Life advice according to Cheryl Strayed

At age 26, Cheryl Strayed hiked 1,100-miles on the Pacific Crest Trail from the Mojave Desert to the Oregon-Washington border, entirely on her own. A story of finding oneself in the wake of tragedy, Wild details Cheryl’s journey, the events leading up to it, and the personal growth she underwent as a result of it.

I first read Wild the summer before I embarked into my own unknown of my freshman year of college, and immediately fell in love with Cheryl’s honesty, determination and perseverance. Between Wild and Tiny Beautiful Things, a collection of letters and responses from Cheryl’s “Dear Sugar” advice column, these are the five most important lessons I’ve taken from Cheryl.

Own your imperfection

Cheryl is maybe the most messed up person I’ve ever read about, and yet I completely idolize her. Because she doesn’t just recognize or accept her imperfections, she totally embraces them. For an obsessive perfectionist like myself, this isn’t a lesson that comes easily. But I realized that when I thought about why I loved Cheryl, it’s the ways in which she is imperfect that are the most interesting, special parts about her. Cheryl has taught me that we need to love every inch of ourselves – every scar, birthmark and stretch mark – equally. We need to treat the things that we love about ourselves and the things we hate about ourselves as equally vital, and equally beautiful elements of who we are.

Life is messy, lean into it

Just like we are imperfect, so is life. It’s disorderly, complicated, and nothing ever goes as planned. We can either fight back against every mishap to desperately stick to our preconceived life plan, or we can surrender a little to the current and see where it wants to take us. Again, this doesn’t come without some difficulty to a compulsive planner like myself, but Cheryl has taught me to embrace the messiness, the mishaps, and all of the hurdles not as failures but as re-routes.

It’s better to get it wrong on the first try

In one of her “Dear Sugar” responses, Cheryl describes the process of writing her book, the failure she felt at age 30 when she had not put anything cohesive together, but the acknowledgement, five years later, that all of those starts and failures were crucial steps in the final product. It’s common wisdom that we learn more from our failures than our successes, and Cheryl further solidified for me that failures and disappointments are crucial building blocks in ultimate success.

Cry often

If I had a dollar for every time Cheryl recounts breaking down in tears I’d be on the path to Oprah-status. That woman seriously cries about everything. But her tears are always followed by these wonderful moments of clarity. Her meltdowns are the bridge between the recognition of “this is difficult, this sucks” and “but we can get through this, we can do something about this”. It isn’t always easy to admit that things aren’t perfect, and these meltdowns are crucial in making Cheryl surrender herself to that reality. In acknowledging the reality that things are not perfect, Cheryl is able to address it head on and make good on it.

There are two kinds of love

The first kind of love I think of as fake-love. It’s when your significant other is your source of compassion, comfort, acceptance, confidence, etc. But then there are those self-assured people who don’t need their significant other to boost their confidence. Sure, they still receive support from their partner, but they know and love themselves without needing to know that they are loved by someone else. So for those people who are their own source of compassion, comfort acceptance and confidence, they receive something else entirely, and that’s what I would describe  as real love. In Cheryl’s earlier relationships, she was so at odds with herself that she relied on her various partners to completely support her broken sense of self. However, by the time Cheryl had emerged from the west coast woods, she had developed such an incredible sense of self that her relationship with her now-husband wasn’t built on a need for shelter and acceptance, it was built on actual love.

Cheryl has taught me that none of this comes easily. It takes a lot of mental strength to forgive, to love yourself, to be vulnerable. But Cheryl has taught me that the most important thing to develop is strength and resilience, but not callousness. Allow yourself to cry, allow yourself to have your heart broken and to make mistakes, but have the willpower to move on.