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It’s a struggle as old as the points and miles game itself: should you use your points for a given redemption, or hold for something grander in the future? We’ve argued before that it’s not wise to stockpile points without a goal in mind.
Instead, you’re better off cashing your points and miles in for a desired trip, flight or hotel stay as soon as you have enough. Given that airlines and hoteliers have devalued their currencies with little to no notice, holding miles unnecessarily could leave you wishing you would have sprung for a trip while values were higher.
But, what if you dream big? Really big? What if you’re okay stockpiling points for years, knowing that valuations will change, in hopes of cashing in for that once-in-a-lifetime adventure? I’m in that camp, and I think it’s perfectly OK if you are as well. In fact, I routinely coach those new to the points and miles world to practice patience, and to consider saving their points for a trip that they would never pay cash for — even if money was no object.
The Importance of Goals
What’s not wise is to aimlessly collect points and miles for years with no idea of how or when you’ll use them. You wouldn’t save cash for years without directing it to an investment or at least having a long-term reason for maintaining liquidity, and you should think of your various points and miles collections similarly.
When the Chase Sapphire Reserve® launched with a now-legendary-but-dead 100,000-point welcome bonus, I wasn’t tempted to use them right away. Instead, I calculated my annual spend on the card and plotted a trajectory of roughly how many points I’d earn over the next couple of years.
At the same time, I eyed my growing balance of Delta SkyMiles — accumulated through hundreds of thousands of flight miles thanks to my job — and did likewise.
I then sat down with my wife and asked: “What’s a trip that would be atop our bucket list that we would never pay cash for, but would love to go on if it were free?” The answer was a business class trip from the United States to the Maldives, with as many days as we could afford in an overwater bungalow. Conservatively, a trip like that (for two) would cost around $20,000 if flying on Delta and its SkyTeam partners and staying in a top-tier property like Park Hyatt Maldives Hadahaa.
You can’t execute on a trip like that with just one credit card welcome bonus, but if you stack a few together over the course of two years and add in everyday spend, impossible dreams suddenly seem feasible.
Patience is a Virtue
While Delta has unfortunately done away with its public award charts, there was a time where you could exchange 120,000 SkyMiles for a round-trip business class award from the United States to the Maldives — assuming you could find availability, of course. It took me over 3 years to earn 240,000 total SkyMiles by flying, but I could’ve shortened that by applying for a Gold Delta SkyMiles® Credit Card from American Express, Delta Reserve for Business Credit Card or Platinum Delta SkyMiles® Business Credit Card from American Express.
During that span, I had many opportunities to cash out SkyMiles for shorter, less exotic trips. Instead, I bit the bullet and paid cash for every single trip, using those paid tickets to maintain my Diamond Medallion status while also building upon a pile of points that was slowly but surely getting us ever closer to our Indian Ocean paradise.
Once I had the miles, I needed even more patience. I called Delta’s reservation line and could only find business class award availability through SkyTeam partner Korean Air some 10 months out. In other words, even when I found the right dates to exchange miles for confirmed tickets, I had to wait nearly a year to actually fly.
That 10-month window wasn’t wasted, though. Thanks to my frequent work travel, I managed to secure Diamond elite status with Hilton. As a TPG reader, I knew that one of the best redemptions in the Maldives was the Park Hyatt — a chain where I had no status, and thus, no points balance. I also knew that you could transfer Chase Ultimate Rewards points to Hyatt at a 1:1 ratio.
With award nights at the Park Hyatt Maldives Hadahaa running 25,000 points per night, I’d need 175,000 Ultimate Rewards points for a weeklong stay. (By the way, this property is soon moving up a category and will therefore demand 30,000 points per night.)
I managed to spend my way to those added 75,000 Chase points over three years, and during the 10 month window between booking both the flight and hotel using points, I plotted a plan to status match from Hilton to Hyatt a few weeks prior to our stay. I knew top-tier Hyatt status would make me eligible for a room upgrade, provide free breakfast for myself and my wife (valued at over $100 per day in the Maldives) and free snacks during an evening manager’s reception.
Status matching to Hyatt is once per lifetime, and I knew I’d never maintain that status after the trip, but I calculated it to be worth having for that single week in one of the most remote, expensive places on Earth.
While we could’ve embarked on many more trips while we were patiently saving for years, the wow factor of a free week in the Maldives was worth it for us. A long weekend in Miami or visiting family in California, while certainly a factor in one’s budget, is typically doable by dutifully saving cash. Saving enough to purchase a four-door sedan, then diverting those funds for a a single week of frolicking, isn’t just more difficult — it’s probably a terrible financial decision even if you can swing it.
After a decade of earning and burning, my most satisfying redemptions are those in which I know I would never execute on without points. While I wouldn’t judge someone for dropping 10,000 miles for a quick visit to Austin from Los Angeles, it’s extremely difficult to ever save enough for the most aspirational of holidays without a high degree of self-control.
I’m OK with risking devaluations for the hope of a trip that simply wouldn’t be possible without points and miles. Case in point: I saved SkyMiles for another three years to book yet another business class ticket to the Maldives for later this year. Delayed gratification never felt so good.
All photos by the author unless otherwise noted.
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