There’s a strange, powerful energy that settles in a family home around 9 p.m. The dishes are done. The house is finally quiet. Kids are tucked into bed after books, water, and last-minute questions. The lights dim. The weight of another long day working, parenting, and adulting feels heavy.

But for some of us, this is where the real work begins.

We are the parents who build after bedtime.

Not because we have to, but because something inside us won’t let us not build. We crave creating something of our own. A product. A brand. A book. An idea. A tiny seed of a business that might, one day, become something meaningful for our family.

This is our life with Captain PillowBelly. And it’s probably yours too, in some form.

This is an essay for the dreamers who stay up later than they should. The exhausted parents who squeeze in 30, 45, 60 minutes of focused creative work between real life. The ones who are chasing legacy, even while packing school lunches. The ones who know that “I’ll do it later” eventually becomes “I wish I had tried.”

The reality of parenting + entrepreneurship

The dream of running a business feels simple on paper. Freedom. Flexibility. Autonomy.

But the reality—especially for parents—looks very different:

• Work a full day job to pay the bills

• Parent intensely from 5 p.m. to 9 p.m.

• Steal 30–60 minutes from your own sleep to inch your project forward

We’ve done this every night for months now building the Captain PillowBelly children’s book series. Some nights we crash. Some nights we win. Most nights, it feels like nothing happens at all.

That’s the secret no one tells you: building a side business with kids isn’t sexy.

It’s slow. Uncertain. And deeply unglamorous.

And yet—there’s something magical about taking a blank page and slowly filling it. About designing characters, writing stories, or building community one follower at a time. About creating something that belongs to your family, not your boss.

You are not alone: the growing rise of parent-preneurs

We are not outliers.

According to recent studies from SCORE and the Family Business Alliance, nearly 42% of small business owners are parents with children under 18. The pandemic accelerated the trend, with thousands of parents realizing they wanted to control their schedule, work remotely, or pass something down to their children.

But this doesn’t mean it’s easy:

• Nearly 65% of all small businesses fail within 5 years

• Among family-owned businesses, only 30% survive into the second generation

• Less than 3% reach the fourth generation

And yet thousands of families are still doing it. Why?

Because even if the chances are low, the upside of ownership—freedom, legacy, independence—is so high, that it’s worth trying.

In many ways, building after bedtime is the ultimate parent hustle.

How parents get it done (hint: it’s not by having more time)

The biggest myth is that parent entrepreneurs are superhuman. They’re not.

The difference is structure and persistence. The most successful family side hustles don’t happen with huge uninterrupted blocks of time. They happen in micro-doses:

• 10 minutes planning tomorrow’s tasks on the train

• 30 minutes designing a product before bed

• 45 minutes of focused writing early Saturday morning before anyone wakes up

You don’t find time. You make it.

You become ruthless about protecting creative windows.

For us, running Captain PillowBelly looks like:

• Monday nights: book editing

• Tuesday mornings: social media scheduling

• Saturday afternoons: website updates

• Daily: 30-60 minutes working on the next idea (whatever that might be)

Consistency beats intensity. We rarely have perfect 3-hour work sessions. But we show up for 30-60 minutes almost every day. And that adds up.

The unfair advantage no one had before: AI as the parent-preneur’s assistant

If you are building a family business in 2025, you have an advantage that no generation of parents had before: Artificial Intelligence.

This is not about “robots taking over jobs.” It’s about AI as your silent co-founder who works 24/7, never complains, and saves you hours you literally don’t have.

Here’s how we actively use AI every day for Captain PillowBelly:

• Writing support: brainstorming book plots, drafting marketing copy

• Image creation: helping refine illustration ideas

• Market research: identifying trends in children’s publishing

• Social media: batching and optimizing posts

• Email drafting: customer service templates, newsletter ideas

AI doesn’t remove our creativity; it removes the friction to execute.

It allows us to go from “idea” to “draft” in minutes instead of hours.

This is why, even in our small window of 30–60 minutes a day, we’ve been able to build dozens of story drafts, design visuals, and prepare content for eventual publishing.

We cannot overstate this: if you are parenting + building + tired, AI is your superpower.

The messy middle: balancing family, work, and your project

Nobody talks enough about this. The messy middle is where most parent-preneurs give up.

The messy middle looks like:

• Staring at your laptop at 10 p.m. while your partner goes to bed

• Missing a self-imposed deadline because your child was sick all week

• Worrying no one cares about your brand or product

• Comparing yourself to influencer founders with perfect launch days

We’ve felt it all. Still do. This is normal.

But here’s the mindset shift:

The struggle is the work.

The discomfort is the growth.

You can’t “schedule” entrepreneurial momentum. Some weeks you’ll feel invincible. Some weeks you’ll publish nothing and beat yourself up. That’s part of the journey.

The only thing that works is:

1 Lowering the emotional stakes per day. Each day is just 1% progress.

2 Measuring small wins. One finished page, one new subscriber, one new follower.

3 Not quitting when it feels slow.

The people who win in side business building aren’t the ones with the best product. They are the ones who just didn’t quit.

How we stay motivated with Captain PillowBelly

What keeps us going building after bedtime?

• The thought of holding the first printed book in our hands

• The idea of creating something our kids will be proud of

• The dream of building a community of global, adventure-loving families

• The small joy of publishing a new Instagram reel and watching 5 people smile

• Knowing that even a modest $500–$1000/month revenue stream changes our family’s freedom

Our mantra has become: “Small actions, every day, for years.”

Not: “How can we go viral this month?”

But: “How can we build something meaningful over 3 years?”

Advice to fellow parents building side hustles

If you’re nodding along because you’re doing the same—or thinking about starting—here’s the truth we’ve learned:

• You will never feel fully ready. Start anyway.

• You will never have enough time. Work with what you have.

• You will question yourself at least once a week. That’s normal.

• You will build skills you never thought you could.

• You will inspire your kids just by showing up.

You don’t have to launch big.

You don’t have to “go all in.”

You just have to start.

A side hustle doesn’t have to be life-changing to be life-affirming.

Final thoughts: Your kids are watching (and that’s the legacy)

The money matters. The freedom matters.

But the real reason most parents stick with building side businesses?

Our kids are watching.

They see us persevere. They see us try something scary.

They see us do something for ourselves outside of “just being mom or dad.”

They see that you can work a job, take care of family, and still make time for passion.

That’s the lesson we hope to leave them.

That’s the true Captain PillowBelly story: a gentle reminder that adventure exists, even in small stolen moments between the chaos of life.

And we’re still sailing.

Sources:

• SCORE Small Business Statistics 2024

• Family Business Alliance Research 2024

• Pew Research: Parents and Side Hustles (2024)

• Personal experience: The Captain PillowBelly journey