How It Really Felt To Quit A Career And Plunge Into The Wild Unknown

Sometimes it requires therapy and a whole quest for permission and validation.

Image created in Canva AI

This isn’t one of my usual posts this week. Instead, it is dedicated to one of our Substack colleagues -

Alexa Juanita Jordan

.

I have specifically mentioned Alexa because very soon she’s embarking on a massive journey of her own. Into the wild. The great unknown. The realm of “holy shit, what have I just done?” 😂

Everyone has fantasized about it.

Even though this post is a lot longer than I normally write, I’m positive many of you will either glean inspiration or recall a time when you also took off searching for your Wildhood.

Following are two chapters from a book I published in 2011 (when my writing was anything but polished, but hey….it still got all 5-star reviews!) ⭐⭐⭐⭐⭐

The book was called, Chronicles of a Shipwreck in Jamaica, and it documented the leadup, execution, and aftermath of my decision to dump my longtime corporate career and flee to Jamaica on a one-way ticket with roughly $3000.00 in the bank. 😬

Alexa….I hope you have a little more than that in your wallet.

Although the book is no longer for sale, I occasionally refer back to it when I’m feeling less than brave.

Without further ado….Alexa, I’m thinking of you as you embark on your big adventure!

Chapter 16 - Letting Go of it All

I had considered an alternate title for this book. It would have been, “How to Recklessly Abandon Your Life in Ways I Don’t Recommend.” 

Almost everything from this point on is the “ways I don’t recommend.”

Now that it’s been eight months since I abandoned my life and moved to Jamaica, I can look back and see everything I did right and what I did wrong.  Of course, there are parts I would take back or do differently but there’s plenty I wouldn’t change no matter what.

One thing I know for a fact is that I would always be bound by fear whether I left or not, so I chose the lesser of the two evils – trying it and finding out. 

My fear of leaving was giving up the security of $35.00 an hour paychecks that I’ll likely never see again, and trying to survive in a foreign country with no real plan. 

(In 2011, $35.00 an hour was a very pretty living)

My fear of staying was that I’d become an old lifer at my union job and be angry at myself for never doing anything adventurous that added meaning to my life. 

I toyed with the abandonment idea for years and as the time came closer I jousted with the decision to fully quit my job or just take an unpaid leave of absence, just in case. 

Somehow I felt highly opposed to the leave of absence because having a backup plan left room for failure.  I was so set on getting the hell out of dodge that no forethought or backup plans entered my mind.

Even though I’d been working up to this move for years nothing could prepare me for the day I resigned from.  It was almost a split-second decision. The feeling of unbridled freedom and sheer panic overwhelmed me the moment I hit the “send” button on my resignation email. 

I couldn’t even hit the send button myself; I made my co-worker do it. 

And then it was done. Two weeks’ notice. 

Following is my actual resignation letter:

“Please accept this letter as my formal resignation from my current position with the City of Calgary.  My last day of employment will be Friday, March 11.  I will be leaving the country to pursue other opportunities that are in line with my current interests.

This hasn’t been an easy decision and the past ten years with this company have been very rewarding.  I’m grateful for the experience and security the City has provided me over the years but I feel it’s time to pursue a future that I’m passionate about. 

If I can be of assistance during this transition please let me know.”

I remember like it was yesterday and as soon the news filtered through my department, people trickled in and out the rest of the day asking if it was true.  I bucked up and faked the confidence in my reply, “Yes, it’s true.” 

In two weeks I’d be gone from this career, and in four weeks I’d be gone from the country. Even though the excitement was welling up inside me, I can’t lie, so was incredible fear. 

After finishing my final weeks of work, coworkers threw a big going-away party on the last Friday.  It was an awesome night and people I didn’t even talk to regularly came out to wish me luck and tell me what an inspiration I was.  Some even cried; I wondered if it was because they wished they had the guts to do it. 

They made me feel proud of myself. 

The most memorable point of that night was leaving the bar and walking to the train station to go home.  I remember feeling pure loneliness standing on the train platform in the cold night air, leaving downtown Calgary for the last time. 

I was toting my messenger bag with the last of my work belongings and taking the train for the last time until who knows when.  I arrived home around 11 p.m., sat down and watched CNN news coverage of the latest Japan earthquake and tsunami. 

I couldn’t even fathom the thought of no more Monday mornings.

It was only after my last day of work that all the harsh realities of leaving home crashed down on me.  Once it became real, my heart sank every time I looked at my dog.  I wondered how she would react to me never coming home after work. 

She was old and very set in her ways. Every single day around 5 p.m. she instinctively laid at the front window waiting for me to get off the bus.  How long would she do this before realizing I was never coming home?  Do dogs even have the same perception of time that we do?  Would being gone for months feel the same for her as when I’m gone for two weeks? 

I made a pact with myself to take her for as many walks as possible in those last two weeks and it broke my heart to think of her missing me.  Humans understand why other humans are gone but dogs can’t reason the same way. All she would know is that I’m gone.  It might sound stupid to some because she’s just a dog but I was torn up about it.

(Just so everyone knows, my dog lived with my mom after I left. I feel the need to clarify that!)

The other one I was worried to leave was my son.  At the time, he was eighteen and had been living on his own for a couple of months.  My relationship with him is unrealistically tight – we have a bond that I wonder if all mothers and sons have, or is it just us?  We’re almost appendages to each other.

He was a difficult one to raise and we went through a lot of hardship with me being the only parent.  I was often worn out, stressed out and uptight. We struggled to keep it together even though underneath it all was a true bond that no one can break. 

I felt like I was breaking it by leaving.

During the last month of my job, I took advantage of free counselling provided by the company EAP, on how to deal with pursuing my dreams.  I felt tremendous guilt about even having hopes and dreams when I should just be a responsible mother instead. 

The counsellor basically bitch-slapped me back to reality, reminding me that my son was legally an adult and cancelling my dreams was out of the question.

I cried a lot in those sessions because no matter what a therapist says, I’m still a mother who remains loyal to her son.  But deep down I knew she was right. I needed to spread my wings and show my son that this is what adults do. We pursue dreams!

If you’re one of my long-time followers reading this now I bet you thought I lived a normal life and just jetted off without a care in the world!  That’s far from the truth and without going into minute details, just know I struggled up to the very last minute before I skipped town. 

My passion prevailed and I’m still proud of myself for going.  I had the guts to pursue a big thing in the face of adversity and believe it or not I still feel guilt that I left.  I’m not sure I’ll ever feel completely okay with being a free spirit.

Chapter 17 - Departure Day

All my preparations were coming to fruition now and departure day rolled in like a tornado.  I managed to pack my entire life into two rolling duffle bags and a carry-on.  This was pretty easy considering I’d had my apartment in Jamaica for seven months before this day. It was already full of things I’d carried down on previous trips. 

I don’t think I slept at all the night before, consciously aware of the feeling of sleeping in my own bed for the very last time.  Using my heated mattress pad for the very last time. 

5 a.m. came quickly and I was up and dressed in no time.  I zipped my two fifty-pound bags, laid them by the front door and watched my dog lie beside them.  I cried. 

Mojo not even looking at me 😥

My mom was driving me to the airport that morning and once she was up and ready to roll I loaded my bags in her car, came back into the house for the final farewell with Mojo, and I cried some more. 

She would be waiting for me to come home that evening and I wasn’t coming home.

The night before departure, I went to my son’s apartment to say goodbye.  I gave him the option of coming to the airport in the morning but as I suspected, it would be too early for him and he chose sleep over me.  Looking back at what a mess of tears I turned into at the airport it would have been worse if he had come. 

I knew he would be okay because I raised him. He had the tools to take care of himself.  We savoured our last couple of hours together and I promised I’d call the minute I landed the next day.

Driving to the airport on that dark, cold morning was surreal.  I’d done this exact same airport drive fourteen times before but this one wouldn’t be the typical “drop and go, see you in two weeks”. 

I asked my mom to park and come inside so we could enjoy breakfast together.  She took this picture of my last egg and cheese McMuffin on Canadian soil. 

When the time came for my mom to leave I completely lost it.  I was bawling like a baby and hugging her while she just laughed at me.  She was like, “Why are you crying?  You’re moving to Jamaica!”  The drama queen in me behaved as if I was going off to war to get shot. 

I think my outburst was one big ball of emotions releasing; sadness, excitement, anticipation, and total fear.  It was a weird feeling but at the same time, it felt so right and I couldn’t believe it was finally happening.  

I watched my mom walk out of the airport and I just stood there for a few minutes before I headed outside to have a last gulp of Canadian air.  Big mistake because while I was out there I saw my mom’s car leave the parkade and I bawled again. 

This was finally it. 

I was completely and utterly alone on this journey. 

I bucked myself up, went through security, took a picture of my plane through the window and waited to board.  I kept thinking to myself, “I can’t believe I’m not coming back in two weeks.” 

Seated in row thirteen, I gazed out the window at the snow-covered ground and was not sorry to be leaving the cold behind.  As we taxied on the runway tears streamed down my cheeks. I think the people beside me thought I was either mentally unstable or had a huge fear of flying. 

Who the hell cries on their way TO Jamaica?

But this was my first time grabbing hold of an actual life and doing something at least as adventurous as being a single mom for the last eighteen years. 

Don’t those two chapters make you wonder how on earth it took me SIXTEEN chapters to get to departure day? You should see all the following ones. Reading them still feels like a dream even though I’ve done this twice now!

I sometimes feel like I should spiff up the original book and add on what became eight more years of my Jamaica journey after it was published. But I’d need a mountain of cash and months of idle time to recollect and repurpose the entire journey.

ANYWAY…

This was really long! My apologies! But if you’re still here I’m honored to have shared a microscopic snippet of what turned into a massive chunk of my life.

Alexa….I’m raising a glass to you! Safe travels when your time comes and be confident in your decision. You got this!

My Mother’s Day mimosa in 2018, in Montego Bay, Jamaica.

Now it’s time to hear from the peanut gallery…that’s YOU.

I REALLY want to hear about your quest for Wildhood! Have you ever dumped life as you knew it to forge a new path?

It doesn’t have to involve something as big as moving far away. It can be anything that felt like a huge leap for you.

Please share in the comments!

If you’re fairly new here and have no idea WHY I moved to Jamaica or what I did there, I have a section of this newsletter called, Your Other Passport and following is what it’s about….

Did you know that a hidden gold mine exists for people who write about their favorite destination? Whether you visit the same vacation spot on repeat OR you’re madly in love with where you live, you can absolutely turn your favorite pin on the map into the most rewarding job and lifestyle on earth....without begging the tourist board to hire you.