The Terror Of Jumping Out Of A Perfectly Good Airplane

How I Completely Changed The Course of My Life After 40 Years

Have you ever wanted to be someone you weren’t? Or wanted something you’ve never had?

The quote “If you want something you’ve never had, you must be willing to do something you’ve never done” has been falsely attributed to Thomas Jefferson forever, but there being no evidence he ever said or wrote it doesn’t make it any less a wise quote.

And honestly, my first two questions are rather ridiculous as who hasn’t wanted both, right?

I was wanting to be someone else for as long as I could remember going into 2017. Someone who had accomplished more than I had. Someone who had been to more places than I had. Someone who knew more about the topics I was interested in than I knew.

There isn’t a soul among us who doesn’t have a list of dreams they hope to achieve someday.

And we can all be divided into three categories: those who pursue them, those who don’t, and those who haven’t learned how to pursue them.

Or as Les Brown says, “There are winners, there are losers and there are people who have not yet learned how to win.

I was ready to do something I had never done. I was ready to learn how to win.

It was 2017 when I listened to Steve Harvey in a clip titled “You Gotta Jump To Be Successful” (you can listen to it here). In it he speaks to the fears we often have in doing something new, and the people we think of as successful are the ones who, despite their fears, did the thing they were afraid of anyway.

They jumped. 

Here is how he starts.

Now, a lot of times you stand on the cliff of life and you see other people soaring by.  Gliding down like a bird flying through the air. 

You see people soaring, going to exotic places, you hear about them doing wonderful things.  They’re flying by, and you know why…’cause their parachute opened. 

But the only way to get your parachute to open so you can soar, you got to jump…You got to take a leap of faith.  You got to dash off that cliff and you got to jump out there as far as you can. 

After working at the same company for almost nine years, and feeling like I was wasting away, not doing anything to become who I wanted to be or achieve any of what I had told myself I wanted to achieve, and doing work that didn’t matter to me just to get a paycheck, I finally mustered the courage to jump.


Jumping Out Of A Perfectly Good Airplane

I had been working for a large publicly traded company in the healthcare space, managing a marketing team. My days were spent inside of spreadsheets and powerpoint presentations—sharing them with executives who didn’t care about the same things I cared about.

My team’s job was to get people to visit our website, and for those people to click on as many pages as possible.

The more pages people clicked on, the more advertisements would load on the page, and the more money the company would make.

Every quarter I was invited to sit with the CFO, CEO, President, and a handful of others responsible for the company and report on my team’s efforts.

Whenever they wanted to present to investors that the company was doing better than it actually was, I was instructed to send out e-newsletters to anyone we had an email address for—and we had email addresses for millions of people.

Those emails had links to our website, with all of the click-bait titles we are familiar with, that would result in millions of page views.

I never went to school for business, or marketing, or healthcare–or how to spam website subscribers. My degree is in literature and history. My passions have been creative writing, exploring cultures different from my own, wine, and building things with my hands.

When I failed at finding sufficient ways to turn those into profitable ventures (and let’s be honest, I didn’t try very hard at that), I abandoned them for what was easy.

The more successful I was at my company, doing what I disliked, the more my paycheck grew.

As as I was living in one of the most expensive cities in the world–New York–I ended up prioritizing that paycheck over my passions. And I was afraid of unplugging from it all.

I had been drifting away from what spoke to my soul and towards more and more money for so long, I began to doubt those passions and if I was capable of doing anything else than what I had been doing.

If they were true passions, then wouldn’t I being doing something about them? If they truly mattered to me, then wouldn’t I do more to protect them from the greed I was being consumed by at my job? If I hated my job so much, disliked the little I thought I had accomplished in my life and craved to do more with it, then why wasn’t I?

There is a romanticism to the idea that “one day everything changed”, but it was over four painstaking months of my working through a twice daily journaling process where I challenged all of my known fears and mapped out what I would do if I decided to change everything about me.

I had become too comfortable with being comfortable. I had become too passionate about being able to afford to live in my city, and too limiting in my view of my options.

Turning forty years old wasn’t an insignificant factor, and so the journaling and the age culminated in my using the next year to jump.

It was “one day,” however, that I made a list of the things I had never done that I was ready to try. And in those next twelve months I did each of them: 

  • Quit my job.
  • Enrolled in a wine program at the Culinary Institute, and after completing the program passed my Sommelier Certification exam.
  • Traveled to Europe visiting twenty-one cities and towns in five countries, stopping off at as many wineries as I could fit into my schedule.
  • Packed up my apartment and moved to San Antonio, Texas after living in New York City my entire life.

I didn’t have a job waiting for me in Texas, and I didn’t know what I would do for work when I got there.

But I thought at the time that it was, as Steve Harvey said, “out there as far as I could go” in the little more than a year since I quit my job.

They say that we are always capable of at least 20% more than we think we are.

So over the next twelve months I found myself pushing a little bit further: what else had I never done?

I moved again, this time to Austin, Texas for a job opportunity (because a bank wouldn’t lend me any money to buy a house…something I had never done…if I didn’t have a paying job)

I bought my first house (back in San Antonio), and a month later bought my second house (again in San Antonio).

I became a landlord…and turned both houses into long-term rentals, attempting to manage them from Austin.

When the pandemic forced us to work from home, I moved back to San Antonio and bought my third house, turning this one into a short-term rental…and became an Airbnb host.

I got engaged to the greatest representation of humanity I’ve ever met, my now life and business partner, Fernanda.

Fernanda and I, along with her son, moved in together, into the fourth and final house I bought within those twelve months.

I had jumped.

Further than I had ever jumped before. Further than I ever thought I would or could ever jump.

I became a home owner, a landlord, an Airbnb host, a small business owner, a fiancé, and a step-dad.

I would like to say that I was proud of what I had done, that there was some satisfaction in having changed nearly everything about who I was and what I was doing just two years earlier, but I spent nearly every one of those days being a combination of scared and terrified.

Everything I had done over the those two years seemed to be new, unfamiliar (spoiler: that hasn’t changed; and still terrified).

I didn’t recognize myself (another spoiler: I still don’t).

Two years into it, and I still felt like it was just yesterday that I was putting yet another spreadsheet or powerpoint presentation together for a company thousands of miles away.

Looking back on the time, I can admit that I was enjoying some of experiences (like my engagement).

But Steve Harvey’s words didn’t conclude with a simple call to jump. And I had adopted his calling more seriously than just a passing video, and was waiting for the rest of his words to happen.

Not Single Spies, But in Battalions

Harvey goes on to warn about the process.

Now here’s a problem.  When you jump, I can assure you one thing.  Your parachute will not open right away. 

No, that’s the fear part. 

I promise you your parachute will not open right away. 

You gonna hit them sides and them rocks, you gonna get some skin tore off on those cliffs, you gonna tear your back out on that cliff, you gonna cut yourself, you gonna get wounded, you gonna get some tears and stuff like that.

You’re going to be bleeding pretty bad. 

We celebrated our first meal in our new home together excited about the life we were starting together, and despite my fears, I was feeling blessed. Lucky, even.

We were officially entrepreneurs, landlords and short-term rental hosts. We had survived the covid-19 pandemic without exposure.

Yes, I was scared about all of the financial responsibility I had taken on, but the pandemic had yet to affect us (neither one of us had lost our jobs like so many others; and the most we felt the pandemic at that point was deferring the rent for our long-term tenants for a few months during the early months of the lockdowns).

But it wasn’t long after that I began to feel some of the scrapes and cuts Harvey talked about and that I had been waiting to happen from the beginning. 

First Fernanda, and then I, was laid off from our jobs.

Then my tenants didn’t renew their leases on houses #1 and #2.

After four months of making my mortgage payments without any rental income, I still couldn’t find new tenants who could afford what I needed to make to just break even with my monthly expenses.

House #3, our first Airbnb, was approaching it’s half year mark and was still not bringing in enough money to pay the monthly bills without dipping into savings, and we had our first bad guest experience where their damages required us to cough up money to repair.

Fernanda and I finally made the decision to convert houses #1 and #2 into short-term rentals in the hope that we would have better luck renting to travelers; but it required us to invest about $10,000 per house to make them vacation rental-ready (short-term travelers don’t bring their own furniture).

With four mortgages; tens of thousands of dollars in total set up costs for the now three short-term rentals (and not counting all of the downpayment and closing cost money that would take years to see back); no full-time jobs yet; no staff and with Fernanda and I serving as the property managers, plumbers, electricians, landscapers, cleaners and whatever other skill set was required and where we didn’t have the money to pay for a professional, I was feeling more than I ever had before the scrapes and cuts and tears and wounds, and wondering if my parachute was ever going to open.

I had taken what I had saved for years and risked it all on real estate in the hope of one day it contributing to my parachute opening and my soaring.

And while I knew it wasn’t going to happen overnight (or even over a few years), I didn’t know if I would have enough blood to last until my chute opened. 

Years one and two of this journey, in comparison to year three, felt easy. I jumped further than I ever imagined possible for myself, and nothing bad had happened. Those two years I was mentally kicking myself in the ass for not jumping sooner.

But then the physics kicked in.

Think about it in terms of standing on the high diving board for the first time in your life.

You jump up and out as far as you can go, and for a short while you are flying. Nothing but the cool air touching your skin as you ascend up and out. And then gravity pulls you back down, and without any form you awkwardly strike the water hard.

If you thought the beginning, the seconds after the jump, was going to be how the entire experience played out, you are quickly and painfully reminded how wrong you were.

Well that is what I experienced. I jumped. For a time, I felt like I was flying without even the need of a parachute. Gravity hadn’t happened yet. But when it did, my parachute hadn’t deployed.

Gravity was pulling me towards the sides of them rocks. 

Wile E. Coyote Has Nothing On Me

Now, if you are expecting this story to transition to how it all worked out, and how I am now writing to you from my multi-million dollar villa, retired decades before 65, living off of other people’s money, and that you can too, I am going to have to disappoint.

If you are scratching your head at how rich I must have started out to be able to buy four houses in a year’s time and live off of ample savings, also going to let you down. There are enough get-rich-quick and self-help gurus on the web for those stories.

And I don’t know how honest of a “jump” mine would have been if I used wealth to buy the properties I did. I can assure you that it is far easier than you think (than I thought) to have lenders lend you money to buy multiple houses.

There is always another lender who will say “yes” after someone else’s “no”. Mortgaged-to-the-hilt is an expression I have come to know and live (and just like the origins of the expression, alluding to the handle, or hilt, of a sword, where the only portion that remains out when the weapon is plunged all the way in is the hilt, I have felt on more days than I care to remember that in the last two years I have gone and stabbed myself with a sword).

And I have been measuring my savings in months-long rather than years or actual dollars, as in “how many months can I afford to keep living off of savings before I hit the dirt like Wile E. Coyote?” 

But here is how the story continues.

I am still waiting for my parachute to open (or rather, I am still learning what I need to be able to pull on that rip-cord.)

I am still hitting “them sides and them rocks”.

I am meeting you here still very much in the early part of my jump.

I don’t know if and when my parachute will open. I don’t have all of the answers to my questions, or yours.

This blog is not meant to share the secrets of how I went from being poor to rich, and how you can too (I’ll let you know when I get there). It is not coda, not the end of the story told to you in retrospect. It is not meant to be a reflected conclusion but rather a living journey. And it’s one I am deciding to not share with only myself in my daily journaling anymore.

I have decided that perhaps it would benefit both me and others if I shared the most instructive, most entertaining, most consequential parts more publicly.


Because I have really adopted Steve Harvey’s words as my own. And he concludes his talk with this:

But here’s the other caveat, let me teach you this right here.  If you do not jump, I promise you one thing: you’re parachute will never open.  So you’re safe, but you’ll never soar. 

You got to jump.

I knew that my parachute would never open while I was working at a job I hated in a city I couldn’t actually afford not doing anything that spoke to any passions. At least now my parachute has an opportunity to open.

And I would rather spend the rest of my life with the uncertainty of whether it will open than the certainty that it will not.

And because that feels so much better than anything else I have ever felt, I thought it a good time to share my jump with others. I am also hopeful that anyone who finds these posts valuable will share their dreams of jumping with me.

And together, perhaps we will both help one another soar.

What I Promise To Share With You

I am not a professional writer. So this blog will have errors. I welcome your feedback, comments, recommendations, advice and direction. Without it, I am just journaling for myself, and that is not the objective of this blog. 

But I hope to work out my passion for writing here.

I am not a real estate mogul (despite my adolescent nephew thinking otherwise). So I only know about what I have done, and what I have done has only been a few years of experience.

I am learning something new everyday about the space I am in, about how to be better at what I am doing, and will not pretend like I have more answers than I do.

But I will look to share what has worked for me in the hopes that it will benefit you, in whatever jump you are either thinking about making or perhaps are in right now.

I may technically be a Certified Sommelier, but I don’t practice it for a living, don’t teach it, and don’t generally spend more than $25/bottle on the wine I drink.

But I will share with you what I am drinking, what I have drank and where (especially those incredible times in Italy, France, Spain and Portugal, where I drank the wine on the same piece of land where the grapes grew that made it). And both why and how wine is as appropriate an analogy as any for life and our time defining our own version of it.

And I am not native to San Antonio or Texas. But if you found this blog because you are thinking about visiting, I will share what a native New Yorker loves most about his new home.

So is this a blog about writing? About real estate? About rental homes? About wine? About San Antonio? If it is, does that not sound like it is all over the place, a little too much so for the attention of any sane blog reader?

Perhaps (more than likely, actually). 

But I would describe my objective for what I want this blog to be about as the importance of jumping, and how my jump has taken me through the worlds of international travel, real estate, wine and Texas.

Your time is valuable. And there are countless options for content across all of the areas I could or would speak on that are freely and readily accessible to you. 

So every post you decide to read I promise my objectives will be:

  1. To inspire you.
  2. To humor you.
  3. To inform you.

And every post I write, I promise to be:

  1. Interested in the topic.
  2. Interesting in how I share the topic with you.
  3. Intimate in sharing myself with you.

So are you my ideal reader? You are if:

You are interested in becoming a better version of yourself.

You are interested in having something you’ve never had, and so are ready to do something you’ve never done.

You are interested sharing your journey with us (Fernanda and myself, and all who are jumping).

You are interested in thinking about any of life’s experiences as opportunities to learn how to be good at the thing you want to be good at (as in, how meeting a master wine maker in Piemonte, Italy can teach you how to be a successful operator of a vacation rental home).

And in the interest of full transparency, let me say at the jump that while I am deeply interested in everything that I will be writing about, I can just as easily continue writing about it for my own amusement.

Journaling my thoughts and never sharing them with an audience. But in sharing them with an audience, and where that audience may one day be interested in visiting San Antonio and need a place to stay, or may know someone interested in visiting San Antonio who needs a place to stay, then this blog is one of the ways for me to reach that audience. 

So now that we have introduced ourselves to one another, let’s dive right in.

And I can think of no better place than with a master winemaker in Piemonte, Italy who taught me how I should aspire to be when opening my home to strangers—before I knew that I would be opening my home to strangers.

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Published on: April 15, 2022  -  Filed under: Life Lessons  -  Tagged: , ,

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