Sixes are known as the “Loyalist or Skeptic,” because they value faith and are great at playing ‘devil’s advocate.’ Their greatest fear is abandonment or lack of support and thus they fall into the temptation of doubting themselves and their abilities. For Sixes my advice is to get grounded! Sixes are amazing at seeing every situation through a variety of perspectives and having a Plan B in place for every disaster. Sixes tend to become clouded in their creative process from fear and thinking they need more support, experiences, or tools. By recognizing their own inner strength and trusting themselves, Sixes will be able to build their self-confidence and carry out their projects and ideas without any doubt in themselves or their abilities.


  • Personal Power. Sixes are so good at talking themselves out of opportunities because of their inner fear--but let’s take that power back! Do a fitness challenge, train for a 5K, set a pull-up goal, do a 4-week workout, etc. Regain your power: wrestle and fight your way through and prove to no one but yourself that you have the power!

  • Creative Workshop. Sign up for a creative workshop, whether it’s woodworking, ballet, cross-stitch, drama, etc. Take an entry level class and learn something new. Mastering something new is a sure way to prove to yourself how talented you truly are!

  • Letter from Your Admirer. Write the best encouragement letter you could ever receive from your greatest admirer/hero. Write what you need to hear to feel encouraged and confident, and go back to your letter whenever you need some direction.

  • Self- Portrait. Create a self portrait however you like--use mixed media, 3-D art, crayons, paint, or any medium, colors, and patterns that you feel best represent you. While creating your self-portrait, visualize your power and recognize all the ways that you have made a difference.

  • Security Grounding. Sixes deeply value their security blankets or structures, but many times they still do not feel quite so stable. Use these questions as a creative prompt, “What is security?” and “When will I know that I have enough security?” and explore the answer to them however you like, such as a dance, a play, a short story, a sculpture, a painting, a drawing, as a journal entry etc. Find secure grounding.

Artist Dates for a Seven: Get Present

Enneagram Sevens are known as the “Enthusiast.” They value wisdom and planning and are constantly aware of all the options in front of them. They know that saying ‘yes’ to anything means saying ‘no’ to others, leading to serious FOMO. They fall into the temptation of literally thinking the “grass is always greener.” My advice for sevens is to get present! Sevens are so focused on the opportunities and experiences that lie ahead in the future that they can miss out on the creativity and opportunities available now. Sevens tend to struggle with accountability, following through with projects, and focusing on the inspiration in front of them. But by setting up accountability, rhythms, and practices, sevens will be able to unblock from the future-focus and plug into the creativity at hand.


  • Find Your Zen. Sevens are always running around with a million thoughts racing through their heads. It’s time to slow down and get quiet, find a meditation app or video, or find a yoga video or class where you can get present, grounded, and focused on the now.

  • Create a Timeline. Get a planner, a calendar, butcher paper, a white board, chalk board, whatever you like and create a timeline for your projects. Taking the time to project manage your own projects will help you follow through and know your availability and time limits, and find an accountability partner--if someone is counting on you, you are more likely to follow through!

  • Defining Date. Grab a coffee with someone much older than you (a grandparent, neighbor, teacher, friend’s grandma, etc.) and listen to them share their story. Listening is a great way to slow down and get present, while also making a new friend or growing a relationship!

  • Art Reflection. Think of a difficult time in your life and process your feelings and struggles through an art piece. Choose colors, textures and vibes that get your feelings out and loud. Processing challenges and hard emotions is helpful for a seven to unblock and move forward.

  • Video Time. Create a video of yourself talking about your life, what you’ve been through, and what your goals are--essentially making a time capsule. It will be good to look back on yourself later and see how your priorities have changed.

If you try out these ideas, leave a comment and let me know how it goes! And please remember I am just a human who enjoys reading about personality--but I fully recognize that each type in the Head Triad are more than their numbers and temptations. They are far more complex to be put into boxes. But identifying little habits and changing them up can help us be a smidge more open to creativity!


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