Redeeming Old Regrets
“Your dad does not expect you to pay him back!” my college roommate pleaded. “You don’t know my dad—he absolutely does!”
It was my senior year of college and Ryan Adams was playing the Orange Peel in Asheville. His album Heartbreaker was —and still is—one of my favorite albums of all time. Matt begged me to go with him, but I was scheduled to work a shift at the coffee shop and I needed the cash. I had borrowed money from my dad to continue traveling around New Zealand the summer before, and I was intent on repaying my debt. I stayed behind, missed the show, and probably made a measly eighty bucks. I regretted it immediately.
Over the years I had the chance to see him play again, but it never felt right. I didn’t want Taylor Swift covers or new music in a big venue. I wanted to go back in time to Heartbreaker and the albums he recorded with the Cardinals—a time before his scandals and dropped endorsements; a time when liking Ryan Adams was cool; a time when I laid some claim to that term myself.
Naturally, I leapt at the chance to redeem my regrets when I saw that Ryan Adams was playing a nostalgic Heartbreaker tour this year and he was coming to a medium-sized venue in Tulsa. I bought tickets and hyped myself up. Every song on that album was amazing. I can probably sing every word. Rarely do you get a chance to go back and relive a time when you missed out.
It was terrible.
Sure, there were moments of nostalgia and creative genius. The music, whenever he got around to it, was mostly incredible. His electric version of Bartering Lines was transcendent. But there were many more moments of incoherent rambling, stream of conscious ranting, and foul-mouthed airing of personal vendettas. Toward the end of the night he spent a good ten minutes insulting his ex-wife (Mandy Moore) and detailing the many injustices of their divorce settlement. It was beyond the point of cringe.
I left feeling mostly saddened by what I had witnessed. Here was an incredibly talented man with an impressive first mountain. I’m sure he made some strides on his second mountain. I know he left behind an addiction and his struggles with mental illness are certainly unwanted. Yet when his character flaws caught up to him, he doubled down. There doesn’t seem to be a period of searching followed by intentional growth and healing. His approach seemed to be to change nothing and wait out the public shame. As he put it on stage, “I had the balls to wait it out. I wasn’t going anywhere.”
Maybe there’s a cautionary tale here for all of us trying to relive any glory days in the past. First, going to concerts of bands/artists you liked in your youth will likely always carry some level of disappointment. It’s a humbling experience to look at the crowd and wonder why everyone there looks so old, until you realize that it’s because they’re roughly the same age as you.
But maybe the greater lesson is to consider how we handle our failures and disappointments. Will you age with grace or bitterness; with intention or indifference? Will you evolve as you age or rely on your past success to give you a stage to rant on?
This issue of The Second Mountain is a joy to share. Today I’m introducing The Second Mountain Questionnaire, and our first participant is David Zahl—a man who has clearly pursued the path of grace and wisdom over the years.
You’ll see his bio below, but I’ll add here that it’s hard to overstate the impact Dave has had on me from afar over the past five years. I rediscovered Mockingbird during Covid through the podcast and it gave me the shot in the arm that I needed to get me through some dark days. I’ve also experience multiple acts of personal kindness from Dave and the team at Mockingbird over the years and I’m excited for you to read and relate to his responses below! And if you need a shot of grace like I do, go read his new book, The Big Relief.
We also have some inspiration for being intentional as we grow into the men, leaders, husbands, and fathers we want to be. May our regrets propel us into a better future rather than making us cling to the past.
Godspeed,
Joshua
The Second Mountain is a metaphor for any transition when your life shifts from striving to becoming—when external success gives way to deeper meaning, and your priorities move from achievement to alignment.
*Ryan Adams image is likely copyrighted
SECOND MOUNTAIN QUESTIONNAIRE
David Zahl
David Zahl is the founder and director of Mockingbird Ministries, editor-in-chief of the Mockingbird website (www.mbird.com), and co-host of both The Mockingcast and The Brothers Zahl podcasts. He and his family live in Charlottesville, Virginia, where he also serves on the staff of Christ Episcopal Church. Zahl is the author of Seculosity: How Career, Parenting, Technology, Food, Politics, and Romance Became Our New Religion and What To Do About It and Low Anthropology: The Unlikely Key to a Gracious View of Others (and Yourself). His latest book, The Big Relief: The Urgency of Grace for a Worn-Out World came out in April 2025 from Brazos Press. His writing has been featured in The Washington Post, Christianity Today, Plough, and The Guardian, among other venues.
1. What’s something you loved doing as a kid that you wish you did more of now?
I was a big skateboarder when I was in elementary school. I tried to get back out there as an adult, fell once (hard), and never got back on a board. The fun part wasn’t just the actual skating but the designing/building of ramps, brainstorming tricks, and hanging out with older kids. We also lived in Europe for a bit when I was in middle school and I loved traveling by train, which I almost never do anymore.
2. What do you wish you’d learned ten years ago?
I wish I’d learned earlier how my inclination toward being a martyr (or helper) in any given situation is not always a noble or heroic one. The posture, even when adopted out of necessity, brings with it significant and sometimes devastating liabilities in relationships, chief among them being resentment and alienation. I also wish I’d learned to play the piano when I was younger.
3. Have you experienced a fall, transition, or disruption that changed your direction (e.g. burnout, divorce, loss, crisis of purpose)? How did you get through?
I’ve gratefully been spared most of the ‘big hurts’ you mention. The most acute struggles of my adult life have had to do with addiction and its fallout, which has been no walk in the park. I’ve also dealt with quite a bit of depression and career-related confusion. The way through is ongoing but has come mainly through rigorous honesty, loving friendships, outdoor exercise, the intervention of wise therapists/mentors/doctors, and a steady diet of good art.
4. What relationships, practices, or callings feel central to your second mountain?
The intentional cultivation of male friendships has been particularly crucial to this stage of life. I’m also very privileged to be part of a church community that’s full of transparency, humor, and verticality. My calling as a father feels pretty central right now– the struggle at present is to prevent it from dominating every other calling in my life (husband, writer, neighbor). And perhaps it’s cliched, but I find I crave time in nature more and more, the older I get.
5. What do you want more of in life in the next five years?
Time with friends. Outdoor exploration. Deeper connection with my wife. Live music.
6. What piece of content do you wish every man knew about? (can be yours or a book, podcast, movie, etc. you want to share)
Everything Jonathan Haidt has written is of utmost importance no matter who you are. Of my own work, I think Low Anthropology is probably the book men would glean the most from. Meditations for Mortals by Oliver Burkeman is a worthy secular equivalent. Nick Cave’s Faith, Hope and Carnage and How to Stay Married by Harrison Scott Key are two male memoirs I keep coming back to. Terry Real is a guru worth following. Oh and The Age of Surveillance Capitalism by Shoshanna Zuboff should be required reading for everyone in our society.
Check out Thou Shalt Be Needed but Never Needy: Sad Clowns, Lonely Husbands, and COVID Friendships by David Zahl.
FATHERHOOD
Fathers Talking Fatherhood
“From Carhartt Handmade Films, Fathers Talking Fatherhood features actor/climber/father/bad*ss Jason Momoa and a group of exceptional fathers as they reflect on what it means to be a dad. They talk with reverence and humility about keeping their kids safe, being present in their lives, and the honor that comes with that role.”
Takeaway: This short film inspired me to be in the present in the moment while also imaging a vision how I want to father my children. It was also a reminder of how much I want the outdoors, art, and music to be a part of my family.
FATHERHOOD
Types of Fathers
Jon Tyson’s The Intentional Father outlines five types of fathers, each representing a different level of engagement, impact, and intentionality in the lives of their children—especially sons. Tyson challenges men to move beyond passive parenting toward purposeful fatherhood marked by presence, guidance, and formation.
Takeaway: Sometimes parenting books can create impossible expectations that no one can live up to. Read Jon Tyson’s book and you’ll likely feel like there’s no way you can achieve everything he suggests. But what if you can take it as inspiration? Could it empower you to greater intention as a father? I think so. Read through his list below and see it less as a test, and more as an invitation to reflect on your own father and imagine the type of father that you want to be to your children. Where do you see yourself here?
1. The Irresponsible Father
Absent by choice or behavior (e.g., addiction, abandonment)
Makes no effort to engage in parenting
Leaves deep wounds through neglect
The child is forced to fend for themselves emotionally and spiritually
2. The Ignorant Father
Wants to be involved, but lacks the tools or models
Repeats the parenting patterns he grew up with (or reacts to them blindly)
Often passive, busy, or unsure of how to guide
May love deeply but fails to intentionally mentor his children
3. The Inconsistent Father
Swings between engaged and absent, depending on work, mood, or energy
Provides for physical needs but not consistently present emotionally or spiritually
Sends mixed signals—children don’t know what to expect
Leaves a legacy of confusion and unmet expectations
4. The Involved Father
Present, supportive, loving
Attends games, shows up for milestones
Values his child’s success and happiness
However, may still lack a vision of formation—doesn’t intentionally guide character, faith, or purpose
5. The Intentional Father 💡
Actively mentors and forms the heart, mind, and character of his children
Leads with vision, purpose, and presence
Has a plan for how to guide a son or daughter into maturity, identity, faith, and responsibility
Creates rites of passage, practices, and one-on-one moments
Quote
“Teddy told me that in Greek, ‘nostalgia’ literally means ‘the pain from an old wound.’ It’s a twinge in your heart far more powerful than memory alone. This device isn’t a spaceship — it’s a time machine. It goes backwards, and forwards... it takes us to a place where we ache to go again.”
—Don Draper in Madmen
REFLECT
“The unexamined life is not worth living.” —Socrates
What are your biggest regrets? What do you want to do with them?
Take some time to reflect on or journal your answer. Pay attention to what emotions come up for you.