Jennifer Simpson and her family in blue track suits leaning up against a minivan

Five Kids. Three Degrees. How Did This Working Mom Do it?

Five Kids. Three Degrees. How Did This Working Mom Do It?

Jennifer Simpson is mother to five children and works as a compliance specialist for the Department of Education in Boston. She got her MA in Communications and Rhetorical Studies from Idaho State and a J.D. from Indiana University. In our interview, Jennifer details how she always felt that she needed to equip herself to provide for her family and how that impulse led to pursue her education while caring for her children. Jennifer turns the narrative of “work first, then kids” on its head, having her first child at 21 and entering law school when her youngest started first grade. Though she has experienced some frustrations entering the full-time workforce at 41, Jennifer says that she would not change her choices if she had to do it again. Enjoy this refreshing and eye-opening interview!

Introduce yourself and your story of integrating work and motherhood.

I have five children. And I came to work from a different lens maybe than some people. When I was growing up, my dad was disabled. He’s a first generation college student . . . [a] real go-getter kind of guy. [In] 1976 he was in an accident—he was a lumberjack, and a tree fell and broke his back. And then in ’82 he was diagnosed with multiple sclerosis, and then in ’95 he died of pancreatic cancer. So he had just this triple whammy of chronic health problems and then died of this horribly painful kind of cancer. 

My mom went back to work when my dad got diagnosed with MS. My dad was on social security [and] disability [benefits], but that’s only health insurance for one person, [so] my mom’s transition back into the workforce didn’t really allow [time] for her to go back to school. There was a job that was available at the high school—it was a state job and it had benefits, [but] it never paid very well. And drawing disability and working a state job does not a wealthy family make.

Watching this at a formative part of my life, I was like, “I’m going to school, and I am getting a job. This isn’t going to happen to me.” I always felt like the clock was ticking for me. “How long before I’ll be the breadwinner?”

How did you integrate having five children with your career?

We had a baby right after getting married, and the next year I went back to school. By the time I finished my undergrad, we had two babies. Then we owned a restaurant for three years [and had our third baby], and then my husband and I went back to get our master’s degrees at the same time. We were both grad assistants, and I had our fourth child in that time. My husband and I finished our master’s degrees together. Then I taught as an adjunct professor at Idaho State for seven years, and we had our last baby while I was teaching.

Jennifer and her husband Darren.

My husband [Darren] was with [our church’s] Seminaries and Institutes. He had this great stable job, but there was just always this discomfort for me: “I’ve got to be prepared. I’ve got to be prepared.” Darren earned his PhD from 2003 to 2008. He had to do it after work, six credits at a time. And I had had the impression to go to law school in 2001. [But it was] in 2009 [when] we got invited by Seminaries and Institutes to move to Indianapolis [that] I had the impression,  “Oh, this is my chance to go to law school.”

I took the LSAT the first year and then went to law school for three years. I passed the bar in ’13, I got a job with the Department of Education in Indiana (which is when I transitioned into working full time), and then we got the call to move with Seminaries and Institutes to Boston in 2015.

That move was disruptive as a working woman, because I [couldn’t transfer] my law license [from Indiana to Massachusetts]. We came from Indiana to Boston, and I had to decide what I was doing with my legal career. I really resisted taking the bar again because it was a bad experience. Just hard. It’s so hard. 

I worked part time at the library, got an administrative job there, and then went to the Cambridge Law Department doing public records. But there was no way for me to transition to an attorney role without the bar. 

After three attempts, I finally passed the bar, and then I got a job with the Commonwealth of Massachusetts in the Department of Education doing compliance like I did in Indiana, and that’s what I am doing now!

Why did you want kids?

I had a religious inclination that I wanted to have a big family. In my religious language, I felt impressed or prompted to start my family right away. And I also felt like each time we welcomed a new child into our family that that was good timing for me. My children have brought me a lot of joy, [but] I don’t think [that when] I started having children—I was 21—I had some grand ideas of why I was doing it. I don’t. I just had a baby, [and] I loved her a lot. It was different than I expected—more rewarding. Harder, of course. But I also was amazed at how it felt to watch a person learn and grow and to be someone when they were born. Babies have personalities, and just to watch them and think, “You’re different than me. You’re yourself.” That’s really a remarkable thing—to get to be a part of that.

I think there’s a lot of pressure now that I didn’t feel, and I can’t really identify why. I don’t know if it’s this social media environment that didn’t exist when my kids were small or just more accessible information with the Internet, but when my first daughter was born in 1994 I didn’t feel pressure to sleep train her and feed her organic food. You know what I mean? I had no apps. I had no influencers. I had nobody telling me or nothing influencing me beyond what I thought and what I would ask people. I didn’t have a lot of externals influencing my parenting or giving me pressure about my parenting.

Having five kids and getting three degrees and working throughout just sounds impossible. How did you do it?

I just used screen time. That’s how I did it. “You want to watch a movie? You want to watch another movie?” [Laughs] [Because of the lack of external pressure] I felt like I could have my daughter and still do the things that I wanted to do and needed to do to pursue a career. [If I had] to write a paper, I would leave snacks in accessible places and just put in movies and write my paper. And I was like, “We’re gonna work together on this family. This is my day [that] I have to write, and this is your day to watch TV.”

I [also] think [that] school is easier to manage than work, because school is, at the end of the day, voluntary. You can miss a class. Right? It’s not like missing work. You don’t have to call anyone and say, “I’m not going to be at your class today.” 

I was really worried that I would be disadvantaged because I was really entering the full-time workforce at 41. And that was not my experience. I found that my age was valued. My soft skills were valued.

When I was getting a master’s degree, [for example], I scheduled my classes on two days, and my kids went to daycare [on campus] on those days. . . . Daycare was on campus. You could visit your kids during the day between classes, bring them lunch, check on them at nap time, see them playing in the yard, [and] wave at them when they were on their walk. It’s right there and it’s built in. I distinctly remember one day during my master’s program, my daughter, who was in first grade, was getting dropped off for the first time at the after-school daycare program. I met her there to help her look at the program. And she started to cry. It was all big kids, [and it] scared her to death. I said, “You don’t have to stay. Let’s go to my class together.” My professor gave her paper and pens so that she could sit there in our class and not have to go to that program. I don’t think I would have asked my boss if my child could come color for two hours, but my professor had no problem with that. I had a lot of experiences like that where school was very supportive. 

[When I started working part time at Idaho State] I worked nine to noon twice a week, so [my children] just went to preschool on campus.  . . . That was supportive and easy as well, and that was still at the university environment. [And I prepped lessons] in the evenings, when they were asleep.

How has the pandemic impacted you, and how have you seen it impact others?

The pandemic has really highlighted [issues of work-life balance] for moms. I was not disrupted by the pandemic in my work. I didn’t have to do anything to disrupt my day to accommodate my high school student. But in my work with the Department of Education, I got calls every day from parents who had younger children. Imagine a working parent with a child who does not know how to read. . . . [Their children] have to have assistance to access virtual learning. Somebody has to sit there and read it to them. People had to quit their jobs to do this virtual school. 

Working woman phone call
Jennifer on the job.

Our society balances on the thin edge in so many ways for working parents, and school is one of the ways that we have adapted to make society work. There’s before-school programs; there’s after-school programs; there’s breakfast, lunch, and snacks at school; there’s sports. You can leave your kid at school from 7:30 a.m. until, in a lot of places, 6:00 p.m. So when [school was] gone, when that piece of infrastructure that allows society to function with two working parents [was] gone, it was devastating—devastating—to so many families, because it wasn’t just assisting with school. It was having a place for your child to be while you were gone the whole day. And that was really, really tough, especially on moms, as we know from the data. [The pandemic has] exposed what [being a working mom] really requires: we have to have a free place to send kids.

What has your experience been like, building your career as you had kids?

I was really worried that I would be disadvantaged [because I was] really entering the full-time workforce at 41. I was like, “Nobody’s gonna hire me. They’re gonna think I’m old and I didn’t take the [straight shot] from undergrad. I should be [peaking in my career] at 41, not entering.” And that was not the case. That was not my experience. I found that my age was valued. My soft skills were valued. We do something in society that is wrong by suggesting [that] if you’re not in the workforce you’re not developing skills. That’s not true. What skills are you developing working with a toddler? That’s highly skilled [work]. . . . It’s not like your life’s a void if you’re not in the workforce.

So we have to acknowledge these life skills—soft skills that people [develop] when they’re not in the workforce—are valuable. You’re doing things at church, you’re doing things in your community that are valuable, and it has been my experience that my employers have valued that.

Looking back, are you glad you did things the way you did, or are there things you would change?

I’m glad I did it the way I did because I have loved the opportunity to be home with my kids unexpectedly. I never thought I would do that. Like I described earlier, I had this urgency to work. 

I think it takes some time to adapt to being primarily a stay-at-home mom. . . . Being in school full time, [you] get validation from your school or from your grades and from your peers [and] from your professors. Being at home full time, that goes away. You’re by yourself with your little kids. There’s networks and moms, but it’s not the same reinforcement—it’s not the same validation that comes from school and from work. It takes a long time to say, “This is my baby that couldn’t put his blocks away and now he’s putting his blocks away!” Nobody is going to tell you that matters. But you’re gonna be like, “I taught him how to do that!” To have the opportunity to be at home long enough to enjoy that and appreciate it was a real blessing to me. 

I would rather have regrets about not being a manager than regrets about not knowing my kids.

One of my favorite compliments I was ever paid was when I was studying for the bar in 2013. We had [friends stay with us for a few days]. Their mom watched the kids all day while I was gone studying for the bar, [and] I was having [some serious] mom guilt. Anyway, she said to me when I came home, “Your kids do a lot more around the house than my kids.” And I was like, “Yeah, because I don’t do anything for them right now.” [So] they were making their own meals, getting to their own jobs, getting to their own activities, doing all of these things. And that is a good thing, right? For an older kid, of course. 

I have had some frustrations feeling like I’m entry level at an older age, and I haven’t advanced to a place where I feel like I have [the] power [or] credibility [commensurate] to my age and what I feel is my experience. I said that my soft skills were an advantage. They were for getting a job, but I do feel like I am behind on [entering] management or [having] more administrative responsibilities. But then I have to ask myself, “How much do I care about that?” I think, maybe, I don’t. That’s another perspective of age. Do I really care if I am the manager of people who don’t like their jobs and want to call me and whine about it? [laughs] . . . I would rather have regrets about not being a manager than regrets about not knowing my kids. And I really know them. We’re really close. And that’s more valuable to me.

What policies do you think we should implement to better support mothers?

[The first thing is keeping the] flexible work-from-home options [we got from Covid]. If you say, “Okay, I know I have to work eight hours today, but I can do three of those hours from 5:00 a.m. to 8:00 a.m., I can do two of those hours at nap time, and then I can do [three] of those hours after bedtime. Then I’ve got these big blocks of time in my day where I can be present with my kids and take them to soccer or take them to doctor appointments.” [I think we need] true flexibility in your workday, and I think that that also can happen with working from home.

[And the second thing is a more flexible approach to leave.] I think the whole idea of paid leave and the requirement to use leave for an absence is really difficult to manage because, as a mother, absences are unexpected. So I can’t plan. I don’t know what day my kid’s going to be sick. I don’t know what day they’re gonna forget their lunch. I don’t know what day they’re gonna miss the bus. I can’t plan in advance to request an absence

I’m [also] glad that we have sick time reserved for the way it’s set up—that you can call out immediately if you’re sick, and everybody needs sick time and recovery time. But I think that I would like, ideally, just to see leave function like that. You just accumulate leave time, and it’s not so delineated. [Right now,] you get this much vacation time, you get this much personal time, you get this much sick time, and you can’t cross over. There are just some days where you just need to not be at work, and you need to [be able to] tell people that day.

What words of encouragement or advice would you have for young moms who are trying to figure this out?

I would say you have time. You have more time than you think. If you don’t get to do what you have always wanted to do with a career until you’re 40, you’ll still do that career for 25 years. You have time. You have time to enjoy your kids now and do something else later. 

That’s my advice. Now, what about money? How can I wait until I’m 40 to make money? And that’s the question that families have to answer for themselves, and that’s really difficult, because some people don’t have the option of waiting that long to have a second income. We just did without some things. You know what I mean? Drove an old car. Ate sandwiches. Wore hand-me-downs. Made those kinds of sacrifices. . . . I think [making those financial sacrifices together] makes [your kids] more adaptable and resilient—not to be the center of your family’s universe but to be a cog in the wheel that makes the whole thing work.

Editing credential to Bethany Bartholomew.

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