At the start of each year, Mr. Nacho and I make time for a retrospective we call “Big Brain Planning”. It’s not a New Year’s resolution session, but is instead an opportunity to reflect on the past year and think about what’s next (even if much later down the line).
We sit down with a set of questions to reflect on what went well, what didn’t, and what the future could hold. This tradition has become one of my favorites (and I like to secretly imagine one of Mr. Nacho’s too : ) because it combines gratitude for the past with purposeful planning for the year(s) ahead.
Here’s a look at our process and why it works for us.
Why a “Big Brain Planning” retrospective matters for us
It’s easy to put most of our focus on the future and forget what’s already happened or what brought us to this point. Taking the time to review both our successes and non-successes helps us identify what’s working well (so we can continue building on it), and what’s not (so we can find ways to improve). It also allows us to appreciate our blessings and acknowledge just how fortunate we are.
Discussing and documenting it all also helps us preserve the memories of our years together. It lets us revisit the highlights year after year, and also shows us how we and our dreams have evolved over time. For example, my 2023 was largely focused on meditation and spiritual growth. I expected that to carry on as a theme into my 2024, but it has not. Once we start our Big Brain Planning, I hope to again reflect more on what this past year has meant to me and what themes I expect to carry forward into 2025.
Thinking big together also sparks creativity and opens the door to new possibilities. What are the big, crazy ideas we’ve kept to ourselves? By big brainstorming a future without limits, we might just get closer to making it real. The hope is to talk openly, aim high, and be supportive of each other’s ideas.
How we approach our end-of-year retrospective
A dedicated time and place
We set aside dedicated time, whether it’s a weekend away or a long meal. One year, we did it over brunch at a restaurant. Another year, we made a weekend of it for a staycation at a local bed and breakfast. Maybe one day we could even turn this into an extended trip, stretching the planning sessions over several days and letting our ideas unfold as we explore together.
A shared notebook
We keep one book where we document our ideas and reflections each year. Keeping it all in one place makes it easier to see what we’ve written in the past, how our goals and perspectives have evolved, and how we’ve grown. Each year we take turns being the “notetaker”.
Dedicated template for question prompts
Core questions
Our first few years started with the following questions as prompts:
- Did we accomplish our goals?
- What worked and didn’t work for us this past year?
- What unexpected blessings came into our lives?
- What are our goals and visions for the future?
We brainstormed and wrote our thoughts down together as we discussed each question.
Additional questions over time
The core questions above are still our main focus, however last year we added follow-up questions to encourage deeper reflection. I was inspired by this episode from one of my favorite financial independence podcasts, where these questions were part of a New Year goal-setting discussion. Going through these questions add a bit more time to the discussion, so for this next round we may pick and choose only a handful of questions to reflect on, or perhaps save the full set for every few years.
- What drains me/runs me into the ground?
- What is a life of meaning?
- If I could work for only 2 hours a week, what would I keep doing (or ditch)?
- What rituals make me feel the most like myself? What’s stopping me from doing them?
- Where am I today?
- Where do I want to be 1 year from today?
- Rate the following from 1-10
- Personal
- Professional
- Financial
- What would a “10” look like for the above (personal, professional, financial)?
- What is working and what isn’t, for each of the above?
- Fill in the blank:
- More than anything, I would love to _______
- I am happiest when I _______
- More than anything I’d love to be _______
- If I could do anything, I would _______
- Choose a word for the new year
- What is your estimated net worth?
One reason I wanted to incorporate these additional questions was because Mr. Nacho and I had a bit of a stressful year to reflect on. I wanted to see if we could dig into ideas for how to improve the year ahead. The thinking was that if we could identify what drains us and what’s important, then it could potentially help us focus on what will bring more balance (and less stress). The final question about estimated net worth is also meant to help track our progress on the path to financial independence.
Final thoughts
An end-of-year retrospective is a chance for us to reflect, align, and look ahead. For us, this tradition is both fun and productive, helping us celebrate successes, learn from challenges, and make preparations for our future goals.
