We should talk about hard things.
The tables turned this week when I got to interview one of my favorite interviewers, Anna Sale. The author of “Let’s Talk About Hard Things” and host of the “Death, Sex and Money” podcast is in Jackson live to help us all get better at talking about hard things. I want to give a shout out to recommend her book and thank the event host, Womentum, for making this happen.
Listening to Anna’s interviews and reading about her skillful conversation reminds me how much mindfulness and effective dialogue rely on each other. Giving someone your full, undivided, nonjudgmental attention is a precious – and deeply felt – gift, especially when you show up with intentional curiosity. Skillful conversation isn’t about finding solutions or right answers but about learning to view conversations as a practice. This approach creates space for new, deeper, or nuanced understanding that allows us to evolve together.
“I am greatly lifted by being connected with others in a particular way,” Anna told me, noting how much richer the unfolding is without judgment or a preconceived notion. She made a simple declaration: “We assume things are fixed, but they aren’t. Especially in our closest relationships or when the stakes are high.” Those assumptions keep us gridlocked, isolated and with no space for deeper understanding.
Conversations, as she writes in her identity chapter, “can also be about transformation and choosing a different way than what came before.” As humans, we yearn for connection, which comes only through understanding each other better. The idea of conversation as practice, rather than a debate competition, is something our communities and organizations desperately need. Only through creating space to consider other perspectives can we begin to let our shoulders down and evolve together.
“We are often forced to confront the gap between how we see ourselves and how we are experienced by others,” Sales observes, something that feels exceptionally important in these times that call for rebuilding of trust and civility. While mindfulness practice is the power tool for self-awareness, it is only through relationships with others that we actually get to test newly gained self-awareness. There is a two-pronged approach to narrowing the gap. Mindfulness provides time to grow our skills, and conversation allows us to practice using them.
Anna covers all the hard stuff in her book: death, loss, divorce, sex, failure, grief, disappointment. And she asks the important question: “What is it like to navigate from a full range of perspectives?” Conversation is how we discover perspectives previously unseen and unacknowledged. This is how awareness grows.
Like many of you, I was especially tuned into the opening chapter, “Death,” which features beloved local Shelley Simonton and the stunningly open and caring way she talked about her own journey with melanoma before dying. Eerily and perfectly, I type these words on the anniversary of her Celebration of Life, an occasion that modeled how things can be both hard – like bottomless grief – and healing when we share that burden with each other. The willingness to have hard conversations was Shelley’s final gift.
In the school of life, the reading, writing, and ’rithmetic are the curtains, not the scaffolding. People like Anna, like Shelley, like the group of Shelley’s friends called “The Birthday Club” reinforce what I feel in my bones to be true – our lesson here is to create space for understanding to emerge, to resist the urge to find the “right” answer. Not everything has an answer. Not everything needs an answer.
“You can’t smooth everything out in a conversation,” Sales concluded. “There is no solution for death.”
And then, after a pause, she adds, “I look for openings.”
Keep singing with the angels, Shelley. We’ll keep talking about hard things.
With gratitude,
Sara
TO HEAR MORE
Livestream Anna’s sold out talk this Friday, August 6th, at 10:30 a.m. at: https://fb.me/e/2Mg8v22H5.
TO SHOW SUPPORT
Remember Womentum in Old Bill’s.
TO GO DEEPER
Buy Anna’s book from a local bookstore, such as Jackson Hole Book Trader, 307-734-6001, bookshop.org, or Valley Bookstore, 307-733-4533, www.valleybookstore.com.