Today's Question

September 15, 2026/Adventure

What would make your life feel bigger without requiring anyone's permission?

A new question every day

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The Uncomfortable Truth

Most people don't need better answers. They need better questions.

One conviction holds this whole place together: the quality of your life rarely rises above the quality of the questions you are willing to ask. This is the work of author, speaker, and creator David H. Rollo, a quiet place to slow down and think, not a place to buy things.

A Life Worth Choosing, a parable by David H. Rollo, standing hardcover edition

A parable by David H. Rollo

A parable about the questions that change everything.

✦

Simon Millar thought he had built the life he wanted. Then one question made him wonder if he had built someone else's.

Publishing October 27, 2026

Pre-order on Amazon

First 50 completed pre-orders get the Questions Worth Asking journal, free

The Companion

A place to sit with the questions you keep avoiding

The book asks the question once. The Questions Worth Asking journal hands it back to you every week, one prompt at a time, until answering honestly becomes a habit rather than an event.

The Questions Journal, a debossed linen journal resting on a second copy opened to a workbook page
  • 01One question per spreadNo blank page to fill. Just a prompt worth sitting with.
  • 02Five categoriesWork, relationships, purpose, attention, and adventure.
  • 03Made to lastDebossed linen, gilded edges, meant to be left out and returned to.
Explore the journal

First edition, limited run

Questions, answered

Frequently asked

Who is David H. Rollo?
David H. Rollo is an author, speaker, and creator whose work centers on a single conviction: better questions create better lives. He writes the parable A Life Worth Choosing and designs tools that help people think more clearly about the lives they're building.
What is A Life Worth Choosing about?
A Life Worth Choosing is a parable about change, reinvention, and the courage to choose a different life. It follows Simon Millar, a man who has spent twenty years getting very good at a life he never quite chose, until a single question undoes all of it.
When does the book launch?
A Life Worth Choosing launches October 27. Pre-order now on Amazon, and the first 50 completed pre-orders receive a complimentary copy of the Questions Worth Asking journal.
What is the Questions Journal?
It is the companion tool to the book: a guided journal that gives your thinking structure across work, relationships, purpose, attention, and adventure.
Is David available for speaking and consulting?
Yes. David delivers keynotes, fireside conversations, and workshops on reinvention, leadership, and the power of better questions. You can start a conversation from the Speaking page.