Learning to Learn: Creating Healthy Boundaries in the Learning Process

This is part of the Learning to Learn series, where I’ve been interviewing working mothers with school-age children to understand how their learning experiences as kids shaped who they are as working professionals and as mothers raising the next generation of learners and doers.

[Read last week’s Learning to Learn post on Goals vs Growth]

Hi Leslie! Want to introduce yourself to folks? 

Sure, my name is Leslie Borrell. I’m the founder of Carefully, which is an app/platform for parents to create trusted networks for sharing care and organizing playdates. 

I started Carefully in 2016, but I’ve been focusing on it more since 2020. Before that, I was leading technology teams, and working in software and products for the past twenty-some years. 

I’m a single mom in Greenpoint. 

Wonderful, thanks for sharing that. A single mom to a? 

A nine year old boy. 

Tell me, who were you as a learner when you were nine?

I think when I was 9, that would have been third or fourth grade. For most of my childhood, I was definitely a very diligent student and an overachiever in terms of academics. 

I wasn’t crazy or anything, but I was very much the traditional or what you would stereotypically consider “smart” or an “overachiever.”

I did all of my homework and would answer questions in class. My parents wouldn’t have to bother me to do my homework. I liked to read. 

I’m sure if it was today I’d have a lot of the same problems that a lot of kids do, because I did watch a lot of TV growing up, but I also did like to read a lot. I was very good at math. I liked school, and my parents used to have to give me extra work. 

So funny that your parents gave you extra homework. Tell me a little bit more about that. If we are defining learning as going from not knowing how to do something, to then knowing how to do it. This may be hard to answer as a nine year old but you can think a little older too. Can you think of any situation you were in when something felt hard in school or outside of school, and you went from not being good at it to then being good at it?

I took gymnastics from a very young age. When you talk about achievements, I was very goal oriented. I don’t know when I started gymnastics but they had a system where you have your gymnastics leotard and you get stripes when you achieve certain milestones and you get a star. 

That’s very motivating. 

Yeah, I went to this specific gym for a very long time, so people would work through this ladder to get their stars and stripes. 

While I was athletic, I wasn’t a superstar athlete. I think with athletics, I was very much the same as with school in terms of being disciplined, but it was probably harder for me. 

I was just goal driven and worked really hard at repeating something until I could learn it and do it with the motivation being the success at the end — the idea of repetition and improvement followed by the intrinsic or the extrinsic reward and the motivation from accomplishing the task. 

Things were easy for me in some ways because I had a good memory, so I could read something and remember it for a long time, but when things were hard, I definitely powered through to understand it and learn it because I wanted to have a good outcome. 

Interesting, that’s cool. I think folks who are high achievers in school often fall into one of two camps where it’s like, “I worked harder.” And sometimes it’s, “Oh, I avoided it completely.”

I think that there was one subject that I gave up on and to this day, I probably don’t understand it. 

What was it? 


I remember taking it in high school. I don’t think the teacher was very good, so I didn’t have a great introduction to it. It was his first year teaching physics, and it’s a hard subject, but it was really the first time I had an experience where I couldn’t understand it, like my brain just didn’t click. I could never understand it and get to a point where I could do well on the test. 

I ended up just dropping the class. Never have I tried again. 

Thanks, you’ve done okay so far without it. So tell me a little bit about your son. Who do you think his teachers see him as? How does he see himself as a learner? 

He’s very different from me as a learner, which is also a learning experience for me to understand how he learns.  Trying to support his learning style has been a very challenging and interesting learning experience for me. 

He’s much more of a self-learner, and this could be a sign of the times, but he can watch things on YouTube or whatever, and he absorbs information just by listening to it and watching it. 

In contrast, I really like to go through the process of listening to a lecture and practice the whole structure. He likes to absorb it, but if he doesn’t understand it he gets very frustrated. 

He’s also the opposite of me because he’s very strong with athletics and that comes very naturally to him, but less when it comes to school. 

He’s very smart because he can pick things up and understand things, but he doesn’t like to go through the traditional learning process. He likes to learn things in his own way to a certain extent. When I try to teach him a different way of doing things, he tells me it’s not the way the teacher taught him. 

That famous line. 

I don’t know if that goes along with his learning theory, or if it goes along with kids not getting along with their parents. 

Totally. It sounds like he’s something of a self starter, where if he wants to pick up information, he’ll go and find it. 

He loves facts. 

What are some of the things that he does look up for himself or try to get information about?

He loves facts. He likes to listen to facts about the world. 

Kids make things up a lot so sometimes he throws things out at me. Half the time he’s telling the truth because he’s watched or read something, but half the time he isn’t. 

He pulls up some pretty crazy facts a lot of the time. He likes to learn about things that are going on in the world and how things are made. 

He finds really interesting things on YouTube, and in the middle of all the annoying things he watches, he watches some educational stuff as well.

I don’t play video games, so he does tend to learn about how to play his video games and I hear him talking to his friends. He learns about games he doesn’t even have, and has these in-depth conversations. 

When he wants to learn something, he’ll learn about it. He just has to be interested in it. 

You’re talking to me about your learning and all of your examples have been outside of school, which is rare! How does he interact at school?

It’s really interesting. We’ve worked really hard for a long time on the discipline around doing his homework, and it was a battle for a long time. 

I was worried about going back to school this year and what it would be like. He’s very independent, and we got into a routine last year with his playgroup that we started through Carefully. 

On the days that we would get together, the kids would do their homework together, and then they could play afterwards. 

I think part of that routine taught them that homework is part of their routine, and he’s very structured like that. 

He’s been very good about coming home and doing his homework on his own. He has that motivation of wanting to do well in school. 

As much as he struggles with me, he has that desire to do well both in sports and in school,  and I think that comes through in his focus. 

Sometimes I think the big difference is that I push through a lot when something is hard, and he gets very frustrated when something is hard for him. He’ll stop, and then he’ll come back at his own pace. He’s not as patient. If he doesn’t do well in school, he gets frustrated, but that gives him the motivation to focus a little bit more. 

What messages have you given him? What are some ways that you tried, that have worked or not, in terms of how you respond when he does get frustrated?  

When he gets frustrated, I’ve learned that I can’t engage. 

He has to calm down and come back in his own time, whereas, my reaction is to say “just push through, sit down and do it, it’s going to be fine.” 

I know that once he gets worked up his brain just goes off. He has to walk away, calm down, and then come back. 

That’s really hard for me because it’s so opposite from me; I just power through to focus and understand it.

The other thing is just accepting that he will not work well with me. He’s a lot better now than he was the last two years. Getting a tutor and using external resources to help him with the things that he’s struggling with saves me a ton of stress, and is more effective. I don’t think he would have made any progress, and my hair would be falling out if I didn’t have a tutor or occupational therapist. 

He’s very extroverted and loves the one-on-one attention from people besides me. He doesn’t like me telling him he’s wrong. I’m his mom and he wants to feel proud. 

When he’s with somebody else, he feels like he’s building a rapport by working together. He doesn’t feel as insecure or whatever the right word is in those spaces. 

Instead of fighting that, it’s just accepting that, and I think I did that early on in the pandemic. It was like, “Look, I’m home from work, I’m actually not working right now, I have the time. Let’s do this together.” 

By day 3, I was crying and he was screaming. We can’t do this to each other. 

It sounds like he takes after you in so much of his learning style, and it sounds like maybe the only difference is his need to stop, pause, and regroup. His drives are probably external, satisfying the other adults that are with him, but picking up information and learning new things sounds like it comes from you. 

Yeah, I think there’s something about how he learns that’s very different. 

He starts from a place of wanting to be perfect from the beginning, whereas I don’t think that I have the belief that you had to be perfect. I don’t know exactly where that comes from, and that worries me a lot. I don’t know how to break that down. 

He has such a need to feel like everything he does is perfect. I feel like that’s different from being an overachiever. 

[You may also like Unlearning Perfectionism]

Yeah, you’re right. I want to get into your working life – in terms of the perfectionist streak or frustration when things don’t feel easy immediately, or when things are hard at first. From what you’re saying, it’s been getting a little bit better when he works with other adults. Do you see it being related to making mistakes? Do you think it’s coming from wanting to impress people? Or is it wanting to impress himself? 

I don’t know because there’s so many times when he uses those exact words. He’s so willing to put himself out there. It’s only with academic stuff that he feels that way. I think it’s an insecurity in him. To some degree with sports, too. 

When he feels like he’s not really good at a sport, or there are people that are better than him, some frustration comes out too. He understands conceptually the idea of making mistakes because he repeats some of the things that we talk about, but he hasn’t quite internalized it in some respect. 

The only thing I can do is help him continue to work through it. He’s great at reading now, even though he doesn’t love it, and his writing has improved. He’s better with his tutor, but he also really likes his vocational therapy.

To switch gears a little bit, tell me about your drive and ability to go from not knowing something to knowing how to do it. How has that served you at work? Is there anything you feel like you missed in your learning, that you wish showed up?

It definitely made the transition from school to work easier I think. 

I didn’t really have an office job until I graduated. I may have had some internships, but nothing serious. 

Going into my first day of work, I had no idea what work was like. Understanding that this is something you have to do when you don’t know something, or you just figure it out. Going from high school to college and understanding how to just do things. You just sit down and you figure it out, you try it, and you work it out. 

From that perspective, trying new things doesn’t scare me as much when it’s within the realm of intellectual work. I went into software development even though I didn’t have a clue what it was about in 1998. I was able to get into it and I actually really love the challenge of it. It’s almost the first time that I really challenged my brain. I had to think, learn, and push myself. I loved that aspect of it because I got to put the skills I had acquired to the test, and it all worked together. 

The overachieving part played against me because when you go into work as a female in technology, and probably as a female anywhere, if you are an overachiever, you can burn yourself out. People can take advantage of you by pushing you. You don’t understand your true worth. When I say “you,” I mean me. You feel like nothing’s ever good enough, and you always doubt yourself. 

With school, you’re overachieving, and you get a 100% on the test and get a “check”. With work, you never get that validation. I might get a raise, or “I got this and that,” but there’s never enough validation for me as an overachiever to feel a sense of calm. It made me just push, push, push, push. 

I can so resonate with that.

When there was misogyny and sexism, I missed all those things that were causing me to burn out for 20 years. It took a very long time for me to recognize what that had done to me, and only in this conversation am I pulling it all together. 

What do you do now that you’re your own boss to avoid some of the same pitfalls?

That’s a good question. I think it’s part of the reason that I hesitate to take on outside investments sometimes. I worry about whether I’m equipped to handle the pressure of other people’s expectations, because my expectations of myself are so high. 

Even with my app/platform, Carefully, I don’t feel like I’m meeting my expectations right now, and I worry that’s what’s causing some of the pain in my body. 

Trying to create balance in my life is a constant learning process. The way that my life is structured right now, I’m not focussed on work full time, and I’m not in a toxic environment. I try to surround myself with people that aren’t toxic, environments that aren’t toxic, so I have less opportunity to put myself into situations that are going to take advantage of my weaknesses. 

It’s so ingrained in me at this point. Old dog new tricks. At least I’m aware that there are more steps. 

It was in 2019 when I said I couldn’t go back to that environment. I started my own company and built up a whole new network. Reasserting myself, getting back out there, and learning how to set boundaries for myself. It’s hard when that’s just how you operate. 

That’s one of the things I learned when I started my own business. Someone told me “Make sure you like your boss.” Don’t turn yourself into the boss that you’re running away from. 

I think it’s part of the whole cooperative structure that I put in place for Carefully. By creating a cooperative structure, I’m actually sharing those responsibilities with other people. I’m still the CEO, and still responsible at the end of the day, but I’m trying to create a culture of accountability, responsibility, and empowerment across the company so I don’t have to always put everything on my shoulders. Maybe that’s why some of those things resonate deeply with me; I’m trying to find out external solutions for my internal issues.

This is great, Leslie. Thank you so much for sharing all this. I think it’s going to help a lot of folks to read through the way you think about learning. Any final words before we sign off? 

No, thank you for letting me talk about this. I would love to hear from other people. It’s always comforting to know if other people are having similar struggles. How they dealt with it and other reactions that people have to it as well. 

Through her 20 years as a technology and product leader for industry leading companies including Etsy, Travelocity, and ThoughtWorks, Leslie has demonstrated a unique talent for building diverse, strong teams capable of solving complex problems with simple solutions and delivering above expectations. Since shifting her focus to Carefully in 2020, Leslie has grown to understand the challenges and opportunities in the childcare space through her work with Carefully as well as her involvement with the FamTech Collaborative where she was invited to take on the role of Best Practices Collaborative Lead. She combines her deep understanding of agile values, engineering ethos, and practices that promote early delivery with her core values of empowerment and accountability to grow inspired teams. Leslie has always worked at the forefront of the technology industry, looking for the newest areas where she can adapt her experience, tackle new challenges, and expand her thinking. 

Carefully was founded by Leslie Borrell in response to her own challenges as a busy, single mom living and working in New York with a young son. Bringing care circles to the digital age, Carefully allows parents to connect with people they know and trust to exchange care and organize playdates. Carefully is on a mission to create a cooperatively owned platform for parents in need of affordable, accessible, and inclusive childcare options. Based on the principles of mutualism, Carefully believes that we need a reliable and resilient safety net to find innovative solutions to our childcare crisis. As we develop a trusted network for childcare and playdates that expands beyond our inner circle, we develop deeper connections to our community, find more time in our week, and save money. While prioritizing the needs of underserved and underrepresented communities, Carefully is building an inclusive solution that strives to re-ignite the age-old need for connection and community, while using leading technology and design solutions  to make the experience fun and seamless as busy parents connect, plan, and share.

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