Back at the end of June I started my trip around the world by hopping in an Uber in front of my house en route to Tampa International Airport. I was actually going to drive over and park in the Economy Lot, but 19 days x $10 per day…(you get the idea), so on a whim I checked my Uber App to see what was available, and what the cost to the airport would be.

I live south of downtown Tampa in a strictly residential area, and being just far enough from the city means that Uber drivers have never been very abundant in my neighborhood. The one time I took an Uber to the airport a couple years ago, it cost around $60, so I was pleasantly surprised on Sunday when I checked the price and the app said the estimated cost would be $28…and a car was only 3 minutes away!

Anyone with an American Express Platinum card should know that one of the perks of the card is a $200 per year Uber credit. Unfortunately Amex likes to make it as hard as possible to use it, so they spread it out over 12 months ($15 per month Jan.-Nov., and $35 in Dec.), and if you don’t use it each month you lose it. I hadn’t used my $15 credit for June yet, so subtracting that from the $28 ride would bring my cost down to $13 (before any tip).

To make the deal even better, just a week earlier Amazon was running a special for Discover Card holders whereby using 1 Discover Cashback point on an item sold by Amazon, would save you $10 on a $30 purchase. This worked on several gift cards, and I happened to use this promotion to buy a $30 Uber gift card for $20, further reducing my out of pocket expense on my airport ride.

As I was writing this I was sitting in the beautiful city of Edinburgh, Scotland, so I wasn’t exactly focused on my trip home from the airport, but when I eventually returned back to TPA it was a new month allowing me to use my $15 July Uber credit!

That’s just one very small illustration of how keeping track of the possibilities in this hobby will make you critically think each situation, and allow you to do things you didn’t think were possible.

All this brings me to my inspiration for this post. When I tapped the Uber app and requested a ride to TPA, it very quickly connected me with a driver. It told me that his rating was 4.98, and that he was “Known for Great Conversation”. Yes… it actually said that!

Now that may be a common thing in the app, but having used Uber over 200 times, I had never seen that.

Charles arrived a couple minutes later, and what followed had to be the shortest 40 minute ride to the airport ever! When I hopped in and he confirmed what the app had told him (that my destination was the airport), we had a very cool conversation about travel, and how so many people dream of it…but never realize their dreams.

I found out that Charles was 47 years old, had 3 college degrees, including an MBA, worked 3 jobs including coaching high school football…and of course driving for Uber on the weekends. He said “yeah, I’m kind of a workaholic!”

He asked me which airline I was flying out of TPA, so he could drop me off at the right spot, and when I told him British Airways, he was naturally curious about where I was going. I said “well, I’m going to London tonight, but in the next couple of weeks I’ll be visiting 6 countries in Europe before continuing east to Hong Kong and then eventually on to New York before returning home to Florida.”

I went on to tell him that my flights later that week from Brussels to Hong Kong and Hong Kong to New York (about 25 total hours) were going to be in flat-bed business class!

He seemed shocked by all that, but I assured him that without using airline miles and hotel points, something like this for me would never be possible. And let’s be honest, for MOST people something like this wouldn’t even be something they would know to dream about!

Only a tiny fraction of people have any idea that for 92,500 Alaska Airlines miles and $120 or so in taxes and fees, you can fly almost all the way around the world in incredible luxury!

Charles went on to tell me that he has done some traveling, mainly around the Caribbean, but that he has always dreamed of going to faraway places. I asked him where, and he told me he always wanted to visit places like Korea, where his dad was stationed in the military, and Japan, and the Philippines, where he had heard it was beautiful…

I told him that for a long time I had those same thoughts, but one day I decided to stop waiting for “the right time”, because I realized it may never come. I wasn’t trying to minimize his dreams, but only to stress that for me traveling has become such a passion, that although I kind of wish I had started this quest sooner, I couldn’t be happier about what travel has brought to my life.

I knew I only had a short time, and a 35-40 minute Uber ride with a stranger is hardly the ideal venue for life inspiration, but as I usually do when I hear people talk like this, I tried to give him some idea of the endless opportunities out there to actually realize those dreams, and not just once but over and over.

I suggested to Charles that he should do a little research into the miles and points world, and that if he did he would be surprised what he might find. I’ve made similar suggestions many times before, but I was thinking this time might be a little different since I had just told him where I was headed. Maybe this would be a little more inspirational than the other times? Who knows!

I’m realistic in the knowledge that even a basic search and a little reading is not enough to inspire most people to learn this hobby. It requires a full commitment to get the most valuable return, and with the goalposts constantly being moved, that gets harder all the time…

The Wrap Up:

The world has never been smaller and more accessible than it is today. Budget airlines and falling airfares bring dream destinations within reach, and miles and points (and other money saving strategies) can create opportunities most people don’t even realize exist. I enjoy sharing what I’ve learned, but most conversations about the matter are “one and done”, and understandably so since it can all be quite confusing.

The description of Charles in the Uber app as being “known for great conversation” was right on the money, and after hearing about his education and work history it was obvious that this man possessed a ton of drive and perseverance. Those qualities are important when going down the rabbit hole of miles and points possibilities. I tried to get the point across by stressing that the dream can be real, and it is achievable, and that a huge dose of skepticism is natural when you’re talking about traveling for pennies on the dollar.

As he dropped me off for my flight he seemed interested, and he said he was going to “check it out”. I have my doubts but I’m hopeful…and now I’m sitting here wondering if he did that first Google search…