Skip Cherryholmes: Month 8 Of Lead Dad Life

Welcome to Month 8 of the Lead Dad Diaries. We’ve been following Skip for eight months now as he goes from well-known touring musician to a new career where being a Lead Dad for his wife Stephanie, their son and their daughter, is integral to what he’s doing. Last month we revealed that Skip has joined us as our social media director.

This month we’re talking as the holiday season is ramping up. Thanksgiving is behind us. So is Festivus. Hannukah, Christmas and New Year’s are coming up quick. Skip had a birthday. And we’ve got lots going on for 2024. Where do we start?

How about with a little historical perspective?

“It was around this time a year ago, in the fall of 2022, that I made this decision to go in and start the phase of dialing things back with the band,” Skip recalled before we got into our five questions. “I’m looking back at where I was. I’d made this decision but there was a lot of obvious uncertainty around it.”

A year later and eight months into Lead Dad Diaries, Skip noted this: “I’ve always been a reflective person. I’m always looking to absorb knowledge. It’s a constant thing and not just an exercise to be content with the moment. The Lead Dad Diaries is the closest thing I’ve kept to a journal in a long time.”

So let’s get into reflecting on the past month with our five questions. For the full version, watch on YouTube.

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

It was going to be a month of craziness – I knew that getting into it. I had a pastoral conference at the beginning of the month. Then I had a really busy week to play catchup. Then we celebrated my son’s birthday, then I went down to Disney World for three days, and went home and switched suitcases and then I went to the studio to record three new songs for Sideline. The following week led into Thanksgiving. Then at the end of the month I was ordained a pastor, had my birthday and my parents came to visit. I enjoyed moving and shaking a bit. Going down to Florida was a last-minute decision. We had so much crammed in but said, ‘Let’s just run down there for three days, just go down and have a good time and make some memories and come home.’ I really had a blast. I don’t think it hit me too much until the first week of December that I’d lost out on all the sleep.

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

I came down with the crud. You know how it is with young kids. They catch it. You pass it around and someone always has something going on. The illness that everyone else was kind of dealing with in the back half of November. I managed to keep away from it. I didn’t really catch it or anything until the month was over.

What’s your best Lead Dad moment been?

My son Aidan turned six. It’s hard to believe that six years ago we were at the hospital. Crossing out of 5 into 6, it feels like you’re really on your way. We went to Disney to celebrate. It’s one of the true pleasures – getting together with your kids. You’re not worried about all the development, the structure, everything. We literally jumped into the kiddie pool together. Being able to do that is a very important part of being a parent, of being a kid again. As far as a specific Lead Dad moment, he was so excited to have his sister, who is two and a half, there with him. He wanted to show her all the cool stuff at Disney. He got her ramped up about different stuff. Then on our way home from that trip, just listening to him and hearing that lingering glow about how excited he was and how many times he said thank you for taking him there.

What’s been your most challenging Lead Dad moment?

My parents live in Tennessee, so my son doesn’t get to see them too often. They came out at the end of the month. It was really cool to have my son, myself and my dad all together. But then we got the call that his dad – my grandfather – had passed away while we were all together. I was glad I was my dad in that moment. It was definitely the heaviest moment of the month. It was a full cocktail of emotions. My grandfather was a pastor his whole life. We got the word that he passed after I gave my first sermon, which he had listened to on the internet. Then I got word that he had passed, and I was there with my father and I was there with my son, and it may have made it easier. It was tough but it was beautiful too. I don’t get to see my dad as much as I’d like. So, the fact that of all the places my dad could be, that he was with me was huge for me. That’s real life.

Any lessons learned?

There’s a short-term and a long-term lesson. Life is inevitably going to get crazy. This month was a combination of things you planned and didn’t plan. It stacked up. It was important to have that endurance, to not take on everything at once or until you have to. The sub-lesson there is make sure you give your kids lots of breaks when you’re in the car or it gets unpleasant. The bigger lesson is I had a whole month of insanely exciting, cram-packed beauty. But the event that happened with my grandfather at the end of the month made me very humble. It was because of knowing the legacy he left on this earth. You stack all of that up and look at it. I felt honored to have been part of his legacy. The impact that he left behind. It’s amazing and there’s a huge aspirational component for me.