Past Year Reflection Interview
A guided self-interview about the year that was. These questions help you see what happened — not just remember it — and extract wisdom you can carry forward.
45-60 minutes Late December / Early January
Read each question slowly. Pause. Let the answer arise before writing. There are no wrong answers. This is a conversation with yourself.
Getting Started
Find a quiet space. Close the door. Turn off notifications.
Take a few breaths. Let the past year wash over you — not to judge it, just to remember it.
When you're ready, begin.
Part 1: The Overview
Tell me about this past year — highlights first.
What were the moments that stand out? The times you felt most alive, most proud, most yourself?
Now, what was hard?
What moments would you rather not think about? Where did things go wrong, hurt, or disappoint?
What surprised you most?
What happened that you didn't expect — good or bad? What caught you off guard?
Part 2: The Work
What was your biggest professional accomplishment?
Not what looked impressive to others — what actually felt meaningful to you?
Where did you add the most value?
Looking back, where did your unique contributions make the biggest difference?
What professional challenge consumed more energy than it deserved?
Where did you spin your wheels? What battles weren't worth fighting?
What did you learn about leadership this year?
Part 3: The Energy
What drained you the most this year?
What activities, people, or situations left you depleted?
What gave you the most energy?
What activities, people, or situations left you energized?
How was your physical health this year?
Be honest. How did you treat your body? How did your body treat you?
How was your mental and emotional health?
What was your inner world like? Were you at peace? Anxious? Hopeful? Overwhelmed?
Part 4: The Decisions
What was the best decision you made this year?
What choice, when you look back, clearly moved you in the right direction?
What was the worst decision you made this year?
What choice, when you look back, you wish you'd made differently?
Where did you avoid hard decisions?
What have you been putting off? What conversations haven't you had? What changes haven't you made?
Part 5: The Relationships
Which relationships grew stronger this year?
Who did you get closer to? What relationships deepened?
Which relationships weakened or faded?
Who did you drift from? What connections did you neglect?
Who helped you the most this year?
Who showed up for you? Who did you lean on?
Part 6: The Hidden Wins
What are you proud of that no one else sees?
What quiet victories did you have that didn't make the highlight reel?
What inner growth happened this year?
How did you change as a person — not what you achieved, but who you became?
Part 7: The Hard Questions
What would you absolutely NOT repeat?
If there were a "never again" list, what goes on it?
What did you pretend not to know?
What truths did you avoid? What did you see but not acknowledge?
If this exact year repeated ten times, would you be satisfied?
If the patterns, habits, and rhythms of this year continued indefinitely, where would you end up? Is that where you want to go?
What needs to die for something new to be born?
What are you holding onto that no longer serves you? What needs to end?
Part 8: The Wisdom
If you could capture the wisdom of this year in one sentence, what would it be?
Part 9: The Transition
What are you ready to leave behind in this year?
What do you want to consciously release as you step into the new year?
What do you want to carry forward?
What from this year do you want to bring with you?
How do you want to feel as you enter the new year?
Not what you want to accomplish — how do you want to feel?
What is one word or phrase that captures your intention for the year ahead?
Closing
Take a breath. You've just done real work.
The act of reflection changes what you carry forward. The patterns you've named are now visible. The lessons you've extracted are now available.