In the fall of 2003, when I was 11 years old, my mom, Stephanie Skylar, and I decided to collect every letter she put in my lunchbox.
It started with typical “have a nice day at school” notes and quickly became a place for her to more closely connect with me while she worked long hours. Her wisdom stuck with me long past when she first wrote these letters and this experience greatly shaped how I view the world.
Of course she wasn’t always able to write, but by the end of the year we had saved over 100 notes of her incredible advice. The following story is an edited and chronological curation of the letters. They are categorized by “Lessons” that I’ve learned as an adult; lessons my mom prepared me for ten years ago.
Female friendships have always been a struggle for us. We consider ourselves extremely loyal friends but often lack the finesse to navigate “girl world.” Around this time, I remember a group of my mom’s oldest friends planned to take a trip together and left her out. She was upset but reminded me to focus on sustaining relationships that matter and not to waste energy on the ones that don’t. That always stuck with me.
These first few letters talk about girls at school. Like most middle-schoolers, I struggled to figure things out and fit in. She used the letters to remind me to stay confident and tough. Girls used to mock me; I would read the notes under the table or even in the bathroom sometimes, which made the words even more palpable and significant.
My journey into “girl world” was just beginning. I still had school dances, first boyfriends, and high school cliques to awkwardly stumble through. But I came out the other side relatively unscarred and I owe that to my mom. My closest girlfriends now are some of the smartest, most supportive, and funniest people I know. I admire and respect them, as they do me. I don’t think it would’ve ended up that way if I didn’t learn to value these merits early on.
In 1993, when we bought our house in Lima, Ohio, my parents poured their hearts and souls into making it a home. They remodeled every inch to perfection. When we eventually moved to South Florida in the summer of 2004, we were all heartbroken to leave it.
During my first semester of college, it used to upset me that I didn’t have a childhood home to go back to on breaks, like most of my friends. We moved when I was still in middle school, so going back to Florida felt more comfortable than Ohio; but then we sold my house there too, shortly after I graduated from high school. At this point, my family was living all over the place, but I realized something: I was prepared to react to change, instead of allowing it to paralyze me.
Eventually, I got over the unrealistic expectation that, while I was evolving and growing at college, my family had to stay exactly the same as how I left them. I thought the familiar house would provide that needed safety net for when things got difficult or lonely. But my parents and my brother had to keep living their lives too, making decisions that sometimes affected the rest of us.
I’m grateful I can savor the memories of my first home through these letters. Like most people, I will live in many places throughout my life. The joy comes from making those once empty spaces feel like home and not being scared to move on from them when it’s time.
I started calling my dad “papi” when we moved to Florida. We suddenly went from a small town in Ohio to an extremely diverse, largely Spanish-speaking area. I’m not sure why, but the nickname stuck.
When we moved, our lives became quite unorthodox. My mom continued working in Ohio, commuting back and forth to Florida on weekends. My dad and I bonded during those early days, adjusting to our new neighborhood’s cookie-cutter pink stucco houses, and the awful humidity.
But then a lot changed. I became a teenager. My dad and I lost each other for a few years, even though we were together more than anyone else in my family. It wasn’t until my sophomore year of college that we really connected again. We have always had a unique, complicated relationship. In so many ways, we are the same person. He is one of the most compassionate people I know, even if it’s buried under a thick layer of sarcasm and harsh honesty. I relate to this juxtaposition every day.
This project is about my mom’s advice, but my dad has—and continues to have—an equal influence on my life and the person I have become. He taught me how to embrace my love for graphic design at a young age. He encouraged me to go to grad school. He told me to follow my gut and move to New York City after college. I know he will appreciate me saying this publicly, so I will: he was right and he usually always is.
In October of 2003, my mom’s dad, David Skylar, began having health difficulties. My grandpa– and namesake– is the creative patriarch of my family. He was an original “mad man” who ran an advertising agency in Cleveland in the 50’s and 60’s. My grandma even wrote a memoir about his life.
Around this time, my parents started discussing the possibility of moving. They wanted my brother and me to have better educational opportunities. They also wanted to be closer to my grandparents on both sides of the family. My mom wrote in one of her letters, “If you ever have doubts about a situation, follow your instincts.” To this day, she still reminds me to “listen to my gut.” What I didn’t realize at the time was that she wrote this note for herself too. I didn’t know we were moving yet, but she did.
She really struggled with the decision to uproot our family. We were comfortable in Lima, but she had to follow her instincts. Our move to Florida allowed me to have relationships with my grandparents I never would’ve had otherwise by long distance. She still asks from time to time if she made the right decision. I know she absolutely did.
I am extremely fortunate. I have a loving and supportive family who have always set me up for success. I’ve worked extremely hard over the years to get where I am, but I’ve had plenty of advantages to do so.
My mom has always made that extremely clear. I was never told that this kind of life falls into your lap, but you have to earn it. My parents started saving for my education before I was even born because they were able to and they valued it. They weren’t going to let me fail, but they didn’t just hand me opportunities without expectations.
My brother and I went to a low-rated public school in Ohio. When we got to Florida, I went from girls being pregnant in my middle school to girls carrying designer purses and the newest cell phones. Suddenly, what made us extremely well-off in Ohio made us one of the lesser families at my new private school.
My mom constantly reminded me the importance of my upbringing. She wanted me to understand that just because you have money doesn’t mean all of your problems go away, and just because you don’t doesn’t mean you can’t succeed. I have friends that stretch across this spectrum and it’s always encouraged me to be gracious and appreciative of my life.
For more than a decade, karate was a huge part of my life; it was basically the only thing I really cared about. Today, all of my friends reject the idea that I could ever do martial arts, but I am, in fact, a black belt and I really earned it, too.
I started training at the YMCA in Lima, Ohio when I was 8 years old. My mom never forced me to participate in activities that didn’t interest me, but she strongly encouraged me to stick with karate for at least a month. After a lot of tears and arguing, I finally gave it a real chance, fell in love with it, and quickly rising to the top of my class. I competed in tournaments and learned how to become a leader.
More importantly, I started to gain some much-needed confidence. My Sensei, Rod Kohler, was one of the most important influences of my adolescence. At age 18, I became his first female black belt student ever, after more than 30 years of teaching. At the ceremony, he presented me with the first black belt he ever earned and told me to “always wear my belt on my sleeve.” And so I do.
One of the funniest things I found when reading through these letters was how many times mom addressed my moods. I’d like to believe that I have overcome my occasional bursts of irrational behavior and short-temper, but I know they’re still in me, just part of who I am.
The difference now is that I’ve accepted it. I know the things that bother me; I recognize when I need to be alone and I’m learning how and when to keep my mouth shut (for the most part). I’m still extremely outspoken and brutally honest at times, but I’ve come to embrace those traits and use them for good and not evil. My mom also asks me if I want her advice or if I just want her to listen when I come to her with a problem. I try to remind myself of that now when I’m helping my friends with a problem.
We’re constantly evolving and learning new things about ourselves, but my mom recognized these patterns in my behavior long before I did. Getting to know yourself is a difficult, time-consuming process. We don’t easily acknowledge and accept our flaws, yet we think about them constantly. I decided loving myself completely is more important than denying the existence of my shortcomings.
I learned this lesson pretty early on, quicker than many of my peers. But as I dive deeper into adulthood, I actually understand it.
Moving to Florida was the start of several complicated years for my family. Now in high school, I saw my parents as something other than superheroes. That’s a hard thing to accept. They didn’t have a perfect marriage or flawless careers; they struggled, just like everyone else. They are two individuals with their own dreams, successes and failures.
After my first semester of college, my parents announced to my brother and me that they were getting a divorce because my dad was coming out as an openly gay man. These were two pretty heavy pieces of information for a 19 year-old to digest.
My dad struggled through many years of understanding and accepting who he was. He is the bravest man I’ve ever met and I am extremely honored to call him my father. On the flip side, my mom is the strongest, most patient woman I’ve ever met. She helped my dad to live a transparent life, something everyone deserves. She allowed him to be who he is, even if that meant ending their marriage.
While I now see my parents as handling this situation extremely gracefully and bravely, I know it didn’t happen that smoothly. We all experienced a lot of emotions and really leaned on each other for support. Life is difficult no matter what age you are. The moment I stopped seeing them as people that could handle everything on their own, the more I could help them through this hard time. We’ve all grown significantly closer ever since.
My parents were together for 26 years and still, to this day, have the best relationship I have ever seen. Their love is deep and honest. We still spend holidays together, annoy each other with group texts, and act relatively “normal,” whatever that means.
I wrestled with the decision to address my parent’s divorce in this project, but ultimately decided it is an important example of how these letters have affected my outlook on life. I have two living parents who both love me and support me. The rest doesn’t really matter.
It took me 11 years, but I finally wrote mom with the advice she asked me for.
During my last year of graduate school, while working on this project, she was preparing to leave her career and I was preparing to start mine. We were both stressed out, to say the least.
I went home to Lima for a weekend visit and we read through the letters together. We laughed and cried, and, eventually, came across this undated note asking me to give her some advice. I knew she needed some, now more than ever.
After 20 years at Chief Supermarkets, as a consultant, Marketing Director, Vice President, and, lastly, company President and CEO, my mom negotiated a sale of the business so she could pursue other dreams. I am so proud of her, not only for her amazing and inspiring career, but also for her courage to start over. I wanted her to know that.A few weeks later, I mailed her a letter. Little did I know, she had sent me one, too and they crossed paths in the mail.
My mom wrote me more than a hundred letters but this was, by far, my favorite. It meant our lives had come full circle. We changed, we moved, we grew, we failed, we struggled, and we succeeded, but at the root of it all, we loved each other…