The Dear Sugars podcast has only been on since 2014, but their advice feels like it’s been a constant for me much longer. When it debuted, I was a brand new mom to an infant, living two thousand miles away from my family, and looking for wisdom and assurance about surviving life’s most seismic shifts, and the Sugars offered the perfect doses of wisdom without judgment, truth tempered with humor, and literary references to real life problems that made my book-nerd heart skip a beat.
Co-hosts and former Dear Sugar columnists for The Rumpus Steve Almond and Cheryl Strayed give advice on all kinds of Hard Things that only two writers could give. They’ve been observing and absorbing and negotiating and screwing up just like the rest of us their whole lives. But when writers give advice, just like when they write great stories, they have a way of telling the truth and giving their perspectives in a game-changing, myth-busting, beautiful ways that stay with you and can really change the way you see the world. This show made me a better, more understanding person, made me feel less alone in the world when everything felt chaotic and weird, gave me permission to want a bigger, more interesting life, and dared to ask questions about relationships I would never have been brave enough to ask.
The anonymous letters from people seeking advice speak for themselves; we only know what’s on the page, and that mysterious specificity makes every episode also resonate so universally. Their guests, who also read the letters and offer their own advice, range from award-winning authors like George Saunders to the inimitable sex and relationship experts like Esther Perel, and they approach each letter with an astonishing, breathtaking level of perspective and empathy.
There are common threads to their advice. Grief is a thing to be carried, not gotten over. You are entitled to a creative life, not matter what else you have going on and what anyone tells you. There are stories we tell ourselves that are not true, but that we’ve believed for so long they feel impossible to escape (they aren’t). The system is rigged, but the way to improve your odds at beating it is by facing that truth, reaching out, and working your ass off anyway. Our darkest traumas are real, unfair, and painful, but they also don’t have to define you forever. We’re responsible for the consequences of our mistakes and misjudgments, but we’re not alone in making them.
Before listening to the final episode (and weep-running, or sniffle-driving, or whatever), I looked back at some of my favorite episodes from the past five years, the ones that have made me stop and burst into tears or fist-bump the air. I’ve forwarded episodes of this podcast to friends going through everything from divorce and infidelity to addiction and mental health crises, and I’ve replayed favorite episodes myself more than any other podcast on my list. Five years in, there’s not much they haven’t covered, and I know their archive will stay in my constant rotation as long as the world insists on its continuing seismic shifts.