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Mom, birthdays, and choices…

A favorite pic of Mom...
A favorite pic of Mom…

So today is Mom’s birthday, she would have been 82. I find it rather odd that I let myself schedule a sailing trip to start today of all days. Maybe I should have put today aside, but I didn’t. Maybe that’s part of the milestones becoming less off-putting than previous years. Or maybe there was another reason I don’t even know about yet.

It’s not due to forgetting her birthday or anything like that. I have been thinking about my mom quite a bit lately, and not just because of her upcoming birthday. It’s because I found myself feeling guilty. Guilty because I promised myself that I’d write a piece about a strange or funny experience that I shared with her on the anniversary of her death back in July. Much like what I did with Pop on his birthday. Though I had tons of material and memories to pick from, I found myself just not being inspired to write about any of them. Which I found both strange and frustrating.

Oddly however, I did find myself mentally replaying a pivotal, if not brief, conversation that I had with her a long time ago. One that when I look back now, appears to have had a strong hand in sending my life off into the rather unorthodox direction that it ended up going, for better or for worse.

I’ll set the stage…

About 20 years ago, I found myself at a crossroads. My life had not been going the way I had hoped the past couple years, since I’d gotten out of the navy. Things just kept not working out. A serious relationship failed, my business had gone down the tubes and my sales career, which at one time seemed promising, started to tank.

I found myself financially desperate and rather hopeless. My future prospects were bleak. There were no decent job prospects, other than bartending and waitering in Orlando on the horizon. I was deep in debt with a house that I could no longer afford to keep and on the brink of foreclosure. Going back to college, which maybe I was open to doing at the time, seemed like a distant pipe dream.

All I can see in my future was more struggling, mediocrity and little hope for freedom or happiness. I knew that I needed to take drastic measures. I put the house up for a quick sale in order to beat foreclosure. Luckily, I had a good agent who found a buyer, ready to do a fast deal at my asking price.

Despite the fact that I was deep in the hole with my mortgage, credit cards and poorly thought out loans, I somehow still managed to eek out a few thousand dollars profit after all was said and done.

Wow, a few grand and no obligations or commitments whatsoever. A huge change from my situation just a week or so before. When did this ever happen to me in the past? Never to be sure. Yet again, I realized that you could completely change the direction of your life with just one simple decision.

Now, I stand with the power to induce even more change with my next few decisions. Or, on the other hand, I would do nothing of the sort. I’d play it safe or stupid, and things would just stay the way they are. The money would get wasted on pointless shit, put into a doomed business, or invested badly. Whatever the case, it would soon be gone with just a few stupid decisions, and I’d be back at square one.

I considered all of my options. What should I do with this small cache of opportunity?

I could go back to school or invest it in a new business, sure. I could do something wise to get back on my feet and prosperous again. No doubt that I could and should do something logical with it.

Nonetheless, despite all the “logical” and “safe” options that banged around my head, all I can really think of doing with it was one thing. Getting a plane ticket off to somewhere new and exotic. Somewhere I can start from scratch, and even pursue my lifelong passions of traveling the world, and even my dream of sailing the seas. Things I have wanted deep down for most of my life.

I saw myself going to somewhere in the Caribbean, somewhere I can work and figure out how to get on boats. After some more pondering and researching, the Virgin Islands started making sense to me.

After thinking long and hard about it, I decided that perhaps this was something that I should pursue, and now was the time. There was also a lot of apprehension, fear, anxiety, and pressure at play. On top of that, I felt like my window of opportunity to “escape” was closing on me fast. Along with Clint, my roommate at the time that the house was sold, we had moved into a temporary apartment while looking for another place somewhere around Daytona. We even considered the possibility of finding a house to buy and fix-up while we were living in it, then turn around and sell it for a tidy profit.

I knew that if I signed a lease, sales contract, or something like that, that I would be stuck in Florida, and probably for longer than I would like. It would be that much harder for me to leave if I signed any dotted line. Despite the fact that it was probably unfair to my friend and roommate to bolt, I had to at least attempt to do it now. Right now.

Not yet really knowing how to wrap my head around this whole concept, I consulted with my parents. I first talked to Pop. He was rather diplomatic and sympathetic to my talking to him about my dreams and zany escape idea, for the first time in a very long time. Despite the passion that he saw in me to make a real change, he thought that I should at the very least use the money to get back into school. He’d always wanted me to get an MBA, and maybe this was how I can start back on that path. Besides, he reminded me that he had just moved back to Florida after nearly a decade in Chicago just so he can be near Nick and me.

He didn’t push or inflict any guilt. But he did basically imply that he thought I should stick around and keep trying to make something of myself, at whatever the cost.

A couple of days later, I called my mom. She was living in upstate New York at the time, running her jewelry business. Things had been strained between us over the previous few months (which was typical). Nonetheless, I still felt like I should call her about this particular matter. I told her my situation and everything that was going on in my head. Particularly about how hard it was for me to come up with any kind of plan or scenario that would be right for me, other than to just pack up and go to the Virgin Islands.

She listened rather intently, which was pretty rare of her, to be honest. She usually loved dominating our phone conversations with nonsense and even gossip about everybody. And usually it involved people that I didn’t give a rat’s ass about.

After I was done telling her all my thoughts, she didn’t hesitate to respond. “Tony, if you think you should go. You should go, just go. Vai!“. I found myself a tad surprised at her response. I fully expected her to give me a driveling speech about how I should be practical, get serious and focus on getting my life in gear and making money, etc., just like Pop did. That’s pretty much what she’d always said to me before in different ways and different conversations anyway.

This time though, she just said I should go.

When I audibly sounded confused by her response, even wondering if there was a catch, or the inevitable “but”, she took control. “Hey! Tony, what do you think I did? When I was about your age, your Zia Maria and I both finished school to become teachers. As soon as I graduated, I decided to leave Italy. I told everyone that I was going to Argentina, and that I would teach there. Everybody thought I was crazy.” This surprised me, we’d never really talked about the circumstances regarding her taking off to South America before.

“My mama cried for three days, Tony, begging me not to leave. My papa threatened to never talk to me again if I left. My brother and sisters all made fun of me, telling that I was crazy for wanting to go so far away at such a young age to a place, with no family. Maybe I was. My parents talked to Maria (her younger sister) into going with me. They also told her to talk me into coming back while we were over there. She went back in less than a year. But I didn’t. Something inside told me that I had to go and not go back. You should go too. Maybe it’s your time, your destiny. You won’t know if you don’t go.”

This was an eye-opening revelation to me. It made everything somehow make more sense. She helped make it clear that this was my time to go. Thanks to her inspiration, and somehow making me it feel more “ok” about it, I bought that plane ticket to St. Thomas. I said goodbye to my family, pets, and friends, and left.

That one decision made all the difference, changed the course of everything and is probably why I’m doing what I’m doing today.

Sure, albeit a bit later due to getting spontaneously married and having my plans derailed for more than a decade. 😛 . Luckily, I found my way back on track, just before it was too late.

So on this particular birthday, I just want to say how grateful I am to my mom. Who, despite everything that went wrong with her and between us over my life (and there was a lot, believe me), came through for me when I needed her to the most.


  1. Leigha Morrison says:

    hmm , makes you wonder…. hope you have a wonderful trip…….

  2. leila says:

    hmmm.. and here i am, freshly landed in st thomas… haha

    happy birthday to yr mama, and cheers to her for giving you good advice! sometimes a little push is all ya need to follow yr dreams!

  3. Debbie says:

    great story tony…your mom certainly did change the course of your life by encouraging you to go on that big adventure to st’s to your mom and her supporting you to follow your dreams…she’s happy to know that you are on the the course you’ve always wanted to be on…. keep on sailing my friend!

  4. Lynn says:

    Another great story!

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