Last weekend, I was out for drinks with my brother and we got into an argument about who was going to pay the tab. I wish I could say it was because we’re both so generous. Quite the opposite: We both wanted the points.

Whoever didn’t pay that night was going to Venmo the other person their share, of course. But because we each have the American Express® Gold Card — a card I recommended because he travels regularly and spends a good amount on food — the bill gave each of us a great chance to earn rewards.

I ended up letting him pay because I knew I wouldn’t use the rewards anytime soon. I’ve been sitting on a healthy points balance that I don’t plan to use until my trip to Iceland next year. 

While we waited for his card to come back, he bragged, “I have almost 200,000 points on that thing.”

“That many?” I sighed and did the math. “That’s at least $2,000 in travel,” I said. “When’s the last time you used them?”

Turns out he hadn’t used any points since he’d gotten the card in 2023. “I just haven’t had time to travel.” He hadn’t used any points in two years? It sounded ridiculous. What was the point of earning them?

Then I realized I wasn’t so different. I’d only ever used my own rewards once since 2023, despite having earned almost 180,000 points. It got me thinking: What’s been holding me back?

Why it never feels like the right time to use points

I’m a seasoned rewards card user, so I know plenty about earning points. But I’m still new to actually redeeming them. 

Maybe because I’ve worked so hard to optimize my rewards-earning strategy, I tend to treat my points balance like coveted treasure. After all, aren’t “points” and “miles” just another way of saying “money?” 

It’s only natural that, as with money, I don’t want to waste points. Plus, keeping track of point and mile redemption values can be exhausting. I’d likely be much more comfortable redeeming my points if I didn’t have to worry about maximizing their value — if I always knew exactly how much they were worth, as I do with a cash back card (or at least if there wasn’t such a wide range of potential values). Then again, if points had a fixed value — say of 1 cent per point — they might not be worth earning over cash back.

I tend to treat my points balance like coveted treasure…[but] keeping track of point and mile redemption values can be exhausting.

— Brendan Dyer, Bankrate credit cards writer

Advice for overcoming redemption anxiety

Though you’d think my credit card knowledge would give me all the confidence I need to redeem my points regularly, it seems to have only made me more worried about getting it “wrong.”

But for my colleague, credit cards writer and Certified Credit Counselor Ryan Flanigan, knowledge is power. 

A travel rewards guru famous at Bankrate for his binder full of close to 50 credit cards, Ryan is always prepping for his next big trip. His strategies for finding high-value transfer partners, redemptions and sign-up bonuses have helped him see the Northern Lights, visit Australia and more, all using rewards, often flying business class or staying in luxury hotels.

I asked him to share some insight about how he avoids redemption anxiety and decides between using points and miles or cash to book travel. Given the great rewards redemptions he’s had, his advice surprised me. Here are a few of his tips.

“Earn and burn”

“When points can save you money, use them,” Ryan says. “You may not always get the ‘ideal’ redemption value, but if you can keep more money in your bank account, you’ll be better off.”

While using Bankrate’s point valuation guide to get a sense of what points may be worth is a great starting point, Ryan says you shouldn’t stress about getting maximum value. Instead, aim for a minimum value you’re happy with. A good rule of thumb, Ryan says, is if Bankrate values a program’s points at 1 cent or higher, make sure you get at least that much value when you redeem those points.

“If you have a sizable amount of points, there’s almost never a reason you should pay cash, unless your redemption has a really low valuation,” Ryan says. Though it’s tempting to wait for the perfect redemption opportunity — and getting a high value for your points can definitely make you feel better about using them — that chance may never come.

“I don’t think of points like money,” Ryan says. “You save and invest money, and over time, it grows. Points don’t grow when you save them. In fact, they can quickly lose value. Redemptions that offer great value can disappear overnight. My points and miles philosophy boils down to three simple words — earn and burn.”

I don’t think of points like money…My miles and points philosophy boils down to three simple words — earn and burn.

— Ryan Flanigan
CCC, Bankrate credit cards writer

Everyone will maximize points differently, Ryan says. So instead of stressing over the perfect time to redeem rewards, I should develop a strategy based on my unique travel needs. 

I plan most of my trips almost a year in advance, so even if I assume a lower-end redemption value, I can get a general sense of how many points I’ll need to earn. Once it’s time to book that trip, I should redeem the points. If I’m getting my own minimum redemption value for my points, there’s rarely any benefit in waiting.

With this mindset, I can see my anxiety becoming more manageable — I’ll know how many points I need to earn and when I’ll need to redeem them. No more what-ifs or second-guessing.

Evaluate your rewards program

Along with giving up the idea of a “perfect” redemption or always getting maximum value, Ryan advises I consider whether I’m earning points in the right rewards program or putting my rewards to their best use. 

After all, if I’m earning points that don’t fit my travel needs or only offer a super low value for my preferred redemption method, it makes sense that I’d hesitate to use them. To overcome my redemption anxiety, I should assess how well a rewards program is working for me.

Your preferred airline or hotel is an important factor to consider when choosing a rewards card. You can earn points or miles with your preferred travel providers via a co-branded airline rewards card or a hotel rewards card, or you can opt for a general travel card that lets you redeem rewards for bookings with them or transfer points to them.

For instance, if you fly Delta Airlines often, you might want a card like the American Express Gold Card (which lets you transfer points to Delta) or a co-branded Delta SkyMiles card. If you fly Southwest, Chase might be a better fit for you. But if you earn AAdvantage miles, they won’t be useful in either case.

If your card doesn’t earn rewards in your preferred program or allow transfers, that may be why you’re struggling to find a favorable redemption option. If you find yourself with a ton of points and can’t seem to redeem them, they may not be the right ones for you. 

If I’m earning points that don’t fit my travel needs or only offer a super low value for my preferred redemption method, it makes sense that I’d hesitate to use them.

— Brendan Dyer, Bankrate credit cards writer

I can see how simply knowing whether I’m earning the right points could help ease my redemption anxiety. In either case, the “earn and burn” philosophy makes sense.

If the rewards program is a fit, burn those points when you need to, then keep on earning. If it’s not, burn those points, then focus on earning points in a program that fits your goals better.

Plan ahead

When I opened my travel card, I knew it was possible to get a 2-cent-per-point redemption value by transferring points to a travel partner, but I didn’t realize I’d have such a hard time getting that value. 

Instead of getting the best value I could, I got caught up in analysis paralysis. This caused me to spend cash instead of rewards — cash that could have been padding my savings and investments. Meanwhile, I’ve just been sitting on those points, so I certainly haven’t offset any of the cost of holding my travel card (and that’s something I should aim to achieve every year).

I need a better strategy if I’m going to make my travel card worth its annual fee. Ryan says that starts with planning ahead.

I should start by aligning my earning and redemption strategies with my future travel plans. Thinking about my 2026 Iceland trip, I don’t have to worry as much about how I’m earning rewards — I have nearly 200,000 Membership Rewards points saved, which should be more than enough to cover my travel when I transfer my points to the Delta SkyMiles program.

But once I’ve burned a chunk of those points, I’ll need to think about what comes next. Which airline will I use for the holidays this year, or what big trip do I have planned in 2027? When I figure out those details, I’ll know which rewards I should focus on earning and what redemption value I can expect to get for them.

Since I mostly fly with Delta or Aer Lingus, I’ll likely stick with my Amex Gold card. But if I plan a trip to the west coast, I might open a Chase travel card and put most of my spending on that card for the first few months to earn its welcome offer and get a better redemption value with Southwest Airlines or via Chase Travel.

Planning ahead like this has already helped ease my redemption anxiety. I can easily get a sense of what rewards I’ll need to earn, how much they’re likely to be worth, how many I’ll need for my trip and when I need to use them. When it’s time to book my trip, I can burn those points with confidence.

Bottom line

In search of the perfect redemption, I’ve done the opposite of what a rewards card is supposed to help me do — save money.

Looking ahead, I’m going to adopt Ryan’s “earn and burn” approach, while still preserving some of the philosophy that I built my rewards strategy on.

Instead of holding out for perfect valuations, I’m going to keep high expectations, but make them more realistic. Instead of holding out for 2 cents per point, I’ll look for redemptions values of at least 1.5 cents per point. I’ve seen this valuation several times in my travel research, so I know that 2025 and 2026 will be the years I finally cash in on the points value I’ve been sitting on for the last three years.

I encourage anyone who’s amassed a pile of points to consider Ryan’s advice. If you’re in the same spot as me, it might help to rethink your strategy and adjust your rewards expectations. The right time to redeem may come sooner than you think.

Ryan Flanigan contributed additional reporting to this piece.

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