Balancing part-time law and full-time motherhood is no small feat, and attorney and author Kara Kinney Cartwright gets candid about the wins, struggles, and lessons along the way. From returning to work just six weeks postpartum to navigating unpredictable hospital counsel demands during 9/11, Kara shares how she built resilience, found champions for workplace flexibility, and created her own “Cartwright rule” for earning trust. She opens up about parenting with humor, writing her book Just Don’t Be An Assh*le as a parting gift to her sons, and finding healing through her upcoming book on grief after losing her husband. With wit, honesty, and compassion, Kara reveals what it really takes to keep showing up as both lawyer and mom.
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The Truth About Part-Time Law And Full-Time Motherhood With Kara Kinney Cartwright ✨
We are truly blessed by such a rockstar joining us who is not only an incredible attorney and an amazing mom, but also an accomplished author. She has fixated her career on so many important topics and so much wisdom that all of us are truly in for a treat in talking with Kara Kinney Cartwright. I want to welcome you to the show. Thank you so much for taking the time to join us.
Thank you. It’s so nice to be here. I hope I can live up to half of that in this conversation.
From Law School Dreams To Health Law Reality
You already have, and I can’t wait for everyone to know about that. I want to give you the floor. If you would share with us a little bit about your journey as an attorney, adventures in motherhood, and when those two worlds came together.
It’s similar to everybody else’s story. My career has been in health law. In particular, mostly health law publishing. I recall being in law school. I had an internship clerk-type job with a small law firm that did medical malpractice defense. I remember sitting in a room and summarizing depositions with my fellow law clerk, who was a nurse law student. We would say, “Why doesn’t somebody write a book to tell doctors, hospital administrators, and nurses, ‘Don’t do this. These are the things we don’t want to do.’” When I graduated from law school, I had the goal of being an in-house attorney at a healthcare organization, which is a tough thing to do with zero experience.
How did you know that at that point? People don’t even know that it exists.
I was fascinated by the idea that it affects real people’s lives being a health lawyer. Caring for others puts them in a better position to do their jobs well, which results in better care for people. I loved that human element of it. Not to minimize the work that our sisters do in corporate litigation, but I like the idea of real people being involved. I came from a small town. My stepfather was a small-town lawyer. Maybe that appealed to me.
That makes sense.
Unable to get the in-house job that I wanted, I saw a posting for an attorney to edit and write the hospital law manual, which was the book I had dreamed up in my mind. By some miracle, I got that job, and that began my career in legal publishing. I worked in legal publishing for-profit. I ended up working in-house at a hospital for a stint, and then I came back to publishing in a nonprofit context. That’s where I work.
Motherhood And Career: The Corporate Shake-Up
That was such a great journey. At what point did children arrive on the scene?
I was still in for-profit publishing at that time. As is so frequent in that industry, there are a lot of mergers, acquisitions, takeovers, and other things that are happening. There had been enough of a corporate shakeup that I realized that the company never loves you back. You shouldn’t plan your life around your career path. You need to make your life.
The company never loves you back. You really shouldn't plan your life around your career path. Share on XI had my first child while working at that publisher. When I was pregnant with my second, there was another reorganization in my department, and my position was eliminated. I’ve started my job as a hospital in-house counsel, which was the one I originally wanted when I was seven months pregnant. To their credit for hiring me in that situation. That was exciting.
I know you shared this. That was a quick maternity leave.
It was. Since I was hired very late in my pregnancy, I hadn’t accrued enough experience to have FMLA eligibility at that time. After six weeks, I was back in the office. That was tough.
I’ve heard of other women in that situation. It happens. That was your second child, which is a whole different ballgame as well. That ups the ante, especially if you have a demanding career. What was that transition like for you? How did you muscle through? You must have been exhausted. That’s pretty much expected. How did you endure and make your way through that experience?
It was difficult, bearing in mind that I took the job knowing that I was going to have the baby very soon, because those positions come up so rarely. It was a dream transition for me to be able to be in that role. In publishing, we give people the analysis, like, “These are the rules, and these are the laws.” At the end, we say, “You are going to have to figure out this tough problem.” To be the person figuring out the problem was appealing to me, but also a big step up from what I had been doing before in terms of wanting to have that real-world impact. It’s a real hospital.
It’s on call. Especially when you’re in a hospital space, it’s 24/7. You already had 24/7, so maybe it was a good marriage of sorts, but it had to be so hard.
It’s challenging. My position was part-time. I’m glad you mentioned the 24/7, because just like doctors have on-call time, attorneys have on-call time, too. The lesson of that position was that although I was part-time in terms of my hours in the office, it was a full-time background noise, a full-time commute back and forth, and a full-time responsibility for two daycare situations that we had to pay for at that time. Those part-time attorney rules are appealing, but I question whether you can be a part-time professional in that role.
In a hospital setting, especially if you are a problem solver and trying to help people, when they call you, “I’ve already put in my twenty hours,” are you going to say, “Time is up?” We’re not good at that. It’s important.
The 9/11 Impact: Lawyer Life In A Crisis
My son was born in March 2001. 9/11 happened when I was working in the hospital in the DC area. After the attack on the Pentagon, all the hospitals were locked down. You cannot leave. You’re staying until the picture clears up. It becomes apparent who is needed and who is not needed. That made a big impression on me in terms of the challenges that those in-house attorneys face, how hard they work, and how they have to be ready for anything at any time. My role was more in contract review, but being in the GC’s office, there are always other things going on, too.
When that happened, were you at work or at home?
I was at work. My late husband was a federal employee, also. I had to call and say, “I’m not leaving. You have to go get the kids. You have to get out of there and go get them.” Luckily, he didn’t work at the State Department or any sensitive position like that. One of my colleagues’ spouses worked at the State Department, so they were also restricted in what they could do at that time. It’s the curse of living in interesting times or an interesting city.
Navigating that moment had to be quite difficult when you have young children, and that was your role. When you were talking about the part-time job, one of the things that I feel like you have such interesting thoughts on is how to advocate in those moments. As a mom, it was knowing what your needs are professionally because you were in this job that was so exciting and that you had dreamed about, but also advocating for flexibility. That’s something that, at the time when you were working in that environment, was not part of the conversation. I was curious if you could share how that panned out, if you had other role models or women who were part of those conversations to help you find your voice in that. Is that resonating as far as your experience?
Yes. The fact that there was a part-time in-house hospital position seemed, at the time, like a huge breakthrough or a huge get. That was one of the reasons I couldn’t let it pass up despite the fact that I thought I was about to have a baby. I treasure the fact that that was even available at that time. I’ve been working in health for a long time, maybe 30 years. I’ve been full-time in the office. I’ve been full-time remote. I’ve been a freelancer. I’ve been part-time in and part-time out on an as-needed basis.
I’ve done all the things. The only way I was able to do that early on was that I had a champion who was also an attorney and a mother. Her kids are older than mine. She, having more influence in her career and being farther along in her career, had enough faith in me to know that I was not going to let the organization down regardless of what my working arrangement was.
It’s important for attorneys to keep an eye out for one another and to trust in one another. It’s a little different now. In the ‘90s, those opportunities had to be made up out of thin air and fought for. Post-pandemic, people have a little more comfort with remote work than we did at that time. Having benefited from all those different arrangements and sorting out different arrangements that worked for me and my family at different times, it’s important to me at this stage in my career to make sure people I work with also have those opportunities.
It’s such an incredible gift we can give each other. When you’re seen in that way, despite your circumstances, which is a great circumstance, being a parent and trying to be an engaged parent, but knowing that it’s your hard work, you’re not going to let people down. You might need a little flexibility, and how we can support each other, and just honoring that. You’re right. Back then, it was out of thin air, those opportunities. That’s why you had to light up and go take that part-time job. It’s a no-brainer. Now, there is more, but there’s still the need to see each other and to honor how hard this is, quite honestly.
It’s impossible.
How did you navigate through the impossible? Are there any things that you felt like, “That helped me to make it less impossible?” Even with how you organized the day or how you figured out who is supposed to be where so you could find the time to work, was there anything that stands out?
The Cry-Commute: Navigating The Impossible
I wouldn’t necessarily recommend it, but I cried in the car a lot. I had an hour commute each way. I was leaving my six-week-old baby, and I had an hour to get over to the hospital and get my mind and get over whatever I had to get over. The stress of the day to walk out of there, leave it behind, show up, and care for these two little kids, I only had to get my crying done on the trip.
Do what you say you're going to do. Be honest about your bandwidth and capabilities, then deliver. Share on XYou had dedicated cry time. I love this. I was driving in the car with my fourteen-year-old, which we’ll get to later. I was crying. There was an emotional song about his child. I was crying while driving. He looks at me and goes, “Should we pull over?” I’m like, “Why?” He’s like, “I’m not comfortable with you crying and driving.” I’m like, “Moms do this all the time.”
This is our skillset. This is my me time, driving on the beltway and crying in the car.
It’s okay to cry. Especially as lawyer moms, when we are trying to sometimes be a little tougher than maybe the person next to us, like, “We can handle all of this,” a dedicated car cry time might be an excellent thing to promote and honor in our processing.
I hope it’s better for the next group of women coming up and coming through. For me, I felt, having been given this privilege of a flexible work arrangement, that I could not let anybody down on either side of it. It was my choice to go into it, knowing what I was getting into. In our family, we refer to it as the Cartwright rule, which is you do what you say you’re going to do. Be honest about what your bandwidth and capabilities are and what you bring to the situation, and then do it. Do what you say you’re going to do. Keeping those promises creates more opportunities because you earn trust and are able to get the flexibility when you need it.
That’s helpful. There’s a thing that you touched upon that I struggle with in some ways. You’re a phenomenal attorney. You’re so bright. Anyone should be so lucky to have you working with them in whatever capacity. What I heard there, too, which I see in other women and sometimes in myself, is that we enter into those jobs with such gratitude. Sometimes, that’s a super blessing. I love gratitude. It’s one of my favorite qualities, but sometimes, we take on so much out of gratitude that it makes life even a little more difficult.
I’ve made that mistake over time. You have to learn the hard way. The women coming up now will be smarter than we were in the position because maybe there’s more availability of options. To know your worth is a difficult thing and something that has come to me quite late in my career. For folks tuning into this who are still in the thick of it, you need to know what you bring to the table and have confidence in that. If you value it yourself, hopefully, other people will see that and value it, too.
Was there anything in particular that helped you come into that knowledge to know your worth?
Age.
I love it. That’s a guarantee. We all got that going for us.
We will all get there eventually. It took me a long time to realize that not everyone can walk into a situation and size it up the same way that I would. Those years of experience, knowledge, reading, writing, working, and building networks, eventually, you realize, “That worked. It’s working for me.” When you first come in, people know more than you. There’s a stage of your career where you’re learning all the time. You’re trying to learn the next thing, get ahead, and open up that next specialty or that next level of knowledge. Eventually, you come to realize that not everyone has the same background that you do. You bring something special and unique to the table that you’ve earned over time.
That’s such an important thing to remember. Even when you’re suffering and struggling in something, you’re acquiring those tools. We are all suffering for nothing, but seeing that challenge as an opportunity to gain the tools that will eventually create confidence. In sitting with a lot of female attorneys who are moms, there’s a tendency not to see their goodness.
If nothing else, in the conversations I’ve been having with them, it’s to say, “Let’s sit down and talk about how awesome you are and how you’ve achieved so much with such grace.” That’s where age helps. Even if you could have come into that earlier and the knowing, that might have been nice, too. I don’t know what that’s like either.
The Magic Of Hard Work: Beyond Easy Assumptions
I’ve had conversations with other women about not showing your work, and you make it appear to be done by magic. It’s like, “You asked for this thing, and here it is. I made it happen.” If you don’t show the work, effort, knowledge, experience, and struggle that went into it, it’s easy for folks to misunderstand how difficult it was to create that thing. Earlier in my career, I wanted to please everyone and never let anybody down. I was in the habit of that magic service. I was like, “You want this? I will make it happen. Here it is.” Over time, I’ve learned it is important to let people know that that was work. It wasn’t magic. It was me who did it.
We want to make it easy for them to think it was easy. That is so smart. I’ve never seen anyone do that where you break it down to say, “Here’s your result. Guess what? I was able to do this because.” It’s not in a gloating way. We always struggle with that. I’m not saying I’m so brilliant, but I’m letting you know what this takes. To even entertain that in the conversation is such a brilliant idea because I don’t think we’re doing that very often. It would help. That’s so smart.
It’s an issue for lawyering overall, too. If you’re going to make a recommendation to someone, you want them to know you turned over every rock, looked at every possibility, and considered everything that applied. It took me a long time to figure out how to apply that basic lawyering technique to my own self.
If you don't show the work, effort, knowledge, experience, and struggle, it's easy for folks to misunderstand how difficult it was to create that thing. Share on XIt’s so interesting. Let’s transition a little bit because that is triggering my thoughts as far as parenting. A lot of our kids are under the impression that there’s a lot of magic involved in our deliverance of certain aspects of their lives.
That’s so true.
How can we help them know, except by showing them by doing? That is an uncomfortable idea or notion in our current parenting environment. Do the work. In your book, you talk a lot about showing up and doing the work. Before this book on parenting, I loved this book called The Collapse of Parenting. The byline is how to raise your children in a culture of disrespect.
It’s a very powerful book. It validated a lot of the aspects that come from being parented by a lawyer anyway, like what the rules were and what the expectations were. It’s setting it up in a different way. It resonated with me because I feel like we have to encourage our kids not to be under that misimpression. There is no magic that makes us happen. It’s hard work and dedication. It’s like, “I’ve been up since 4:00 this morning.”
Looking back on that phase with your boys, tell me how you remember it, first of all. Is it a blur? What stands out for you? When you survived having those two boys so young and so early, and figuring that whole gymnastics out, and let’s say they’re in elementary school and going into middle school, what helped you survive that? That’s a phase that is taxing in different ways.
By that time, I was working freelance, so I had a lot of control over my schedule. By control over my schedule, I mean that after they went to bed, I would start working.
We call that mom all day, up all night. That’s the byline.
That is not the ideal setup. In our family, humor is part of our daily life, and teasing is our love language. If you know that someone loves you, you can take a little ribbon from them, or maybe a lot. We often use humor as a way to open and approach difficult subjects. It’s interesting. There was a lot of, “No other parents are saying this. No other parents are doing this. You’re the worst parent ever in the whole world.”
If you're going to make a recommendation, you want them to know you turned over every rock and looked at every possibility, considering everything that applies. Share on XWe were attentive, loving, and very involved in their daily lives, so I appreciate the flexibility that being a freelancer during those middle years afforded me. I’ll drive the carpool. I could see who their friends were. I could volunteer at the school. I could be there for their games and practices. I don’t know how full-time in-house working attorneys do travel sports. I don’t understand how that works. I don’t understand how people without those kinds of jobs can afford it for their kids to do those types of things.
It’s a catch-22.
It’s all impossible, but somehow, we do it. We did it.
Lawyer Mom Parenting: Skepticism And Love
We’re here to talk about it. One of the things I would love you to touch on, too, is you mentioned the humor and skepticism, especially towards those pre-teen years or even beyond that. What was it like as a lawyer mom, being in the carpool, being present, and being aware? It doesn’t take away the fact that you were trained as an in-house lawyer and think a certain way about life and things. How did that influence the parenting of your children in that space?
Looking back, it was not easy to be a teenager with a lawyer mom. Nothing gets by us. We know how to conduct a pretty good investigation. Having those other kids in the carpool, you know which one is the weak link. You can be like, “Jeremy, is that what happened?” You can usually get some good intel from them. I want to say I was trust and verify, but honestly, I didn’t trust either.
That’s fair.
I was very skeptical of all the middle school and high school. Go exon. I always wanted direct evidence, not hearsay.
They know those terms.
I wanted to know who is going to be where and with whom. I was asking my son. They’re older now. They’re 24 and 27. I asked them, “Do you think my being a lawyer made it harder for you in middle school and high school when I was on top of everything?” He said, “That’s who you are as a person, so being a lawyer suits you.”
That’s a good answer.
He doesn’t think it would’ve been any different, but I do think I had extra skills.
I love the way you articulate it, though. It doesn’t always flow so naturally, but it’s the skepticism, researching, and paying attention to detail. That helps bring in the benefits. To me, as a mom, it’s excellent because you also know that someone cares about you. The underlying piece is that because of our nature with that level of intensity, there is extra love in that, potentially. I like to think that. Maybe I’m wrong. Maybe it’s too soon to tell. I have younger kids, so I’m still waiting for them to feel like that was extra love. I don’t know.
I don’t know what the boys would say about that. I would say that out loud to them when they would say, “No other parent is asking these questions.” I would say, “No other parent loves their child as much as I love my sons.” They would be like, “Do you know how horrible that is? How could you say that about my friends? I disagree with that.”
I love to say that. I’m like, “I love you the most. I’m assuring you.” There are two things I want to make sure we cover. I loved meeting you for a lot of different reasons. You are a bright light in the world and a treasure. I also have a fourteen-year-old boy. Someone said this to me when he was seven years old. They said, “Your kids stop listening to you when they turn fourteen,” so I have been jamming in every bit of advice, thought, and problem-solving approaches before, and then I met you.
I’ve been engaging people who are trusted resources to tell them what I want them to hear. I have been working on a side hustle, but then I met you, and I learned about this book. It’s called Just Don’t Be an Asshole. It’s a wonderful guide that I have delivered not only to my sons and maybe husbands and dads to make sure that they’re on the right side of this and are all confirming their good guy status, but also my nephews.
It draws out so many incredible things that I pray were conveyed that I might have missed. I first want to thank you. I’ve read it. I loved it. There are so many things I could talk about with it, but one of the things I am so thankful that you included was how to apologize. That is revolutionary because I don’t think I have, as a parent, taken the time to map it out so well. I can’t even imagine when you were writing this book how you decided on what to include. Is there any additional background on how you chose the topics and how you structured this? It’s powerful, especially since I’m relinquishing my input with my son and giving him the book.
The “Just Don’t Be An Assh*le” Parenting Guide
You’re at the precise moment this book was written for. Thank you for being so receptive to it. The year I wrote this book, one of my sons was graduating from high school and one was graduating from college. It’s exactly as you described. It was like my last, “Did we tell them all the things we want them to know before they go out in the world? Can we tell them one more time?” Being a lawyer, it’s in writing, so they can never say that we never told them.
It’s the things I would shout down the stairs to the boys when they’re playing video games in the basement or as they’re walking out the door. One of my online friends and I call it blurt parenting. As your kid is walking out the door, you shout some admonition that you saw on television or are worried about. My son, who is now 27 years old, as he walked out the door, I yelled, “Don’t get struck by lightning.” You can’t stop yourself from getting in those last words.
I love blurt parenting. I hope everyone agrees with this. We should all jump in here because I know everyone wants to do it.
Whatever it is, get that last word. At one point, with one of my sons, when he arrived with his other friends, they would say, “What did she say?” They would want to know, like, “What was the blurt?” “Nobody got a head injury. Bath salts are not for you.” Whatever it was, they got some comedic relief. I said, “If these boys get through high school in one piece, I’ll take it.”
That’s amazing. I love that. Were a lot of these things in here, possibly blurt parenting that were born into this book? It’s an incredible approach. It alleviates, in my mind, a little bit of parenting stress. I chuckle when I catch my son, who is fourteen. I leave it on the coffee table. It’s not mandatory reading, but it’s strongly encouraged to pick it up and see what resonates. I’m so thankful that you wrote it. I loved it. I know you’re also writing another book. It’s injecting your humor into it, but also on something that’s not always so humorous. Do you mind sharing a little bit about that as well?
Sure. I’m working on a book about grief. In 2021, my husband passed away from cancer quite unexpectedly and quickly. During the isolation of the pandemic, so many people died during that time. It was such a universal experience. At the same time, grief is extremely isolating. During the pandemic in particular, it was especially isolating. Many people did not get closure or not in the ways that society has developed over time to bring closure after loss.
Grief is extremely isolating. Share on XThere is a cohort of women Gen X-ers, like myself in particular, who the grief literature doesn’t necessarily serve well. Similar to the book for teenage boys, I like giving advice to people who don’t want any advice. They’re the people who are like, “I can handle it. I can do it on my own. I don’t want a guide to this.” What I’m trying to do is use humor because grief is so surreal. I feel like only surrealist humor can capture what it’s like to lose your partner or suffer a very close loss.
This book is to let people know they’re not alone and to validate their feelings. It’s okay if you’re in year three and you’re still in the anger stage. That’s great. That’s fine by me. Also, this book is to sneak in some support, similar to the book for teenage boys. It’s like, “This is terrible. It’s horrible to be a teenager. All the rules are against you, and you don’t want to do any of it, but guess what? You have to do it anyway. This is how we make a life in the world.” There are some parallels between the two.
Best Tips For Lawyer Moms: Lead With Love And Keep Going
Speaking of things that may be focusing on a group of people that may not want or think they need advice, lawyer moms might, in our stubborn, wonderful way, fall within that category. I don’t know if there’s a next book to be written on that topic, but if you had to spin off a couple of your best tips for lawyer moms who are navigating life, whether they’ve either had just their babies and they only have six weeks of maternity coverage, or they’re well along on the experience in embracing the teenage experiences or beyond, are there any core thoughts that you would share with them?
I wouldn’t necessarily qualify myself as an expert with regard to teenage boys’ grief or lawyer moms.
You’re on your way.
I wouldn’t get through the qualification questioning in front of the judge. Looking back, if I were advising myself and thinking about how hard it all was, I would say, “You have to keep going and lead with love.” There are so many tough decisions. Do I go to this meeting, or do I show up for this thing at school? Do I go, or does my partner go? Is my kid old enough to go on their own, or am I pushing them out too quickly? Are we asking for too much independence or not enough independence? Let love be your guide and do the best you can.
Let love be your guide. Do the best you can in the moment, for that is the best you can do. Share on XThe best you can do in the moment is the best you can do. That’s it. All you can do is your best. Whatever you decide to do, that’s your best. Whatever you did in the moment, that was your best. We’re all doing our best, so maybe we could be a little easier on ourselves about our decisions. Maybe only make them once and not go back and keep thinking about them.
That is a curse. I agree with that. Being settled and at peace with that would help tremendously. The second-guessing is where some of those challenges affect our mental state.
That was maybe a lesson I learned through grief. Looking back on my husband’s illness and the period afterward, I try to treat myself as well as I would a good friend. I know I would tell my friend, “You did your best. You did the best you could at the time.” To all those lawyer moms out there, you’re doing your best.
Thank you so much. You are a treasure. There’s no question about it.
You’re so sweet.
I would not be honest if I didn’t let you know that you are someone that I would never have met if it weren’t for doing this passion project of a podcast. Even though I have my own moments of self-doubt and questioning where I’m going, meeting people like you has given me so much inspiration and hope. I know that other people, hearing from you, are going to make a huge impact. I want to thank you for your time. Thank you for doing your best.
Thank you for having me. I want to do it again.
It’s been so fun.
It was so fun talking with you. You made me feel very special and fancy.
You are wonderful. Thank you. I am so grateful. I would love to do it again. When your next book is ready to go, we can talk through that. There are so many important aspects of what you’re doing. I’m so grateful that you’re taking all the time to do it. Keep going, and I’ll do the same. Thank you so much for joining us. Have a great rest of your day.
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About Kara Kinney Cartwright
Kara Kinney Cartwright is an absolute JOY whose career commenced as a health care attorney and evolved into dedicating her incredible intellect and passion for writing to become an accomplished author in the legal field and beyond. One of her recent accomplishments is authoring Just Don’t Be An Asshole: A Surprisingly Necessary Guide to Being a Good Guy: A Parenting Book.
She is an ultimate good human who always says, please, thank you, and excuse me-even on the subway. She married a total good guy and, through relentless lecturing, threatening, teasing, cash bribing, and tricking, they have raised two sons who are not assh*les, for the most part. She lives near Washington, DC, and currently works as a publishing director for the American Health Law Association.
