As the year winds down, there’s no better time to reflect on where you’ve been and where you’re headed. Inspired by a conversation I had with Sahil Bloom on Ep #99 about the art of conducting a personal annual review, I’ve found that asking these 7 questions can become the key to uncovering insights and setting a purposeful course for the year ahead. This practice helps me understand my growth, pinpoint areas for improvement, and ensure I’m aligned with what truly matters and I hope it helps you plan for your best year yet.
1. What Did I Change My Mind On This Year?
This question is about embracing change and updating your “mental software.” If you’re not changing your mind about something each year, you’re probably not growing.
For me, one of the biggest shifts this year was learning to let go of my frugality in small decisions. I realized that obsessing over minor costs was draining unnecessary energy. By reframing my mindset to focus on the bigger picture, I’ve experienced a significant boost in my happiness and reduced stress levels.
How to Approach This
- Reflect on conversations, books, or experiences that shifted your perspective.
- Use tools like photo albums or calendars to jog your memory and avoid recency bias.
2. What Created Energy for Me This Year?
Think about the activities, people, and projects that made you feel alive. For me, spending time on adventures with my kids was a huge source of energy. Whether it was taking my daughter on a bike-and-train trip to get donuts or building a fort in the living room, these moments were pure joy.
Another surprising energy boost came from primary research for my podcast. I love diving into the details—like testing credit card perks, experimenting with loyalty programs, or trying new travel hacks.
Your Turn
- Look back at your calendar or journal and identify patterns in what made you feel energized.
- Ask yourself: Did I spend enough time on these things?
3. What Drained My Energy This Year?
On the flip side, it’s equally important to identify the activities and habits that sapped your energy. For me, one big drain was trying to fit our kids into our “old life” by planning vacations the way we did pre-kids.
Another culprit was social media. Feeling the pressure to post content for every platform was exhausting. I realized I was spreading myself too thin and decided to focus on what I enjoy most: creating podcast episodes and writing my newsletter.
Take Action
- Look at your patterns. Are there recurring meetings, habits, or even relationships that drain you?
- Strategize on how to reduce or eliminate these from your life.
4. Who or What Were the Boat Anchors in My Life?
Sahil calls these “boat anchors”—people or habits that hold you back. These might be relationships where negativity or lack of support creates drag on your progress.
For me, one “boat anchor” I uncovered wasn’t a person, but a mindset: my fear of not making enough money. It’s a self-limiting belief that occasionally distracts me from bigger opportunities. By recognizing it, I’ve started working on reframing that fear and focusing on what truly matters.
How to Navigate This
- Identify the anchors in your life and plan to reduce their impact.
- You don’t need to cut ties entirely—sometimes just limiting engagement is enough.
5. What Did I Avoid Because of Fear?
This question helps uncover opportunities missed because of hesitation or anxiety. For years, I avoided going full-time on my podcast because I was afraid it might not work. This year, Amy and I faced a similar decision about her joining the podcast full-time. I’m proud we pushed past that fear and took the leap—it’s been one of the best decisions we’ve made.
How to Push Past Fear
- Use “fear-setting,” a concept from Tim Ferriss, to deconstruct your fears and evaluate the real risks.
- Ask yourself: What’s the worst that could happen, and can I handle it?
6. What Were My Greatest Hits and Worst Misses?
This is where you reflect on your wins and losses to balance optimism with self-critique.
My Greatest Hits:
- Watching my daughter walk to school with her backpack on—it’s a small, everyday moment, but it fills me with pride.
- Our first group trip to Iceland was a huge success, and I’m thrilled to do more in the future.
- Maintaining consistency: We didn’t miss a single week of the podcast, and the newsletter hit a weekly cadence.
My Worst Misses:
- Everything felt too last-minute. Whether it was planning episodes or personal trips, I want to be more intentional next year.
Pro Tip
- Writing down both hits and misses gives you a clearer, balanced view of your year.
7. What Did I Learn This Year?
This question ties everything together. It’s about extracting the lessons from the entire review process and using them to guide your future decisions.
For me, the overarching theme was intentionality. I want to be more deliberate about how I spend my time, energy, and money. Whether it’s planning a vacation or making a business decision, I’m aiming for alignment between my goals and actions.
Final Thought
- Use this question to synthesize your reflections and chart your course for the next year.
How to Track Progress and Improve Next Year’s Review
To make this process smoother next year, Sahil proposes adapting the 1-1-1 Journaling Method. This straightforward approach encourages daily reflection by focusing on three key elements: one win, one point of tension, and one point of gratitude.
- One Win: Identify a moment from your day that you feel proud of, no matter how small. Acknowledging these wins helps build a positive mindset and reinforces your progress.
- One Point of Tension: Write down any stressors or challenges you faced. This allows you to process these feelings and find solutions, reducing their impact on your well-being.
- One Point of Gratitude: End your reflection by noting something you appreciate, whether it’s a supportive friend or a beautiful moment. Cultivating gratitude improves mental health and increases happiness.
Additionally, you can commit to monthly reviews to stay aligned with your goals and track progress throughout the year.
Reflecting on the past year is one of the most valuable investments you can make in yourself. I hope these questions and examples inspire you to conduct your own annual review and set the stage for a purposeful and fulfilling year ahead.
Here’s to an incredible year ahead!
