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 Media

• Instagram Highlights or Stories Archive: Check what you’ve shared publicly or privately saved as Stories
• Facebook Memories: Review your “On This Day” feature for posts, comments, and photos from the year
• X Bookmarks or Top Posts: Look for posts you bookmarked or those that received the most engagement (via analytics)

Productivity & Notetaking

• Notion, Evernote, Obsidian, or other notetaking apps: Search your notes for key tags, projects, or frequent topics
• Daily Journaling Apps (e.g., Day One or Reflectly): Review your daily or weekly entries to find personal highs, lows, or repeated themes
• Task manager or project management apps: Look back through projects completed, milestones reached, challenges overcome
• Calendar apps: Look through past events, meetings, special dates, etc.

Communications

• WhatsApp or Text Messages: Scroll through photos, links, or memorable exchanges from key conversations
• Emails: Use search terms like “thank you,” “congratulations,” or “milestone” to surface important exchanges

Finance

• Bank Statements or Budgeting Apps (such as YNAB): Look at major purchases or investments, which often signify big life events or changes
• Amazon Orders or Receipts: Review purchases that reflect memorable moments (e.g., items bought for vacations, hobbies, or special occasions)

Health & Fitness

• Step-Tracking Apps (e.g., Apple Health or Fitbit): Review your best months, longest walks, or exercise streaks
• Meditation Apps (e.g., Calm or Headspace): Look at your most meditated days or longest streaks
• Diet Tracking Apps (e.g., MyFitnessPal): Spot trends or standout meals you might have recorded

Writing & Creativity

• Drafts or Google Docs: Look for essays, brainstorms, or personal reflections you started but maybe didn’t finish
• Art/Design/Drawing Apps (e.g., Procreate, Adobe Express): Find completed or in-progress creative works

Travel

• Google Maps: Check your timeline, showing you where you’ve been the past year
• Airline or Hotel Loyalty Accounts: Review your flight or hotel history to recall travels or trips
• Trip Planning Apps (e.g., TripIt, Hopper): See itineraries or trips you had on your calendar

Learning

• Online Course Platforms (e.g., Coursera, Udemy, Maven): Check what courses you started or completed
• Language Apps (e.g., Duolingo): Reflect on your language-learning streaks or new skills

Content

• Music: Check your Spotify Wrapped playlist or “Liked Songs” playlist
• YouTube videos: Review your watch history, or “Liked videos” playlist
• Netflix and other streaming services: Review your watch history
• Books: Review your ratings on Goodreads or the books you’ve read on your Kindle
• Photo 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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I’ve read hundreds of books on productivity and self-improvement over the years.

Many of them are filled with vague prescriptions or clichéd advice, but a small number were truly transformative for me. They served as intellectual lighthouses on my journey, helping me understand what was happening to me as I explored my past, my psyche, and my pain.

Here are the 10 personal development books that have been most inspiring and impactful for me, in the order in which I encountered them (all the following links are affiliate links, for which I earn a small commission at no cost to you):

Mindfulness: An Eight-Week Plan for Finding Peace in a Frantic World, by Mark Williams and Dr. Danny Penman

I found this book on an obscure online forum late one night soon after arriving in San Francisco to begin my first professional job. 

I had read a lot of philosophical or mystical accounts of meditation and mindfulness, but this book was different. It describes a series of empirical, first-hand experiments I could run to reach my own conclusions, free of unprovable metaphysical claims.

I still remember the classic “raisin experiment” – a series of prompts in which you examine a single raisin in extreme detail using one of the senses at a time – which opened up a doorway into the infinite intricacy and subtlety of my everyday perception. Since then I’ve always returned to the idea that running experiments to uncover my own truths is far more powerful than just accepting someone else’s philosophy.

The Untethered Soul and The Surrender Experiment, by Michael Singer

Michael Singer’s first book, which I wrote about in The Untethered Soul: The Roadmap of My Personal Growth, has been like a user’s manual for my mind over the last decade. I’ve reread the book multiple times, and each time I’m astounded at how Singer is able to describe almost exactly what I’m experiencing inside the confines of my mind in such vivid detail.

It has served as a roadmap in my journey, reassuring me that each dissolution of a part of my identity is a good thing even when it feels disconcerting. 

His second book, The Surrender Experiment, is an autobiography of his spiritual journey, including his incredible achievements in business. It gave me hope that success in business is not incompatible with the spiritual life and that the former could even be a gateway to the latter. 

Emergent Strategy and Pleasure Activism, by adrienne maree brown

Adrienne maree brown’s book Emergent Strategy is a mainstay in political activist circles. I picked it up at my then-girlfriend Lauren’s suggestion and was skeptical at first, expecting a lot of sociopolitical theory and shrill finger-wagging.

Instead, I was shocked to discover a powerful framework based on nature metaphors for understanding and shaping change, systems, interdependence, and power, which I summarized in Emergent Strategy: Organizing for Social Justice.

Her followup book, Pleasure Activism, is an even more radical exploration of the “politics of pleasure,” and has influenced my thinking for years as I learned to tap into pleasure as a source of motivation in my work. I wrote about my takeaways in Pleasure as an Organizing Principle.

Man Enough: Fathers, Sons and the Search for Masculinity, by Frank Pittman

This was another book I read at Lauren’s recommendation. It is an exploration of what is known today as “toxic masculinity,” including all the ways our upbringing and societal expectations shape our understanding of what it means to be a man and a father.

Pittman was a psychiatrist, and thus his writing isn’t about abstract theories or political diatribes. It’s rooted in the real conversations and experiences of his patients, which gives his ideas a vulnerable, personal grounding.

His book helped me see and understand how masculinity had been communicated across generations in my family, how that legacy had affected me, and which parts I wanted to embrace or reject in my own life and parenting.

It Didn’t Start With You, by Mark Wolynn

Mark Wolynn’s book, which I wrote about in It Didn’t Start With You: How to Understand and Heal from Intergenerational Trauma, opened my eyes to the tremendous importance of family history in unraveling one’s own individual trauma. 

You would think that discovering how unresolved trauma is passed down through generations would feel like a great burden, adding to the already formidable burden imposed by a single life’s experiences. Instead, I experienced this revelation as a tremendous relief. Finally I had the context to understand why so much of my pain seemed to come from before I was even born.

Up until that point, I had never realized what a weighty responsibility it had been to feel that all my problems and shortcomings were mine and mine alone. To hold myself responsible for my own pain and its healing. This book helped me see my own healing efforts as a service to past generations of my ancestors, giving them so much more meaning and significance.

The Yoga of Eating, by Charles Eisenstein

Charles Eisenstein’s book, which I wrote about in The Yoga of Eating: Food as a Source of Information, gave me a whole new perspective on eating and food and its importance in cultivating my intuition and self-awareness.

I had never thought much about food, considering it a mere source of fuel for my brain. But as I got older, what I ate started to have a bigger impact on how I felt and performed. So I knew it was time to revisit that relationship.

Eisenstein’s book is such an unorthodox approach to this topic. It’s not based on science, nor does it recommend any particular diet. It’s about reframing how you understand the very nature of food – not just as macronutrients but as a potent source of information flowing from the external world into your cells.

The Body Keeps the Score, by Dr. Bessel van der Kolk

Dr. Bessel van der Kolk’s book is an encyclopedic tour de force of many aspects of trauma and its treatment, which I summarized in The Body Keeps the Score: Brain, Mind, and Body in the Treatment of Trauma.

This book rose to international mega-bestseller status, despite its semi-technical and often winding prose. I think that’s because it has become the banner for a broad increase in awareness of trauma, a complex and nuanced subject that can take many forms and has many potential causes and forms of treatment.

Our society is becoming “trauma-informed,” and this book is the best deep dive into what that often charged and misunderstood word really means in the context of our lives.

How Emotions Are Made, by Dr. Lisa Feldman Barrett

Dr. Lisa Feldman Barret’s book gave me a completely new way of understanding emotions and how they work, which I recounted in How Emotions Are Made: The Theory of Constructed Emotion.

This book is mostly about the science of emotions, which is helpful for avoiding many of the unfounded assumptions and ancient cultural baggage around the topic. Dr. Barrett’s work creates a bridge between the heart and the mind, giving us a way to think and reason about our emotions, but also a way to feel into our thoughts.

I believe that emotions are the most important frontier of personal development in society today, and understanding what they are at the most fundamental level is crucial for exploring that frontier.

Follow us for the latest updates and insights around productivity and Building a Second Brain on X, Facebook, Instagram, LinkedIn, and YouTube. And if you’re ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.