Holly left banking, built a daycare, and now runs her own EA business — all while homeschooling three kids. Here’s how she did it.
What led to the shift
“When we got married, I became a teller at a large bank. I loved the work. When my son was born, it got harder. He wound up in daycare a day and a half every week. Didn't love that.”
(*Pausing for a moment of collective relatability. One of the biggest reasons we see people leave their jobs is they love the work — but juggling daycare, especially when illness hits, can be so hard. In my opinion, it’s not the illness itself, it’s what the illness represents — the start of a long road where unpredictability becomes part of parenting. Kids’ health, schedules, emotions — it all starts to affect how we think about showing up for work. Let’s continue.)
“When we found out we were expecting another little one AND my husband was returning to school for his second degree, we knew something needed to change. I stepped away from the bank - without another job lined up.”
What came next
Holly took a leap — and trusted that she could figure it out. She thought about what kind of work would be a better fit for her growing family, and in the short term, leaned into her caregiving strengths.
“I had an interview for a nanny job on Monday and started on Tuesday.”
That was a great fit during pregnancy. And after her daughter was born and they moved, she took her experience one step further.
“After she was born, we moved houses and I began an in-home daycare. That was a great fit for a long time. I was able to be home and raise the kids while still helping provide for our family. And it was great for the kids too.”
But as the kids got older — and as many families navigating school transitions know — the needs shifted again.
“Once my kids got to be school-aged, we knew we wanted to homeschool. It got harder and harder to prioritize my kids' education as well as all the daycare things.”
How she found something new
Rather than search for the “perfect” job title, Holly leaned into relationships and kept her ears open.
“A friend of mine knew I wanted to get out of daycare, and she knew she needed help with some admin things of her business. She said, ‘Welllll... do you want to give this a try?’ I said yes. And it opened a whole new world to me.”
“I had no idea that my options for work while homeschooling would be anything other than daycare or medical transcription. I called myself a ‘personal assistant’ (because that was the term my friend had used initially), but found what I actually liked and was good at was being an Executive Assistant.”
And what started with one opportunity turned into something steady and sustainable.
“Now, I'm in a place where I'm balancing about five clients, working 27ish hours a week, and homeschooling my three kids. It has been just wonderful.”
Challenges she’s faced along the way
Like most Both& stories, Holly’s shifts weren’t seamless. There were growing pains, dry spells, and moments of doubt. Here’s what she shared:
“Both daycare and being an EA are ‘self-employed.’ Not always having new clients to replace the funds when families or clients leave is stressful. Finding the right clients — knowing if they're right during the interviews — is tough. Wanting to help everyone but finding the boundaries can get grey. Taxes are terrible to figure out. My husband gets stressed during the ‘dry’ seasons which makes an already hard time even harder emotionally for us all. Finding ways to prioritize my own children while maintaining care for clients — both daycare and business owners — is always a struggle.”
What she wishes she’d known earlier
This is one of our favorite questions to ask in the Both& series — because sometimes, a small piece of advice earlier on could’ve saved a whole lot of stress. For Holly, it was this:
“I wish I would have known how to interview clients or families better to make sure I was getting a good fit for myself and my family.”
Resources that helped along the way
We ask every parent in this series what resources have supported them — whether they’re formal tools, informal community, or personal systems. Here’s what helped Holly most:
“I was part of a Facebook group of in-home daycare providers. That was a huge help and encouragement during my time in daycare. Now, I use Asana to keep myself (and my clients) on track. I'm also part of an online community for Christian business owners which refreshes not just my ‘business’ self, but my whole self.”
Advice for others navigating a similar shift
We’re big believers that no one figures this stuff out alone — and Holly agrees. Her advice?
“Don't do it alone. Find people who will encourage you and mentor you — paid or unpaid. Share your story. People will rally to support you. Don't be afraid to ask questions!”
Both& Takeaway
Every parent we speak to has a core message they carry with them. For Holly, it’s about recognizing when something no longer fits — and trusting that a new chapter might be just around the corner.
“What worked for me for years no longer is the best fit. Transitions can be tough (and can be smooth!), but when you know it's time, go for it. There are always people to help you along the way.”
.jpg)
.jpeg)
