The last episode of Your Next Business Bestie went live in October 2025. Six weeks later, I had a baby. By Christmas, we’d gone from a family of three to a family of five.
So, yeah. There’s a little catching up to do.
The podcast is back, and I’m opening season three with a solo episode about the year that changed my family, my business, and the way I move through both.
Three kids. Three very different chapters.
I never planned to be a mom. I was going to be the aunt who went on adventures and brought home cool shit.
Now I’m raising a baby, a third grader, and a high school senior. Some days I’m helping with math, figuring out college applications, and making formula within the same hour.
My business has had to change along with my family. I work from the couch. I close my laptop to read with Ollie. I pick work back up after bedtime. I’m grateful for that flexibility, and I’m also exhausted.
Both are true.
In this episode, I talk about what that adjustment has looked like, including my complicated relationship with maternity leave, client commitments, and figuring out where my own needs fit.
Something I’m learning to celebrate
When I moved to Colorado in 2018, I brought $76,000 in credit card debt from a business I’d built with my ex.
As of August, the last of it is paid off.
I still have complicated feelings about that chapter. There’s shame, relief, pride, and financial scarcity that didn’t magically disappear with the final payment. But I’m learning to let myself acknowledge what it took to get here.
My business coach, Diana Davis, introduced me to the idea of celebrating myself years ago. At the time, it felt uncomfortable and a little ridiculous. Now I understand why she kept encouraging it.
It’s easy to finish something hard and immediately turn to the next responsibility. I do it constantly. This time, I’m trying to pause.
Coming back with more stories to share
We’re also planning a move back to Maine in 2027, which brings its own feelings. I share why returning initially felt like failure, and the words from a friend that helped me see it differently.
There’s a lot happening in this new chapter, and I’m excited to bring those conversations back to the podcast.
You’ll hear from business owners about the experiences that shaped them, along with solo episodes as I figure things out myself. New episodes every other week-ish, because life.
Listen to “A Baby, a Teenager, and $76,000” below, or watch the episode on YouTube.
And before you move on to the next thing: what’s something you deserve to celebrate? I’d love to hear it.
Email me at jenn@jennsway.com.
