We Can Do Hard Things: Cheryl Strayed Tells Us What the Hell to Do Next (Best Of)
Release Date: June 22, 2025
Hosts: Glennon Doyle, Abby Wambach, Amanda Doyle
Guest: Cheryl Strayed

Introduction to Cheryl Strayed

The episode kicks off with an enthusiastic introduction of Cheryl Strayed, renowned author of the bestselling book Wild and the critically acclaimed advice column Dear Sugar. Amanda Doyle highlights Cheryl's impactful work and encourages listeners to revisit previous episodes featuring her.

[02:04] Cheryl Strayed: "Yay."

[02:58] Cheryl Strayed: "I love you so much you know this and I'm now even more obsessed..."

Navigating Alcohol and Mindful Drinking

A significant portion of the conversation delves into the complexities of alcohol consumption, addiction, and the cultural binaries surrounding drinking habits. Cheryl shares her personal journey of reducing alcohol intake, emphasizing the importance of mindfulness over strict dichotomies of "alcoholic" vs. "non-alcoholic."

[04:11] Cheryl Strayed: "I've been on an alcohol journey of the last year... I started to just be mindful about that and to pay attention to how I was using alcohol and why. And I slowly but surely have pretty much stopped drinking."

Abby Wambach and Amanda Doyle echo Cheryl’s sentiments, discussing the misleading notion that responsible drinking neatly categorizes individuals, and the broader implications of mindful consumption.

[07:48] Cheryl Strayed: "Almost always that binary is a false narrative."

[08:51] Amanda Doyle: "Holly Whitaker does a beautiful job... asking ourselves, do I have a problem? We could always ask, is this benefiting me in my life?"

The Healing Power of Laughter

Transitioning from alcohol, the hosts and Cheryl explore the therapeutic role of laughter and genuine joy in healing and personal growth. They discuss practices like smiling and laughing with abandon as ways to cultivate a sense of well-being.

[18:25] Cheryl Strayed: "My new theory is, like, actually seeking that out. Seeking out laughter is one of the most healing acts of love we can give ourselves."

[19:25] Amanda Doyle: "Gloria Steinem said that one of the many reasons why laughter is so magical is because it's proof of freedom..."

Deep Dive into Dear Sugar

Cheryl narrates the inception and evolution of her Dear Sugar advice column, emphasizing the power of storytelling over traditional advice-giving. She reflects on her motivations and the profound impact her column has had on readers.

[24:44] Cheryl Strayed: "When we do feel lost, well, you know, then our main task is to go about the business of finding our way... Who am I really?"

Amanda and Abby commend Cheryl for her authentic approach, highlighting how stories can illuminate personal truths and foster deeper connections.

[27:30] Amanda Doyle: "It's why everyone listens to you, because what you do is again and again in beautiful new ways."

Listener Questions and Cheryl’s Advice

The heart of the episode features Cheryl answering listener questions, offering compassionate and insightful advice on various personal struggles.

1. Navigating a Midlife Crisis

Bethany's Question:
"I am in my mid-40s. My kids are growing up and they don't need me as much. I never really fell particularly in love with my career or what I was doing. And now I left that for a little while, and I don't know where to go from here. Is this a midlife crisis?"

Cheryl responds by reframing midlife crisis as an opportunity for self-discovery and alignment with one's true self.

[45:02] Cheryl Strayed: "This is this wonderful moment, Bethany, in your life where things are breaking open and you say you feel lost... Who am I really?"

2. Ending Unhealthy Relationships with Grace

Kate's Question:
"When you have the clarity to understand that your relationship is not healthy and you can't stay in it, but you love the person, how do you walk away with grace and dignity and let go of the resentment and remorse?"

Cheryl emphasizes honesty, compassion, and maintaining inner clarity as keys to gracefully exiting a relationship.

[49:00] Cheryl Strayed: "Tell the truth with all of your heart and all of your compassion... Your intentions are to lovingly end a relationship."

[52:04] Cheryl Strayed: "So you tell the truth with clarity, you hold within you that little beautiful, glowing gem of clarity..."

3. Loving Someone Battling Addiction and Depression

Erica's Question:
"How to best love and exist with someone who is in the depths of addiction and depression? It's my adult son, whom I love deeply."

Cheryl acknowledges the profound pain and offers guidance on self-care as essential to supporting a loved one.

[53:10] Cheryl Strayed: "What is inside of our control is to make myself strong and brave and whole so that I can be that strong, brave, whole person that will be there for this person I love so much."

[56:23] Cheryl Strayed: "You're never going to feel good if your son is an addict and struggling with depression... Take care of yourself in those radically deep, simple, complicated daily ways."

4. Managing Money-Related Stress

Miranda's Question:
"I started to think about what in my life is the most stressful and what controls me the most, and it's money. How do I not let it have so much control over my mood and mental state?"

Cheryl shares her upbringing and the importance of adopting an abundance mindset over scarcity to alleviate financial stress.

[53:03] Cheryl Strayed: "We aren't poor because we're rich in love."

[63:08] Cheryl Strayed: "Shifting that thinking, that you are rich in these things... make mindful decisions about money's meaning in our lives."

Cheryl's Personal Reflections and Insights

Throughout the episode, Cheryl intertwines personal anecdotes with profound insights, offering a candid look into her own struggles and triumphs. She discusses her experience with COVID, the impact of her writing, and her continuous journey towards self-care and authenticity.

[12:13] Glennon Doyle: "I've been sober almost seven years now... I am so grateful every morning to wake up and to know that I have nothing that I have to worry about."

[17:24] Glennon Doyle: "I love that."

[18:50] Cheryl Strayed: "Just go out there and laugh. Find laughter. And also just smile to yourself."

Closing Thoughts

As the conversation winds down, the hosts express their admiration and gratitude towards Cheryl, acknowledging the healing and empowering nature of her work. They reinforce the podcast's mission to tackle life's hardest challenges through honesty, connection, and support.

[66:11] Cheryl Strayed: "The work that the three of you are doing with this podcast is tremendously healing and powerful... Anytime you need Dear Sugar, back on the show, I am here for you."

[67:27] Abby Wambach: "I think they've blocked her number, so probably."

Key Takeaways

1. Mindful Consumption Over Binary Choices: Rather than categorizing drinking as purely good or bad, embracing a mindful approach allows for healthier relationships with alcohol.

2. The Healing Power of Laughter: Incorporating genuine joy and laughter into daily life can be a powerful tool for healing and resilience.

3. Authentic Advice Through Storytelling: Cheryl Strayed's Dear Sugar emphasizes the importance of storytelling in providing meaningful and relatable advice.

4. Embracing Midlife Transitions: Viewing midlife challenges as opportunities for self-discovery and realignment with one's true self.

5. Graceful Endings in Relationships: Honesty and compassion are essential in ending unhealthy relationships while preserving dignity and self-respect.

6. Self-Care in Supporting Loved Ones: Prioritizing self-care is crucial when supporting someone battling addiction or depression.

7. Abundance Mindset for Financial Stress: Adopting an abundance mindset can significantly alleviate stress related to financial struggles.

Notable Quotes

• Cheryl Strayed:
  "We aren't poor because we're rich in love."
  [53:03]

• Amanda Doyle:
  "The edge is there for a reason. It's a gift to you to point you in one direction or not."
  [09:41]

• Cheryl Strayed:
  "Just go out there and laugh. Find laughter. And also just smile to yourself."
  [18:50]

• Cheryl Strayed:
  "When you speak your truth, when you live out what you know is the right way, you know that that puts you in the safer zone because then you're aligned."
  [29:52]

• Cheryl Strayed:
  "This is about how much we are defining ourselves by what we have, rather than who we are."
  (Implied throughout the discussions on abundance and self-worth.)

Conclusion

In this heartfelt episode, Cheryl Strayed joins the We Can Do Hard Things hosts to explore profound personal topics with honesty and vulnerability. From navigating personal challenges like alcohol use and midlife transitions to offering compassionate advice through the Dear Sugar lens, Cheryl provides listeners with invaluable insights and encouragement to face life's difficulties with courage and authenticity. The conversation underscores the importance of self-care, genuine connections, and embracing one's true self in the journey toward resilience and fulfillment.