My big-picture points strategy — and, really, my big-picture life strategy! — is to figure out what I like and what I want and then do more of it. My interest in points has always been to turn my everyday spending into amazing “free” travel experiences.

Around the beginning of each year, I reflect on my travel priorities and points strategies for the year ahead.

• We’re going to try to visit Jackson Hole, Wyoming and Puglia, Italy for vacations during 2020, and I might try to turn my annual Tokyo trip into two — we’ll see. Plus work/life trips, and whatever comes up.
• Over the past few years, I’ve become even more interested in thoughtful boutique hotels with taste and culture, and even less interested in big, boring, global chains. So you’ll notice that priority in my coverage.
• I’ve also become hopelessly hooked on lie-flat seats on overseas flights (or, really, any long flights), so I can sleep, work, and relax in comfort. So I’ll continue to focus more on clever ways to sit in business class than exploiting gold-flaked luxury travel pr0nz.

I then take those big ideas and decide which cards and loyalty programs to use, keep, cancel, or add, as benefits often reset around the beginning of the year.

As you start to plan out your travel goals for the year, think about what might help get you there: What airlines fly most conveniently to your destinations? Are there specific hotels you’re interested in checking out? What rewards programs or credit cards can help with those? It’s going to be different for everyone, but that’s how to keep your points strategy working for you.

For 2020, I’m mostly going to keep things the same as last year.

For credit card spending, I’ll continue to focus on mostly earning Chase Ultimate Rewards points — which are valuable and versatile — plus some American Express points.

I’ll continue to mostly spend those Chase points for airfare on American Airlines, hotel bookings through its travel portal, and by transferring them to other loyalty programs, such as British Airways and Hyatt, to book award flights and rooms.

I’ve had a tougher time getting good value from Amex points, but I’ve found a few sweet spots lately — mostly by transferring them to other programs — and will do a full issue about that soon.

Specific-card-wise:

• I use the Chase Sapphire Reserve for travel, dining, and international purchases, the Chase Freedom (refer-a-friend link) for its rotating quarterly bonus categories, and the Chase Freedom Unlimited (refer-a-friend link) for everything else. More here on the Sapphire Reserve and here on my overall Chase strategy, but the big idea is to roll all of those points onto the Sapphire card, where they’re worth the most.
• I also have a Chase Ink Business Preferred (refer-a-friend link) that I use for business purchases.
• I use the Amex Gold card (refer-a-friend link) mostly for grocery store purchases, which earn 4 points per dollar, and whenever there’s a special Amex promotional offer.
• I use the Apple Card mostly for Apple purchases, including recurring iPhone Upgrade Plan and iCloud payments, which get 3% cash back. More on the Apple Card in a future issue.
• I might add the Amex Platinum to my wallet this year, but I’m not particularly inspired by any other cards.
• I’ll likely get rid of the Amex Bonvoy card — I simply have no interest in Marriott — and the Barclaycard Aviator Silver, which is no longer as helpful for earning credit toward American elite status.

For travel loyalty, I’ll continue to focus mostly on American Airlines and the Oneworld alliance.

While many people just fly what’s cheapest, I’ve found that the benefits of accumulating points on a single airline is worth it, even if it costs a bit more. And if you fly enough, earning elite status, which has perks including free access to extra-legroom seats, international lounge access, and occasional business-class upgrades — plus generally better service from the airline.

I flew less in 2019 than in 2018, thanks to my new business and time overseas, and I’m not sure how much flying I’ll do for work in 2020. That means the end of American’s Executive Platinum status for me, for now. But from my home base in New York, American still makes the most sense for the places I fly the most: Los Angeles, London, Paris, San Francisco, Chicago, and Tokyo.

For many New Yorkers, Delta is a better option. If you’re based in San Francisco, it’s probably United or Alaska.

American, like most big airlines, has done a bunch to make its points less valuable over the years, such as increasing the number of miles you need to book award tickets. But its points are still useful for free flights and upgrading coach tickets to business class. For our upcoming flight to Paris, we’re already confirmed in business class via cash-and-miles upgrades.

Last, I’m not going to be loyal to any hotel chain this year.

When I was traveling every few weeks for work, I focused on Hyatt to consolidate points earnings and perhaps receive some perks. But even with the second-highest Hyatt status the past couple of years, I haven’t found it worth it, beyond occasional later check-out and earning some bonus points. I keep a Chase World of Hyatt card (refer-a-friend link) active — you get a free night every year, which more than pays for itself — but I didn’t use it otherwise this year.

Mostly, I just have no interest in big, boring chain hotels, unless it’s something special.

Instead, I’m going to keep trying interesting boutique hotels and chainlets, like The Line, Palihotel, Tokyo’s Trunk, The Proper, Ace Hotel, etc., booking either with Chase points or through a third-party booking site with its own loyalty program, such as Hotels.com or Hotel Tonight. And for anything more than a few nights, you’ll probably find me in an Airbnb.