Skip Cherryholmes: Month 5 Of Lead Dad Life

Welcome to Episode 5 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.

This month, we talk about a house fire, a lost beta fish, a return to a favorite vacation spot, the chance to perform again, and, of course, school.

Month 5 of Lead Dad Life

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

We actually took a week and went to Myrtle Beach, S.C. and went to Ocean Lakes Camping. It’s really, really nice. This is something that I’ve done every year since I got married. They’ve always held a music festival at the campground. My group Sideline would be hired to play on a Saturday or Sunday. We’d get a house and go down the week before. We’d hang out at Ocean Lakes the whole week, then play music and go home.

When we were coming off the road and disbanding, one of the contracts we kept was this one. We thought it would be a really low stress show to play. We’d hang out and then get together at the end of the week and jam. This one was just a lot more fun for me, even with all the changes I’ve made. I’ve got a 2 and 5 year old, and they’re playing really well together. It’s a really great place. I was able to break away and do some work. But then I was able to shut it down and have fun. I thought it would be great to shut it down for the whole week. But then I thought I’m blessed to be able to work this way.

When we got down to Friday, when we were going to play, we played an hour and a half concert and it was slam packed because we’re not playing anymore. This was a very special show. They came from Ohio and Kentucky, Pennsylvania and Ohio – they came all the way down to Myrtle Beach to catch our show.

Before, work was life and life was work. Now, work is work and life is life. When someone asked me previously who’s Skip Cherryholmes, everyone knew I was a touring musician. Now, if I want to be known for something, I want to be known for being a husband and father first.

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

Aside from the house fire…

Even though it was August and you were at the end of the summer, it was a slammed month. We had this vacation planned to Myrtle Beach. I had this wedding I had to sing at and a funeral over there. Aiden was under the weather and then we had to get him ready for school. You go out for almost a week it takes a while to get back to where you were.

What’s your best Lead Dad moment been?

My son got his first bicycle.

We’ve gotten him bikes before and he wouldn’t do it. I don’t know what happen, but I was able to get him a bike and get him excited about riding it. Then I got my bike out and now we’re riding bikes together. Just watching how excited he got. When it came to riding, he’s all focused on it. We go out and ride for a while and then we come back and work on our bikes. When he says daddy do you want to go ride bikes, I say yes let’s go. I can take a quick break. It’s hot so we’re going to ride for 15-20 minutes not an hour. He’s excited and he’s excited to have me be a part of it. He’s wanting to see the more hands-on side of life. That’s really cool that he says, I want dad to be a part of it. I feel that I’m the one who’s fortunate to be his father.

To pair along with that there have been a few moments from the Ocean Lakes/Myrtle Beach thing. I wasn’t sure how everyone else would feel about sharing their vacation with my kids. But they welcomed the whole situation. They played with the kids, watched them at the pool. Sometimes, you can feel as a parent that everything is coming to pieces but then when someone else externally recognizes what’s going on that’s the pinnacle. You feel you don’t have your mess together and then someone recognizes your kid

What’s been your most challenging Lead Dad moment?

Preparing Aidan for school. He started 1st grade. Understanding how your child learns and not how you want him to learn. We’re homeschooling our kids. It was something we talked about before having kids. Steph was homeschooled and I was homeschooled. It’s a huge undertaking to homeschool your kids. One thing you have to understand is not every kid learns the same way. And chances are they don’t learn like you did. We’ve found we have to teach our son in a way that he doesn’t know we’re teaching him. You have to make it fun but also relatable. If we’re doing math that’s one thing. But what if we do math with Mario Cart characters?

For her it’s just about being involved. Give her a coloring book. She counts really well. Even if she’s just a part of it. It gets her accustomed to this idea of school. And two it teaches her before it teaches her.

Any lessons learned?

Watch how much you pack on yourself. In an effort to be more present with my family, I need to be conscious with how much I take on for my sake and theirs. And watch how hot the oil gets on the stove top! And if you’re ever going to take your beta fish over to someone else’s house bring your own water.