How To Raise A Baby And Grow A Business—At The Same Time

There’s an obvious tension in being an entrepreneur and a new parent at the same time. Both require as much attention as you can possibly give.

Last year, my wife and I had a rapidly growing business, a toddler, a high-energy dog, and another baby on the way. It seemed like growing the business would just have to wait.

Or maybe not.

To find some inspiration and advice, I asked three successful entrepreneurs about their experiences raising babies and growing businesses—at the same time.

Here’s what they told me.

When Cassie’s son was born in December 2019, she had two jobs.

She was working a consulting business that helped pay the family’s bills, and she had just bought out her partner at Wild Rye, essentially moonlighting as an entrepreneur.

Then the pandemic hit.

With no maternity leave and no childcare in the very early days, Cassie was working the equivalent of three jobs at once. She described that period as so painful that she barely remembers it, lost in a strange fog of exhaustion and stress. It was a combination of forces that seemed determined to smother her resilience.

She kept going.

Wild Rye’s sales started rising, and Cassie can remember wearing her baby in a carrier while packing up orders with her husband and sister-in-law. The first year was a patchwork of childcare via parents, a part-time nanny, and co-parenting. Work happened in the slivers of time in between.

Cassie described her early experience as a new mother and entrepreneur as “scrappy,” less about rigid schedules and more about using every free minute to push forward however she could.

Today, Wild Rye has about a dozen people on staff, and Cassie’s work and family life are in much better balance. To contrast the challenges Cassie experienced in the early days, she promotes a culture of flexibility that prioritizes personal time, family time, and exercise. If you get your work done, go outside.

Cassie didn’t say this on our call, but it sounds like her approach to entrepreneurship and parenting is mostly about prioritizing mental health. Being the first one in the office and the last one to leave isn’t the example she wants to set as a leader. Being the best version of yourself is.

For her part, Cassie makes sure she always does drop-offs for her son’s school, she blocks off exercise time on her calendar every week, Thursday night “ladies bike rides” is sacrosanct, and she’ll step away from work and towards her family (and the outdoors) if she needs a quick recharge.

Chris’s first-born arrived in 2016, when ADVNC Lacrosse was already a few years old. In true entrepreneur fashion, he remembers thinking about his business while he was in the delivery room.

His thought was: It was no longer ok if the business didn’t succeed. It had to.

The first few years brought a lot of challenges, many of which were rooted in scheduling. Chris’s wife was still working full-time, and the lacrosse business requires a lot of travel for camps and tournaments. This was a difficult time, when the underlying growth of the business was harder to focus on.

Then they had a second child.

As time progressed, a parenting and business-owner philosophy took shape for Chris. He framed life as three concentric circles: work, family, and personal.

One circle can’t get bigger unless another circle gets smaller. And as every new parent knows, the personal life circle is the one that has to shrink.

Chris reverse engineers the sizing of his concentric circles each week. Even though family is the top priority and work comes second, he actually prioritizes personal life first when planning the week.

Surfing specifically and exercise more broadly are Chris’s top personal priorities, so he starts there when scheduling. When the surf is good, it goes on the calendar, the box gets checked, and the rest of his time can be split between work and family. If the surf isn’t good, Chris will exercise during the workday, so family time isn’t compromised.

As his kids have gotten older and the business has matured, Chris maintains his concentric circle mindset, but he has also leaned into delegating responsibility at work to make more room for family and personal life.

Michael’s first company, JuiceBox Games, was about a year old when his first baby was born in 2014.

Having a newborn and a start-up invited a certain type of mindset—there was a lot to prove, which meant that working 10 to 12 hours a day wasn’t really a choice for Michael. It was essential, as was his involvement in every decision.

Michael acknowledges today that he had it all wrong, but his learning experience opened the door for doing things differently with his second start-up, FunCraft.

By then he and his wife had a 2-year-old and a 4-year-old, and time with family had replaced the “all-in” start-up mentality as the essential thing in life. With this revised mindset, the results have been better across the board.

Michael’s approach to parenting and entrepreneurship leans on what I’ll call “casual rules-based systems.” He and his wife trade-off time blocks with the kids so the other can focus on work when need be, and there are other standard procedures that guide the week—who does drop-off, who does pick-up, who’s reading bedtime stories that night. He also puts his phone away when he gets home from work and until the kids go to bed, having adopted the mentality that whatever it is, “it can wait.”

There are also steps Michael takes to ensure that he’s being critically productive at work, which makes more room for being present during family time. He likes to make a clean to-do list each day that focuses on the most important tasks, which ultimately doubles as a mental health exercise. Crossing tasks off the list is not only satisfying, it is also a marker of a successful day. That feeds the positive headspace needed to enjoy the harder job: being a parent.