Skip Cherryholmes: Month 6 Of Lead Dad Life

Welcome to Episode 6 of Lead Dad Diaries with Skip Cherryholmes.

This is part six 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 6 of Lead Dad Life

Welcome to Month 6 of the Lead Dad Diaries with Skip Cherryholmes.

We’re almost halfway through, and neither of us can believe it. Skip wore a Star Wars shirt; Paul was not as well dressed. Before we got to the 5 questions, we talked music, movie scores, and the power of music in cinema. And somehow it led to laugh tracks, shows kids like and the redeeming features of kid TV.

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

Coming out of August and out of the summer, it was the wrap up of real craziness. September was the most domestic I’ve ever felt since coming off of the road and owning the Lead Dad position. The weeks were pretty similar. I was able to be very hands on with Aidan for school and shaping that routine. The way the weather changed was really nice.

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

We had a month at home. It was real even keel. I felt everyone was ready for things to open up again. I think this is a good thing. But in a lot of ways, it was showing that we need to be more spontaneous. That’s more from the day-to-day standpoint.

I did have a personal issue – with the house fire. That was kind of comical. But I had inhaled a bit more smoke than I thought I had. My lungs were hurting a bit more. I was having a lot of trouble breathing. Being a singer, I sing at church on Sundays. When you sing professionally there is professional technique you have to sing with. The technique is designed to save your voice. When my lungs were not at the capacity they should be, my ignorant self just tried to push through. That overextended my vocal cords. I couldn’t get through a sentence without hurting. I couldn’t do a lot of things. I went on two and half a weeks of vocal rest. I kept my talking to a minimum, and I didn’t sing. I definitely saw the benefit from it. I did a performance in Virginia, and I was able to sing with no pain or no strain.

What’s your best Lead Dad moment been?

I got to take the time and create the time to do really normal things that I put a lot of value on when it comes to my kids. Like playing Legos with Aidan and not rushing around because I had a time frame with the kids. You can take moments like that for granted and miss them when they don’t want to play Legos anymore. Or cooking. I smoked a beef brisket. It gave me time to chill out. When I can feel settled, it’s valuable. To actually feel moments of peace and acknowledge them and say this is amazing. And take the time with the kids and have the consistency to be at home and do what we’re doing. Riding bikes and getting ice cream. I do feel that especially as they get older that I’ve taken this time and didn’t buzz through everything. Taking time where it’s appreciated and then appreciating the time I’ve been given.

I was working outside in the yard, and I got Aidan out there and he said the coolest thing: “I want to be like Dad and do more things like Dad does.” It means he’s paying attention. Sometimes as dads you feel like your main role is to interject discipline, break up fights or provide. To hear your son say dad can do things, that was heavy for me. Then going back to think about what that conversation would have looked like had I been on the road. It wouldn’t have come up. He never witnessed my work when I was on the road. And if it came up it would have been a FaceTime conversation.

What’s been your most challenging Lead Dad moment?

The hardest thing with Adeline has been the sleep. The most challenging Lead Dad moment was also a harsh realization. You have the first one with all of these expectations. You think you have a grip on things but then you learn that’s not the case. I’ve heard these stories of parents who say he just woke up to eat and went right back to sleep. It was amazing how different things look from before you had your first child and all the things you had figured out and now all the compromises you’re willing to make to accomplish a simple goal. It relaxes with the second child. She got so excited. She lay down on the floor as if to say I’m not going to get into my bed. We left here there. There was no way we were going to move her. We never would have done that w Aidan. He had to be in his bed.

Any lessons learned?

Change is inevitable, but that doesn’t mean it’s a bad thing.

You’re going to stand on your toes. I realized that the thing that I’ve done to put myself back at home was at a time when they’re still so much development to do with the kids. I’m learning a lot in this process and things are constantly changing. You can’t let that discourage you. Just because you don’t have a grip on that change doesn’t mean you’re failing. Then your son or daughter will come to you and tell you that he really wants to be like you. Then things aren’t that crazy. My son is very social and very well spoken. … when you have the opportunity to have those peaceful moments – they may not come very frequently, or they may come in quickly – don’t push through them. Absorb them. They may last an hour, or a day or only 5 minutes. Recognize them and acknowledge that you may not know when the next time they’ll come. They are your refreshing points. You need to acknowledge them or else it’s just grind, grind, grind.