The Back 9 - Midlife, Best Life.

Divorce has a nasty habit of turning bad decisions into permanent ones.

This week on The Back 9, mother-and-son appellate attorneys Amy Shield and Roger Levine, authors of Divorce SOS, share the legal mistakes people often don't recognize until it's too late — from financial records and settlement agreements to choosing the wrong attorney.

But some of their best advice happens outside the courtroom. When an ex knows exactly h...

Being engaged with the world doesn't mean we have to let all of it into our heads.

This week on The Back 9, it's just Dennis and Josh, talking about everything from the crime against humanity that is mixing 12-year Scotch with Coke to movies, anxiety, meditation, social media and the things we allow to occupy way too much space in our lives.

Dennis shares what happened when he dramatically cut back on social media...

Sometimes we get to a point in life and realize that we are spending so much time focused on the future for our family, that we've lost sight of the life we're living right now.

This week on The Back 9, entrepreneur Philip Crutchfield talks about becoming a father young, building successful businesses, and confronting his own role in the end of his second marriage.

Philip spent years working long hours and traveli...

Divorce can feel like the worst thing that's ever happened to you. For Kurt Heide, it once did.

When his first marriage ended, Kurt suddenly found himself raising three young children as a single father while trying to hold together his career and his life. This week on The Back 9, he shares what he learned about putting his kids first, keeping anger from driving important decisions, and eventually building the relationshi...

This week on **The Back 9**, ESPN 1000 Chicago's **Marc Silverman** joins us to talk football, fatherhood and the non-Hodgkin's lymphoma diagnosis that changed the way he thinks about his time.

Now six years in remission, Silvy shares how therapy, mentorship and even acupuncture helped him through treatment—and why he no longer puts off the trips, experiences and time with his wife and sons that once could have waited.

Dennis...

Three years ago, The Back 9 was born over late-night hot dogs and cheese fries at Chicago's legendary Wiener's Circle. This week, we sit down with one of the guys who owns it.

Investor and restaurant owner Ari Levy talks about preserving—and reinventing—a Chicago institution famous for its irreverence, and how the Wiener's Circle became part of the conversation around the Bears last season with viral stunts inv...

Everybody says time is more valuable than money. We decided to put that idea to the test.

So we kick off Season 14 of The Back 9 with a hypothetical that quickly becomes a lot less hypothetical. Our answers lead to a bigger conversation about time, money, family and what we value at this stage of life.

As we make the turn into another season, we also look at how far The Back 9 has come, the progress of our book, a...

We went into Season 13 wanting to take a deeper look at divorce, particularly about what comes next when relationships end. Nine episodes later, we've heard some very different answers.

On the 19th Hole for this season, we look back at conversations about going through divorce in real time, protecting yourself legally and financially, avoiding the costly mistakes that can make splitting up even harder, building a successfu...

Divorce is already expensive, exhausting and painful. You don't have to make it worse.

On this episode of The Back 9, author and educator Eric Saperstein shares the lessons from his own three-and-a-half-year high-conflict divorce—and the practical steps that became the foundation of his new book, Simplify the Split.

We talk about the mistakes that cost time, money and emotional energy: treating your attorney...

A four-year college education can cost a family as much as $400,000. But how do you know what you are really buying?

This week on The Back 9, we sit down with New York Times personal finance columnist and bestselling author Ron Lieber to discuss one of the biggest financial decisions most families will ever make.

As tuition continues to climb and artificial intelligence reshapes the job market, Ron explains why parents and students...

The smartest legal decisions you'll ever make about divorce happen long before anyone files the paperwork.

On this episode of The Back 9, family law attorney and author Diana Romanov shares the legal advice every man should know before marriage, during separation, and throughout the divorce process. We cover prenups, protecting assets, financial transparency, mediation, documentation, and how to avoid costly mistakes when ...

You spend most of your life thinking anxiety is something other people struggle with. Then one day, in midlife, suddenly…it's you.

On this episode of The Back 9, licensed psychotherapist and mental performance coach Rachel Blogg explains why so many of us are caught off guard. Anxiety disguises itself as overthinking, overworking, sleeplessness, the need to control everything, or the nagging feeling that something is wrong&m...

Cal Callahan had everything he'd spent years chasing: a successful career, a beautiful family, and all the outward signs that he'd made it. The problem was...he still wasn't himself.

In one of the most vulnerable conversations we've ever had on The Back 9, Cal shares the deeply personal journey behind his new book, UNLEARN—and, for the first time, why he's bringing his 6½-year podcast, The Great Unlearn, to a close. ...

Some of the most important conversations in a relationship don't happen because of conflict. They happen because life keeps moving.

This week on The Back 9, the briilliant entrepreneur and financial advisor Henry Yoshida joins us to talk about the conversations couples—especially those in second relationships—need to have long before retirement arrives.

Yes, we discuss trusts, beneficiaries, taxes, and planning. But the...

After a divorce, many people wonder whether they'll ever build the kind of family life they imagined.  Dave Ryan got a second chance.

On this episode of The Back 9, the longtime broadcaster joins us to talk about balancing a career that kept him on the road with fatherhood, what he learned from his first marriage, and how remarriage opened the door to a new chapter he never expected. He and his wife had kids, then fos...

If you're in the middle of a divorce, or thinking about divorce right now, you need to listen to this episode. Not after it's over. Not when you've figured everything out. Right. Now.

Geoff Fountain is in the middle of an 18-year relationship that is coming to an end. Two kids. A shared life. And now he's rewriting his future. And at one point, Geoff turns the tables and starts asking us questions. Questions we've both had to answe...

This Father's Day week, we're doing something we've never done before.
For the first time in Back 9 history, we have a full episode with just the two of us.
No guest. No expert. No one else to play off of… It's just two guys sitting across from each other talking about what it feels like with our kids grown and living on their own, and looking back at the fathers we tried to be.

We talk about raising daughters a...

Season 13 starts with an announcement:

Over the past year, we've been building something bigger than a podcast — a book about how men heal, rebuild, and find healthy relationships after midlife divorce. It's now in front of major publishers, and the response has reinforced something we've believed from the beginning: Men need hope.

This season will continue that conversation through stories about relationships, fatherhood, pu...

This season started with a daughter getting engaged, included 3 graduations, and ended with a toast by the campfire.

That's what the 19th Hole is for.

Every season, we take a breath and look back at the conversations that stayed with us. And this season had plenty.

We talked about the pull of the wrong relationships after divorce. Knowing yourself before saying "I do." The discipline of co-parenting without letting ego take over.

A...