Sitting down to interview a female business owner on how she balances work and family is a little daunting. There’s the obvious question: Would we even be having this discussion if she were a man? And, how do we not make it sound like a version of the book I Don’t Know How She Does It – part awe and part comedy? Talking with Jackie Roberto, founder and partner of Madison Design, the importance of having these authentic conversations becomes clear. Over a glass of wine (but, of course) at Hotel Covington, Jackie candidly shares how she creates space for herself, her family, and her business. Sometimes it’s rocky; sometimes it’s smooth. But it’s all worth it.

There is no single definition of an entrepreneur or the obstacles they face. As part of our year-long series sponsored by Main Street Ventures, our community chose 12 of the biggest obstacles female-identifying entrepreneurs face, and we found 12 women who spend their days conquering them. Explore the whole series here.

Interview by Judy Zitnik. Photography by Chelsie Walter.

What’s your elevator pitch?

Madison Design creates, evolves, and protects brands. We create brands from scratch; we evolve existing brands to respond to things like changes in the market or changing business strategy, or we protect them. And by that, we mean that when we create touchpoints, like marketing touchpoints that are an extension of the brand, we make sure they are laddering back to the brand strategy and the identity so that they're strategic.

Our topic for this interview is “family.” Tell me a bit about yours.

I have a husband; his name is Phil. We've been married for 22 years. I met him through a mutual friend at DAAP right after college. We have two daughters: One is a junior and one is a sophomore at Walnut Hills.

Since you’re nearing the end of your daughters’ time at home, let’s start there. What advice – regarding family – would you give yourself looking back? What would you today tell yourself starting out?

“Do a better job of taking time for yourself along the way.”

I think when you're raised as a woman, your inclination is to put others in front of yourself. That's sort of the core definition of what it means to be good – at least, in the way that I was raised. So that's what I always thought.

But the dilemma with working and having a family is that there just is not enough time in the day to get everything done. And so, when you put others first and yourself second, the list is never finished enough for you to take time for yourself. And because I'm such a worker kind of person, I never get to that part of my list. I rarely get there. Only if I'm – as my husband says – “squishing down sideways” do I make the time to do it. And in hindsight, I should have made a practice of it. And I didn’t. And so now I'm still trying.

Tell me about how you integrate your family into your business and your business into your family.

When our daughters were born, Phil and I both went to three 10-hour days. There was only one day a week that we needed childcare. And you know, when you think about an eight-hour day: By the time you get up, drive in rush-hour traffic, work until 5 o’clock, drive home in rush-hour traffic, you might as well just work 10 hours. You go in earlier and miss the traffic, stay an hour later and again, miss the traffic, and it's kind of a net-net at the end of the day in terms of time at work and time with family.

It's not easy, but it's doable.

We did that for about four years. And my business partner, Julie – she and I had kids about the same time, and we both ran that schedule. So she worked, I think, Monday, Wednesday, Friday, and I worked Monday, Tuesday, Thursday. The bummer was I saw her a lot less. But it forces you to get efficient and use your time wisely.

What was awesome about it is that Phil and I are both there raising our girls. We both had this connection with them since the minute they were born, and it continues to this day. And so that organic schedule change, just trying to think creatively and step away from it and go, “What do I need? What does the business need? What does the family need, and what does my husband need?”

We’ve evolved it over time, depending on how old the children are and what they're doing. I mean, there's not a ton of flexibility. I don't want to make it sound like we can do whatever we want. It's not that at all. There's a lot of discipline involved. But if you get disciplined and you use your time efficiently, you can hit these marks and you can have these connections that you want in your life with your family. It's not easy, but it's doable.

Is there anything you tried that just really didn't work in terms of setting boundaries?

Oh, yes! How much time do you have? [Laughing.] We've tried lots of things along the way. Number one is probably me expecting everyone in my house to do all the little things I write on their to-do lists!

I think when I overextend myself too much, everybody suffers. So if I have a full work week, and then I have a lot of things in the evening, that can get away from me. And sometimes I can push it too far, and I'll just be exhausted.

So I think it's just a constant cycle of try and fail, try and fail. One of the things that I failed with early on was when I first was hiring childcare, and I was way too accommodating. It took me awhile – and several terrible experiences – to realize that they were working for me, and that I needed to own that and tell them what I needed and what I wanted.

How is family a part of your company’s culture?

We're very family-friendly. And we try to be that way in attitude and in policy to the degree that we can still keep the doors open. So when, for example, Julie and I had kids, we did six weeks and then went right back to work, but we came back part-time. One of our directors is having her first child in a few weeks. She said, “Hey, why don't we use this as an opportunity to rewrite policy to be 12 weeks paid for maternity and paternity and adoption?” And it was challenging, financially and legally, but we worked hard, and we did it.

To be a good creative, you have to have a life. You have to be immersed in life.

If you have to go home to a sick child, you do. We expect you to make up your hours when you can or work from home. We like it when people bring their kids in to visit. But, we still have discipline. Our view is: Let's be really focused and efficient while we are here, so that we can leave and have a life.

Another policy that we have is if you don't use your vacation, you can't roll it over. So it's an impetus to use it; go have a life. Because to be a good creative, you have to have a life. You have to be immersed in life to know how to communicate or to write or to design. You have to be informed in that way to be better at what you do. So we try to make sure that we work really hard, and then we leave. And then you do whatever you want. It's not work hard; play hard. It's work hard, and then have your life in whatever way you define it.

I was once your client. And what really impressed me was the way you communicated boundaries to your time – setting the expectation that you wouldn’t be answering 11 o’clock emails. At first, it surprised me, but as a woman, I really respected your decision. Can you talk about that?

Yeah, that stuff is so intrinsic that I forget to talk about it.

When you're a working mom, especially, but probably when you're a working dad, as well, you’ve got to be present. You have no choice but to be present with a baby, a toddler. I mean, you cannot let a two-year-old walk around by themselves. They'll be dead within an hour. Let's be honest, right?

So they taught me to be present. But that meant that I worked, then I left work, and then I was at home. And I still maintain that, for the most part. There are times when I have to work from home. But if I have to work at home, I'll try to go to a coffee shop or something. I try to keep home as home as much as I possibly can. My husband isn’t like that – he is a big amorphous fluid. But I cannot do that. I need to find stops and starts.

So maybe some of the best advice is: Know yourself. Know your strengths, know your weaknesses, and know your limits, and create a life around that. It's different for every single person. Who you are doesn't change when you become a mother. You just take your own parameters and your own attitude towards life and apply it to motherhood. You don't magically become someone else. So, for me, it was really important to have things delineated and defined: I'm on at work, and now I'm on at home.

I've always joked, “Well, clients never wipe their nose on my legs.

And to this day, I'll go home, and I’ll try hard not to look at my phone or be on email. I'll be back tomorrow morning at 7:30, and I can look at it then. If there’s a big deadline or a hot project happening, I will say to my clients, “Text me because I know that we have this deadline.” But if it's ongoing, and there's not a deadline, I'm upfront about it.

So that's the other thing I've learned is just to communicate clearly. And that can be tricky. Especially early on as a new mother. Being that direct was off-putting to some people sometimes, but I had to do it. Same with helping at school. I would say, “I can volunteer for you on this day at this time; that's all I can do for you,” or, “I can't volunteer, but I can write you a check this year.” Like, here's what I can do, and here's what I can’t.

If we think about family more broadly, how has your business impacted your extended family, and how has your extended family impacted your business?

I am a business owner because my dad is a business owner. My dad is a direct influence on me, a direct inspiration. I pretty much owe all of my success to him for all the ways he’s helped me along the way.

I also owe it to my two business partners, who are like my oldest friends. Julie and I went to DAAP together and met our first day of drawing class freshman year. And then, Jonathan was one of our first hires. And he was working for us while we were both working three 10-hour days, and we were like, “Oh my God, we can't lose this guy. Get him some sweat equity fast.”

So we're all equal partners now. But, those two, I couldn't do all this without them. Because not only do we run the business together, but we're a deep emotional, mental support for one another. They're critical. I couldn't do it without them.

I couldn't do any of this without my husband. He's secure enough and confident enough that he's been fine with all these arrangements along the way. There was never a moment where he said, “I'm the man, and I have to go do that,” ever. I might have married someone else who could have said, “I'm not comfortable with this. I’d rather have you stay at home.”

And I would have been like, “All right.” [Laughs.] Seriously, it's probably what I would have done. This is really hard. The moment you have the baby, you’re like, “Stay home with the baby or work?” Well, staying home looks a lot easier until you realize it's actually harder. It's way harder. You know, I've always joked, “Well, clients never wipe their nose on my legs. They never cry. (Or if they do, they never cry in front of me.)”

Honestly, though, it is way harder to stay at home. I think it is the unsung amazing work for our society. And it has almost always been on women. It's changing slowly. It's a noble and important job. But it is still a thankless job. And you know, we know some stay-at-home dads, and I'm sure they feel the same way.

How do you and your husband split up the emotional labor of caring for a family, with both of you working? And doctors’ appointments and playdates, etc.?

We're pretty shared on emotional labor. He's actually better at it than I am. He's more sensitive. He’s more empathetic. He's more aware than I am. So I rely on him.

When the girls were little, and we both had an equal amount of time at home and at work, we would just split commitments based on whatever fell on that day. But I think that I stepped in and did a little bit more because I wanted to. You still get caught up in like, “Well, if I'm a good mom, that means I'm doing this, this, this and this.” And then after doing that year after year – not that Phil was unwilling to do it, it's just that I took it on – then I was like, “Okay. Help!” If I ask for help he totally dives in. My problem is I just get to the mark quickly because that's how I'm defining myself as being a good mom. And that's what's challenging.

I was happy when they were young, and that we were both raising them equally. We were both really happy about that. We were both forging nontraditional roles, and we were both working against societal norms. Both of us were, not just me. We both wanted to be connected to our kids. And so we both got that. And now at 15 and 17, they’re clearly connected to both of us. So I think we got what we wanted, which is good. So I think it was all worth it.

Throughout this journey, how have you, as an entrepreneur, personally defined success?

I think, for me, it's about experience. Have I spent quality time with my children as they've grown up? Have I forged quality relationships with my business partners? Do I still have a good solid connection with my parents and my family and my friends? Can we travel and have an experience together, whether it's far or near? And, do I have freedom? For me, it's not really about money or all the outward signs of success. It’s not that I'm immune to all that, but it's just about living modestly so that I have enough money to have interesting experiences.

Looking back, are there resources you wish were available to you as a woman starting a business?

Yes. I wish that all these interviews that you're doing now were around when I had babies, because I was desperately searching for advice. And I couldn't find it because it wasn't really there. I think everyone was just suffering in silence, honestly. And not enough people were speaking out. I think now there's plenty, thank goodness. But there just wasn't enough advice. And so we were all just trying to make it work and commiserating with fellow moms over wine. That saved me the entire time. Still does. But the advice just wasn't around, which is kind of unbelievable. It was only 15 years ago.

What are you most proud of about Madison Design?

I have two business partners, and we’re running the business together that’s been around for over 20 years. And some of the most important people on our team have been with us since they graduated from college and now they're all getting married and having children, and it's like, wow, this is deeply rewarding. It's the relationships with them. It's the relationships with clients. And it's the relationships with our vendors that we've had over the years. It's just the people. It's really all about the people.

Tell me about an influential woman in your life.

I have several, and they're all family members. So my grandmother Helen, my great aunt Helen, and my great aunt Alma. And my mom.

So, my great aunt Alma was a nun. She was a music professor at Marian University in Indianapolis, and had traveled the world. She was such a bright mind, an open mind, an open heart, and just very loving. She influenced me because of her independence. Here she was, a Catholic nun, and yet, when I was a teenager in college, I talked to her about all kinds of stuff. And she was in a college environment, and she was very used to talking with young people. So she was inspiring.

And then my great aunt Helen. She was a buyer for Shillito’s. When I was a little kid, she was still working. And she was probably the only woman I knew who was working in a traditional environment. I just found that to be eye-opening. She was just sharp.

And then my grandmother, my dad's mom, was just super creative. She was born ahead of her time. She had an entrepreneurial spirit and an incredibly creative spirit. Of course, she couldn't work because her husband didn’t want her to, but she was just a loving and creative woman.

And of course, my mom. My mom was a stay-at-home mom, but she ran that family. I have four brothers. My dad is super kind and easygoing. Mom was like, “I have expectations of you. What are you doing today?”

We all laugh; we're like, “Oh, Mom's the one that pushed us to become something.”

She went back to work when I was in college. My dad started a business when I was in college. My mom worked with him. So that was pretty inspiring that they worked with one another. They have a wonderful marriage. But health care became a thing, so she went to work at a brokerage firm full-time and worked there until she retired. And what's cool about that is all of my sister-in-laws and I, we all work to some level. And my mom says, “I think I'm more understanding because I worked, too.” When she went back to work, my little brothers were in high school.

So I had all these independent women around me. I guess I just thought, well, that's how you do it. I mean, I grew up in a very conservative environment, and my mom did stay home, so I think in the beginning, I had a lot of head trash around, “Should I stay at home?” But I didn’t, for lots of different reasons. And I'm here now.

There is no single definition of an entrepreneur. Check out our year-long series, "This Is Entrepreneurship." Sponsored by Main Street Ventures.

This Is Entrepreneurship: Jackie Roberto on Family