Year-End Reflection Questions for Leaders Entering the New Year
As the year winds down, there’s a lot of noise about how you’re supposed to reflect.
Summarize the year.
Set goals.
Optimize for what’s next.
I didn’t feel like doing that.
Instead, I’ve been sitting with a different kind of reflection. Quieter. Less performative. More honest and inward. The kind that doesn’t try to fix anything (yet), but actually notices what’s been true.
Here are a few questions I’ve been spending time with. Sharing them in case they’re useful to you too.
Year-End Questions to Sit With
When did you feel most like yourself this year?
Time when it was just you.
With others.
In your work.
Take a moment to notice each area.
What moment from this year do you want more of?
Something you only got a taste of.
Look across your life: personal, relational, professional, learning. Nothing lives in a silo.
Where did you know what you wanted, but held back?
A decision you delayed.
A boundary you gave in on.
A place where you sacrificed and still feel it.
What’s a guilty pleasure or goal you need to accept, or let go of?
Sometimes pressure comes from fighting parts of ourselves that are asking to be acknowledged… or released.
What was not worth caring about this year?
Where did stress or energy turn out to be poorly spent, and what does that clarify moving forward?
What changed in your life because you invested time or energy into it?
What you water grows.
Where did your life actually bloom?
When I get stuck answering questions like these, it’s usually because I’m too close to them.
So I try looking at my life from a different seat.
If you were the boss of your own work:
What feedback would you give yourself?
What would you change about your job?
If you were your romantic partner, or former partner:
What feedback would you offer yourself?
What would you do differently to grow the relationship?
If you were your best friend:
What would you say, honestly and with care?
And one more I keep coming back to.
If you knew miracles were possible next year, what would you ask for?
Not what you think you should want.
What you actually want.
If a fearless year means anything to me now, it’s this:
Less forcing.
More listening.
Creating opportunities for stillness.
And the courage to keep building a life that feels like mine.
— Ben
P.S. If this reflection brings up that you’ve been leading more from fear than excitement, and you want a thought partner while you rebuild trust in yourself, that’s the work I do. You can reach out anytime. Let's talk.