In September of 2015, I had the privilege of celebrating a milestone birthday in my life. Turning 40 was probably not as shocking to myself, as it was for others (thank you, Mom and Dad for the youthful genes!), but it certainly didn’t arrive without much gratitude and a whole lot of reflection. During that time, a friend had texted me an old picture of herself on a #ThrowbackThursday and I ended up sharing my high school graduation photo in return. Looking at that girl that night, I felt compelled to write…and write…and write some more; endless reflection on the last 22 years of my life flowing effortlessly from my fingertips. Here is the result of my reflection—a letter I would have written to myself, back then, had I been given a glimpse into my future. What would you have said to your 18 Year-Old Self if YOU had been given the opportunity to prepare yourself for the years ahead? Perhaps you’ll even connect with a few thoughts of my own.
Dear 18 Year-Old Self,
You are about to embark on an adventure. You are going to gain so much–and lose some too. Be prepared for the good, the bad, and the ugly. Life is going to bring you a lot of sunshine, but it won’t always be roses. Life is beautiful, but it is hard. Just don’t forget to keep going, because that’s just the ebb and flow of your privilege to take this journey.
In university you’re going to make a best friend. She’ll be from Toronto–a big city you’ll finally visit when you’re 21 and your school career is nearly over. The buildings will be taller than any you’ve ever seen in your little hometown. You’ll take a subway for the first time and accompany her to her first real-life job interview. Her name is Angela and she’s going to stick around a long time. You’ll be her Maid of Honour in her wedding and her confidante when it all ends and she must rearrange the pieces to begin again. She’s going to take you to Florida for the first time and open a whole can of worms there.
My first trip to Florida! Longboat Key (1996)
Angela & I, Key West (2019)
You’re going to miss your family a lot while you live away at school and your boyfriend will struggle, in his own way, with your moving to the city, so you won’t get a lot of support from him. It’ll be difficult, but you’re going to study your ass off and, even though you get a 64 for the first time ever in your life on that Sociology midterm the first semester, you’ll brush yourself off and learn to manage your new workload better. You’ll still graduate at the top of your program, so don’t let it get you down. It’s okay not to be perfect. You can’t learn much in your life if you don’t make any mistakes. You’ll actually start to refer to these humbling moments as “learning opportunities!” (Shocking, isn’t it???)
You’re not going to have much time to play after you graduate from University, because you’re going to move home and get into Teacher’s College a year early, despite what the haters say when you try. When you finish Teacher’s College, you’re not really going to get anything more than a summer break in life before you have to be an adult and hop on the program of making a living. You’ll begin your full-time teaching career when you’re 22, immediately after graduating, and that’s pretty much going to be your life. That’ll be just awesome…for a while. You’ll walk a picket line at 25 and learn to manage your time more efficiently and get some of your life back. This is when you’ll get a glimpse at understanding there’s more to life than your job. You’ll continue on in this profession and watch it change over the years; enough to make you sad and disheartened with the system and realize that the most important things you teach aren’t actually in a teacher’s manual.
My Pirate Themed Classroom!
Capt. D celebrating 100 Days at Sea (School)!
You’ll take your first flight when you get brave after Teacher’s College ends and think this is a great way to celebrate, but hardly believe it was your idea to get on a plane the night before you leave for your first Caribbean Island. Yes, first. You’ll return, several times, to many islands, and realize this is what makes your heart soar. A passion that’s sitting dormant inside of you right now.
Oppenheimer Beach, St. John, USVI
Trunk Bay, St. John, USVI
Rooftop in Puerto Rico
Sapphire Beach, St. Thomas, USVI
You’ll lose all of your beloved grandparents and the traditions you loved as a child will begin to fade; become an Auntie to your baby brother’s two beautiful boys—a brother you view now as a father and feel an immense sense of pride for the man he has become every time you see him; leave the boyfriend whom you allowed (yes, you!) to steal your shine and, after continuing to work at getting it back, wonder why the hell you put up with that for so long? Your sister will be your party sidekick for a short period of time, you’ll grow apart, and then, you’ll start growing fiercely together. She will be one of your greatest cheerleaders when your ideas don’t look like everyone else’s. Only a handful of friends from your teenage years will remain, but the friends you have now, will be the closest reflection of yourself you have ever known—both types of friendships will have a special place in your heart.
My sister, Kristi, & me!
My brother, Kevin, & his boys, Ashton & Cameron
You’ll bond with a few furry felines and acquire your very own kitties without having to sneak them into the house before your parents even recognize what is going on. These pets will teach you to choose compassion and selflessness when their time with you must end, how to buck-up and be brave when a little life depends on it, and get over yourself enough to give injections and test blood sugar levels for the diabetic one without fainting.
Shamus & I battling his Feline Diabetes Diagnosis.
Shamus (In remission–4 years Off the Juice!)
You’ll move into an apartment and, after thinking you have nothing to show for that, decide to buy a house. Then, the urge to rent an apartment will return again because you love to travel so much and start to understand that a simple life is where it’s at.
Just like your dad, you’ll learn to drive a boat. You’ll even buy a couple of boats. After a few years of fun, you’ll sell them and ultimately decide it’s much cheaper just to be a guest on others. You won’t miss the expenses.
Your mom will continue to be your best friend. She’ll be there to pick you up when you fall, wipe your tears, and then wipe hers, when she recognizes the wings you’ve grown.
River Cruise with Daddy
Out for a cruise!
Momma & Me at the Christmas Parade
You’ll give your all in every relationship and most every boy will break your heart in return. You won’t break too many hearts of your own. In most of these interactions you’ll never have to worry about feeling like you’re not enough. You’ll learn that, in nearly every case, you’ve been too much—and the timing has never been such that any one person has been fully ready to receive all your heart has had to offer. Rejection will hurt. A lot. You’ll go to that dark place that follows when a relationship comes to an abrupt end and each time it will hurt more, until one day, you choose differently, your heart cracks open and into a creative space, and you start working on yourself–hello counselor (no, this doesn’t mean you’re crazy–most of your friends will have their own experiences to share here), naturopath, reiki healers (what???) and a whole host of self-help books and inspirational articles that you’ll love sharing in deep conversation with those special people whom you let into that part of your world. You’ll have a hard time saying goodbye and letting people go, but you’ll start to do it more gracefully—and never with words left unsaid. You’ll be able to see the gift in each goodbye and how each relationship was preparing you for the next experience life was about to offer. Despite all of this, and what will baffle you the most, is how incredibly open your heart will remain after all of the heartache. You’ll continue to wear it on your sleeve and still carry hope in this very moment…
You’ll have some health scares, some biopsies, and wonder if you’ll ever be able to have kids way before you should have to worry about that decision–all before you recognize you’re actually content in your life without having children, in contrast to what others may say about you making a great mom.
You’ll have an opinion and a voice more than you have ever expressed. Don’t be afraid to use it in a gentle way. You’ll begin to care less about what people think about you. That insecurity won’t completely go away though, so you’ll find yourself continuing to work on that from time to time, even now, but you’ll have a stronger sense of self and what makes you “you” more than ever. You’ll realize you never fully stop uncovering the layers in the identity you’ve wrapped yourself in all of these years—and you’ll start to get excited about getting to know yourself better. You even have some talents on reserve you know nothing about—just you wait!
Some people will let you down, so remember that not everyone has the same heart as you. Continue to give anyway. You’ll look back and know it wasn’t really about them after all.
You won’t look back at your past nearly as much as you do now. Be grateful for being able to live a life with less attachments and responsibilities. You’ll acquire all this “stuff” and realize you have way too much of it anyway. Every “thing” that you ever wanted, will lose its sparkle in time and “experiences over things” will replace the need for the tangible.
Proud Home Owner (2006)
My Water Convertible (2012)
You’ll have heard a million times that “everything happens for a reason”, but you’ll actually start to understand it, feel it, and believe it. You might not like it, but you’ll accept it, and life will get a little bit easier because of it.
You’ll start to see how the Universe works FOR you, not against you–every time; even when things don’t go your way. You’ll see how it supports you when you follow your heart and connects you with the most incredible circumstances, opportunities and people. You’ll fall in love with synchronicity and pay attention to the signs the Universe is always sending your way. You’ll believe in magic—but not the kind that someone else pulls out of a hat.
Finally, you’ll still be smiling like you are in this picture. Your hair will be lighter (and smaller!), your face have a few more lines, and the lasik surgery so miraculous you won’t need those dorky glasses anymore. Beyond any of these things, your heart will hold more love than you could possibly have imagined it would, despite some of the biggest losses and setbacks you know are still inevitable as you continue to grow older. You’ll be open and ready for what life is manifesting behind the scenes, even though it could hurt like hell. You’ll recognize the courage in this vulnerability and know that it’s the only way to live the life you’re still gifted enough to be living and truly call it a “life”. You’ll wonder what’s next and be confused about the direction in which you’re travelling, but you’ll have more faith than you ever learned about during those years in Catholic grade school and you’ll be making the best of it. You’ll laugh about it, you’ll cry about it, but you’ll still end up smiling through it all. You’ll work hard on trying to stay present without worrying so much about the future and look fondly upon the past, but, above all, you’ll be strong enough to look to the Universe and shout at the top of your lungs–#BRINGIT!!! (And no, that’s not actually a direct call to the stars above–it’s a hashtag–and that, my dear, begs an entirely different letter!)
18-Year-Old Me (High School Grad)
Present-Day Me (“Better Than I Used to Be”) 😉
So, keep smiling sweet girl–you’ve got this! The best part of your journey is still, and always will be, yet to come.