People assume experience leads to wisdom.
It doesn’t.
Because if it did, every person over a certain age would end up happy, wealthy, and wise.
Experiences only become valuable when we extract the lessons from them.
During the year, we’re in constant motion, putting out fires, solving problems, and responding to the demands of daily life. In these moments, we are very much in our business — operating from default patterns and conditioning.
It’s sort of like the movie of your life is playing out, and you’re an actor completely absorbed in playing the starring role.
You’re so immersed in it that you don’t have any distance from it, which makes it difficult to make changes.
Luckily, at the end of each year, you have the opportunity to “step out” of the movie and see it from the vantage point of a more objective observer.
It’s almost like the film has been fully recorded and released, and the actor (i.e. you) is now in the cinema watching it as an observer. This distance allows you to extract the lessons from your experiences, and make changes for the year ahead.
What follows are the 19 questions I’ve used to extract the lessons from 2025, and plan 2026 from a place of depth and clarity.
1.) What wins are you most proud of from the last 12 months?
2.) What activities, projects, and experiences energised you and brought you joy this year? When did you feel most fully alive?
Optional: If you’d like to ensure you’re working with concrete data, it can be helpful to review your calendar from the year that’s just passed. When you discover an item or event that energised you or brought you joy, list it below. Ensure to set your calendar to the “week view” setting:
3.) Can you schedule any of these (or similar activities) in your calendar for the year ahead? If so, when?
Note: To ensure follow through, it helps to have “skin in the game” and some sort of commitment in place, whether it be social (e.g. contacting a friend) or financial (booking a flight).
4.) Energy Amplifiers
a.) Who did you love spending time with?
b.) How can you consistently invest in these relationships in 2026?
5.) What were the most important things you learned?
— Generally?
— About yourself?
— From suffering?
— Biggest “aha” moments?
Which books had the biggest impact on you and what were the key things you took from them?
Which teachers/mentors had a positive impact? How can you share your appreciation with them?
Part 2 – Looking Back (The Dark Side)
6.) What were your biggest mistakes this year?
— What did you learn from them?
— What can you do—or put in place— to ensure you never make them again?
7.) What activities, projects, and experiences drained you and led to misery this year?
Optional: Like question 2, review your calendar, and list these items below.
8.) Energy Vampires
a.) Who are the “energy vampires” in your life?
b.) Is there any way you can reduce the amount of time you spend with them going forward?
9.) 80-20 Stress/Pain analysis
a.) Which 20% of inputs are causing 80% or more of the unnecessary suffering in your life?
b.) If you were able to make a meaningful change in this area, what kind of difference would it make?
c.) What’s your best guess about the best way to approach making this change? E.g. hiring a coach, therapist, or getting advice from someone on the other side of the problem.
Part 3: Looking Forward
10.) What do you want said about you at your funeral?
I’ve found this to be—by far—the most effective way to cut through the noise and get at the signal of what matters most to me in life, and the kind of person I want to show up as every day.
11.) Deathbed goals
If you could only achieve 3-5 goals before the end of your life, what would they be?
Source: Gay Hendricks
12.) Future Self Vision
Here, you create a detailed description of what your life looks like in 10 years, considering:
— Spirituality/Inner Life
— Health
— Family
— Friendships
— Work + impact
— Skill stack
— Finances
— Contribution
— Personality
— Community
— How you make others feel when you interact with them
13.) A Letter from Your Future Self
Now that you have a vision of the person you want to become, the next step is to write an “advice letter” from them to current you.
What advice would this older, wiser version of you give to you about how best to approach the year ahead?
14.) Ideal Average Week
5 years from now, if you couldn’t fail, what would a typical week look like for you – best case scenario?
— Start by listing out all of the activities you’d love to do in a typical week.
— Then, once you have your list, map them onto a simple table like below:
15.) What path options are available to you now?
Taking the big picture (future self, deathbed goals, & ideal average week) into consideration, what are all of the different paths available to you at this point in your trajectory?
Now that you’re clearer on where you want to end up, this places your current options in a more holistic context.
16.) 3 Things Focus
Of all the options available—and considering your deathbed goals, future self vision, and ideal average week—what three things if you achieved this year, would have the biggest impact on creating that future?
17.) Misogi
This is a Japanese practice of choosing one year defining goal to work towards.
Something right on the edge of what you believe might be possible for you.
It’s not important whether you achieve your Misogi or not.
And it doesn’t have to be related to your work.
What matters is that you have a north star to build towards, a daily/weekly sense of progress, and a focus which makes it easier to say no to lesser temptations.
Source: Michael Easter
18.) 6 x Mini Adventures
Inspired by Jesse Itzler, this involves planning six experiences to look forward to—one at the end of every two months. They don’t have to be life-changing or expensive, just something that will take you out of your routine for a day or 2, and give you something to look forward to every couple of months.
It could be a camping trip, visiting a new city, or getting lessons in a new skill/sport you’re curious to try. If you do this, it’ll mean that at the end of a ten year period, you’ll have created 60 meaningful memories that will be with you for the rest of your life.
19.) 4 x Micro Habits
Also inspired by Itzler, the aim here is to identify areas of life where you might be falling short and then develop one micro habit each quarter to strengthen this area.
For example,
— If you’re always late, you might develop the micro habit of always being 5 minutes early in January to March.
— If you’re neglecting your finances, you could get into the habit of saving or investing a certain percentage of your income each month from April to June. And so on.
Over time, this compounds for a dramatically improved quality of life. 1 year = 4 new life-giving habits, 5 years = 20 new habits, and 10 years = 40.
