The Annual Recalibration: 2025 edition
a portal to revisiting the year
tl;dr: It’s annual review season and I’m excited to share this year’s edition of my Annual Recalibration. It’s designed to be a gateway to reflect on how life has played out over the last 365 days, revisit the moments that defined you, and make sense of the disparate strands of what’s happened that only make sense looking backward.
Next weekend, I’m hosting our second annual End of Year Intentions Retreat. We’re experimenting with different formats for virtual and in-person events.
Interested in joining us? Let us know here!
We’re entering the portal of one of my favorite times of the year. For a few weeks, the world slows down and there’s a collective ease into the holiday season.
It all began with a letter my senior year of college. I was overcome with anticipation as we edged toward graduation. I’d spent my whole life working toward the distant reality of 2014 and now, it was finally on the horizon.
I had recently committed to my first full-time job and made the decision to stay in Boston. I wanted the space to process everything that had happened over the last three and a half years in preparation for entering the real world.
That winter break, my family traveled to Cancun to celebrate the holidays. On a whim, I packed a notepad. As I waited for them at the airport, I felt a jolt of inspiration to write a letter to myself as a capstone to the year.
I started by flipping through my calendar, jotting down the milestones, peaks, and valleys that had unfolded over the course of the year. By the end, I had a shortlist of experiences that had defined my 2013.
Over the next few days, I turned over how the year had gone: the joys, the heartaches, the triumphs, the disappointments, and how I’d showed up in the face of it all. It was clear I was ready to usher in a new chapter.
With a few hours left to the new year, I sat down and wrote myself a letter, trying to make sense of what had transpired in 2013 and detailing my intentions for 2014. Once I was done, I sealed the envelope, only to be opened again in 365 days.
In the ensuing decade, this letter writing ritual turned into an annual goal setting exercise. At the start of each year, I curated a new set of bucket list items, motivated by the never enough mentality that pervaded my life at the time.
For several years, I chased after external success and experiences like traveling to new countries and national parks, running my first marathon, getting promoted at work, and moving to a new city. It became harder and harder to outdo myself. After an epic 2019 that would have been impossible to top: moving cross-country, a new job, three international trips, and my first international marathon, it all came to a head in 2020 when we found ourselves in a global lockdown.
No longer able to anchor the success or failure of my year based on the number of new experiences abroad or new marathons run, I found myself directing my energy inward. After months of being forced to slow down and learning to appreciate the small daily moments, I found myself curious to explore my inner world. Why did I feel so energized after that experience? Did I disassociate during that conversation? Why did that interaction leave me spiraling?
And so began my first annual recalibration.
Guide to the Annual Recalibration
I typically reserve the last week of December to go deep on reflecting, processing, and integrating. Some years, I’ve found the spaciousness to start earlier in the month which gives me more time to sit with how life has played out over the last year and revisit old memories.
The process is designed to be a non-linear way to reflect on your year. The first step is to gather all the artifacts across 2025 to avoid defaulting to recency bias.
Once that’s done, you’re welcome to wander through the sections in whatever sequence feels most alive in your sense-making journey.
In some instances, it’s helpful to have completed a prior exercise like setting intentions for 2026 before diving into curating a vision board for the new year, but perhaps spending time with your vision board actually inspires you to set some new intentions.
Here’s a preview of the experience:
⭐️ Gather the puzzle pieces
Gather your memories, experiences, reflections, ideas, and feelings throughout the year
Collecting these puzzle pieces allows you to build a complete view of your year rather than default to recency bias
Retrace the year
Reflection is the heart of the Annual Recalibration
Take the time to retrace your year and revisit the moments that defined you over the last 365 days
Share gratitudes
Reflect on the people you’re most grateful for this year and couldn’t imagine living 2025 without
Set intentions
Rather than just focusing on what you want to achieve in 2026, define who you aspire to become
Compliment goal setting with identity aligning
Curate a vision board
Once you’re clear on your intentions for the new year, the fun begins. What’s your vision look like? How do you want to feel?
Use whatever tool feels most satisfying to you: magazines and poster boards, Pinterest, Figma, Canva, etc.
Write 2026 you a letter
Using your intentions or vision board as inspiration, imagine a world where you’ve actualized your intentions over the next year
Drop into the clarity of who you aspire to become
Hand write the letter and seal the envelope to be read in 365 days
Say a final farewell
All things must come to an end — what are you ready to leave behind this year?
Take time to reflect on the beliefs, experiences, and relationships you’re ready to release
Let go of what no longer serves you
How are you approaching your annual review process? Share with us in the comments!