Skip Cherryholmes: Month 10 Of Lead Dad Life

Welcome to Episode 10 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 10 of Lead Dad Life

Welcome to Month 10 of Lead Dad Diaries. It was a big one for Skip and his family. He finally got to take his kids on a cruise where he was playing with his band Sideline. When they got back home to North Carolina, Skip got his first, unexpected Lead Dad weekend with the kids. It was a learning experience. It went great. But it got him reflecting on his new role in life.

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

I’ve done cruises for 20 years. This trip I got to have my family with me. I’d always thought, How cool would it be to take the kids? It played out as I thought it would. The cruise with our kids was a bucket list thing. Getting together with the guys in Sideline was a good thing. I have no desire to go back on the road and gig and gig. My brother is in a band, and he went to Australia for two months. I have no desire to do that. It’s fun to get together and jam a little music. My son was out there signing the lyrics. He knows all the songs.

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

Maybe leaving the ship! We softened the blow a bit. We got off the ship and went over to Disney World for two to three days. There wasn’t an agenda. We didn’t feel like going home so we didn’t. Inevitably, we had to go back home and feed our fish and collect all our mail and come back to the crappy cold weather. I had a different experience here in this last month. Right after we got back, my mother-in-law’s mother-in-law had been in poor health. My wife took off and went to help. It was a new experience for me. It was my first weekend with just me and the kids for consecutive overnights. I’ve done overnights. But this was a solid weekend from Friday night to Monday morning with just me and the kids. It was a different experience. It definitely gave me that sense of Lead Dadness. I’m usually the first person at church. I open the doors at 7am. I had to get them dressed and get them over there. They usually don’t come until 9am. It was a good experience. I had some support. I reached out to some of the parents of the kids at the church.

What’s your best Lead Dad moment been?

I think it’s a mix of it all. When it comes to the cruise definitely felt that satisfaction of hey, I’m here, with my kids and my family. One of my biggest things is to show other families that this kind of stuff is possible if you put your mind to it. Most of it is mindset. It would have been a blast if it was just my wife and me, but it was great. I think it’s worth encouraging. On the cruise, Stephanie and I had to miss out on some of the things that other families were doing. But I was more fulfilled doing it with my family. We dressed up for dinner every night. It was an event. It gave me that sense of pride – this is one of the perks of owning my own schedule. This shows where that paid out. Then with my wife going to Alabama and me having the kids for the weekend it was both peace and humility all wrapped into one. Here was the nitty gritty of being a Lead Dad.

What’s been your most challenging Lead Dad moment?

The thing that’s been the most challenging are the distractions. Trying to keep that day to day motivation, to check yourself every day. We’ve had a lot of illness. My daughter had a double ear infection. All the traveling does have repercussions. You as a father have to show up. It doesn’t matter how I’m feeling today. I have to compartmentalize it. It’s harder to do it in the cold weather. You still have to push to show up and shout out for your kids. I’m hitting the most consecutive number of days in this new capacity of life. It’s not that I’m doing this for now until something changes. It’s this is what I’m doing. Creating that mindset of endurance is the challenge.

Any lessons learned?

One of the cool things of working with The Company of Dads is to sift through all this dad material. You had this dad with this career in aerospace and he had to make a decision for his family. When you look at stories like that it’s motivating. When you want to just go somewhere and scream into a pillow, when you’re just done, those moments are going to come. You need to get up in the morning and check yourself. When you’re around your kids, they don’t need that. They need you. That’s been a real big one.