🔍 October 19 – Evaluate Your Life Day: Mid-Month Crisis, Anyone? 💭📋

Yep, this is a real holiday—and no, it’s not just an elaborate excuse to lie in bed and spiral into a full-blown existential crisis (although... no judgment if that’s your vibe). October 19 is Evaluate Your Life Day, a quirky little calendar moment dedicated to checking in, looking back, and maybe—just maybe—getting your sh*t together. Or at least thinking about it.

Let’s be honest: life moves fast. One day you’re confidently drinking green smoothies, the next you’re deep in a bag of stale Halloween candy wondering how you got here. This day is your gentle (but slightly judgey) nudge to pause and ask, "Am I living my best life, or just watching reruns of it?"

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Just so you know, this post may contain affiliate links. That means if you click through and buy something, I might earn a tiny commission—enough to keep the lights on and maybe snag a celebratory cupcake. It doesn’t cost you anything extra, pinky promise.

📜 A Very (Self) Reflective Origin

Evaluate Your Life Day was created by Thomas and Ruth Roy of Wellcat Holidays, who are basically the masterminds behind some of the oddest and most delightful holidays out there (think: Bathtub Party Day, or Sneak Some Zucchini Onto Your Neighbor’s Porch Night). They invented this holiday as a moment for honest introspection—but, like, with a wink.

The goal? Take a beat. Ask yourself some real questions. Maybe cry a little. Maybe buy a planner. Maybe finally delete that toxic ex’s number (do it).

🤯 Weirdly Fun Facts About Life Evaluations

  • The average person makes 35,000 decisions a day—so if you’re exhausted, now you know why.

  • Studies show that writing things down actually improves your follow-through. Yes, journaling counts as productivity.

  • Ancient philosophers like Socrates were all about evaluating life—“The unexamined life is not worth living,”anyone?

  • 92% of New Year’s resolutions fail, which is why this October check-in might actually be your secret sauce.

🎉 10+ Quirky Ways to Celebrate Evaluate Your Life Day

  1. 🧘‍♀️ Schedule a Life Audit
    Not as scary as it sounds. Break your life into categories (career, relationships, health, creativity, etc.) and rate each one 1–10. Bonus points if you do it with snacks and a fancy pen.

  2. 📱 Reorganize Your Home Screen
    Delete the apps that bring stress. Move the ones that bring joy front and center. Make your phone a tiny sanctuary instead of a black hole.

  3. 🎧 Make a “Main Character Energy” Playlist
    Soundtrack your next chapter. No sad bops allowed unless you’re crying in the rain in slow motion.

  4. 📓 Start a “What I’ve Learned So Far” Journal
    Think of it as a living guidebook you’re writing for your future self. Spoiler alert: you’ve learned more than you think.

  5. 💡 Write a Letter to Yourself—From the Future
    Picture yourself five years from now. What advice would they give you? What do they want you to start (or stop) doing?

  6. 🧺 Clean Out One Life-Dump Zone
    That junk drawer. The dreaded closet. The metaphorical emotional closet. Clear space = clear head.

  7. 🫶 Ask 3 People What They Love About You
    (And actually listen without awkwardly brushing it off.) Sometimes others see your magic better than you do.

  8. 💬 Play "Would You Rather: Life Edition"
    Would you rather work 60 hours a week at a job you hate, or take a pay cut to do something that lights you up? Great for late-night debates or awkward first dates!

  9. 🌮 Plan a “Quarter-Life” (or Mid-Life) Crisis Party
    Celebrate all the chaos with tacos, thrifted tiaras, and dramatic toasts about your new chapter. Existential angst, but make it festive.

  10. 🧭 Make a ‘Do More / Do Less’ List
    Do more singing in the car, less doomscrolling. More calling grandma, less comparing yourself to random influencers. You get it.

  11. 🎨 Make a Vision Board... but Make It Weird
    Use glitter. Magazine cut-outs. A photo of a llama that represents your calm energy. Interpret however you want—just go full art therapy mode.

Evaluate Your Life Dinner Theme - ✨ “A Meal of Meaning: Comfort Food for the Soul Audit” ✨

🥘 Main Dish: Roasted Butternut Squash Risotto with Sage & Brown Butter

A cozy, grounding dish—perfect for pondering your life choices while stirring slowly and staring into the middle distance.

Ingredients:

  • 1 small butternut squash, peeled & cubed

  • Olive oil, salt & pepper

  • 1 tbsp butter (for roasting)

  • 1 cup arborio rice

  • 1 small onion, finely chopped

  • 2 cloves garlic, minced

  • 1/2 cup white wine (or extra broth)

  • 4 cups warm vegetable or chicken broth

  • 1/4 cup grated Parmesan (plus more for serving)

  • 2 tbsp butter + 6-8 fresh sage leaves (for the brown butter moment)

  • Optional: a handful of chopped walnuts for crunch

  • Existential clarity (or just a spoon)

Instructions:

  1. Roast the squash with olive oil, salt, pepper, and a bit of butter at 400°F until tender and slightly caramelized (about 25 min).

  2. In a large pot, sauté onion in a bit of oil until soft. Add garlic, then arborio rice. Toast for a minute.

  3. Add white wine, stir until absorbed. Add broth one ladle at a time, stirring constantly. This takes time—as do breakthroughs.

  4. When rice is creamy and al dente (20-25 min), stir in roasted squash and Parmesan.

  5. In a small pan, melt butter and fry sage leaves until crisp and butter browns. Pour over the risotto.

  6. Top with extra cheese, walnuts, and sage. Pause. Reflect. Eat.

🥗 Side: “What Am I Even Doing With My Greens” Salad

It’s bright, it’s bitter, it’s refreshing—a salad that knows we’re all just trying our best.

Ingredients:

  • Mixed greens (arugula, spinach, kale)

  • Thin-sliced red onion

  • Orange or grapefruit segments (something zesty, like your therapist)

  • Crumbled goat cheese

  • Toasted sunflower seeds or pepitas

  • Dressing: olive oil, balsamic, a teaspoon of Dijon, and a spoonful of honey (to remember life can be sweet)

🍷 Drink: A “Reassess Your Priorities” Mulled Apple Cider

Warm, spicy, and nostalgic. Best served in a mug you’ve had since college.

Ingredients:

  • 4 cups apple cider

  • 1 orange, sliced

  • 2 cinnamon sticks

  • 4 whole cloves

  • 2 star anise

  • Optional: 1.5 oz bourbon or dark rum per glass

Simmer it all together for 10-15 minutes. Strain, pour, sip slowly. Ask yourself: Is this who I want to be drinking cider in October? If the answer is yes, pour another.

🍮 Dessert: Salted Honey Panna Cotta with Thyme & Caramel Drizzle

Elegant, understated, and surprisingly easy to pull off—just like the version of yourself you're aspiring to become.

🥄 Ingredients:

  • 1 cup whole milk

  • 1 cup heavy cream

  • 1/3 cup honey (go bold—local or raw if you can)

  • 1 tsp vanilla extract

  • 1 ½ tsp powdered gelatin

  • Pinch of flaky sea salt

  • Optional: a few sprigs of fresh thyme (for infusing)

  • Optional topping: warm caramel sauce, extra sea salt, or candied thyme leaves

🔮 Instructions:

  1. In a small bowl, sprinkle gelatin over 2 tbsp cold water. Let it bloom (aka, sit and think about its life choices) for 5–10 minutes.

  2. In a saucepan, combine milk, cream, honey, and a sprig or two of thyme if using. Heat gently—don’t boil—just warm enough to steep the thyme and dissolve the honey.

  3. Remove from heat. Take out thyme. Stir in vanilla and a good pinch of salt.

  4. Add bloomed gelatin and whisk until fully dissolved.

  5. Pour into ramekins or small glasses. Chill for at least 4 hours, preferably overnight.

  6. To serve, top with warm caramel and a sprinkle of flaky sea salt. Or drizzle with honey and crown with a tiny thyme leaf like it’s your inner child finally getting closure.

🕯 Bonus Mood:

  • Light a candle.

  • Write down 3 things you actually want.

  • Eat slowly. Take stock.

  • Laugh. Cry. Stir some risotto.

🍎 Elementary (Grades 2–5): “My Life in Emoji: A Feelings & Goals Flip Book”

🧠 Theme:

Self-reflection through SEL (social-emotional learning) and creative expression using emojis and student voice.

📚 Objectives:

  • Reflect on emotions and experiences so far this school year

  • Set a simple personal or academic goal

  • Practice sequencing and writing in short bursts

🛠 Materials:

  • Half sheets of paper or pre-cut flip book templates (5–6 pages)

  • Markers, crayons, or colored pencils

  • Glue sticks or staplers

  • Optional: printed emoji sheets for inspiration

  • Title page template: “My Life in Emoji”

📝 Instructions:

  1. Start with a Class Chat 💬
    Begin with a simple question: “If your week was an emoji, what would it be and why?” Let a few students share. Discuss how emojis can represent feelings, just like words!

  2. Create a Flip Book 📖
    Pass out materials and guide students to make a small flip book (5 pages):

    • Page 1: 📅 “This Month I Felt…” (Draw 1–3 emojis and explain)

    • Page 2: 🏫 “Something I’m Proud Of”

    • Page 3: 🤔 “Something I Want to Do Better”

    • Page 4: 🌟 “A Goal I Have” (can be small—like remembering to bring homework!)

    • Page 5: 💖 “A Reminder to Myself” (positive affirmation)

  3. Share & Reflect 🎙
    Allow a few students to share their favorite page. Celebrate honesty and effort, not perfection.

  4. Display (Optional) 🎨
    Create a “Wall of Emoji Wisdom” or tuck books into portfolios for parent-teacher conferences!

✨ Quirky Twist:

Offer an “Emoji Fortune Teller” station where students pick an emoji and receive a silly but affirming message (“You picked the sleepy emoji! That means you need a weekend nap and a donut.” 🍩😴)

🎓 Secondary (Grades 6–12): “The Life Audit: A Mini-Zine of Who I Am & Where I’m Going”

🎯 Theme:

Authentic self-assessment meets zine-making! A creative outlet to evaluate values, habits, and goals.

📚 Objectives:

  • Reflect critically on personal growth and habits

  • Explore identity and voice

  • Set future goals based on honest evaluation

🛠 Materials:

  • Blank paper (1 per student, to fold into 8-page mini-zines)

  • Pens, markers, scissors

  • Optional: quote cards or reflection prompt slips

📝 Instructions:

  1. Intro Discussion: “When Do You Evaluate Life?” 💭
    Start with a quote or mini journal prompt like:

    “What would the ‘you’ from last year be surprised to know about you today?”
    Discuss how evaluation isn’t just for tests—it’s a life skill.

  2. Zine-Making Time! 📰
    Students fold a paper into an 8-page zine. Each page = a themed reflection:

    • Cover: “The Life Audit – [Student’s Name] Edition”

    • Page 1: ⚖️ “What’s Working in My Life Right Now”

    • Page 2: 🚧 “What’s Not Working”

    • Page 3: 📅 “How I Spend My Time” (visual or list)

    • Page 4: 🔄 “Habits I Want to Change”

    • Page 5: 🧠 “What I’ve Learned About Myself This Year”

    • Page 6: 🎯 “One Goal, One Step”

    • Page 7: 💬 “A Quote or Lyric That Feels Like Me”

    • Back: 🎨 Doodle, decorate, or leave a message to future self

  3. Silent Zine Walk 🔄
    Students can lay zines out on desks and do a gallery walk. They don’t have to read every page—just appreciate the individuality. Add quiet background music!

  4. Optional Exit Ticket: “One Thing I’m Taking With Me” 🪪

✨ Quirky Twist:

Give each student a tiny “certificate of realness” after the walk—funny and sincere superlatives like:

  • “Most Likely to Conquer Chaos with Coffee” ☕

  • “Deep Thinker with Killer Playlist Energy” 🎧

  • “Self-Awareness Jedi” 🧘‍♀️✨

🎯 Quirky in the Workplace


“Because nothing says team spirit like a tiny existential crisis between Zoom calls.”

Let’s be real—Evaluate Your Life Day sounds like something your therapist would assign as homework… but here in the workplace, we’re flipping the script. Instead of quietly questioning your choices while staring at your fourth cup of coffee, we’re bringing communal chaos and introspection with a twist of glitter.

"Choose Your Own Midlife Crisis" Bingo

Each employee gets a custom bingo card featuring mildly relatable workplace existential triggers. The goal? Achieve bingo by the end of the day through observation, participation, or personal realization.

Sample squares include:

  • “Reorganized my desktop and called it ‘self-care’”

  • “Googled 'How much does a goat cost, asking for a friend'”

  • “Scheduled a meeting to feel in control”

  • “Updated my LinkedIn but told no one”

  • “Had a staring contest with the printer”

  • “Asked ‘What even is success?’ out loud”

First to get Bingo wins a “Certificate of Intentional Rebranding” and a mystery box of office supplies that may or may not contain a rubber chicken wearing glasses.

Tagline for the day:
“Evaluate Your Life Day: Because if we’re going to spiral, we’re doing it as a team—with office snacks.”

🎬 Movie Pick: The Secret Life of Walter Mitty (2013)


Why it fits:
This film is the embodiment of “Evaluate Your Life Day.” Walter Mitty, a timid photo archivist stuck in a monotonous routine, breaks out of his shell when a real-life adventure forces him to confront the limits of his imagination—and his life. It's visually stunning, emotionally resonant, and challenges viewers to ask: Am I really living, or just existing?

📺 TV Episode Pick: BoJack Horseman – Season 4, Episode 11: “Time’s Arrow”


Why it fits:
This critically acclaimed episode is a haunting, surreal exploration of memory, identity, and the weight of past decisions. Told from the perspective of a character suffering from dementia, it dives deep into how a life can be shaped—and misshaped—by trauma, regrets, and missed opportunities. It’s raw, reflective, and perfect for evaluating the life you’ve lived and the one you still have time to shape.

🪞Final Thought (Because We’re Deep Now)

You don’t have to have it all figured out. Evaluate Your Life Day isn’t about shame—it’s about curiosity. Think of it as emotional spring cleaning, but in the fall. There’s still time in the year to change course, chase something new, or give yourself a little more grace.

And hey, even if you just take a nap and make a to-do list that says “nap,” that counts too.

📲 #EvaluateYourLifeLikeABoss

#MidMonthCrisis #GetItTogetherDay #CelebrateQuirky #ExistentialButMakeItFun #SelfReflectionStation

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🎉🧁 October 18 – Chocolate Cupcake Day: Let’s Get Frosted, People 🍫🎈