The Ordinary Magic of Introspection

When I was seven years old, my great grandma passed away. She wasn’t a central figure in my life, and I had only a few scattered memories of bosomy hugs, carousel rides, and her powdery, old-person skin. We traveled to South Dakota for the funeral and helped the rest of the family sift through her house with its everyday artifacts of a life left behind. It felt dim and unfamiliar to me, but when my mom told me I could pick something to take home, the light of possibility flickered on and those rooms became a veritable treasure trove. I chose a tiny white bear with smiling golden eyes and a delicate peach bow.

It was my first real experience with death, and I thought about it with all the heart and depth that a contemplative seven-year-old can muster. Although I didn’t have a strong emotional tie to my great grandma, there was a burdensome and confusing sadness that sat with me when I wondered how this real person that we had loved and touched and known could be here one moment - and not the next.

I cried, looking at that smiling bear perched so sweetly on my bed. I cried on the playground at school, wondering why everyone was swinging and jumping rope as if a human being hadn’t just left this earth. I cried in the woods behind our house, hoping my grandma was someplace warmer and cleaner than the cool earth underfoot. Finally, the school counselor called my mom and suggested that she get me a journal to help me process my feelings.


That journal was a child-sized blessing with thick, square pages and a ballerina kitten on the cover. I set pen to paper with an earnestness that made me wonder how I had made sense of anything before this bit of wizardry fell into my hands.

My introspection process has changed a bit since then, but the spirit is the same. There is a gentle beauty in creating space to think deeply about the kind of humans we want to be and how we want our minutes to stack up. Time has a way of slipping through our fingers, and we often treat reflection as a luxury when in truth, it's entirely necessary for a life well-lived.

In his wise and powerful book, The Five Invitations, Frank Ostaseski reminds us precisely why this matters:


"Over the past thirty years, I have sat on the precipice of death with a few thousand people. Some came to their deaths full of disappointment. Others blossomed and stepped through that door full of wonder. What made the difference was the willingness to gradually live into the deeper dimensions of what it means to be human."


Here are a few of my favorite rituals for introspection. It has taken several years for this framework to come together and it will undoubtedly continue to evolve as I do. I hope you will find something of value for your own quiet practice.

Each day is a little life.

Arthur Schopenhauer

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This guide is broken into daily, weekly, monthly, quarterly, and annual processes. They work in conjunction with each other, but they can also stand alone. Feel free to pick and choose what speaks to you. To download the entire guide, scroll to the bottom of the page and get the goodies!

Daily Journaling:

  • Gratitude makes us happy and retrains our brains.
  • Loving-kindness creates space to focus outward. It's good for us and good for the universe!
  • Considering longer term goals (and how to accomplish them) aligns our small, daily actions with what matters most.

Weekly Planning:

  • Choose 1-2 simple, meaningful goals to focus on for the week.
  • Plan for failure. Be honest about what will trip you up and create a specific strategy to overcome it. 
  • Dream a little! Expect magic and it just might show up.
  • Habits and small changes add up exponentially over time.

Weekly Reflections:

  • Evaluate progress on your "most important thing" for the week. This can be a grade, a rating, or a simple narrative.
  • Celebrate! Identify what you did especially well this week.
  • Give thought to what lit you up and what drained you. 
  • What small shifts would make next week even better? 

Monthly Evaluation:

  • Identifying your feelings packs a dual punch of fostering mindfulness and cultivating emotional intelligence.
  • Consider what stood out to you this month - the victories, struggles, and ordinary moments. (Bonus: This creates a helpful reference for your annual review!)
  • Think about what you were thinking about this month. This often highlights rumination traps and new idea seedlings.
  • Choose an especially helpful lesson and keep it front + center.
  • Set your goals and intentions for the coming month, and align them with your values and longer term aims.

Big 4 Reflections:

  • Begin your retreat with a gentle meditation. Sit quietly and set an intention to receive guidance. Ask yourself these four questions silently and pay attention to what comes up.
  • When you are finished meditating, write down your answers. Don't think, just write! Let your inner voice speak.

Wheel of Life Evaluation:

  • The wheel of life is a helpful tool to see your life at a glance, and the visual representation lends a unique perspective.
  • Take your time with the wheel and then reflect on these questions. Keep this nearby as you move into goal-setting.

Goal Evaluation:

  • Review the quarterly and annual goals you set for yourself.
  • Think about how you made it happen. In the PERMA model of happiness, the A symbolizes achievement, and it's a core component of living a meaningful life.  Acknowledging that our actions yielded the result also enhances our self-efficacy, which motivates us and ramps up our cognitive functioning. 

Next Quarter Priorities:

  • Use what you've learned in your reflections to consider the goals you'll focus on in the quarter ahead. Are your new goals aligned with your core values and over-arching life aims? 
  • Be clear and specific about the everyday shifts you'll make that will support your goals. This is where the magic happens!

Annual Reflection Processes:

  • The retrospective Year in Review and forward-looking Annual Prospectus documents take a deeper dive into a broad-scope life planning and living intentionally.
  • Scroll on down to grab copies of all three documents. As always, I'd love to hear from you if you run into questions, need more resources, or just want to geek out on introspection!

"Life can only be understood backwards,   but it must be lived forwards."   Soren Kierkegaard

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Get the Goodies

This guide walks you through the creation of your own daily, weekly, monthly, and quarterly reflection processes. Use research-based  techniques for goal-setting, emotional intelligence, self compassion, and loving-kindness. Say hello to your best self.

Take a guided tour through this master plan for your year. Think deeply about what matters most and where you're at today, then use your reflections to channel robust goal-setting in eight key areas. Make a final stop at the happiness checkpoint and let the magic in.

Think about your life in a way you never have before. Take a journey that will help you reflect on your triumphs and missed opportunities, your epic moments and ordinary ones. Consider what made this year different from all the rest and what it has to teach you.

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I love the dark hours of my being.
My mind deepens into them.
There I can find, as in old letters,
the days of my life, already lived,
and held like a legend, and understood.

Rainer Maria Rilke

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