Skip Cherryholmes: Month 7 Of Lead Dad Life

Welcome to Episode 7 of Lead Dad Diaries with Skip Cherryholmes.

This is part six of our year-long series examining one man’s Lead Dad journey. Here’s the backstory – or skip to the questions.

Skip Cherryholmes spent nearly two decades on the road as an acclaimed Bluegrass musician. Starting as a pre-teen, he was a member of Cherryholmes, a Grammy-nominated band started by his parents. He then launched a successful touring career on his own, with his band Sideline. During that time, he married Stephanie, who he met because her father performed with his family’s band. They have two young children, ages 5 and 2.

Earlier this year, he came off the road for good to be a Lead Dad. It was a decision that he started to consider during the pandemic when he slept in his own bed for more consecutive nights than at any other time since his childhood. “The adventure of being a father spoke to me,” he said.

But the moment when he realized it was time for change came when his son was talking to him and Skip couldn’t hear a word – he was so engrossed in planning the logistics of upcoming travel and shows. Shortly after that, he announced his intentions to come off the road and effectively retire – in his early 30s – from performing. He played a series of Bluegrass venues in 2023 as a farewell tour and then he came home to Raleigh, North Carolina, with no plans in sight.

What was that transition going to be like? What would be great? Where would he struggle? Would it work out as he hoped? What would it mean for his family?

Skip and Paul Sullivan, founder of The Company of Dads, decided to track this and agreed to talk every month for a year to see how things worked out. To track what happens, Paul asks the same five questions each month. What follows is the start of Skip’s new Lead Dad story.

Month 7 of Lead Dad Life

Welcome to Month 7 of the Lead Dad Diaries with Skip Cherryholmes. We’re following Skip for a year as he goes from well-known touring musician to a new career where being a Lead Dad is as important as what he is doing for work. We’re just over halfway through, and we’ve got some big news that neither of us can believe it. Skip has taken over the social media for The Company of Dads and we’re thrilled.

What do we talk about in the pre-question chatter this month? All kinds of stuff but I guarantee that what you’ll remember is Skip’s favorite food from the state fair: two Krispie Kreme donuts wrapped around a bacon cheeseburger. (“I would not recommend it,” he laughed. “It’s not safe!”) There was also some sickness in the house this month – unrelated to overdoing it at the state fair. And a lot of gratitude for being off the road and at home for Halloween. Here we go!

What’s been the best part of the past month?

We’re in the throes of fall. This is my favorite time of the year. We’ve pushed past a lot of the pumpkin spice, and we’re moving toward the peppermint and the chestnuts! As a touring musician you’re gone all the time from the end of August to Thanksgiving. That was true even in 2020, before it got really cold but after we’ve been around this whole Covid thing for a while, people were testing the water on more social activity. My fall has traditionally been a time where I’ve been gone a lot. I’ve been able to dive into the reality of the season. Take my kids trick-or-treating, go to the state fair, make campfires. It’s just been a great experience for me. I relish in the small things.

What’s been the worst part of the past month?

The sickness that’s gone around the house. Aiden had been complaining that his stomach wasn’t well. It spread to my wife and my little girl. I managed to stave off what they got. It was the first week I started here at The Company of Dads. I had an event at church I was trying to produce and I was trying to take care of them. When they’re sick it’s heartbreaking to see them so drained of life and sitting there.

What’s your best Lead Dad moment been?

I feel sometimes that when you’re a Lead Dad you have a barrage of things on a daily basis that come your way that could almost qualify as Lead Dad moments. Helping Aiden in school has been a huge one for me. I’ve watched him develop so rapidly. He’ll sit down and ask me something so substantially above anything I thought he was listening to. He wants me to go into depth and I’ve realized I’m talking to a little man. We had a close family friend issue that opened up a conversation about mortality and illness. He’s sitting there and you don’t want to say things that are going to be upsetting. I’m reading his body language. He’s not going to listen to a lie. He wants an answer. I said, okay, I’m going to give it to you straight. Here’s what it is. He had follow-up questions. Some of it I could answer and some of it I couldn’t. He was sitting there and so maturely processing information as I was presenting it to him. That development piece is so remarkable. I thought before I had kids: What’s it going to be like to watch someone else learn? What’s it going to be like to watch someone develop these fundamentals that they will use massively? How will I know as a dad when it’s good to talk about certain things? When will I give too much information or not enough? I can see that my being home and being present has given me a better example of where he’s at and where his personality is. He’s come at me with some pretty heavy stuff.

What’s been your most challenging Lead Dad moment?

I honestly haven’t really had that urge to get back on the road. I miss my guys as far as the bandmates. I still talk to the on a consistent basis. It’s odd not to have seen a couple of them in months. We were going to track some songs. I’m looking forward to that. I’m more excited to be part of the creativity with the guys and the fellowship. As far as getting away again, I’ve always tried to find a way to bring my family along with me. I’m glad my kids are flexible and happy to travel. But going back to the question about the worst, I’m having trouble labeling something as the worst.

Any lessons learned?

Any time I’ve felt that I’ve been supremely overwhelmed or maybe just on the fritz as a parent or spouse, I look at the calendar and say in a previous life, what would I have to be dealing with right now? When that list starts to populate, particularly in the cons column, I realize that what I’m stressed about isn’t as bad as that. You need to take time and clear your head. Selfcare is very important, and it keeps your endurance up. That reflection has been really solid for me. I got to do something really cool with Adeline experiencing her first real trick-or-treat at Halloween. Her mind was just blown that she could knock on people’s doors and get candy. There have been years when I left to go on tour and I wasn’t home for Halloween. I had to experience those moments on Facetime. Same with some of the more important questions with my son. I don’t have to do those on the phone. His first birthday I was in San Francisco doing a show. The most I had was a FaceTime call and a present I left for him at home. And then I wasn’t going to be home for 3.5 weeks. Whatever is overwhelming me isn’t that big of a deal because I could be 3,000 miles away missing out on A, B and C.