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

Ryan Holiday
14 min readApr 12

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.

“We are ghosts or we are ancestors in our children’s lives,” he said at the beginning of his broadway show Long Time Comin’. “We either lay our mistakes, our burdens upon them, and we haunt them, or we assist them in laying those old burdens down, and we free them from the chain of our own flawed behavior. And as ancestors, we walk alongside of them, and we assist them in finding their own way, and some transcendence.”

Will you be a ghost or an ancestor to your children? Will you be the kind of example they need? Will you leave the kind of legacy that will guide them? That will inspire them to be decent and disciplined, great and good? Or will you haunt them with your mistakes, with the pain you inflicted on them, with the things left unsaid or unresolved?

Of course, we all know which of those two we want to be, just as Bruce’s flawed father surely did. But then our demons, our issues, the ghosts of our own parents, get in the way.

Ryan Holiday

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