GPP: How would your kids describe you in three words?
Ashlyn: I wasn’t sure what my kids might say when I asked them this. You know, as a mom, you’re always trying your best, but mom guilt often makes you second-guess if you’re doing enough. So, it was a sweet surprise when both my kids’ first answers were “loving and sweet.” Aubree followed with caring, and Connor said nice — all words that make my heart so happy to hear. No matter what life has thrown at me over the years, especially during the long stretch of being a single mom, I’ve always tried to make sure my kids come first and get the best parts of me.
GPP: What’s been the biggest difference between parenting a 13-year-old versus a 9-year-old?
Ashlyn: Honestly, the biggest difference between having a teenager and a 9-year-old is more about boy versus girl than their age. Connor is a very mellow, go-with-the-flow kind of kid. His passions are baseball, fishing, and Fortnite. Aubree, on the other hand, is outgoing, wears her heart on her sleeve, and wants to take care of everyone.
I’ve learned how tough third grade can be for girls. It’s so important to remind them often how loved, how special, and how valued they are — that their beauty comes not just from the outside but also from the inside. To let people see Jesus in you and not be rude to others just to fit in. That your worth isn’t defined by your looks. Things I don’t feel like were talked about until middle or high school, even for me — they’re already dealing with it in elementary school.
GPP: What was your first reaction when you found out you were pregnant again, and how did your kids react?
Ashlyn: Finding out that my husband and I were expecting was definitely such an exciting moment! He is already the best (bonus) dad, so I can’t wait to see him with this new little baby. Telling the kids we were pregnant was a moment I will always cherish. We got a box of Krispy Kreme donuts and put a sign inside that said, “Eat up! Mommy doesn’t want to be the only one with a belly,” and they each got big sibling shirts. Aubree was beyond excited — she’s asked Santa for a sibling for a few years now. Connor was also very excited, as he loves babies.
GPP: What are you most excited about this time around?
Ashlyn: I’m most excited about where I am in life this time around. All babies are blessings from God, and I truly believe that. But praying for a baby with your spouse and dreaming of holding a little one, then finding out it’s real, makes it even more special. My husband has been so supportive, especially since I struggle with hyperemesis gravidarum (extreme vomiting) during pregnancy. He’s stepped up for the older kids and given me the time to focus on getting through the toughest stages. I’m also just glad to be older now, more settled in life. I can soak it all in even more than I did with the first two, with the confidence that comes from having done this before.
GPP: What’s something motherhood has taught you about yourself?
Ashlyn: It’s taught me about my incredible strength. To realize that failure isn’t an option when you have little ones depending on you for everything. During some of the toughest storms, they watch how you handle things and still need all their needs met. When you want to give up and can’t – because of the example it sets — I’m proud that my kids saw me walk across the stage and earn my master’s degree as a single mom. I hope they’ll look back someday and say, “My mom did it — she did it for us, no matter what the obstacles.”
GPP: What’s one piece of advice you’d give moms raising kids at different stages?
Ashlyn: Remember that none of it lasts forever — the good, the bad, or the ugly. Also, don’t let anyone tell you that taking too many photos or videos is a bad thing — one day, those moments are all you’ll have to look back on. The little years fly by so quickly.
GPP: How do you refill your cup when life feels overwhelming?
Ashlyn: I try to add small things just for me. Getting overwhelmed is part of being a mom, but it’s essential to remember that you deserve grace, just like your kids. So much of our job is caring for others. For me, I set aside a few minutes every morning to enjoy my coffee and breathe before the day starts. I also take an extra 20 minutes during my morning routine to do my makeup — it’s a simple way to do something just for me.
Rapid Fire Questions
- Cozy Cabin or Beachside Bungalow? Both!
- Coffee or Tea? Coffee
- Vacation or Staycation? Vacation
- High heels or Cowboy Boots? Cowboy Boots
- One word to describe yourself. Determined
Ashlyn Webster-Sidner and her husband Brandin got married in April 2025. Brandin and Ashlyn’s brother co-own McDavid Meat Processing, and Ashlyn has been able to work from home for the past six years as a property manager for a family business.
Ashlyn is a wonderful mother to Connor (12) and Aubree (9), and Brandin is the best bonus dad. Together, they are expecting a little girl in May.
Connor plays year-round baseball, and the whole family enjoys being at the ball field – Brandin is an assistant coach, Ashlyn keeps score, and Aubree is there to socialize and cheer on her brother. When they aren’t at the ball field, they love to be out on the boat or at the racetrack. They also really enjoy trips to Disney World throughout the year.
