Celebrating Hard Work and Healthy Risk-Taking in Children with Jennifer Hill

Welcome to the Learning to Learn series, where we discuss how our early learning experiences shape who we are at work and how we parent.


Hey there. Welcome! Let’s start off with you introducing yourself to folks.

My name is Jennifer Hill, I am the Executive Vice President of Remedy Analytics. We are an analytics company whose mission is to make prescription drugs cheaper through data for optimum health.

Amazing. Tell me a little bit about your kids.

I have a nine year old son, who’s in fourth grade and I have a seven year old daughter who is in second grade. 

Great, so nine and seven. If you could think back to late elementary school – who were you? How did teachers see you? How did your parents see you? What messages did you get about yourself as a learner? 

I always loved school. I was one of those kids that just absolutely loved it. I started the Montessori program which was very focused on visual learning being part of a larger whole of being self directed, so that kind of defined who I was as a learner, which was strong for me and also one of the reasons why I chose Montessori for our children’s early education. I always wanted to get to the next hardest thing, which meant that I craved additional challenges. I would look for things outside the classroom. There was very little technology then, so I did not have the customary distractions of iPad and computer and all those things. I was a very avid reader. I absolutely loved to read. That was my happy place if I felt things were stressing me out or if I felt the world was out of control, I would get a book, find a corner and a pillow and read. 

Wonderful. I love the term “next hardest thing.” What happened when you started to do the next hardest thing and it felt hard? What did you do when things didn’t quite work out as planned?

As much as I remember, I would ask a teacher. I would look it up. I do remember using a library and a lot of resources that we had to figure out if there was something else. I recall doing some group projects so I would ask friends in class, and sometimes I would ask my parents. 

Okay, so looking around you for resources. When you were young, around 9, and you were thinking about, “Here’s how I kind of navigate the world.” It sounds like you had a few self soothing practices, like taking a book and reading in a corner. Was there anything else that helped you go from not knowing how to do something to knowing how to do it? If we are defining learning as going from not knowing how to do something to knowing how to do it? Was there anything else that you leaned on that helped you move forward? Nine or a little older if you think to yourself in middle school or as you grew up. 

Great question. One of the things that I remember doing at the beginning of every school year was flipping to the end of my literacy or math book and seeing all these really hard things and thinking, “Wow, I really have no idea what that is.” Then by the end of the year I would get there, so it made me feel less daunted by the fact that I didn’t understand something or something was hard. I think that added to making it easier to approach challenges where I didn’t really understand something, and realizing that I’m not always going to have the tools for it, and that’s okay. But, that part of it is figuring it out and since I enjoy learning, I didn’t expect it to be a straight line, that everything would be taught to me and I would regurgitate it. 

Interesting, your perspective is very unique. I think that there are so many kids who are learning as young people, and when it comes easily to them or when they love learning a lot of times that develops a fear. Is that something that affected you? 

No, I feel like I had a really positive attitude around that, and it’s something that I try to instill in our children: hard things are great, hard things are exciting. Taking that leap to do something more challenging rather than staying in your comfort zone is fun. I relate it to things like, “you jumped off that slide, I didn’t want you to jump, but you did it, and you weren’t afraid of it.” 

Nice. Let’s get into your kids. Tell me a little bit about who they are as learners – similar or different to how you were? 

My son absolutely loves math and chemistry, and he’s really excited about electricity. He loves anything related to math and science,the internet, and a little bit of coding. He does like to read, and that’s something that we encourage in both children, but sometimes they need a little prompting. Our daughter loves math and science, but very much finds art and literature much more her thing. She actively picks out and gravitates towards different kinds of books. They’re both pretty positive about it. They’re trying to figure out, particularly the last two years because of the pandemic, what learning is like, and they’ve been learning how to rely on themselves, more than they have in the classroom because my husband and I work, so it’s not like we’re doing their work with them. 

Totally. So learning, they’re both into it in different ways and so for your son, we’ve talked a little bit about this before. For your son, when things like reading come up and for your daughter when things like math come up, what does that look like for them? 

Our son’s a great reader, and we have a dictionary nearby, so if he doesn’t understand a word, the default is not to ask us, and certainly not to ask Amazon Alexa, which we turned off since it can be a cheat for a lot of things. We have a kid’s dictionary, so he knows how to look it up or to try to figure it out from the context. A lot of the effort that we spend is just helping him select books that match his interest and that are grade level appropriate or beyond so that he’s not getting caught in a reading rut. For example, he loves to read Dave Pilkey, which is great. Dave Pilkey gets tons of kids reading, but that’s just one of many genres, so we try to balance that with introducing books that are still super fun but that are more challenging in level. We look around asking other friends, particularly the ones who have older children and older boys, for recommendations. 

We go to the public library a lot, too, so they get the experience of looking at books and seeing if it’s something they want to borrow, as opposed to just expecting to buy something. The library is such a great way for them to explore books in a way that one can’t really do at the bookstore or online. It’s also helpful to see what they gravitate towards. 

Yeah for sure, just browsing. With that, he’s finding books that he likes and books that he’s interested in. He’s got some resources when things get hard. Is there anything else that you try to give him or that he seeks out when things start to feel really difficult in school? 

We try to remind him that working through things that are challenging is normal, and he shouldn’t expect to have all the answers, and that it’s meant to extend his thinking. Sometimes we’ll draw something and say, “Your idea is right here, your learning is to get to that next step.” Kind of like running, you need to run a hundred yards and two hundred yards, but you have to find a little bit of extra energy to run two hundred yards. With this set of problems that you’re working on, that’s the extra one hundred yards that will help you get there. Helping him normalize what’s uncomfortable because he doesn’t know it. We can certainly help him with the content and explain concepts without giving him the answer, but what I think is more important is he’s okay with being frustrated, not knowing something, and understanding how he would solve a problem. We actually did this yesterday in math; there were some concepts that he actually understood, but didn’t understand based on how the questions were asked. I looked at the questions, and I kind of understood how they were confusing in a way, but before we dove into that, we talked about, “Let’s just check in on how you’re feeling about this.” So  it doesn’t go from zero to frustration. 

Totally, that’s nice. Checking in on how he’s feeling, kind of normalizing difficulty, that’s big stuff. Does this come up in any other way? Obviously a lot of learning happens in school, but where else do you see your kids learning and how do you feel like those school based messages translate? 

I think it translates in the playground in terms of human interaction and social emotional growth. We’ve spent a lot of time talking about that this year in particular because you have a lot of kids coming back to school for the first time in a while, new kids because people have changed schools, and sports. Knowing that there are some kids who just do one sport so they are super good at it, versus others who do many, so their skill and technique are at different levels. Talking about practice, learning skills, and the lack of comparison. There’s no need to compare your skills to somebody else’s because you’re on a different journey, but if you want to improve at something, then put in the work to do that.  

How do those messages go over? Sometimes children want to put in the work, and sometimes they don’t. 

Well, they’re nine and seven so I try to normalize frustration. I feel like that’s the biggest thing because the expectation is that it will come easy. I remember when I went to college things came easier before, and then the level of challenge was a lot  harder. I remember having to normalize that for myself, and I feel like one of the life skills that we can help develop in our children is to normalize the fact that everything is not going to be easy and teach them that discomfort is okay. Hopefully, they get to a point on their own where they think, “If I were to solve a problem, what are three or four ways that I can do that?” and not having any judgement about which one is right or wrong, or good or bad, they’re just different things to try. We have a Dyson vacuum and I tell my kids, “It took Dyson 5,000 tries at making vacuums before he commercialized one. He did not make this on the first try, he went through lots and lots of models, so the fact that you’re not getting this or these things don’t work doesn’t matter.” 

I love the vacuum analogy. Let’s switch gears for just a minute. How has this willingness to sit with frustration and knowing that you don’t have all the answers right away, how has that impacted you as someone in the working world. 

Great question, I’ve worked with and in startups for most of my career so that’s pretty much the norm, and I think that’s one of the reasons that I’m most conscious of it in developing those skills in my children because I regularly don’t have the answers, and I regularly have to go find them on my own or with the help of other people. I actually did this yesterday with both our children with an issue that I was grappling with at work. I defined the problem and put it in a little box with things radiating from it saying, “Here’s way number one I might save it, way number two, and way number three.” And they’re like,”Which one do you think it will be?” And I tell them, “I don’t know and I don’t have an investment on which one it is and I have to figure it out. It may be zero, and I’m okay with that.” I do try to talk about how I get frustrated at work, and what I do to help manage that, so they feel like that it’s not just them and somehow adults have all the answers. I feel like that’s something I always thought as a kid for a while. “I’m a  child, and adults have all the answers; they’re omniscient, they know everything.” That is not true. Hopefully that will help them in terms of how they navigate the world. 

Great, as someone who really values that productive frustration, which is THE important part of the learning process. It’s not learning if you don’t feel frustrated a little bit. They are nine and seven now, when they were younger, what were ways that you tried to instill that message because it sounds like this is an ongoing family conversation that didn’t just come up in first grade. 

 I think when they are younger they are more open to trial and error because they don’t know differently and the school activities better lend itself to that. I wondered if once they enter a classroom and start to see peers, they start the self comparison and it changes the framework for them.

Yeah that’s so interesting. I definitely think so. Most schools by definition are either you have the way or don’t have the way. “Here’s the way we solve the problem.” Even if there are six potential ways you can solve the problem. As we close out, is there anything else that you found for yourself as a learner that’s helped you get from not knowing how to do something to then knowing how to do it? 

I ask this question all the time, and realize that I’m probably going to have to do a lot more work than I expect in order to find the answer, and that it’s not a linear process. Just not think about the time or anything like that, it’s putting in the work. But by the same token, particularly in a work context, if there is someone on your team that can make a shortcut, then there’s no reason to put the whole weight of the world on your shoulders. Getting help and having more minds can be a benefit, and it’s always good to leverage your colleagues which I do all the time. I’m grateful that I have a supportive team to do that, and we’re very open about it, so within the workplace and classroom I would say that fostering an environment with people asking questions even if they feel silly, or asking for an opinion or thought partner is a really good thing because you’ll get to better solutions faster and people will learn faster. 

Love it. Asking a silly question, that’s good advice. Thanks so much for talking to me Jennifer. 

You’re welcome, thanks for making the time.

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