How to be a Girl Dad with Madeline Anderson

April 18, 2023
James Whittaker

Check out this episode on the Win the Day Podcast

Fathers, be your daughter’s first love and she’ll never settle for anything less.”


My guest today is Madeline Anderson. Maddie is the author of new book, Girl Dad, which is the father’s guide to becoming your daughter's hero.

As a reluctant girl dad myself, I can now say it’s the most beautiful journey I’ve ever been on. That’s why I’ve brought Maddie on so she can share the insights from interviewing hundreds of dads for their biggest lessons, regrets, and ideas to thrive as a parent, especially as a proud girl dad.

In this episode, we’re going to talk about:

  • The best tips to help girl dads thrive
  • How to bring your children more into your daily life – without it interrupting your schedule
  • The biggest mistakes parents make, and
  • How to strengthen your family bonds right now.

Before we begin, the right bit of inspiration can completely change the trajectory of someone’s life, so if there’s a friend or loved one who needs to hear this episode or could use some help to Win the Day, share it with them right now.

Let’s WIN THE DAY with Madeline Anderson!

James Whittaker:
Maddie, great to see you! Thanks for coming on the show.

Madeline Anderson:
Great to see you. Thank you for having me!

Congrats on the book. It's an amazing read and I'm so happy you did this.

A lot of people love their dads but don't go the extra mile of writing a book about it. How come you decided to take that step?

I have an incredible relationship with my dad. I had no idea how rare that is and I want to change that. I started, and it was just a book about me and my dad's relationship and how he raised me and my two younger sisters, but I realized there are so many other incredible dads out there.

I started interviewing dads and daughters to get perspectives from all over. It's really their stories that shine throughout the book. It's supposed to be an uplifting and inspiring book on how to have a great relationship with your daughter.

Was your dad a willing participant in the project!?

Yeah, definitely. Throughout the entire book writing process, which was a little over two years, I was constantly calling him and asking him, "Remember that one time!?" 

It was an ongoing interview for about two years.

Someone reading your book, who do you want them to be afterwards?

I want them to be present and excited. This isn't supposed to be this daunting parenting book where you're scared to be a girl dad and scared to have a daughter. You're supposed to close the book and be like, "All right, let's go! I'm so excited to do this. I want to have the best relationship with my daughter. It's going to be great." 

Also, one of the main takeaways is to be present. I want them to be present with their daughters and set themselves up for having a great relationship.

I’ll admit, I was a reluctant girl dad! Both my wife and I thought we were having a son. But our daughter Sophie has been the best thing. I love every moment with her and we have so much fun together.

What is it about the identity of being a girl dad that you think men struggle with?

That's a great question.

After interviewing all the dads, there's this fear of messing up. Instead of leaning into it and taking it as a challenge and starting a great relationship, they decide to stay away and maybe let mum handle those kinds of things and just never really explore that deeper relationship. 

The dads in those cases are doing themselves and their daughters a disservice, because having that great relationship is one of the best things that you can have on this earth. I've heard a lot of dads describe it as the most rewarding challenge possible.

Instead of leaning into it, taking it as a challenge, and starting a great relationship, they decide to stay away and maybe let mum handle those kinds of things.

I think you're doing a great job by leaning into it, and obviously you overcame that fear or reluctant feeling that you got, but it's very common. Leaning into it and being excited about being a girl dad is important. 

You touched a little bit on the identity of being a girl dad, and I think step one is claiming that identity. Call yourself a girl dad, and then you're going to start acting like a girl dad, thinking like a girl dad, and taking action. That's the best way to set yourself up for success.

There's something you shared in your book about the difference between the regular dad versus the girl dad approach to it. The girl dad response makes it more inclusive and brings your daughter into your life rather than giving up your favorite hobbies. It sounds like just adding her to the team is the best way to go about it. 

Now with our daughter, she does things like cheer for the football when we're watching it, she loves cooking, and she loves participating in literally everything that we do. That's a big part of what you found with your research and what you put together in your book, is that inclusiveness rather than trying to separate the roles so much?

Absolutely. I think that's a really exciting thing for dads. 

Another reason they might be fearful of having a daughter is, "Oh, I can't relate to her," or, "I have to stop doing my favorite things because I need to spend time with my daughter," and that couldn't be farther from the truth. You should go all in on your favorite things, but include her, like you said.

You should go all in on your favorite things, but include her.

If you love football, for example, teach her all about football, teach her the rules, sit her on your lap while you're watching your favorite team and tell her about the favorite players, and throw football with her outside, she can do it too.

The more you can include her and make her feel like she's a part of your life, the better you're setting yourself up for later on when she is talking about football with her friends and you're looking at her so proud of her. 

It's a special bond and the more you can include her in your life, the better.

You’re reading an excerpt of this interview. To access the full Win the Day episode with Madeline Anderson, including bonus content that doesn’t appear here, check out the YouTube or podcast version. 🚀

Was there anything that surprised you the most from all the research that you did?

I think it was just the vulnerability that these dads were able to share with me was really impactful. Some of them cried because they loved their daughter so much and you could tell how much of an impact their daughter had on them as well. That was really fun for me to see and really inspiring and it made me feel like, okay, this book is real, it needs to reach more dads and I hope everyone can have this kind of relationship.

Was there a regret that a lot of these people have, perhaps maybe not saying enough about how they felt about their daughters or their children more broadly or just any other trends of regret that you noticed?

A lot of the conversations I had, to be completely honest, were really positive. Some of them touched on times when they couldn't show up for an event and they had to make it up to their daughter, but there was always a redemption in the conversations for the most part.

A good redemption story?

Yeah, of course there's going to be regrets. 

The conversations that I had were really positive and that's what shines throughout the book, it's how to have that great relationship with your daughter, but of course there are times where it gets tough and you have to struggle through it.

What do you, as a daughter, regard as the best quality time to have with your dad? Are there any certain activities or anything like that that you would suggest?

Anytime you can get one-on-one, that's a great opportunity to have quality time. Some examples would be making breakfast in the morning on the weekends, hopefully you're not working and you can be present and ask high-impact questions, the ones that aren't yes or no answers.

There's actually a full chapter in the book called Roses and Thorns, and it's all about how this one dad asked his daughter every night before bed, "What was your rose for the day and what was your thorn for the day?" This is essentially what's one good thing that happened today and what's one thing you wish could have gone better or you could have done better. That's how you really find out about your daughter's passions, what she likes, what's bothering her, and how you can help.

This one dad asked his daughter every night before bed, "What was your rose for the day and what was your thorn for the day?"

If you use those high-impact questions, like what's your favorite part about today or yesterday, and you're talking to her at breakfast and you're sitting down with her one on one, that's great. If you can take her out on a little daddy-daughter date, that's another great opportunity.

Also, playing sports, for me especially golfing with my dad, we bond so much. There's obviously a lot of time to talk on the course.

Who wins these days!?

He still wins!

It's gotten closer and closer, but he's a really good golfer.

Each year in December, I have a recurring calendar notification to write a letter to my kids. It began before our first kid, Sophie, was born because I wanted to write a letter to our future child to talk about a lot of the sacrifices that her mum had given up. She was waking up with leg cramps constantly, it was very challenging for her in particular, that first pregnancy. 

I wanted to communicate with our future child to give them a sense of what was happening and what our feelings, hopes, and apprehensions were around parenting. 

That has now become an annual letter that I write, where I include all their milestones for the year and show them how I was feeling, what happened in the family, and everything else. When we found out Jenn was pregnant with our second child, Henry, I started his first letter and now that's an annual thing for him too.

Were there any rituals like that or other activities in terms of maintaining that bond or doing something a little bit unique that you noticed that some dads were doing with their kids?

Yeah, absolutely. One of them was really cute, the ritual was eating ice cream together. Again, speaking of ice cream and girls, we love ice cream!

Ice cream sales are going to go through the roof after this interview!

One daughter I interviewed, the ritual with her father was to eat ice cream together on the couch. She did that since she was a little girl all the way until she was leaving for college. Her dad helped her moved into college and he actually wrote her a letter saying, "I wish I was here eating ice cream with you," and he put it in her freezer. 

She found it a couple days later when she went to go eat ice cream. She told me she was crying and it was the sweetest thing. She has moved three or four times since then and she's taken that note and stuck it in the freezer ever since then.

That just goes to show you how powerful those little notes can be. Hat's off to you for doing that now, that's awesome.

Well, a lot of people are trying to figure out what's an expensive way that they can show their love, but it's not about the money. As you mentioned, a thoughtful note that didn't cost a dime is now a memory that she will never forget, that she was able to have as a result of what her dad did.


Another example with a note is one of the girls I interviewed, she had an anxiety attack right before college. She was freaking out, she didn't want to leave home and was going through all of these feelings and thoughts of despair.

She ended up taking the note with her to college and she put it in her backpack, it went everywhere with her and she still carries it around today.

Her dad wrote her this really heartfelt note about how she's going to do great and he's always there for her. She ended up taking the note with her to college and she put it in her backpack, it went everywhere with her and she still carries it around today. It just goes to show you how much of an impact something so little can have.

What are the biggest mistakes parents are making in terms of the relationship with their kids?

One of the biggest mistakes is related to work-life balance. I know the word ‘balance’ is getting some hate right now, so work-life integration.

But really what it comes down to is how parents can communicate work with their children, especially at a young age, because you have to think back to when you're a kid – and maybe that's tough – but basically there's this thing called ‘work.’ And when you're a kid you don't really know what that is, it's just this concept that your parents have to do, they have this work that they have to do.

If the parents are constantly talking about how stressed they are, how much they hate their job, how much they hate their boss, but their actions are showing that they prioritize work over their kid, then the kid's looking up and they're saying, "Okay, there's this thing called work, my dad or my mum doesn't like it. Yet, here's where it's at on the priority list and here's where I am. What's up with that?" 

Whereas even if you hate your job, first, maybe look at other jobs because life's too short! But second, if you hate your job, just be really careful about the way you're talking about your job. When you're around your child, or your daughter, just make sure you're highlighting the positives if you can, and also, you're including her in conversation so that she even knows what you're doing.

That was one thing that my dad did really well. He would sit me on his lap, show me the projects he was working on. He would even bring me to work on the weekends if he had to work on the weekends, which he did sometimes. He was always working. He would let us draw on the blueprints, because he's an engineer.

We felt really involved in his work even though we weren't, but it created that relationship where we had open communication. I didn't feel like he was prioritizing work over me unfairly. I admired how he liked his job, and it actually motivated me to find something that I like just as much, rather than discouraging your kid because there's this thing called work that they hate. 

Why would your kid want to go find a good job if that's what she's looking up to?

That's so interesting. 

It's like the idea of this devil being work that's always spoken about but they don't understand it. And when it comes to your career, especially if you’re an entrepreneur, there’s always more work to be done – you can make an excuse to be working all the time, which is horrible for your own well-being and your family bond.

I often say, “You can't be productive without being present.” If you're on a phone call or doing emails on your phone as you've got kids around you, of course you're going to bring a lot of stress into that environment and it just leads to a horrible situation.

Yeah, absolutely.

Your positive energy, where did that come from and what things did your father say to you that you still remember?

Yeah, I'm sure he had a huge impact on that.

One thing is probably just teaching me confidence and that I can do whatever I set out to do. It makes me look at life really positively because I'm just really excited for the next opportunity and I'm always looking on the bright side of things.

Both my parents are very optimistic people and they always say there's a lesson in everything, so even when I fail, I learn from it. 

Both my parents are very optimistic people and they always say there's a lesson in everything, so even when I fail, I learn from it. That was one thing that my dad really taught me and made sure that I learned, especially on the golf course, because you can fail a lot!

Sometimes 10 times on the one hole!

It's about how you approach the next shot or approach the next hole, and just always having a good attitude and showing up and trying your best and being okay with failure. I think that has really made an impact on me.

My kids are only three and one, as I mentioned, but something that I really worry about, in terms of the biggest fear that I have for them growing up, is that when they grow up, they're going to have to discover that the world is a very big, dark, scary place. 

How was that introduced to you, that transition? Was there anything that you were exposed to in terms of homeless, charities that are in need, or people who come from backgrounds that aren't as advantageous as where you grew up?

Yeah, I think it probably started in high school when I was a part of model United Nations, it's essentially this nerdy debate team, but we were debating world issues. You represent a specific country, and it's usually not America because everyone has a different country.

You have to show up to this conference knowing that country's policy on a given issue. These issues are really tough, like the Israel-Palestine conflict. You're just reading about this and you have to present the opinion of Australia, for example, if that's the country or company you're representing.

But you would just realize that, oh my gosh, there's a lot going on in the world and we are privileged to have freedom and feel safe. That was the start of it.

Then I went to UCLA, and I feel like I was introduced to more backgrounds and homelessness and just lots of other issues. Then when I started traveling more frequently and got to go to places like Fiji and you see this sense of poverty that you've never seen before. You see little kids who are starving, clearly, animals walking the street with no owner and you can see their bones showing and it's really, really sad, but it's a wake-up call. 

I think that's another reason I am so positive, it's like I know what's out there and I feel really lucky.

Yeah, perspective makes you grateful.


What about your time in Australia? Was it much culture shock there or did you immerse yourself very easily into the Australian lifestyle?

Oh, it was the best! I would move back there in a heartbeat.

Great coffee in Australia!

Great coffee. 
I feel like they're ahead of the game on everything, their avocado toast is out of this world. Then any Australian cafes that pop up here, I'm like, "Oh, I'm going there because they know what they're doing."

We've spoken a lot about what parents, specifically dads, can do. What about for the children who might be teenagers right now, perhaps listening to this podcast in the car with their parents, what's some advice that you would have for those kids in terms of strengthening the relationship that they have with their parents?

I would say number one, be grateful. It's so easy as a kid to take advantage of what your parents are offering you and take for granted all the little things that they do for you just because you feel like, "Oh, well, that's mum and Dad, that's what they do," but they're really going out of their way to show up for you every day. 

You’re reading an excerpt of this interview. To access the full Win the Day episode with Madeline Anderson, including bonus content that doesn’t appear here, check out the YouTube or podcast version. 🚀

I didn't realize how much intention and attention went into parenting until I got to interview all the dads and hear their perspectives. I'm like, "Wow, it's a job." They really put a lot of effort and work into this. As a kid, it's really easy to brush that off, but remember that every time they show up for you, they're taking time out of their day to do that. Be grateful for that kind of action, because not every parent does that. 

That's what I'm hoping to change, but it's rare and you've got to be grateful.

It's only when you get older, especially when you start having kids of your own, that you realize, oh my God, the sacrifices that my own parents went through. You mentioned that one of the biggest things in your life was all the sporting activities that you were doing, having your parents turn up week after week to training.

It's a big deal to have that presence and to put that time in from them.

It is, and it impacted our relationship so much. I cannot thank them enough, but I wish I thanked them more at the time.

What did your dad bring to the table that was different from your mum?

He taught me a lot about hard work and loving your job and doing whatever it is that you want to do. 

My mum, she's a teacher and she loves doing that, but that's her thing. I think I relate more with my dad when it comes to being all over the place and multi-passionate, but we both have this entrepreneurial spirit and so we'll do a lot of phone calls in the morning when I'm on my walks where we're just brainstorming ideas.

Anytime I have an idea for a business or whatever I call him and we bounce ideas off one another. That's created a really special bond.

What about some ideas for daddy-daughter dates? Did you get some good ones from all the people that you spoke with?

Yeah, absolutely. I think a cute one is just a picnic, just taking her out. You get to sit down one on one and you can pack her favorite stuff, and I would recommend always doing little surprises. 

If you know that she likes a certain thing, I don't want to say candy but adding in a treat that you know she loves, or her favorite sandwich, apple sauce, or whatever. Figure out what it is she likes most and integrate that into whatever day you have. If it's a picnic, hide it in the basket.

Getting out of the house and being in different contexts helps to create better memories. 

Then another one is just going to your favorite coffee shop. If you're ordering a hot drink, like a coffee, then get her a little vanilla steamer, which is just hot milk and vanilla. Then she's going to feel like you because she's going to have the same looking cup and she's going to feel proud to look like her dad.

Then my dad and I would go out to the golf course or play sports or he would set me up outside to Rollerblade or hula-hoop. We would always just be outside doing something and he was always there with me. Just getting out of the house and being in different contexts helps to create better memories. 

When you think about the relationship with your father, is there one particular memory that stands out in terms of when you felt the bond the closest or perhaps something from childhood?

There is one story that relates to him building my confidence, his trust in me, and then feeling like we're a team, like you said at the first part of this interview. 

It was when I was 16 and I had just gotten my license. It was the summertime, so I was off from school. He wakes me up and he's like, "Madeline, I'm double booked for a meeting. I need you to fill in for me." I was like, "What? I'm 16, I don't know anything!" But again, he had been sitting me on his lap, well, obviously when I was a child, not an adult, but he's been teaching me what he does so I have a general idea of what he does.

He's like, "There's this pre-proposal meeting in Long Beach. I need you to drive to Long Beach." Essentially, it was this park that was getting renovated and there was an old bridge on it. He's an engineer, so he was going to work on the bridge and then we need to partner with a landscape architect to do the landscaping around the bridge.

He was like, "Okay, your job is to go to this pre-proposal meeting, sign in and then meet as many landscape architects as you can, get their business cards, give them yours and then we'll follow up with them later." 

I'm like, "Dad, what!?"

He was like, "No worries, you got it!" I was like, "Okay." I put on the most professional outfit I had, luckily from model UN I did have a blazer and a skirt and heels!

I drive there, I'm like, "All right, here it goes." I basically had to play a detective, because if I start talking to someone and they are an engineer, then I need to end that conversation and move on to the next, because I've got to get as many landscape architects as I can. 

I'm going around and there was only one or two women there and it was like 30 men who were probably my dad's age, so around 45, 50 or so, and then there's just me, the 16-year-old girl, and I'm just like, "Okay."

Very intimidating, I would imagine.

Yeah, you'd think, but I also had a sense of calm just because my dad had so much belief in me. He made it sound like, "This is no big deal, just go do this," and I was like, "Okay."

Then I came back with 10 business cards, they were all landscape architects, I successfully exchanged mine. Then he was like, "Okay, can you follow up with them?" I was like, "What!?" He had me email them and say, "Great meeting you today, just wanted to follow up." 

It was a great learning experience, but I think it made me feel really close to my dad because, again, he trusted me with his job. He was like, "Go out here and do this and be part of the team." He built my confidence because he made me feel like, yes, I can do this. It doesn't matter if I'm 16, it doesn't matter if I'm a woman, whatever, I'm capable, I can go out there and do it.

Then also, it just increased that bond of what we have that is a common interest that we share together. We both like entrepreneurial things and feeling successful and checking things off the to-do list. That was a huge thing that made me feel like, okay, I did that.

Final question, what's one thing you do to Win the Day?

My morning walks. I listen to a podcast every morning and I feel motivated. I'm getting sunlight in my eye to start my circadian rhythm, get my sleep good, get my blood flowing. 

Then also, I'm listening to really motivating podcasts, like yours, where you feel pumped up to take on the day! You won't ever catch me listening to true crime or anything, absolutely not.

Final steps to Win the Day...

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James Whittaker

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Resources / links mentioned:

🔥 Join me at the Win the Day Mastermind (Sept 2023)

⚡ Girl Dad website

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📚 ‘Girl Dad’ by Madeline Anderson

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