Skip Cherryholmes: Month 12 Of Lead Dad Life

Welcome to Episode 12 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 12 of Lead Dad Life

Welcome to Month 12 of Lead Dad Diaries. This is it. We promised to follow Skip for a year on his Lead Dad journey. We did it. And from our end a lot has changed. For one Skip went from being a Dad we liked to a Lead Dad who is running The Company of Dads social media.

For our last episode in this series we wanted to bring in a special guest, his wife Stephanie. Welcome Stephanie. And two other very special guests – their children Aiden and Adeline. We’re also going to mix up our regular five questions and ask them over the full year not just this month. So let’s hear from the Cherryholmes family what this past year has been like.

Note, if you watch one episode, this is the one!

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

Aiden: Playing Minecraft with my Dad. It’s really just about building. I’ve never ever really beaten that game because it’s so much fun building.

Skip: We just build stuff. Buildings, traps, lots of tunnels. Being able to be home more has opened up the options for recreation. My main goal when I got off the road was I wanted to work from home. You think about the amount of time you lose either driving to somewhere or home from somewhere. To be able to clock off and say let’s just cook dinner or let’s play a game or let’s have a dance party. It’s bought me a lot more time with my family.

Stephanie: It was different, definitely, at first. It was nice to have help with the kids. It wasn’t, “He’s home for two or three days and we need to cram everything in.” Weekends were the weird ones. Usually Saturday we wouldn’t have anything going on. Then suddenly we had family day on Saturday so let’s go to the park for the whole day. It was an adjustment getting used to the five-day work week. As a musician he was gone all the time on the weekends. He had shows on Saturdays. It was just nice to have him around. Me personally I watch a lot less Netflix. We’re spending more time together as a family.

What’s been the part of the past year that you didn’t really expect?

Aiden: We got a new umbrella outside. It broke and we replaced it with a new one and I didn’t know.

Skip: It just broke. And the color was different. He did not expect to see a red umbrella where a blue one use to sit.

Adeline: Daddy surprised me.

Skip: What surprised me the most is how it’s not been an easy journey. There have been a lot of obstacles we’ve really had to sort through. But how the rhythm came together. When you think about it, with such a drastic adjustment – a career change, a lifestyle change – one year is not a lot of time. And for things to have fallen together the way that they have – when you hit that one year mark it reaffirms or establishes this is how I can go through life. How am I going to pull this off without some scathing repercussion? I’ve been pleasantly surprised and excited that for the most part things have been very rhythmic and show a lot of promise for this being the future for me and my family.

Stephanie: I’ve been asked a lot by people are you guys driving each other crazy? Are you tired of having him around all the time? Honestly we enjoy spending a lot of tie together. We spend every single day together all the time. We haven’t gotten on each other’s nerves. I didn’t expect to enjoy it as much as I did. Communication is key. We’re really good with open communications with one another. When we first got married, before having kids, it was you do your thing, I do mine. After having Aiden he was gone a lot when Aiden was a baby. It was an adjustment for sure. Whenever he got off the road and something happened I’d say I just need 30 minutes. Let me go take a shower. That kind of communication is key. You need those moments to reset and refresh.

What’s your best Lead Dad moment been over the past year?

Skip: That’s a hard one. It’s hard to sum it up. I could be really cheesy and say my best Lead Dads moment was when I quit my job and got off the road to be with my family! I think just in general, any time we’ve ever done something, being able to have my family with me and when people come who know the whole reasoning of why I got off the road and they see it in action, they see what kind of difference it’s making in our life. It reaffirms that I’m on the right path. It empowers me to take more and bolder steps forward. I think I thrive on whenever someone compliments my family I want to be involved more. There have been a lot of people who have been upset or straight up made that I got off the road. They were diehard fans and didn’t understand the whole reasoning. Now they see what has changed and what has transpired over the past year, it shows that as a lead dad I’m doing what I should do.

Stephanie: It’s just having him around more. As a musician, people see him on stage and think it’s just that 45 minutes. When he was home, he’d be planning for the week ahead. There was so much more he had to do. Family dinners have become a really important thing around here every night. Finding that balance as a family and doing random things.

Skip: Just being here. I’ve been here for most of Aiden’s kindergarten and all of first grade.

Aiden: Disney.

What’s been your most challenging Lead Dad moment over the past year?

Aiden: So, like something very hard?

Skip: One of the biggest challenges throughout and it’s still something I’m trying to figure out is it’s a big adjustment. When I was traveling and playing music and getting ready to go out on tour, I was busy but I wasn’t stationary busy. I was running all over the house. I was a lot more accessible. Now with the current structure of things, the rhythm and understanding that during these business hours I can’t always stop and go do it. We take breaks, but I can’t just do it then. They know dad is on a call and we can’t go in and interrupt him. For me it’s realizing I don’t just have to sit here and pound away at something. I can walk away for a second, even if it’s just having lunch. I get really bad sometimes getting focused on work. I go in, slap together a sandwich and go back to my desk. For me it’s realizing the benefit of working from home and stepping away. For them its understanding dad has hours, he has things he has to do. So, patience on both ends.

Stephanie: I didn’t necessarily notice things right away. It was over time. It was like oh I never watch TV anymore. Or Saturday was usually cleaning day. Now we spend all day Saturday at a park. I realized a couple of months in that these things I normally saved for when he was out of town, I had all these things stack up. I had this list of things I wasn’t getting done any more.

What are the top three lessons you learned over the past 12 months?

Aiden: I’ve been working on my garden that we’ve been putting in.

Skip: For me a lesson slash realization was family first. Always. That looks different for everybody. Whenever you hit a crossroads and you don’t know which direction to go, family first all the way. It has not let me down. There have been a lot of challenges. I think of all the different options I was faced with just over a year ago when I was trying to decide what to do. I don’t think I would have seen the quality of life, and growth and success that I’ve seen otherwise. And that comes down to what’s best for my family.

Stephanie: Putting the family first – getting the kids to understand this is work hours. She gets to the point where she doesn’t understand what work is, sometimes she just needs her Dad. A small break can have a big impact on a small human being.

Paul: Cherryholmes Family, thank you so much. It’s been a wonderful year-long journey. I hope everyone has enjoyed the last year on the Lead Dad Diaries.