Rediscover Your Year: A Cheat Sheet for Reflecting with the Help of Tech

At the end of each year, I sit down to reflect on my milestones and memories—big and small—that shaped the past 12 months. It’s become one of my favorite rituals to celebrate progress and set the stage for what’s next.

Thankfully, technology can do a lot of the heavy lifting, making this process easier and more fun. If apps are already tracking so much of our lives, why not turn that data into a tool for reflection?

Here are some of my favorite shortcuts to use technology as a mirror for self-reflection and self-understanding:

Social MediaInstagram Highlights or Stories Archive: Check what you’ve shared publicly or privately saved as StoriesFacebook Memories: Review your “On This Day” feature for posts, comments, and photos from the yearX Bookmarks or Top Posts: Look for posts you bookmarked or those that received the most engagement (via analytics)Productivity & NotetakingNotion, Evernote, Obsidian, or other notetaking apps: Search your notes for key tags, projects, or frequent topicsDaily Journaling Apps (e.g., Day One or Reflectly ): Review your daily or weekly entries to find personal highs, lows, or repeated themesTask manager or project management apps: Look back through projects completed, milestones reached, challenges overcomeCalendar apps: Look through past events, meetings, special dates, etc.CommunicationsWhatsApp or Text Messages: Scroll through photos, links, or memorable exchanges from key conversationsEmails: Use search terms like “thank you,” “congratulations,” or “milestone” to surface important exchangesFinanceBank Statements or Budgeting Apps (such as YNAB ): Look at major purchases or investments, which often signify big life events or changesAmazon Orders or Receipts: Review purchases that reflect memorable moments (e.g., items bought for vacations, hobbies, or special occasions)Health & FitnessStep-Tracking Apps (e.g., Apple Health or Fitbit): Review your best months, longest walks, or exercise streaksMeditation Apps (e.g., Calm or Headspace ): Look at your most meditated days or longest streaksDiet Tracking Apps (e.g., MyFitnessPal ): Spot trends or standout meals you might have recordedWriting & CreativityDrafts or Google Docs: Look for essays, brainstorms, or personal reflections you started but maybe didn’t finishArt/Design/Drawing Apps (e.g., Procreate, Adobe Express): Find completed or in-progress creative worksTravelGoogle Maps: Check your timeline, showing you where you’ve been the past yearAirline or Hotel Loyalty Accounts: Review your flight or hotel history to recall travels or tripsTrip Planning Apps (e.g., TripIt , Hopper ): See itineraries or trips you had on your calendarLearningOnline Course Platforms (e.g., Coursera , Udemy , Maven ): Check what courses you started or completedLanguage Apps (e.g., Duolingo ): Reflect on your language-learning streaks or new skillsContentMusic: Check your Spotify Wrapped playlist or “Liked Songs” playlistYouTube videos: Review your watch history, or “Liked videos” playlistNetflix and other streaming services: Review your watch historyBooks: Review your ratings on Goodreads or the books you’ve read on your KindlePhoto apps: Look through your “favorited” album on your smartphone; or photos/videos you’ve shared via text message (which tend to be the best ones) 

A lot of these depend on which apps you currently use and how you use them, but I always find many meaningful tidbits that I’d completely forgotten about.

Want to see how all this comes together? Check out my annual reviews here for inspiration and ideas on how to craft your own.

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