21 Questions (To Ask Yourself Annually)

Readers, I wanted to share a list of questions from How To Retire Happy, Wild, and Free by Ernie Zelinski.

This unusual and indiosyncratic book comes from the same family of foundational works as Early Retirement Extreme, Your Money Or Your Life and Mr. Money Mustache’s blog. And as any Casual Kitchen reader knows, these books and sites have massively influenced my thinking. Zelinski’s book is yet another work that pushes readers to think wildly differently about the world we live in, and like these other books, it offers thoughtful, open-minded readers an opportunity to "play chess instead of checkers" in the game of life.

The following list of twenty-one questions is structured in a way to get you to think and reflect. Are you surrounding yourself with the right social and informational inputs? Are you spending your time properly, in a fulfilling way? Are you making truly active choices about these things? Or are you making passive choices while telling yourself they’re active?

I consider Zelinski’s list of questions to be an important contribution to the canon of early retirement/anti-consumerist literature. And while these questions come from a book about retirement, the questions below are really about living a mindful life of quality. In other words, anyone--at any stage of life--will benefit from thinking about them.

Questions to Ask Yourself Annually

1) Am I in control of my lifestyle?
2) Do I make the most of my money to give me the best quality of life?
3) What can I achieve in my retirement that would make me proud?
4) What can I do that is unique?
5) Do I have enough great friends in my life?
6) Do I devote sufficient time to see my close friends?
7) Do I watch too much TV?
8) Does my lifestyle complement my partner's?
9) Do I travel as much as I would like?
10) Do my time commitments allow me to make a contribution to making this world a better place?
11) Do my time commitments allow me to indulge in creative endeavors?
12) Am I developing spiritually as a human being?
13) Do I exercise enough, in my own enjoyable way?
14) Do I complain too much?
15) Am I as grateful as I should be for what I have in my life?
16) Am I continually learning something new?
17) Do I do something special for myself each and every day?
18) Do I take enough time to meditate and keep my mind in tiptop shape?
19) Am I living in the right country or in the right part of the country?
20) What will make me feel better?
21) Do I have everything I need to be happy, but don't realize it?


Readers, what do you think? Which questions do you find particularly helpful or provocative? And why?


READ NEXT: The Official Your Money Or Your Life Reading List