Skip Cherryholmes: Month 4 Of Lead Dad Life

Welcome to Episode 4 of Lead Dad Diaries with Skip Cherryholmes. It was the late summer edition. There was fun. There was sun (and heat). And we continue to talk about Skip’s music – turns out when he and his wife were dating she opted to listen to his album’s debut over going into Disney World. He also reveals his wife’s favorite song – a racy ballad!

This is part four 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 4 of Lead Dad Life

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

This past month has been what I’d call the most normal month yet. No vacations, no business wrap up, no surgeries. This was the first month since 2020 when I had a month where I worked during the week and hung out on the weekends and just existed. I loved it for how normal it was and for just being home. We’ve done some different things but all community based. We went to the library – I couldn’t tell you the last time I went to the library before this last month. While some people might not think this is a big deal, I got a huge kick out of it. I helped a friend from our church rebuild a fence on a property. Before I would have been traveling on the weekends. It’s been a great way to get more involved in the community.

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

Outside of the heat, which can provide a bunch of challenges, I’m not sure where I’d pinpoint a worst part because there was not a whole lot of bad that went on. Because it’s been so hot we’ve spent a lot of time indoors and when you do that, things can get a little antsy. My daughter is in the terrible twos. She’s had her two-year molars coming in and then the other day she slipped and fell and busted her lip. She was just in this mood of I’m not doing anything. With my son, his mind is very curious. He’s so focused on details. That’s a good thing, but it’s definitely something to be aware of. When he’s paying attention he’s paying attention to everything his mother and I do. It’s a full-time job tending to his curiosity. I’ve had to establish – you’re growing up very fast but you’re still five. All in all it’s not been a bad month. I’m seeing the positivity in a lot of the changes I’ve made.

What’s your best Lead Dad moment been?

I’m seeing it so much more from my children’s perspective. I had this opportunity to play some music one weekend. I think I left on Friday morning. I played Friday evening, slept in a motel, played Saturday afternoon and then drove home in the wee hours of Sunday. My kids are getting used to me being home. They missed me. It was great to see that I’m having an impact from being home as much.

From the perspective of where these changes are having the impact on me, it’s maintaining the recognition when they come. If I have moments where there’s something I know I would have missed out on in a prior life, I recognize that I had the opportunity to have that event. It reaffirms the decisions I’ve made. It’s a big thing to jump off into the abyss.

As someone who performed as long as I had, I never lost my passion for performing and creating music as an artist. So to return to the stage, as I probably will from time to time, it’s very satisfactory on a lot of levels. It reaffirms that I still have it. It helps me get it out of my system. And it’s great when I still see the appreciation and people will come out because I’m not as available as I once was. But then on the other side I’m thinking I got a full weekend of music in and now I’m going to go home and be with my family. What a blessing.

What’s been your most challenging Lead Dad moment?

The most challenging moments for me have been that I’ve landed myself into so many different things. I wanted to try it all. I never knew I was capable of doing so many other things. But I have to be very deliberate about shutting it off. One of the defining moments of me coming off the road was my son trying to talk to me and me not being able to focus on him. I want this family to succeed. If I’m going to make such a drastic change and not know exactly what it looks like, I have to make sure it succeeds and that there’s not a bump in the road. I’m finding the buffet is wide open and I’m trying my hand at so many different things. But there’s only so many hours in the day or the week.

My bigger challenge is I do have to be deliberate about shutting off when I shut off. I don’t need to make everything utilitarian. It’s in my nature to find a reason for why something is worth more or bigger than what it is. Here’s a simple answer. My son wants me to read him a book. I sit down and read him a book. I’m trying to use that book to teach him how to read or teach him vowel sounds. He doesn’t want a lesson. He wants a story before bedtime. It’s enjoying times with dad. I have to keep myself in check on those levels. I’ve been given the opportunity to have a huge impact on my family, but everything doesn’t have to be some deeper level.

Any lessons learned?

The most challenging moments are the lessons I’m learning. If I’m recognizing and learning those lessons I’ll accomplish and I’ll succeed. The lesson I’m learning in the most normal month of my time off is the train can get away from me very easily if I allow it. I have to remember that I don’t have to be certain things I have been in the past. I just need to be attentive to myself and make sure I’m compartmentalizing in the correct ways. I’m coming off a habit of I may only have these two evenings with my son this week so everything I do with him or my wife or my daughter has to have a deeper purpose. I need to cram as much into this one book as I can. Same thing where I’m on the road – if I’m gone for 5 days I’m working solid for 5 days. I don’t have to live that way anymore. I have the right and the ability to shut it off and read a book on my own. Spend time with my wife. Check in with the community. See people I want to see.