Skip Cherryholmes: Month 3 Of Lead Dad Life

This is part three of our year-long series examining one man’s Lead Dad journey.

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 month three of Skip’s Lead Dad story.

Welcome to Episode 3 of Lead Dad Diaries with Skip Cherryholmes. This is month three for him. We had started counting in weeks but like with kids, it gets confusing as they add up in age, so we’re pivoting to months. In addition to our five questions, Skip also reflected on the lasting magic of his family trip to Disney and what music a musician like him listens to. (Spoiler alert: it’s not his own songs!) You can hear those answers and more on the video version of our chat. Now on to our regular questions.

Month 3 of Lead Dad Life

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

I’ve really put some purpose behind my reflection. One thing I talked about on the last episode that’s rung more truly is the reset since the last vacation. Changing careers, changing lifestyles has come with a massive set of changes. You start getting tunnel vision and focusing on one thing or the other. I think we knew that when we spontaneously decided to up and go to Florida. It got us out of the rut of some habits we were starting to form. It’s been full of wins and more on a professional level. I’m coming out of my career, and I’ve had months of trying to line things up. A lot prior to this has been scatter brained. When I stepped back, it all made so much more sense. All the pieces started to slide together. Things are clicking.

Another thing that correlates with that is once we got back, I was looking at some of the photos from the vacation, and I said I should be in a lot better physical shape than I am. I started getting up a lot earlier and hitting the gym every weekday and giving myself the weekends off. My physical and mental shape has gotten better. Because of all of that I’m able to compartmentalize work and home a lot easier. I know where I can do better, and I know where things are making sense. It’s spilling over to spending more time with my son and doing things with him and his sister. My wife Steph and I have had some time just for us.

If you’d have asked me three months ago, if where I’m at right now makes as much sense as it does, I’d say no. I thought it would take me at least until winter to see that I could do it.

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

The worst part goes hand and hand with the best part. When it came to my career and work, in the months from the time I made the decision to get off the road to the time it came to fruition, I spent a lot of time trying to take what I did know and apply it to a lot of different areas. I probably put in 150 applications. I’ve never seen it as an obstacle until now, but I don’t have a college degree. I know I have the capability, but I don’t have all of the credentials. Somehow, after we got back from vacation and things started to fit together a lot better, all of a sudden a whole lot of responses started to come back to me. Now all these positions are coming to me. My schedule is full. The hard part with that is for the last month my workload has been massive. I’m trying to create those boundaries where I’m allowing time for my family. I’m working just as much if not more than when I was trying to get away from all of that. I’ve caught it early on enough to where I can shape my business around the exact boundaries I wanted in the first place. It’s sorting itself out. But there have been a lot of weeks of deadlines and trying to impress all these people – I have a hard time saying no. I see it as an opportunity to provide. But as I said in the last episode, your children don’t need for a whole lot if they have you.

What’s your best Lead Dad moment been?

I’ve been able to spend a lot more time with my son, Aiden. Adeline is two, and she’s pretty low maintenance. She plays with her toys, and you interact with her. Aiden is very detailed – you have to be all in 100 percent focused. It has to go the way he has it in his head. It’s a wild ride. His imagination is just exploding. I want him to have that liberty. He’ll find ways to make it work when he gets older. On Independence Day, he was very attentive in asking questions as to why it’s so important. I knew I couldn’t give him a passive answer. I felt proud as a dad passing on important pieces of our history to the next generation. It filled my heart to be his dad.

What’s been your most challenging Lead Dad moment?

This has been interesting. The whole Disney vacation has been part of Adeline’s 2nd birthday. And now she’s officially in the terrible twos. Two-year-olds have a lot they’re not happy about and a lot they have to say. You have to put a lot of energy into what is worth fighting over and what you need to let go. Aiden is five – he sees his sister getting away with a lot of things he can’t get away with. The hardest part is running that balance between the two and the five-year-old. She’s not going to understand certain things, and it’s not a pass. Just because we’re being stricter with him it’s not because we love him less or are harder on him. She’s picked up talking so much faster than he has. I know that’s common. She’s a lot more verbal than he was. Just because we don’t handle her the same way it doesn’t mean we’re not doing things for him. I’ll purposely take him out after her bedtime, so he feels he has a special privilege.

Any lessons learned?

Definitely a lot of lessons learned. Mirroring what I said last time, your family doesn’t want for a lot if they have you. But you have to have you to give them. I talked about my mental and my physical state. Even in the worst times I had to get some motivation from them to push myself forward. It looks different for everyone, but it’s important for all of us Lead Dads to be attentive to whatever gives you that reset to push through the day or to be ready to take on whatever. That’s what you need to invest in so you’re there for your family.