Each parent walks his or her own path. Each entrepreneur is on a unique journey. And thus no two self-employed workparents, or parent-entrepreneurs, have identical experiences. Even if you and your next-door neighbor are both in the same field, both freelancing, and both have ten-year-olds, you’ll still make different choices, lead your families in different ways, and feel differently about your work.

On the flip side, all workparent entrepreneurs face some important commonalities. Raising kids while working outside of a standard employer/paycheck job inherently comes with certain realities, pressures, and, yes, upsides also. Whether you’re an entrepreneur thinking about expanding your family or a parent mulling over going out on your own, it’s a smart idea to know precisely what those are—to know what you’re getting into. Why drive with a blindfold on when you could have a nice clear view of the road up ahead?

In this chapter, you’ll get that real-deal view. You’ll hear the important truths on entrepreneurial workparenting straight from the source: from a diverse group of moms and dads who are there, and who will tell us what they wish they had known earlier on. After hearing their best, unvarnished advice, you’ll have the chance to ask yourself some challenging questions—ones that will help you improve your entrepreneurial plans and confidence.

TRUTH:  There’s never a perfect time to become a workparent entrepreneur.

You’ll have to decide if and when to make the move—without praise or permission.

In prior chapters, we’ve confronted the fact that there’s no ideal or “correct” time to expand your family, take on more at work, or move jobs, and the same holds true here. If you’re looking for the Golden Window of Opportunity to become a working-parent entrepreneur, you’re going to be looking for a long time. Carefully weigh the pros and cons, and then make your own call. And be confident in your choice, because you don’t need, and probably won’t get, a lot of encouragement.

“Although I was working for a well-known company and already had a successful client practice, I wanted to start my own firm. But with three little kids, I was always too busy. I finally came to the realization that, just like with my decision to have children, there was never going to be a perfect time when everything eased up and became less constrictive and the stars aligned. I had to draw the line in the sand and make the leap.”

—Adrianne, financial adviser, mother of three

“I started this company with my husband when I was twenty-five and we were dating. A lot of people told me that was a terrible idea. Seven years later we had our first child, and I spent a big chunk of my thirties pregnant and taking care of my boys when they were infants and toddlers, all while growing this business. I got a lot of unsolicited advice on that, too, mostly from people who hadn’t been through the same situation firsthand. People will throw a lot of comments at you, but the right way to go is in trusting your instincts.”

—Jessica, videogame company founder and CEO, mother of three

TRUTH:  Your business model matters.

It’s not just about having that marketable skill or great idea. You need a revenue plan—one that takes parenting into account.

As basic as it sounds: know how you’ll make money, and don’t assume that because you’re self-employed, your situation will be workparent-friendly. Be honest with yourself about how much time you want with the kids, and carefully manage your income stream and cost structures to let you do so.

“I love this work, but the very nature of it is that if you’re not sitting across from a client, you’re not earning money. Cutting back your hours to spend more time at home means cutting back your income. So I’ve always worked five days a week, and half-days on Saturdays, and then do my admin and catch-up in the evenings. That’s a stress. Looking back, I wish I had thought a bit more about other business lines, or been a little more entrepreneurial in my thinking. Last year I took on a partner as a way to create another source of income, and that’s worked well.”

—Kerry-Lee, speech pathologist, mother of two

“Thank God for social media. With that, blogging and doing online videos—clients started coming to me. That meant I could focus my time on the creative work I actually wanted to be doing and got paid for, instead of on business development. If you’re a parent, and want to start a new venture, don’t lead from the question, ‘What am I good at?’ Ask yourself, ‘Who’s hiring me?’ ”

—Lorri, interior designer, mother of two

“I’ve fluctuated between business models based in part on my son’s needs. When he was born I was working as a private chef, but then I started a meal-delivery business that I ran out of my home when he was little. He would be in his car seat as I drove all around town, delivering meals. Now he’s in school, and it feels a little easier—I have the mental space to think about next steps, and the new business I want to build.”

—Gretchen, chef and entrepreneur, mother of one

“Singing brings me the most joy, but singing jobs aren’t always the most lucrative. It’s not that getting rich is so important, but I do want to give my kids half the life my parents gave me. My husband suggested I try out real estate, and I went into it kicking and screaming. Now I’m one of the top producers in the state. He has a ‘portfolio career’ also: he runs a barbershop, and is an inventor, and does real estate videography. Earning money in multiple ways gives us security. And because some of them are passive ways, we still get good time with the kids.”

—Aundi, singer, real estate agent, and entrepreneur, mother of two

TRUTH:  Systems and infrastructure are essential.

Without them, you’ll spend a lot more time away from the kids.

Being your own boss can bring tremendous freedom, flexibility, and focus on big-picture issues. It also brings responsibility for handling all the underlying operations: IT, tax reporting … all the infrastructure you may have taken for granted when working for someone else or inside a larger organization. Unless you’re realistic, creative, and disciplined about those demands, they can become overwhelming.

“Getting good systems in place, collecting and really organizing all the information you and your team need—that’s not a nicety. When you’re organized, you’re efficient. When you’re efficient, you can get good work done even when, like a lot of parents, you’re exhausted. If I can call up important information in two seconds rather than fifteen minutes, that’s time I’ve just gotten back to spend with my girls. Learn how to really work on your phone as much as you can, too, so that you can get things done on the go, and are less boxed in.”

—Brian, real estate agent, father of two

“When I started this company, I was young, single, and worked ninety hours a week. Work consumed me, and that was OK. When I had my first child, I jumped right back in—I was the CEO, and it was all I knew. But my willingness to spend every single minute working changed, and I didn’t want to work my family into a hole. Fortunately, we had already spent eighteen months taking this company to the next level: getting a functional website up and running, our automated booking system in place, the back-end-payments stuff sorted out. Without those things, being a parent and entrepreneur would have been very hard. You don’t want to be in the thick of it, dealing with those business nuts and bolts, when you’ve got a three-month-old.”

—Lindsay, childcare agency founder, mother of two

TRUTH:  “Watch the pennies.”

As a working-parent entrepreneur, you’ll want to redouble your attentions on costs and spending.

When you work for a bigger organization, the budget may be tight, but it’s still the company’s money, not yours. When you work for yourself, that distinction usually melts away: your personal and work finances can become inextricably linked. That means taking an extrathoughtful approach, both to spending money and to saving it.

“Be on your game and watch those pennies, because nobody else is going to do it for you. I was going over a courier’s bill today and saw a $500 error. There are many small businesses—and busy parents—that don’t catch things like that because they’re consumed with putting money in the register. It’s easy to focus on the business operations but ignore your accountant, particularly when it sounds like he or she is speaking Latin! But it pays to watch the small stuff, and be aware of your financial infrastructure. Two years ago I finally looked at the interest charges on my floor samples, and noticed they were upwards of x thousand a month. Naturally my immediate thought was: How great it would be to have that money for other things—to grow my business, for the kids? It took two years, but now I own every appliance on display.”

—Vito, home-appliance store owner, father of three

“It’s worth it to me to pay people to help with the real-estate work—to do a lot of the running around with clients. Early on I would never have given a commission away to another agent, but I realized that some part of a deal is better than none. Go ahead and pay for help, because letting go of that money can help you make more, and let you take better care of the kids.”

—Aundi, singer, real estate agent, and entrepreneur, mother of two

TRUTH:  Grow at the right pace.

And be deliberate and decisive as to what that is.

The whole “he or she started a company and sold it two years later for zillions” story is compelling. Who doesn’t want that kind of quick success, or cash? As a parent, though, you may find rapid growth working against you, leading to excess time away from home, and to strain or burnout. Set your growth intentions, and stick to them.

“A big reason running this company works for us is that we’ve never been sucked into the trap of ‘you’re not a unicorn, therefore you’re useless’ thinking, or made it our goal to sit on a yacht. We’ve grown at a nice steady percentage each year. When the boys were little we alternated taking four-day weeks, and spending that extra time at home. We’ve been in business for twenty years now, and through some up and very down cycles. I think what’s worked for our family reality has actually made this business stronger and more sustainable.”

—Jessica, videogame company founder and CEO, mother of three

TRUTH:  Family-friendly benefits aren’t exclusive to big companies.

You may be able to (re)create some of them on your own.

That corporate backup care plan, the lactation room, the working-parents network—they’re all great perks. But those perks don’t have to be career-deciding if you can find or build similar supports at an entrepreneurial company or working for yourself.

“This is a startup, based overseas, and I’m the first local employee here—so in charge of everything, including benefits. At first I had a mental barrier about that. I’m not an HR expert, and I had worked for bigger companies before where all that stuff is set up for you. I felt like I didn’t know what I was doing—but putting the working-parent programs I wanted and needed in place wasn’t nearly as hard as I thought. For backup care, I found an on-demand nanny service with a low annual subscription and reasonable per-day fees. I pitched that to the founders and they approved—why wouldn’t they? Now if one of my kids has a fever at 11:00 p.m., I can book a next-morning sitter through their app. That’s taken away a lot of anxiety and pressure, and it was a good lesson: in a startup, don’t expect or ask for parenting support—offer to make things happen.”

—Laura, chief marketing officer, mother of two

TRUTH:  “Flexibility” may take on a new and different meaning, require an all-new approach, or prove elusive.

In fact, you may have to work even more.

Entrepreneurship is not—repeat, not—the Land of Milk and Honey when it comes to time- and stress-management. When you’re the boss, you’re accountable, and when you’re accountable, you typically have to put in a lot of sweat equity. Yes, there may be an upside, but think through the specifics of how an entrepreneurial career would affect you, and your family situation.

“Flexibility used to mean being in the office a certain number of days per week. Now, it’s about working on the run. While I’m in the car waiting for the kids to come out of school, I’ll be on the phone trying to coordinate furniture deliveries. And work goes in waves: there are times I’m hustling like crazy toward a big deadline, and then a lull after. It’s that ebb and flow that makes this work so well and lets me spend concentrated time with the kids.”

—Lorri, interior designer, mother of two

“I’m much busier than I was before, but I see these first few months as an investment period. When you start your own firm, you recommit yourself to your clients in a big way for sticking with you. You have to overdeliver.”

—Adrianne, financial adviser, mother of three

“I have days when I’d love to ‘punch in and punch out’ and get more time with the kids, but I can’t. The big-retailer albatross looms over me every day. Running a mom-and-pop operation comes home with you, too. There’s a lot of pressure to stay relevant.”

—Vito, home-appliance store owner, father of three

TRUTH:  Good news! You get to set the boundaries.

Bad news: that may be very hard to do.

At a bigger organization, or when you’re working for someone else, the “on” and “off” switches are more clearly marked. Now they may be hazier, dynamic, or harder to find, and you’ll have to set them without guidance, precedent, or anyone else’s express approval.

“We try to live one life, not two, which is why we wanted our own firm to begin with. And we’ve consolidated our lives in many ways: our apartment, office, and son’s school are all within a few blocks of each other, which both saves time and gives us a sense of place. Naturally, there’s a lot of connection and bleed-through between home and work.

At the same time, we find it’s healthy to have some separation … we don’t always want to talk things out while we’re in the office, or bring work home with us, because our son is smart and he knows when we’re stressed out, and there’s risk of stressing him out too. We try to leave work issues at the door.”

—Lyn, architect, father of one

“Being a freelancer sounds great, but your entire life is self-guided. There’s no boss. The deadline might be three months away. There’s nothing on your calendar but ‘work.’

When Daddy can’t go to a dance recital because I’m in rehearsals in another city, it’s easy for the kids to understand. But when I need to draw boundaries when I’m home, and around, and there isn’t that visible boss, it’s harder.”

—Eric, stage director, father of two

“Since Day One, I’ve incorporated my children into my work as much as possible. I kept a porta-crib next to my desk. I brought my daughter to the court building with me when she was three weeks old. In the elevator other lawyers peered at the baby sling I was wearing over my gowns and asked, ‘What’s in there?’ I even appeared in front of judges wearing the sling to argue my cases.

My kids are teenagers now, and there’s plenty they can do around the office. I just brought my fifteen-year-old with me to an international conference, and she was the only kid there. She learned a ton from that trip, recorded my presentation on her ‘fancy’ phone and I think the other attorneys found it refreshing.”

—Véronique, law firm founder, mother of four

TRUTH:  Taking time off may be tough.

Or it might carry some very real consequences.

It’s hard to be “off” when you’re the one bottom-line accountable or there’s no paid leave, but you can try taking different kinds of breaks than the ones you’re used to.

“When you’re not an employee, you have all the flexibility you want. You could take years of parental leave, or one minute, and get paid nothing or a lot. The sky’s the limit, which can sometimes make things a little scary, but always exciting.”

—Brian, real estate agent, father of two

“When my first child was born, I decided to take four months’ leave—and lost many of my clients. This is relationship- and trust-based work, and it took six full months to build the practice back up. So when I had my daughter, I didn’t take any leave. The stress of reestablishing myself outweighed the stress of bringing the baby to work along with me. I arranged my appointments so I could spend time with her in between.”

—Kerry-Lee, speech pathologist, mother of two

TRUTH:  Entrepreneurship and parenting can mirror each other.

… both practically and emotionally.

Both are all-consuming, particularly at the start.

“Our first child was this office. At the beginning, it needed us like a baby would: all the time. Now it’s a little more independent.”

—Lyn, architect, father of one

“A startup is sort of like an infant: it’s fragile. You always have anxiety that something’s going wrong. Even if the baby’s asleep, you’re worrying. It’s hard to explain that feeling unless you’ve been there.”

—Eduardo, online retail company cofounder, father of one

TRUTH:  You’ll need your family and Village to help raise this child, too.

Be realistic about the support you need and creative in how you get it.

The more help you can get, the better. Look back to the 8-C method we covered in chapter 9, and use the same approach here, thinking out-of-the-box but systematically about who can lend a hand.

“There’s the clinical work, and then everything that goes into running the practice: the office, billing, scheduling. We have a terrific staff, and my sister—we founded the practice together, and she’s a working mom also—and I brought our dad in as unofficial CFO. He’s helped get the financial part together, and train our team.”

—Elizabeth, physician, mother of three

“We sell wholesale to natural-food stores, but most of our sales are direct-to-consumer through a market in the city. The margins are better there—and it’s also where my brother and his wife live. He’s a teacher, so he’s off for the summer, when we’re busiest. If someone calls out sick, he’s always willing to pitch in. We brought our business to our family.”

—Lindsey, farmer, mother of two

TRUTH:  Working for yourself gives you the power to create a new and better Workparent Template.

In forging your own path, you get to be part of the Solution.

“One of the reasons I wanted to start a company was that I couldn’t find models for having a kick-ass career and being a present, engaged parent. All I saw were trade-offs. So I decided to build it myself.”

—Jessica, videogame company founder and CEO, mother of three

“Everyone in the office knows my son. I bring him in all the time. In my old job, that would have been impossible.

I was only the second person to take parental leave here, but we make it mandatory. We want to make sure there’s equality, and that people take the time they need with their families.”

—Eduardo, online retail company cofounder, father of one