7 Questions to Transform Your Year-End Reflection

In the hustle of life and leadership, the chance to pause, reflect on the year that was, and chart a thoughtful course for the year ahead is a beautiful opportunity that we shouldn't take for granted.

Sahil Bloom, an investor, inspirational writer, and content creator who's releasing his debut book in February titled The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life, swears by a simple yet game-changing process he calls The Personal Annual Review.

For over a decade, this seven-question exercise has been life-changing for his personal progress and growth. Its simplicity is deceptive—it’s not just a review; it’s a recalibration.

Let's take a look at these seven powerful questions that have the potential to shift our perspective—and even transform our lives:

1. What did I change my mind on this year? The best leaders aren’t those who cling to being right; they’re the ones who evolve. Asking this question forces us to examine moments when our beliefs shifted. Were we flexible enough to embrace new truths, even if they contradicted old assumptions? Growth thrives at the intersection of curiosity and humility.

2. What created energy this year? Energy is a leader's most valuable currency. Reflect on the projects, people, and habits that filled your tank and left you feeling invigorated. This question helps identify where to double down in the coming year.

3. What drained energy this year? Equally important is identifying what sapped your enthusiasm and focus. Whether it’s unnecessary meetings, unhealthy relationships, or poor habits, identifying what drains our energy enables us to manage, address, or let go of these distractions more effectively.

4. What were the boat anchors in my life? Boat anchors represent anything that holds us back—people, mindsets, or actions that create drag in our life. This question challenges us to identify and address the weight slowing our momentum. Is it time to let go of a project, delegate a task, or shift your perspective?

5. What did I not do because of fear? Fear often masquerades as practicality or caution, but it can quietly limit our potential. Reflect on the risks you avoided and consider what might have been gained if you had taken the leap. Meaningful growth lives on the other side of fear.

6. What were my greatest hits and worst misses this year? Revisiting our highlights and lowlights helps us identify patterns. What worked well, and why? Where did things fall short or not go as planned, and what can we learn from those moments? This question isn’t just about celebration or regret—it’s about extracting lessons.

7. What did I learn this year? Learning, unlearning, and relearning are essential on our self-leadership and personal transformation journeys. Reflect on the new skills, insights, and wisdom you gained this year. What books, podcasts, experiences, new places visited, or mentors influenced your journey? How will you apply these lessons as you navigate life, leadership, and culture moving forward?

The Personal Annual Review isn’t just an exercise—it’s a gift we give ourselves. It ensures that as we pour into others, we don't forget to pour back into ourselves with grace and deeper appreciation about what the days, moments, highs, and lows taught us about living and leading this year.

By thoughtfully answering these questions, we’re not only acknowledging the past year but actively and intentionally shaping the days ahead.

So, take some time and sit with these seven questions. Be proud of where you are, even if it’s not where you want to be. You have life, you have breath, and with that, you have a unique opportunity to change the course of your life at any given moment.

As Sahil Bloom puts it, this practice has been “transformative” for him. It might just be the reset we need to make 2025 our best year yet.

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