5 Important Lessons To Learn From Cheryl Strayed’s Tiny Beautiful Things: Advice On Love and Life from Dear Sugar

The Dear Sugar advice column didn’t begin with Cheryl Strayed, bestselling author of Wild and Brave Enough, but it did get passed onto her from its previous writer, Steve Almond. While advice columnists usually stick to the rule of focusing on the letter writer, Cheryl instead wrote from the perspective of “a real human being laying herself bare, fearlessly, that we might come to understand the nature of our own predicaments” (Tiny Beautiful Things 5). Steve Almond writes, in the introduction to Tiny Beautiful Things: Advice on Love and Life from Dear Sugar, that Cheryl “was announcing the nature of her mission as Sugar. Inexplicable sorrows await all of us. It all matters–every sin, every regret, every affliction…within the chaos of our shame and disappointment and rage there is meaning, and within that meaning is the possibility of rescue” (5-7). It’s no wonder, therefore, that valuable and far-reaching life lessons can be found in her responses. Here are the five most important lessons to learn from Dear Sugar.

Follow Your Feeling

When Cheryl (Sugar) was eighteen, she and her mother stopped off at a yard sale. Amid the junk was a red velvet dress with white lace trim, “fit for a toddler” (321). Cheryl was drawn to the dress, although she didn’t know why. “I cannot explain it,” Sugar writes, “even now except to say something about it called powerfully to me.” Her mother paid the dollar it cost, and Cheryl put it in a box, not to be unearthed until her mother had passed and her daughter was three. Sugar writes, “[The dress’s] meaning was made only by my mother’s death and my daughter’s birth. And then it meant a lot. How ordinary for a child to wear a dress her grandmother bought her, but how very extraordinary it was to me” (323). Follow your feeling. Follow that gut feeling you have, whether it’s about love or your career or anything and everything else. Follow your feeling because you never know what will be revealed, what will manifest in your life from such a feeling.

Live Your Story As Authentic

One of the most heart-wrenching moments in Dear Sugar is the letter written by “Stuck,” who miscarried when she was six-and-a-half months pregnant. “As one person pointed out,” she writes, “‘it was only a miscarriage.’ So I also feel guilty about being so stuck, grieving for a child that never was when I should just walk it off” (19). Cheryl Strayed as Dear Sugar writes that although the people who surround Stuck love her, “they live on Planet Earth. You,” Sugar writes, “live on Planet My Baby Died. The healing–the genuine healing, the actual real deal down-on-your-knees-in-the-mud change–is entirely and absolutely up to you” (21). Many of us cannot relate to the suffering that a miscarriage brings, but our lives are filled with other tragedy that hurts just as much. And in the end, it doesn’t matter what that tragedy is. What matters, argues Sugar, is that our feelings are authentic and real and legitimate, and no one can tell us or make us feel otherwise. People may expect you to get over your pain, to move on from the suffering, but the pain is yours and only yours to heal from. Your story is yours. And your feelings and emotions are authentically you, meaning only you can decide when to feel them and when to feel ready to get unstuck from them.

Being With People Is One And Only

Dear Sugar, in response to a letter signed “Desperate,” tells the story of a boy who attempted to steal an empty camera case from her yard sale years earlier. He returns the next day and sets the camera case down, placing it back where it had sat the day before. A few young boys, including this one, hang around her porch all day. And she continually asks the boy “Why did you steal it?” (270). After repeatedly denying that he did steal the case, he eventually tells Cheryl he stole it because he was lonely. While it seems like Sugar’s reason for replying to Desperate’s letter is more complex, I think the obvious lesson learned from this anecdote is that being with people and communion with people is of critical importance. It is the one and only thing that can lead to healing. Being open about our place in life, our suffering, our emotions, with the people in our lives with whom we find comfort will lead to our healing. And life requires healing.

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Go. Go. Go.

In a somewhat rare occurrence, Dear Sugar consolidates three letters she received, all from women who seem to have one thing in common: their uncertainty in their partners. All three of these women seem to have the same little voice in their head saying “go, go, go.” Sugar writes, “An ethical and evolved life entails telling the truth about oneself and living out that truth” (171). And while this advice is originally tailored for these women who want but are scared to leave their partners, it works on every level of this thing we call life. First and foremost, don’t stay when you want to go. To stay isn’t fair to you, but it also isn’t fair to your partner. To your boss. To your first apartment. To the city you live in. Unhappy in your current position at work? Leave. Find another job. Let someone who will find happiness and fulfillment take your old position. Sugar writes that divorcing her first husband was the “most excruciating decision” she’s ever had to make, “but it was the wisest one too” (173). This advice can apply to all things in life. Tell the truth about what you want, even if it takes a while to figure out what that is, and act on it. Live out your truth, always.

Embrace Your “I Made It”

In the same response written to “Stuck,” Cheryl remembers her job as a youth advocate for girls who were deemed “at highest risk” by the faculty at their school. These girls, Sugar writes, didn’t have fathers because they were “in prison or unknown to them or roving the streets of our city strung out. Their moms were young used and abused drug-and-alcohol addled women who were often abusive themselves” (23). These girls were looked down upon and constantly told they were not going to amount to much, if anything. Six years after leaving this job, Strayed ran into one of the girls at a Taco Bell. “I made it, didn’t I?” she asks Strayed. “You did,” she answers back. “You absolutely did.” Again, while most of us may not be able to relate to this as such, the advice Sugar gives is applicable no matter our backgrounds. Sugar means this: don’t compare your “I made it” to anyone else’s. Making it is your extraordinary achievement and shouldn’t be based in what anyone else thinks. Your “I made it” is your own. This girl’s “I made it” was working as a shift manager at a Taco Bell. It’s unfair for anyone to look down on that because, despite her upbringing, despite all the times and in all the ways she was told she couldn’t, she did. And you can, too, no matter what your “I made it” means.

Dear Sugar began as just an advice column, but what it became with Cheryl Strayed at the helm is a lesson in radical empathy. Empathy for others, but also for ourselves. If this article interested you, buy her book, see the play, or share this article. All quotes throughout this article came straight from Cheryl Strayed’s Tiny Beautiful Things: Advice On Love and Life from Dear Sugar.