"Direction often emerges not from knowing what you want, but from finally admitting what you don’t." - Ken Woodward
"Direction often emerges not from knowing what you want, but from finally admitting what you don’t." - Ken Woodward
The Inquisitive Almanack: 2026 Edition closes the year with something Curated Questions has never quite done before—an affectionate, slightly irreverent, and deeply thoughtful almanack for the inner life.
Inspired by Benjamin Franklin’s Poor Richard’s Almanack, this episode blends dry wit, invented bureaucracy, and hard-won wisdom to offer forecasts not for the weather, but for the heart, mind, and questions we carry.
You’ll hear interior weather reports, proverbs for the asking class, arbitrary rules of inquiry, lunar phases of curiosity, and predictions for the questions most likely to surface in 2026—across leadership, relationships, parenting, teams, and personal life.
Released intentionally as the final episode of the year, this Almanack isn’t a recap or a resolution guide. It’s a pause. A breath. A lighter place to rest before the calendar turns and begins asking new things of us.
Come curious. Leave rested. And carry one good question forward.
This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.
Keep questioning!
Episode Notes
00:00 Introduction: On Not Knowing What You Want
01:08 Welcome to Curated Questions
01:42 Introducing the Inquisitive Almanac
04:46 Weather Forecast for the Inner Life
08:28 Proverbs for the Asking Class
11:29 The Arbitrary Rules of Inquiry
13:39 Guidance for the Perplexed Traveler in the Realm of Curiosity
17:23 Phases of the Inquiry Moon
20:57 Predictions for the Questions of 2026
26:37 Improper Questions for Polite Company
28:32 Errors, Omissions, and Curiosities
31:00 Closing Reflection
Resources Mentioned
Questions Asked
Are you better served by pretending you can see further than you actually can?
What am I doing?
What am I still not sure about?
What uncomfortable question am I willing to ask myself?
Why didn’t I prepare better?
What expectations am I absorbing that aren’t mine?
Where do I need better boundaries?
What am I powering through that requires drainage instead?
What am I building too close to hope’s shifting shoreline?
What am I anchoring my plans to?
Am I confusing altitude with progress?
What question am I avoiding?
Why am I pretending the basement is dry?
What honest conversation would raise the floor?
What grows in the desert of certainty?
What if the absence of questions isn’t peace?
Am I checking the forecast honestly, or just hoping for sun?
What hurried question am I asking that will make for a long walk home?
What shadow am I still chasing by avoiding inquiry?
Why do answers age poorly while curiosity does not?
What question have I left unasked that I will meet again?
What question am I ignoring that is not ignoring me?
What truth might a quiet question find before a loud certainty does?
What wonder have I neglected that now costs me more?
What question quickens my pulse?
What heavy door might a small question open?
What grows heavier when carried alone?
Do all questions really have answers?
What distance could be shortened by sincere asking?
What borrowed certainty will I have to repay with interest?
What question do I think I’ve answered that has merely changed clothes?
What inquiry am I defending instead of exploring?
What door will only open to a real question?
Which inherited questions should I keep, and which should I release?
What question have I planted that has not yet bloomed?
What happens if I ask “why” one more time?
What do I no longer wish to carry?
What has outstayed its welcome?
What have I tolerated out of habit rather than choice?
What heavy question am I carrying alone?
Who might walk beside me without needing to fix me?
What would my future self say if I truly listened?
Who am I becoming?
Would I want to meet that future self?
How should I enter this difficult conversation?
Am I behaving like a guest or a conqueror?
Is certainty impersonating wisdom here?
Can this belief tolerate a follow-up question?
What phase of inquiry am I currently in?
What question is forming that I cannot yet name?
Why am I rushing to close the loop?
What am I pretending is just curiosity when it isn’t?
What growth is happening in this uncomfortable middle?
What truth have I seen that I cannot unsee?
What belief is thinning?
What map am I between?
What have I integrated rather than resolved?
What new question is already forming in the dark?
What have I been postponing that can no longer wait?
What would I choose if no one were watching?
Is this habit still earning its keep, or am I afraid to evict it?
What am I pretending not to know?
What must I unlearn to be trusted again?
Whose voice is missing from this decision?
Am I leading, or merely occupying the place where a leader should be?
What decision are we avoiding because we dread the meeting about it?
What story does our silence tell?
Where have we confused agreement with alignment?
Am I protecting my child, or protecting myself from their discomfort?
What am I modeling that I haven’t explicitly taught?
Can I stay curious about who my child is becoming?
Are we still asking each other questions that matter?
What conversation keeps knocking that we refuse to answer?
Where does resentment enter our home?
What would it take to meet it at the door?
What if curiosity is our last remaining common language?
What future are we rehearsing with today’s choices?
What truth have we misfiled under “later”?
Is this meeting an email that achieved sentience?
At what point did I decide to care about this argument?
Can I reverse that decision?
Do I actually enjoy this tradition?
Is this emotional furniture I’ve never moved?
Is this my opinion, or one I borrowed without reading the terms?
Would I do this if no one could see me do it?
Who benefits from my silence?
Do I want advice, or do I want the performance of being listened to?
Am I resting, or hiding and calling it rest?
Is this a boundary, or a wall I’ve decorated?
How much of my personality is unexamined coping?
If I weren’t afraid, what would I do this afternoon?
What am I hoping someone else will say so I don’t have to?
What question will I carry into the new year?