15 Questions That Will Make You A Better Parent (and Person)

Ryan Holiday
14 min readApr 12, 2023

As parents, we worry about having all the right answers.

But I think it’s better to focus on asking the right questions.

The right question at the right time can change the course of a life, can still a turbulent situation, can provide a totally different perspective.

While every situation can generate its own, here are 15 questions that have challenged and helped me the most every day both as a parent and then as a writer, as I researched and wrote what became The Daily Dad: 366 Meditations on Parenting, Love, and Raising Great Kids, (it would mean so much to me if you could preorder it!!!). These 15 questions from some of the wisest philosophers, most incisive thinkers, and greatest parents that ever lived.

I’m not saying I know the answer to any of them, but I can say there is value in letting them challenge you. Certainly they have challenged me and continue to challenge me…

Start now by asking:

Will I Be An Ancestor or A Ghost?

In his Broadway show, Bruce Springsteen — whose songs have often focused on the painful legacy of our parents — explained the choice that all of us have as parents.

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Ryan Holiday

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR