Skip Cherryholmes: Month 2 Of Lead Dad Life

This is part two 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 the start of Skip’s new Lead Dad story.

Month 2 of Lead Dad Life

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

The best part has been the realization that I’m taking this step. We packed the whole family up and took a short vacation down to Disney world. It’s been so prominent because this has been a period of so much adjustment. … It’s been very mentally laborious – from the moment I made the decision to start the process, every aspect has been absorbing my energy. My wife and I had an anniversary at the end of May. We decided we’d rather stall for a little bit and do something as a family – to take the whole family away and cut loose for a little bit. That’s exactly what we did. That’s what I needed. I needed to be a little kid for a while and be with my kids. I needed the whole relief factor. We did two days at the resort, one day at the park, a day off and then another day at the park. The day off was when we said I feel inspired now, motivated now. It was time to move forward. I knew it was the right decision to make.

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

There hasn’t been a whole lot of bad. Different challenges have come along – a lot of them steeped in the work stuff. I’m developing a structure to my marketing business to create something I can build on. While I have a lot of experience in some of those areas, we’re starting from square one and building up. Plus, there’s a process of phasing out all the music stuff – which is already so exhausting. It’s those final pieces you have to put on the shelf. There’s a withdrawal from things that aren’t happening because you’ve been doing it for so long. Not a whole lot of bad, just some moments when I’m really fried. I’ve really had to take my time and be patient with myself on a lot of things. It’s a new concept for me. I have time free when it comes to the rest of the world – that’s both exciting and a little bit scary.

What’s your best Lead Dad moment been?

We went to Disney World. That was a great trip. It was a great experience for the whole family. Dads know you feel the defeats more than the successes. But you feel the successes more deeply when they happen. One of my best Lead Dad moments was at the end of May. My church had a father daughter dance. It was really sweet, like a ball. My little girl was just all about me. I’m always all about her. She was all about dad. We danced and played games. We were dancing and she fell asleep when we were dancing. Just that overwhelming wash that I was that comfort for her, and she was gripped on to me. I was literally born to be a dad. I have a lot of questions marks with all these changes I’ve made, but that was proof to me that I’ve made the right call. In years past that would be a phone call or FaceTime from mom. Or I’m going to take her because other girls will be there. Or I can’t take her because it’s a dad thing. This is why I got off the road to do all this stuff.

It takes a different shape when it comes to my son. He’s all about learning and the knowledge but also where those boundaries are. He’s wanting to see where his limits are. I understand that’s the process kids go through. We went grocery shopping and he brought it in from the car. He picked it up and put it where it should go. I’d made a breakthrough. I see he has the desire to do it. I can also see he has the desire to push it. I have the opportunity to see it. When you stop to recognize the wins, they feel so great.

What’s been your most challenging Lead Dad moment?

It’s understanding that this household has for years operated on a rhythm of me being here infrequently. A lot of things have been structured around me not being a part of it. I’m learning to work myself into the process because I’ve just always been gone. I’ve always considered myself to be a very present father even when I’ve been gone. But there are still things I’m learning about my son’s personality. My nature is to automatically want to fix things, to be the hero, to take care of anything that wants to be taken care of. When you haven’t been the one whose been there, you have to figure out how you’re going to fit in. It’s been a challenge with navigating that. Part of my response has been if I’m still developing in this area, I need to overcompensate in the area of spending more time with him or doing more activities with him. When it comes to dad wants to work, I don’t want to continuously shut him down in certain pockets of the day. I need to communicate there are different boundaries that he’s not used to. Adeline is not used to that. Now that I’m home, I have certain boundaries I have to set. Trying to communicate that with him while also not wanting to shut him down. Realizing there’s a certain amount of his life that I have to work myself into. But every day I wake up with the purpose that I have to be attentive in this area, or patient in this area or not overbearing in these areas.

Any lessons learned?

It’s not smart to do a 16-hour day at the Magic Kingdom with two kids!

On a more serious note: Don’t be afraid to believe in yourself enough to take a bold step if it’s to be with your family. Even the hardest struggles, if it’s founded in the right way, you take the bold steps, the landscape that lies ahead is much bigger. You need to have a family who supports you and believes in you too. I know that I’m supposed to do this. This is the greatest most terrifying, most exciting part of my life and I encourage anyone to take that step if it’s for your family.