Skip Cherryholmes: Week 3 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.

Week 3 Of Lead Dad Life

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

The flexibility. The big questions is, Can I do this? You jump off the ship and wonder can I swim? By and large I feel like I can. The best part overall is I’ve had the opportunity to be super hands on with both of my kids in a way that is almost brand new. As long as I get something figured out [workwise], I’m going to be present. I take my computer and sit on the deck. I can interact with them when I’m doing what I’m doing. What’s going on is the whole reason I made these changes.

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

I’m still navigating some of the day to day. It’s the rhythm you find yourself in when you inject yourself into a new life. My wife and I have had to dance around for a long time. In the past it’s put an immense amount of pressure on our life. I’m adjusting to some of that, relaxing a little more. Hey it’s brand new. I’ve had a few moments where I say, This is different. I may not have realized it before – I had my 3,4,5 days at home in these previous weeks and then breaking away and traveling was a reprieve from the home stuff. That anticipation isn’t looming. I’m going to wake up and do this again tomorrow. Maybe some of that adjustment is still settling in. The best way to handle it is to embrace it.

What’s your best Lead Dad moment been?

My little girl is coming on 2. She hates bedtime. One night she’s crying. We put her pajamas on. My son who is 5 and a half asks if she wants to come and play in his room before bedtime. They’re talking. She calms down. He’s got her in his bed. He’s embracing her and just patting her head. Wow, this was really strong stuff. The fact for me that on a Sunday night I could have been halfway across the country and miss it. The idea that there’s them and there’s me. I see in this first month for it to be even bigger.

What’s been your most challenging Lead Dad moment?

Bed time. [Laughs.] Both of my kids cannot stand bedtime. I have to really work to keep my patience in check in certain circumstances. I’m still adjusting to this not being so pressurized. Running the business and being in the band was making life kind of miserable for me.

There is something that’s a little different. I see it developing daily. My son gets mental hang-ups. I really have to stop myself and say he will not get through this hump if you’re putting insane pressure on him. That’s a lot longer lasting effect than what you’re working on. Let him have a break. Be open to that. Don’t put all this pressure you have on yourself on him.

Any lessons learned?

The lesson I’ve learned – and it started with what planted the seed in my mind to go this route – was your children don’t need a lot if they have you. You can provide what you provide. It starts with how much of you that they have. I’ve seen in just this past month a vast difference in the serenity of my home because of how much more of me they have. It’s spoken out of humility, of how much of me they didn’t have before. There’s contentment in the solidity of the home.