Skip Cherryholmes: Month 11 Of Lead Dad Life

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 11 of Lead Dad Life

Welcome to Month 11 of Lead Dad Diaries. We’re in the penultimate month of following Skip’s shift from full-time touring musician to Lead Dad who also happens to be The Company of Dads’ social media guru. “I was always gone, touring,” he said. “I don’t miss that part. I don’t long for it. I have been thinking about things in terms of, ‘This is a new me’. It’s been a year of insane growth. I love that.”

A couple of highlights for all Lead Dads. Skip talks about how and when to ask for help. It’s not an easy ask for many of us and how he unpacks it is fascinating. He also talks about a lesson his son learned in patience – which is one every parent can learn from. He ends with a poignant story of looking back on a more challenging time in their life. So let’s dive in.

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

Last month has had a lot of great parts. Stephanie’s cousin got married at the beginning of the month. I was able to do something at their reception dinner [as a pastor]. It was the Super Bowl – I tried out all different flavors of wings. I make mine in the air fryer, which makes me feel a bit better. I went through 35 or 40 wings during the Super Bowl.

Sideline actually released a song. We hadn’t released a song in two years. Last time in studio was 2020. That was exciting to release a new song. No one was expecting it. Two weeks before it dropped, I did a teaser on our social media page, and it escalated from there. It’s exciting when people dig into your stuff. They listened to the new song, and it sent them down the rabbit hole. The song is written from the perspective of a father whose son went off to fight in the Civil War. It was a big turning point for me. Not having been in the studio, all the things I’ve been through, I wondered, will it come across the same way? It satisfied me to that level of nothing’s really changed as far as my approach. I’ve still got it!

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

There really hasn’t been a bad part of the month. Things have been busy. I’ve been very busy, keeping up with all the irons I’ve got in the fire. The rhythm that the family has found in the household has been really strong. My wife has been an amazing support through all these changes. One of the hardest discussions ever we had was when I was back touring. Aidan was 1 or 2, and I was touring really heavily. She had to tell me it was more disruptive when I was home than when I wasn’t home. I came in like a tornado and then I went out like a tornado. I’m the one working my way back into her life and my kids lives. It’s been very satisfying in that respect. There’s not really anything about it that’s been bad.

What’s your best Lead Dad moment been?

Going back to the beginning of February and my local Chick-fil-a decided to host a Daddy-Daughter Dinner event, which was so much fun. There have been many things like that that have gone on in years past that I’ve missed out on. It was a Monday night and I did it up. I did full black tie. She had this big puffy white dress. Everything’s a princess with her. The Chick-fil-a cow came around. It was awesome to see all of these dads come out with their daughters. Some had dressed up. Some had clearly come right from work and said hop in the truck, let’s go. It was a beaming moment for me.

Along the same lines, I’m working Monday to Friday on a lot of things. But I also have Sunday for church. Most weeks Saturday is my only day off and most often Saturday gets slammed full of catchup. If I have a Saturday when I need to catch up on it turns the 5-day week into a 14-day work week. I try really hard to keep that at bay. Saturdays are for me and my family. This specific Saturday morning I was very deliberate in not scheduling anything. Stephanie was sleeping in. I said let’s go into the kitchen and make French toast. Adeline is very deliberate in the kitchen. Aiden said he was going to make a sign for the restaurant. We turned it into a big old event. We’re having a great morning. Stephanie comes in. we finished eating. And he goes into the bedroom and digs into this big bin of costumes. He wants to turn it into a Disney character brunch. This Mike Wysocki costume. We start snapping pictures. Then Adeline puts a princess dress on, and said I’m Cinderella, come take a picture with me. That was a supreme Lead Dad moment. Maybe that’s why I didn’t feel like there was a worse part of the month? Any potential worse part of the month was overriden by the high point of being a Lead Dad.

What’s been your most challenging Lead Dad moment?

It’s been a very busy month. I’ve put a lot of thought into this during the month. What we call a Lead Dad here at The Company of Dads we can call it a noble position or a humbling position. But at times it can be a very busy position. If I’m going to bother to do something it has to be the absolute best I can do. I don’t give myself a whole lot of grace in areas where I think I can improve. It’s very much an, ‘I’ve got to do this thing’.

One thing I’m not good at doing, but I learned a really good lesson on it, is asking for help. I don’t think a lot of Lead Dads see that as an option. I have a really hard time with asking for help. I had to really own the fact in some areas this past month with the schedule I’ve had to keep, I’ve had a project that has tied up a lot of my time. I’ve had to say I need some help. It’s come in different ways. The only person holding me back from achieving that help is me – me not asking for it. I had to prioritize first what I needed help with. My priority needs to be here, where my kids want me to show up. Anything else I need to make sure I’m filtering through that. If you don’t show up then you’re not being there Lead Dad-wise. It doesn’t have to be that way. If you can extend the ask of help to different areas of your surroundings, most likely you’ll get through that short period of time and move on forward. It doesn’t have to be some big admittance that I need help for all eternity. That’s a hard and prideful walk to take. When you need it, ask for it.

Any lessons learned?

That was my lesson learned. I’ll give you my son’s hard lesson learned. He’s been playing this came, Paper Mario, for quite a while. He usually needs a healthy dose of help from mom and dad. We’ll get him to the point of defeating his foe and then hand the controller back to him. He gets down to the end of the game. He has to defeat him a second time. He accidentally deleted the entire profile. He went to the main menu and deleted everything by accident. He brought it up one time. He said I deleted my profile. I said, it’s a lesson learned. Don’t be in such a hurry.

I want to share one other little nugget here. It was something my wife put out there. We went to Disney and there’s an attraction called Enchanted Tales with Belle. They assign all these kids roles in the Beauty and the Beast story and then you act it out with Belle. Back in 2016 we went to the Magic Kingdom without any kids. Back then we had been trying for two and a half years very unsuccessfully to have kids. It was hard for my wife to see all of these kids. It wasn’t for another 8 or 9 months that she got pregnant. Last month we were able to go back to that same event with two kids and see the full circle effect of the struggle we went through and seeing how things had changed. There’s always a reason and there’s always hope. Things you’re going through in the moment may not look the same down the road. The important thing is to keep your chin up and keep going. It was a really special thing for me.