Cheryl Strayed is an author, columnist, radio personality, but ultimately a woman whose journey and wisdom has served as a guide to lost souls everywhere. Strayed’s work has manifested in many places, movies, musicals, and her popular podcast named after her old advice column, Dear Sugar. In advice column tradition, those who seek guidance sign their letters with a made-up pen name, like Sincerely, Scared and Confused or Bewildered Ex-Bestie. There’s nothing you can’t ask Sugar.  

However, she is a busy woman, and can’t possibly answer all her Dear Sugar requests, so if you’re on your own personal journey, Strayed’s backlist is where you should begin. I’ve assigned a Cheryl Strayed book to make-believe askers. You’ll quickly find that no matter where you are in life, Strayed is right there to help you.

Sincerely, Lost Myself 


Finding out who you are is no easy task. It takes a lot of soul searching, and occasionally you lose yourself along the way. But sometimes it takes losing yourself to find the answers you’re looking for. Wild: From Lost to Found on the Pacific Crest Trail is a personal account of Cheryl’s life. At 22 she thought she lost everything, her mother had passed, her family scattered and her own marriage was soon destroyed.  With no experience or training, driven only by blind will, she would hike more than a thousand miles of the Pacific Crest Trail from the Mojave Desert through California and Oregon to Washington State–and she would do it alone. A tale so captivating you may think it’s fiction, but her resolve to keep walking until she finds herself is a journey we could all relate to.

Sincerely, A Bad Listener


There’s nothing worse than being like a bad listener. Friends come to you with their problems and you don’t know how to help or even console them. This can be a frustrating experience for all involved. Tiny Beautiful Things: Advice on Love and Life from Dear Sugar is a collection of Strayed’s best work when she was an anonymous columnist at The Rumpus. If you’re looking to be more empathetic, Cheryl is the person to learn from.


Sincerely, My Not So Perfect Life  


There are times when our public persona is vastly different than who we are in private. People may always be mentioning how put together you are but internally you feel like you’re just making it up as you go along. In her debut novel, Torch, Strayed writes about a character who gives advice on a local radio show while her own life is far from perfect. Sound familiar? The main character, Tessa Rae Wood, always tells her listeners to “Work hard. Do good. Be incredible!” but sometimes as people we aren’t able to take our own advice. Torch is a beautiful depiction of what it means to lose everything you’ve ever known and still be standing strong. 

Sincerely, No Guts

D.J. Khaled isn’t the only pro at affirmations. If you can’t afford to have a personal hype man that tells you how awesome you are, Brave Enough is a quick fix. The book is a collection of quotes, described as a “mini-instruction manual for the soul.” Whenever you’re feeling unsure of yourself, Strayed is right there to lift you up.  


Be brave enough to break your own heart.

You can't ride to the fair unless you get on the pony.

Keep walking.

Acceptance is a small, quiet room.

Romantic love is not a competitive sport.

Forward is the direction of real life.

Ask yourself: What is the best I can do? And then do that.

Feeling braver already, right?

Wherever you seek Strayed’s guidance you will not be disappointed. Her knowledge, empathy and wisdom is what always propels her books to the top of best-seller lists. A trip through her work will arm you as you venture into the next chapters of your life.