• Alexandra Frost is a former teacher who lives in Ohio and has five children.
• During each pregnancy, she faced logistical challenges due to maternity leave rules.
• Self-employment gave her more flexibility, but it blurred the lines between work and parental leave.

I was 38 weeks pregnant when I stopped being able to walk, at age 28, with my first child of five.

I remember the exact moment, standing in a long hallway, where I couldn't race back to my class where 30 high school kids sat waiting for instruction. I grabbed a rolling chair from a nearby classroom and inched my way back from the bathroom, sitting.

I'd developed a painful pelvic bone condition, and I thought for sure I'd be sent home to bed for the rest of my pregnancy.

But that's not what happened next. Instead, I got a call from HR, detailing my options. I could stop working now — since I couldn't walk and all — but that would count as starting maternity leave early. And that would mean two fewer weeks I'd get to spend with my baby.

So I rolled from student to student in that same chair for the next three weeks, until I delivered my baby overdue.

This was the beginning of my abrupt education into the world of maternity leave, and how policies, procedures, and the workplace dictate what's best for you — not your body, your mind, or even your doctor.

Over the decade that followed, I'd go on to have four more babies, work for multiple employers, and experience multiple parental leave policies. Each one shaped the story of my pregnancy, birth, and motherhood in different ways — some that I valued, and some I'd like to forget.

Baby 1: Toughing out the last weeks of pregnancy for a longer leave

Data from around that same time showed a growing trend of moms working right up until birth, a fear I had with my first child — would my water literally break at a student's feet? It's also why, in education, many teachers try to strategically conceive their babies to line up with school breaks.

In 2014, I learned on leave from my first baby that it was the first of many decisions I'd make as a new mom that involved choosing between my own health and well-being or my child's, who benefited from having me home longer after birth. Ultimately, I was glad to have prolonged the start of my maternity leave as long as I could to get the most healing time possible before heading back to work.

Baby 2: Arbitrary leave rules with big impact

Around 18 short months later, I was back in the delivery room in 2016, and navigating leave with another school district. This one had a unique rule that didn't quite make sense to me — if you had banked 12 weeks of sick leave, you could use all 12 for maternity leave, but only six of those could be paid. As a young working mother now with two babies, also married to an educator, this meant going six weeks without pay to get the most time off with my new baby, while trying to pay for our $4,000 hospital bill and double the diapers.

I called HR multiple times to clarify. Clearly, I'd heard wrong that if I had the sick time that I'd saved up, I couldn't use it still for paid time off? Except I hadn't. Their justification was that they had to make sure we had enough "extra" sick time in our bank so that we wouldn't be in a bind if we or our kids got sick. And here I was thinking it was my decision when and how to use my own sick time.

It taught me that the system isn't really built for moms' or babies' needs; it's for the benefit and convenience of the business, corporations, and districts where we work.

Baby 3: Revolving a leave around benefits

My third child arrived within weeks of a job change in 2018. If I had the baby, due ironically on Labor Day, before the start of a new month, I'd have a certain set of leave benefits. If I had the baby after, I'd have a different set, including insurance with a deductible that would reset. The timing was bizarre.

In this birth, I made the decision to be induced early to reap the massive financial and leave benefits I'd accrued at my first job — I'd met my deductible and the birth would be free if the baby came in time. Induction before the body is ready can come with a slew of risks, I found out. It soon turned into a hellish 28-hour labor, with a failed induction that wouldn't progress and I couldn't turn back from.

I learned that I could try to play God and manipulate my circumstances for financial gain and convenience, but that the body and the baby don't follow your best laid plans. In another world, both employers would have had equally great benefits and leave, and the baby could have come when he was ready. I greatly regret how I handled this, and had to work to undo the trauma of this birth that I caused by trying to rush it.

Baby 4: How it was supposed to be

If you have enough babies, eventually, parental leave will go your way. That was the case with my fourth son, in 2021, when I encountered a largely "chill" contact at my employer who was determined to infuse as much flexibility as possible around the company's standard leave practices.

Late in the pregnancy, when my pelvic pain returned, I was able to take up to five regular sick days off consecutively at a time without them counting toward official leave. This meant I could work for a day, take five days, and repeat — which I did, a handful of times — making the end of pregnancy much less stressful and painful.

I learned from this leave that encountering a contact or boss who would allow the policies to stretch as far as possible to benefit the people who need it. Though real nationwide change would be better, this was a step in the right direction.

Baby 5: Self-employment…better, but worse

A few years into parenting four sons, I quit teaching to establish my own writing, content marketing, and strategy business. I was now my own boss — so the policies better be good, right? Turns out, it's not as easy to take leave as a business owner as I thought.

When it was time to have my fifth baby, I had clients on retainers and editors with deadlines. I had a subcontractor who was luckily loyal and helpful who helped me navigate this. But around a month in, even with the help of a few part time, remote assistants, the emails, projects, and missed opportunities were piling up. I tried to walk the line as carefully as possible to avoid missing opportunities for the sake of full-time bonding with my baby. In reality, this meant only five weeks truly off.

From there, the lines blurred between leave and flexible work. I'd sneak in some work at naptime to keep the bank accounts balanced. I'd work as I nursed a fussing toddler during witching hour in the evenings. I worried as a mom of five about the choice to take time off at the expense of our finances. But in the end, I was in control, which felt better.

From this leave, I learned that maybe I didn't need super long leaves; I just needed choice. I didn't regret going back to work "early" when it was my own decision, not being forced on me by an employer or policy.

Do you have a story to share about your career? Contact this editor, Debbie Strong, at dstrong@businessinsider.com.

• My husband and I spent nearly three years traveling the country in a camper van.
• I got pregnant earlier than expected, forcing us to make a decision quickly.
• Letting go of vanlife helped us realize what we actually wanted in our next chapter.

I sat in the bathroom staring at the blue cross sign on the pregnancy test, as expletives leaked out of my mouth in a whisper. Disbelief sat around me like the 4 a.m. dew outside our window.

We always wanted kids. Traveling in a camper van was our "last hurrah" before pivoting toward parenthood. But that wasn't supposed to happen yet.

The shock bubbled away, and excitement found home in my body. I smiled and covered my hand over my mouth.

We don't always get to choose our own timelines. I rushed to my husband, John, to wake him up.

This was our one last adventure before having kids

My husband and I were both busy with the 9-5-and-working-odd-jobs hustle. We lived in a large house that we would someday fill with kids. There was a whole world we wanted to see before we tied ourselves down with the responsibility of child rearing. We chose to say goodbye to the life we were told to settle for in pursuit of a life we wanted to celebrate.

Partially on a whim, mostly on adrenaline, we sold most of our belongings and built a 1996 Chevy Express conversion van into a tiny house.

We wanted to explore the country coast to coast before we took on the role of parents. We also wanted to see what our options were for where we would settle down. Do we want to raise kids in a city? In the middle of nowhere? East coast? West coast? Mountain town? Rural Midwest?

We buckled ourselves into our van with our pups and hit the road to rediscover ourselves without the chains of our previous life and to find where we'd like to replace our anchor.

From April 2017 to April 2019, we discovered the magnificent, hidden corners of almost every state. We camped in humid Florida, snowy Vermont, busy California, and sleepy Wyoming.

Every pocket we investigated had something remarkable that ignited our excitement and something tricky that made us second-guess a home there. Each area brought us one step closer to our end goal.

Everything shifted overnight

In March 2019, we were back in St. Louis to visit our family. My period had been irregular ever since I had experimented with hormonal birth control, so we could never quite pin down my cycle.

We were planning our next departure, and I took a pregnancy test to prove I was not pregnant, for our own peace of mind.

This wasn't the timeline we had planned, but one thing living in a van had taught us was to find comfort in the unexpected. Flexibility is one of your greatest tools when you travel full-time. You never know what obstacles are going to throw you off course.

Giddy with excitement, John chose to scrap our plans we had laid out for the rest of the year. We now needed to make our most important decision. Where do we want to have this baby?

Life made us decide which path we wanted to take next

Throughout our travels, we found ourselves returning to New Mexico. The warm sun, the dry air, the beautiful winters, and the towering mountains all took our breath away. It was diverse, eclectic, artistic, and inspiring. We joked it was like Colorado, but without any of the people. We both felt the call and picked up the phone.

Shortly after the positive pregnancy test, we lost the baby. Grief filled the van as we stared at the fork in the road.

We had to decide what we wanted now. Do we want to keep traveling? Or do we want to stay on this new path? The contemplation was minimal. The excitement and the loss had shown us what we wanted. We were ready to grow our family.

Trading in four wheels for four walls

We spent that summer exploring various properties. There was an unexpected grief in the search for a new residence. The van was our home. The road, our driveway. The wild, our backyard. Our identity was tied to the title "vanlifers", which meant we were constantly moving and on the go.

But now we were settling down and growing roots.

We outgrew our lifestyle quicker than we had planned, but we unlocked a new and exciting chapter when we bought an off-grid home on 40 acres. We weren't pumping the brakes on an adventurous life. We were just shifting gears.