Skip Cherryholmes: Month 9 Of Lead Dad Life

Welcome to Episode 9 of Lead Dad Diaries with Skip Cherryholmes.

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 9 of Lead Dad Life

Welcome to Month 9 of the Lead Dad Diaries. It’s cold. It gets dark early. There is no vacation in sight – at least for me. But we’re here to find some warmth, light and at least a break from the day to day to reflect on what it’s been like to be a Lead Dad. We’re not going to spend too much time talking about Skip’s tropical cruise where he gets Sideline back together to perform. But we might spend some time on Skip’s lessons on flying a drone – and what to do when it flies out of range. So let’s get into it!

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

The touring life does not mesh well with the holidays, even if you’re not doing shows. A lot of times we’d wrap up first or second week of December. But then you’re getting ready for the season. There’s always been something that’s left me thinking I’ve missed out on the best part of the holidays. When I made the decision to come off the road, I thought the best part was how much I was going to enjoy next Christmas with them. And boy did I!

My kids are 6 and 2. This is the best time to enjoy the holidays. Sitting there and absorbing those two weeks leading into Christmas and the New Year, I was legitimately off. There wasn’t a lot of pressure. I was just really thankful to have all that time.

My parents live north of Nashville. I have two brothers in Cookville. A sister in Nashville. My other sibling lives in Colorado. My family wanted to do a family get-together. My sister said she was going to fly in. I said how cool would this be if we all surprised them. It was a seven-hour drive, and I was there. My parents came over to my brother’s house. My mom was shocked. It was the last thing anyone thought id pull off. I surprised my parents, but they didn’t know my sister was coming in too. Then my sister walked in. She stood there to see when they’d recognize her. It was the first time in 26, 27 years that my whole family had been together for a Christmas event. It was a really cool moment for me to spring something on my mom and my dad and then to have everyone there and to be together.

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

When you’re diving into the holidays and crossing into the new year you might as well throw the schedule book out the window. It goes for your kids, too. They get out of that rhythm. I say hey it’s the holidays I’m not going to worry about it. But then it ends. Trying to realign everyone’s schedules is a huge challenge. Steph and I tried to do some potty training over the holidays. It didn’t really take. And I didn’t go to the gym for two weeks. When I went back it hurt. I got three quarters of the way through it, and I said I’m done.

What’s your best Lead Dad moment been?

There is so much there with the holidays and you get to bask in the magic of it all. It was so much fun to be a part of the family that I had kind of missed. I know there were several moments – my son has taken up with a young lady at church. I don’t think he realizes how fond he is of her and how fond she is of him. There was one day we went as a church group caroling to shut ins. We’d sing for 15-20 min and go to another home. We did about 5 or 6 homes. Aidan went with me, and we were driving around. He said dad do you care if she rides with us. They were sitting in the backseat and playing with toys. I could see him basking in the moment with this young lady. She’s such a sweet little girl. I got to do a father-son thing but then he brings along his friend and it was really cool. In the holidays there’s nothing better than something like that.

What’s been your most challenging Lead Dad moment?

One of the hardest things that goes with the territory of being a Lead Dad is when you get into the holidays one of the things that’s really big are traditions and memories. When you start diving into it you realize how quickly your kids are growing up. They’re 6 and 2 but you realize it’s not going got be very long before he’s 10 and she’s 6. It’s weird when you realize the kids are growing faster. We looked at videos of his first Christmas. He was born in November. We say, how did we get here? It really made me appreciate this Christmas and I pray for Christmases to come when I can be this hands on and present as I was this year.

Any lessons learned?

I talk about the packed schedule. Prior to this year it meant me being gone. Even if I wasn’t physically gone, I was mentally or emotionally gone. I wasn’t present. The huge takeaway is who you’re doing it with. I did learn a hard lesson on Christmas day – don’t fly a drone in the wind. Stephanie’s parents gave me a remote control drone. While they were making breakfast, I took it outside. I cranked it up. The wind cranked up. It got out of range. And I never saw it again. I got in my car and drove around for it. I used my GPS to try to track the wind. It got further and further away and then it disappeared over the treetops. My father-in-law learned, don’t buy Skip a toy.