Author: Sherri DeWolf

Happy, New Year, island friends! With the beginning of a new year, comes the passing of another season filled with the bustle of giving. Over the holidays, I’m sure many of you were on the receiving end of someone’s act of kindness, but chances are, for more than a few of you, the giving of “gifts” was much easier than the receiving. Interesting, isn’t it?

As I’ve continued to grow (yes, this doesn’t stop at adulthood), I’ve continued to learn a lot about myself. The things that I enjoy that take very little effort and are welcomed directly into my heart, and the things that I enjoy, that well, I want, but somehow think I don’t deserve. I like to consider myself an open-hearted person (I certainly wear my heart on my sleeve), but there are a few things that can challenge me and make me recognize I’ve still got some walls that could stand to come down. One of those challenges is in receiving.

Most of my life I’ve been the classic “giver”—especially in relationships with others. Kind gestures, thoughtful gifts, going out of my way, sharing words of encouragement, inspirational pep talks; if I can do something to improve someone else’s well being, I’ll certainly give my best. However, when the tables are turned, and I need help or am on the receiving end of someone’s thoughtful gesture, I can often find myself wondering anything from what their motive is, to why someone would want to be so nice to me, or generally feeling…vulnerable. Perhaps you can relate?

The funny thing, and perhaps the problem in itself, is that many of us think that when we receive, we have a responsibility to give something in return or that we don’t deserve what is being offered to us. Our first reaction is to say, “I can’t possibly take this!” and our mind begins to ponder, “How am I going to repay the favor?” We’ve even been conditioned to say, “No, that’s ok!”, when truthfully, our heart wants to say, “Yes, please.” Nobody wants to be a bother. The reality is, giving with an expectation to receive something in return is not the highest and truest form of giving, and receiving with the intent that we must now give something in return, turns the whole experience into a transaction. I’m certainly not saying that we shouldn’t express our appreciation, simply that it’s okay to allow ourselves to receive kindness for the sake of honoring our own self-worth AND in allowing the giver to feel those feelings that come along with being able to do something just to make someone feel good. In fact, I know how wonderful it makes me feel when someone accepts what I have to offer them, so why would I deny that experience for someone else?

The reality is, giving with an expectation to receive something in return is not the highest and truest form of giving, and receiving with the intent that we must now give something in return, turns the whole experience into a transaction.

My month long stay in Key West this past July was paradise, but it wasn’t all palm trees and sunsets. It was really interesting to process my internal reactions to the kindness shown to me by complete strangers, as well as new friends. Being in a place where I had no roots, I had to consciously practice discernment when invitations were given and people offered to help me out. Something as simple as asking for a ride to the airport from a new friend was strange for me, when I was so used to doing everything on my own. Generous strangers purchased drinks and appetizers at Happy Hour in the Seaport. Incredible friends treated me to dinners and rides to the grocery store, paddleboarding excursions and adventures off the beaten path, a trip to the Tortugas, and gourmet cupcakes too! Even upon returning home, a good friend drove an hour and a half just to pick me up when my flight was delayed and I missed my airport shuttle—just because she wanted to.

Accepting all of these experiences and the generosity that was shown to me, especially in many cases where it was impossible to “repay the favor”, allowed me to open my heart and let the goodness that we ALL deserve step inside. I have no doubt that we get what we give, so even if we’re not scrambling to balance out the “gifts” given to us directly with something tangible, the universe will do its thing and you’ll find yourself bringing that same generosity forward to someone else, while the cycle of giving inevitably makes its way back to the person who went out of their way for you in the first place.

Be generous…be gracious—especially with your thoughts and your words. Be open to receiving all that you are worthy of. Give without remembering…take without forgetting.

Have you ever met an angel in your everyday life? My eyes and heart are always open to the little miracles that present themselves even on the simplest of days, but the messengers that “show up” when I’m traveling never cease to amaze me.

Some people may like to refer to chance meetings as coincidence, but if you know me, I just don’t believe anything is that random. Synchronicity is my thing and when you think about all of the circumstances that have to line up for a person to show up in your life at the “right place” and the “right time”, well that’s pure magic—a reminder that there is a greater force in the universe that is guiding you along, if only you’ll pay attention to the signs. For me, these signs often arrive in the shape of a human (wings undercover) to share a word of encouragement, meaningful story, or even begin a new friendship with, while I’m traveling.

December marked the one year anniversary of my long awaited return to Key West and my very first ever, SOULo vacation. Yes, I finally took the plunge to get back to the place my soul was calling me for nearly five years, and yes, I did it alone. Or did I? That’s where the magic happened.

Shortly after I stepped on the Key West Express out of Fort Myers Beach, I met a family from Michigan whom I connected so well with that we spent the entire four hour ride down the Gulf of Mexico sharing the commonalities we had about our philosophies on life and spiritual growth (this trip being one of those opportunities for me). It didn’t take much time into the conversation for me to understand that these were some people that were “planted” on my path for a reason. By the time we arrived in port, we had exchanged numbers and I spent my first night in Key West having a ball exploring the night life with them—an aspect of the trip that, before I had left, I was unsure I would even partake in considering I was going it alone.

The next three days of my short “water-testing” SOULo trip were just as magical when I set intentions for the universe to gather up enough people to run the dolphin watch I had currently been the only person signed up for, and that, even if I was pushing it, sending me a kayak partner for the eco tour I was taking the next day would be great too! Well, the universe delivered more than a few angels upon that request when a couple booked the dolphin watch only hours before we were set to leave the dock and when waiting to board the eco tour I sat next to the only couple that had their local son playing tour guide for them and whom would be needing a paddle buddy too.

I’m sure you know by now, I couldn’t possibly leave Key West without another close encounter of the “angelic” kind. As I lined up to take the ferry back to Fort Myers I stepped into line behind Amy. A local girl, wise beyond her years, when, after being separated upon boarding a boat filled to capacity, still “somehow” ended up in the seat next to me. When she pulled her “Little Mermaid” sunglass case out of her bag I knew we were a match. By the end of that ride, another new friendship had formed and Amy had her awaiting family graciously escort me to my hotel so I wouldn’t have to take a cab. They say that people come into your life for a reason, a season or a lifetime—but what we can’t forget is that they all serve a purpose no matter how long they are in our company.

These “travel angels” that I encountered on my first SOULo trip to Key West may not have recognized the role they played in validating and rewarding me on a decision that took me nearly five years to prepare myself for, but I paid close attention to the stories they shared and the generosity they showed me. I have returned twice in the last year since this trip and the angels just keep coming! I have kept and made many more incredible connections with people that the universe has certainly conspired for me to meet.

Whether you’re traveling miles from home or just to the grocery store, there are messages and messengers for you everywhere. Open your hearts and your minds to receiving them. Who have your messengers been? Who are the angels who’ve appeared as you’ve traveled through life? What have they taught you or helped you through? And most importantly, don’t forget to stop and thank them, even if it’s only done quietly in your heart. They’ll get the message—because there is no doubt that you, yourself, are one of those angels in someone else’s journey too.

Gratitude.  Appreciation.  Thankfulness.  It’s an easy practice to pack along during the times in your life when the sailing is smooth and the baggage is light, but how does it travel along with you during the detours and the storms?  Just how can you be grateful for the times in your life when the winds become so strong you fear you’re being blown off course or your luggage gets so heavy it becomes difficult to maneuver on your own?

Many of you know, from my first blog post here, that I have a great passion for Key West.  What initially drew me to this island paradise?  A broken heart.  Thank you. What did having to travel on my own to return back to the island bring me?  New friends, new opportunities, and a stronger version of myself.  Thank you.  Thank you. Thank you.  Were any of the situations that preceded my gratitude what I wanted for me at that time in my life?  Absolutely not.  What I’m saying is that it’s easy to be thankful for the obvious good in your life, but we’re not always so eager to stop and give thanks amidst the challenges that arise.  Challenges that are bringing about opportunities we may have never been able to orchestrate, even through our own intricately detailed planning, and those that are carving out our highest potential.  Being thankful for the apparent setbacks in life can reduce the struggle and help you to have a greater appreciation and understanding for your own journey.  It’s all just working itself out, if you can trust the process.

It took a great deal of courage for me to begin my SOULo journeys to the Keys. Courage I don’t usually give myself nearly enough credit for.  Connections with people have always been, and always will be, incredibly important to me. I believe love and relationship are precisely why we are here (in whatever form that may take for you) and that the joy of life itself, is only accelerated by the good company of others. Making the journey independent of a travel partner was a big step for a girl of this mindset.  Prior to taking the trips South, I used to wonder how my experiences would be just as fulfilling without having someone there to share them with.  The answer is GRATITUDE.  Gratitude for every and all experiences along the way–whether they felt comfortable or not–with the underlying knowledge that they were all lessons in preparation for some future class I was yet to know I had signed myself up for.

All of the experiences and feelings that arise when you’re on your life’s journey are there to teach you and help you to grow as a person.  You can never know when you’ll be unpacking a skill set you acquired in a previous life challenge that is going to help you sail smoothly on through to your next destination—be it a job, relationship, location, etc.  You’ve got to be thankful for it all—in advance.

The following quote by author S.C Lourie (Butterflies and Pebbles) sums up my most recent month long stay in the Conch Republic:

“You have those days when you feel so entirely on your own and then you have those days when you realise you have the perfect amount of beautiful people in your life.  I’m grateful for the second lot of days.  And I suppose it’s the first lot of days that make you appreciate the second.”

What a perfect reflection of my time away–for those days that simply felt long or lonely on my own, and those that were filled with new friends and new adventures.

Never underestimate the power in the dichotomies that will present themselves in your life. But don’t limit yourself by expressing your gratitude when “all is well” either.  You can never know what the universe is brewing up on your behalf—sometimes it just arrives in a different package.  So always, always be sure to wrap those experiences in gratitude.  The gift will reveal itself, in time, when you do.

Nearly six years ago, a boyfriend and I took, what would become for me, the road trip of a lifetime.

Sixteen hundred miles to escape the chill of Southern Ontario on Christmas Break to the furthest point South we could travel, in order to guarantee the warmth.  Nearly six years ago, I fell in love with Key West—and all it took were four days—four days of hoodies and jeans in what were unseasonably cold temperatures for our tropical getaway.

As life would have it, I lost the boyfriend shortly after, but not my pull to return to this incredible little island.  Having traveled a fair amount through the Caribbean I tried to put my finger on what this strong desire to return was.  Was it the destination itself? Was it the company? Would it all be the same if I returned?  I needed to find out, but there was just one problem—I could never find a travel partner that was as keen as I was to return, nor had the time off to travel when I did.  This was my dream after all, so no one quite felt the way I did about getting back to the island.

Naturally, my thoughts turned to the idea of taking the trip solo.  Why was I waiting for a sidekick when I had traveled enough that surely I could do it on my own?  Why was I putting my dreams and the things I loved on hold just because I didn’t have someone to travel with?  These thoughts were only reaffirmed when I read the best selling book “Eat Pray Love” by Elizabeth Gilbert.  Now I wanted my own “Eat Pray Love” adventure—but on a smaller scale…all in one place…that little island in the Florida Keys that had etched its name on my heart.  I imagined myself in a historical home, with a bike, a basket, and all of the fish tacos my stomach could handle—living the island life.

Thus, began the virtual vacation planning—FIVE years of virtual vacation planning.  Every road, inn, restaurant, bar, excursion, attraction, etc., you name it, and it was likely I could give you all of the specs.

Unfortunately, I still didn’t feel brave enough, ready enough, to do it on my own during that time.  What if I was sad I had to go it alone?  What if I got lonely?  Or worse still, what if I had created this island paradise in my mind and it was nothing like I had remembered the years previous?  I had never even gone to camp as a kid.  I had always enjoyed my own company, but always in the comfort of my hometown, where friends and family were just a phone call and a few minutes away.

This past Christmas (December 2014), the tug at my soul to return became so strong I could stand it no longer.  I needed to get this dream out of my system so I could dream a new one, or perhaps, even make this one grow.  I took the plunge and booked my first, what I have now coined, SOULo trip to Key West—baby steps, with a three night stay in a beautiful bed and breakfast in Old Town. Arriving via the Key West Express Ferry out of Fort Myers Beach, I can tell you this trip, from start to finish, was nothing short of magical.  If you can imagine the little yellow Google person that you drag and drop to streetview (or rather, mermaid, when you search Key West—yes, you need to try it!), I was that girl.  I guess that’s just what happens when you bring a dream to life.

A quote from Paulo Coehlo’s “The Alchemist” comes to mind:

“When you want something, all the universe conspires in helping you to achieve it.”

From the people that I met and the conversations that we shared, to the beautiful sights and experiences I encountered, it was clear I had made the right decision.  The synchronicities were endless and it all felt good in my soul.  In only four short days, I had made new friends, and there wasn’t a meal I sat down to alone.  It all felt so good, I returned for five nights in March and, just recently, the entire month of July—in my own little apartment in a beautiful historical Conch home in the Seaport.

You can learn a lot about yourself when you take yourself out of your comfort zone and have only yourself to rely on.  It becomes “GrOw” time.  The longer you stay, the more feelings you will encounter.  Some days will be long on your own; others will fly by with new adventures that you don’t want to end.  They’ll be days you feel empowered and other days you’ll need a stranger’s “You’re so brave!”, while sitting at happy hour chatting away, to lift you back up again.

One thing I know is clear, traveling to Key West, as a woman, has felt safe and rewarding.  What better place to feed your island soul both literally and figuratively.  Nothing needed but your suitcase, your walking feet and a willingness to be open to whatever experience is meant to be for you.  You may return with a heavier suitcase full of island treasures, but your soul will be lighter for it.  If you dream of coming to the Keys and are inspired to do it SOULo—Key West will most definitely bring the magic!