When People Are Your Paradise – And You’re Not Allowed to Go

We are in the midst of some unprecedented times. So many introverts are posting memes about how wonderful and relieving social distancing is and I’m over here with a heaviness setting in. The very words “social distancing” evoke a sense of anxiety in me anytime I hear them. To be honest, I’m finding even the thought of being away from people is a struggle when, a social-being by nature, I work from home (primarily in the online realm) and live alone already—not to mention coming off of months of being cooped up because of the winter season. Add in a dash of my own current personal challenges and, well, this does not sound like the recipe of good vibes I’ve been accustomed to cooking up for myself. We’ve all got something going on under the smiles and the uncertainty that we are experiencing right now triggers us all in our own way. For me, it is my perceived “aloneness”.


Now, don’t get me wrong. I know I am never truly alone—I have amazing family and friends, but I am also selective about where I go and who I spend my time with. I have no trouble choosing to spend time on my own before anyone who may not be “good company” for my soul. I have always been comfortable with my independence and “alone time”, but feeling lonely is a different story. And, as life would have it, I have already been hovering under a layer of loneliness for months now—being single can be hard. I’m already in an overall deficit with receiving my daily quota of hugs for healthy living (they say 8 is the magic number) and I am a person who feels that. Feeling things deeply is both my blessing and my curse. When I go out in public, I hold doors, engage with cashiers and store greeters, and smile and say hello to strangers all the time to give and receive my own sunshine. It fills my heart to be able to offer kindness and give love to another. Human interaction lifts me up. I like to be thoughtful and do the little things – knowing the impact they can have on someone – because I know how much those things mean to me when they are extended my way. Working in coffee shops and cafés often helps pass the time for me. So, when people are your paradise, the very thing that lifts you up is threatened.

IMG_5883The world is in a strange place right now, and my paradise within is definitely being challenged. Even if it’s not fear, (which, for myself I can’t say is the feeling I’m tapping into), there is not one person on this globe who isn’t carrying uncertainty and that is a heavy energy to surround ourselves in. As one of my close friends said, “It’s like preparing for a hurricane, but you don’t know when/if the storm will hit.” I share this, not only because writing is a helpful way to acknowledge and unload my thoughts, but, because, as I’ve said before, my life is not all sunshine and palm trees and I work through the tough stuff, too. I want you all to know that for as positive as I aim to be, I’m with you all, just trying to navigate through this, like any other, and it’s bringing up some very real feelings for me. If you feel off, but not overcome by fear, I get this.

It’s like preparing for a hurricane, but you don’t know when/if the storm will hit.

Be patient. Be kind. Send love. Reach out. Show compassion for how everyone is processing these times. We need connectedness now more than ever. Social distancing cannot mean being emotionally disconnected. I’m all for technology playing it’s part here—it pays my bills and keeps me connected to so many people I love—but, the struggle is real in that there are some things it just cannot replace.

You can rest assured I’ll do my part to play it smart and heed any warnings we are receiving at this time. Not because I’m worried so much about myself, but because I care that much about others. You can think what you want about why and how this is all happening, whether people are over or underreacting, but it IS happening and all we can do is come together as people to make the load lighter in any way we can for ourselves, another, and each and every one of us. Now, more than ever, is a time to choose love over fear. We all need it.


P.S. – Thank you to my bestie who randomly checked in with me at just the right moment today. We all need people like that in our lives—the ones who hear your silence…and can still feel you from far away.

Miles apart…but always in heart. Thank goodness for besties. 👯‍♀️


“Who am I, if not THIS?”: Under the Fedora and Beyond the Badge

Well, Ms. D (my teacher persona) made one of her first major appearances in the past three years last night. 👩🏼‍🏫 And I’m not gonna lie. I woke up with a racing heart and All. The. Thoughts. “Are you sure? 😕 What am I doing? 🤔 What have I done? 😬 Where am I going?” 🤷🏼‍♀️ But, all I know is that I’m “going” — moving forward, taking a chance, having another experience.

Walking into LKCS was the trippiest of “trippy-ness” that one could ever trip. 🤯 Through the same doors, with what I swear was the same “Interviews” sign posted in that old swirly font, directed to the same lecture room I was asked to wait in when I started my full-time teaching career over 20 years ago. Sitting there just as anxiously as all the newbies rotating in and out.

Now, before anyone thinks I’m giving up the business and freedom I’ve worked so hard to create for myself these last few years, take a deeeeep breath — none of that is going anywhere. This is no permanent gig nor the level of commitment I was accustomed to before I stepped out of the classroom full-time. Just an opportunity to stay connected to a piece of me, love me some little people, and help out my fellow colleagues with some occasional teaching in my free time. Yep. “Plan B with Ms. D” — substitute teacher. 😂

All humour aside, this is a vulnerable share for me, when everyone expects me to be announcing my next trip south. It’s caused me to do a lot of thinking about all of the hats I wear (and, oh, how we know how much I love those hats! 😉), the labels, images and “expectations” that go with them, and go inward and ask some deeper questions about myself and what it is I want for myself. Most importantly, “Who am I, if not THIS?” Who am I if I’m not wearing my teacher badge, making things look pretty for clients, or wearing a beach fedora and cozying up to a palm tree? Who am I if you take it all away?

Who am I if you take it all away?

What I can tell you is that the answer to that question is actually quite simple (and all I ever aspire to be), but sitting with the discomfort of the feelings a question like that evokes, IS NOT. I have come to learn, however, that it’s actually in that space where the real lessons lie — in those grey areas…between 1 and 100 — where you really start to figure it out.

So, “Who am I, really?” The simple answer — love…and courage. Because, essentially, one doesn’t exist without the other. For me, those really are the only two things that are the answer to any of your questions in life. Do I love what I’m doing? The people I choose to surround myself with? Am I giving myself the same love I so freely give to others? Am I allowing myself to receive that love in return? And if you’re not? It’s time to be brave enough to change that. If something is calling you to stand in love or courage, it’s probably worth it. Life is just too damn short to choose anything else.


So for now, I wait, in love and courage, to see what the next experience will hold. (If, at all, I am gifted the opportunity because, let’s be real, those interview questions were ridiculously wordy, along with my carefully crafted, yet awkwardly botched answers! 🤦🏼‍♀️ Lol!)

To those of you who sent me your good vibes and words of encouragement yesterday, and when I reached out to you in need of them when all I wanted to do was freeze, I love you. And thank you for helping me be brave.


Dear 18-Year-Old Self: A Letter from Present-Day Me

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.

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.

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.

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.

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.

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.

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.

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!)

So, keep smiling sweet girl–you’ve got this! The best part of your journey is still, and always will be, yet to come.


Present-Day Me

Sherri in Paradise: What’s in a Name?

Well, it’s high tide I sat down and updated you all on what this new blog’s all about (and I promise it has nothing to do with Kenny Chesney being in town either–hmmm, wait a minute?).  It’s been some time since I’ve actually written anything, and that’s right, all it took was a little island inspiration and a “local” celebrity to kick my butt back into gear.

shoulder season palm
Back in Key West, December 2018

So, you guessed it, here I am, back in the sunny south–my island home, Key West.  In fact, this is the third time I’ve returned since my last blog post in May, with visits in July and October, along with one quick trip to Miami in November, too.  I signed off on that last blog post not knowing exactly when I’d be returning to Key West and what adventures would lie ahead, patiently awaiting to be embraced by its magic and reunited with this tiny island once again.  But, here I am to let you know, I’m back!–fingers to keypad, and feeling the magic in the place my soul is so deeply connected to.

Spending some time this week with my lovely friend, Lou, we made our way to Mallory Square to stroll through the ever famous sunset celebrations.  Here, we ran into my sweet friend, Linda, selling her beautiful personalized seashells among all of the buskers and entertainment.  A few days prior, there were rumblings that Kenny Chesney was in town (if you didn’t know, Key West is one of Kenny’s common stomping grounds), but, while chatting away, Linda had shared with me that he rode past her earlier that day on the bike her son sold him, with a sweet customized paint job, so this wasn’t just another rumour passed down the coconut telegraph.

kenny schooner wharf
Kenny enjoying some time at the Schooner Wharf, Key West (Photo Cred.: Schooner Wharf)

So what does any of this have to do with my blog, you ask? It all goes back to a balcony in St. Thomas, USVI in March of 2016, and one of those cable stations that plays music on the TV.  On a return trip to the Virgin Islands, I was relaxing on the balcony of my condo after a long day in the sun when I overheard someone singing about “Sherri living in paradise…” The lyrics immediately piqued my interest and I moved into the condo only to hear Kenny Chesney pretty much highlighting my obsession with island life as a girl from the North and this incredible pull I had to search for something, that even then, I didn’t exactly know of (you can listen to the full version of “Sherry’s Living in Paradise” here). So, ya, I was a little blown away. I confess, I don’t listen to a lot of country music, so I wasn’t familiar with this song at all.

Sherry’s living in paradise
Somehow the salty air, it soothes her soul
Says it makes her whole…

sherri balcony
Enjoying the balcony view from Sapphire Beach in St. Thomas

The next day, I hopped into the shuttle van of my most awesome driver and friend, Yisrael, who happens to be a big country fan. He’s even performed on the CMAs and in the video “Painkiller” as a professional moko jumbo dancer for Little Big Town. Of course, Yisrael was playing Kenny, because Kenny also has a home there in St. John, having many fans in the local islanders. When I told him about the song I had heard, he just had to play it for me and said, “That’s you!…Sherri in Paradise!”…and, well, the name just stuck.  Yisrael began calling me “Sherri in Paradise” and I started using the hashtag on my own personal Facebook page with this cute little red-haired bitmoji girl in a beach fedora.  At that time, I had no idea how I was actually branding myself for this blog.  Funny how that works, isn’t it? 😉

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Moko Jumbo time with Yisrael at Iggie’s Beach Bar, St. Thomas
Yisreal and me
Yisrael and I saying farewell at the airport in St. Thomas

Fast forward a couple of years to this summer, August 2018.  My brain is ticking with ideas on what to name my new blog after having written several years for a magazine in the Florida Keys.  I was super excited to be branching out on my own and decided to run a few possible names across my island writing friends and colleagues–“Sherri in Paradise” being the one that called to me the most. That same afternoon I made a quick post of the bitmoji I had been using for more than a couple of years now on my personal Facebook page, taking roll call for a big event we have in my hometown, to see who would be attending. Well, surely the Universe was doing me a solid with my ever so indecisive Libran brain when, later that night, a woman I know saw me and hollered out in the beer tent, “SHERRI IN PARADIIIIISE!!!” I told Tina she had no idea how synchronistic it was for her to call out to me like that–and when she started asking me about places to stay and helping to book and plan some trips to Key West, it was surely a done deal that I’d be launching this blog as “Sherri in Paradise.”SIP Logo TRANS Green Palms.pngI’m thrilled to be able to share this space with you and, even more so, humbled that people are choosing to come along with me virtually on all of my travels. I hope to inspire all of you in search of your own paradise as I share my journey to create my own paradise here at home (Southern Ontario), everywhere I travel (Key West holds a special place in my soul), and, above all, within (You know, the place that’s the cheapest to travel to, but you’re often too busy to book the time to really “go there”?).

So, Mr. Chesney, if you’re still in town and want to share a slice of key lime pie at Kermit’s with a real-life, “Sherri in Paradise”, I can thank you in person for the inspiration.  But, let’s be real, neither one of us is sharing…unless, of course, it’s the whole damn pie!

Kenny Kermits
Kenny Chesney and Kermit of Kermit’s Key Lime Shoppe in Key West (Photo Cred.: Kenny Chesney)

Get social with me!  You can follow “Sherri in Paradise” on Facebook and IG.

Inspired Action: My True “Key West” North

Happy Spring, island friends!  (And, Summer, I know that’s you peeking around the corner.  I’m so ready for your return!)

As my trusty sidekick, the Universe, would have it, I’ve yet to make it back to the Keys in this new year, and I’m still smack dab in the middle of that “walking my talk” lesson in faith I mentioned the last time you all heard from me. And, that doesn’t all have to do with not making my “planned” migration. Truth be told, I’ve really been quite happy with staying put. (Shocking!)  My business continues to grow, my furry babies are healthy and happy, I’m connecting with friends old and new, and, well, all of this is what’s kept my heart warm in the cold.

Out of the lessons, though, emerged a new problem.  I started to question just what I had to offer here, in a space where I write about all of my island adventures in paradise, when I have done nothing but staycation in the North all winter. Yep, that’s right. Not a single trip South since June!  Just what would I write about if I didn’t have any magnificent migration tales to share?  Thankfully, care of another island writing friend who was displaced from her island home during the hurricanes last fall, I was reminded that my island heart lives within me, so I’ll always be living the island life, no matter where I am.  I have strongly felt, that although I’m not physically there, that doesn’t mean I don’t carry Key West in every cell of my body.  And that couldn’t be any more true in this moment.

Along with a healthy, daily dose of Vitamin D, I have been busy creating my own paradise along the river up North. In February, I moved into a new space in an historical ship captain’s home on the St. Clair River and it was my mission to make that space my own–a reflection of this love affair I continue to have with my quirky little island where the sidewalk ends.  If I couldn’t get to the Keys, I was bringing the Keys to me.

After several past stays in historical homes in Old Town, there was no question that the décor was going to be bold, bright, and (surprise!) beachy.  With a few phone calls to friends, I had the items I had used to furnish and decorate my rental last year, shipped up to Ontario.  When I unpacked my coral and aqua colored comforter and pillows, adorned with starfish and seashells, my sense of smell instantly brought me back. It really was a strange, but wonderful, feeling seeing these items that felt like home in Key West, now in a new space I call “home” up North..

From the lime green accents and turquoise window coverings in my kitchen, looking out to the blue waters of one of the main shipping channels to Lake St. Clair, to the specially selected watercolor prints of colorful roosters and a bold, pink conch cottage from an artist in South Florida who also finds inspiration in the Keys, the essence of Key West lives on in my Conch inspired lil space in this 100-year-old ship captain’s home on the St. Clair River. It’s here where my two worlds, and my greatest loves, collide…my True “Key West” North.

Tonight, (not unlike most) I’m listening to my ridiculously talented friend, Chris Toler, stream live at The Green Room Key West and feeling very content with life; trusting I’m exactly where I’m meant to be in this moment. I could not love this space I’ve created any more.  I’m also pretty proud of myself for recognizing my own paradise within and maintaining my sunny disposition despite a lack of sunshine and loads of time outside. My heart has been missing some people lately and I’m impressed it hasn’t gotten the best of me.  I am inspired in so many ways just by switching up life a bit again.  I’ve even got some pretty spectacular sunset celebrations of my own from my new dock!

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Sunset celebrations over the St. Clair River! 

So, I guess the message this time around is that, yes, your true paradise lies within, but you can also create your very own paradise around you with a little inspired action. 😉

I raise my glass to you, Key West, and all of the gifts you’ve given me. Your sensational sunsets, white-picket-fence-lined streets, the stunning seaport and the beautiful, eclectic people who follow their big dreams every day on this tiny 2 x 4-mile piece of coral rock in the middle of the salty seas of the Atlantic Ocean and the Gulf of Mexico. I have not forgotten you, and my island family, and patiently await to be embraced by your magic when we are reunited once again…

Cheers to you, Key West, and all of the inspiration you bring me.