I've Earned 275,000 Points This Year—Here's What a CFP Thinks of My Strategy

Racking up Rakuten points, the biggest sale of the year for flight deals, and the best travel-sized natural deodorants.

Jul 16, 2026

Last year, I recapped how my husband and I racked up 175,000 points in a year. We didn’t turn to sign-up bonuses, expensive purchases, or even strategically spend on cards that 5x the points instead of 4x the points.

I shared in as much detail as I could, because I wanted to show that travel made possible by points is possible. It just takes a little upfront work—once you have a system in place, the miles come flooding in.

Since then, we’ve drastically shifted our strategy: We now own a home, needed a new airline-adjacent card, and we weren’t using others. We primarily use Bilt for housing, American Express (currently up to 175k sign-up bonus for the Platinum) and Chase (currently up to 100k sign-up bonus for the Preferred or the Reserve) for everyday spending, and Rakuten for cash back when shopping (referral links).

I wasn’t ultimately sure if our approach was as optimized as possible anymore, so I asked an expert to take a look.

Ashley Feinstein Gerstley is Rakuten’s Shopping and Savings Strategist, in addition to being a Certified Financial Professional®, so she knows a thing or two about creating a smart financial foundation and leveraging it to power travel. Plus, I welcomed her thoughts as someone who works intimately with a product I use everyday—and a big cornerstone of our strategy: Rakuten.

If you’re unfamiliar, Rakuten gives you cash back when you shop online, sent via check or direct deposit several times a year. They partner with thousands of brands you likely regularly visit—from CVS to Hotels.com, Sephora to PetSmart. Upon switching from cash back to their AmEx partnership (where you can earn Membership Rewards), we’ve earned 189,940 points. Not bad for shopping I was doing anyway.

If you’re nosy like me, I hope you enjoy this look “under the hood” at my own strategy, as well my conversation with Ashley on how to best use Rakuten, the best times of year for certain deals, and how she uses Rakuten for her own business class trips.

Ashley, you’re a CFP® and you run The Fiscal Femme (which I knew of from my time at Money with Katie!). As a CFP® professional, you’re also a fiduciary, meaning you must always act in a client’s best financial interests. I’m curious: If someone has their financial life in a stable place (they have an emergency fund, they’re paying off debts, they have some expendable income), where does strategizing around points/miles fall in your prioritization hierarchy? Is it a worthwhile use of time for most folks, or more for nerds like me who enjoy this stuff?

This is such a great question. I’d say it’s so personal. Points/miles strategizing can be such a practical way to get more from the money you do spend. I’m able to travel more than I would otherwise and in a way I wouldn’t be able to otherwise by using these strategies, so it’s a pretty significant lever for our family.

In a couple of weeks, our family of four is heading to Italy on an Emirates flight that we paid for using points. We typically take an international trip with the kids once per year where our flights are covered by points. We’re also planning a trip to Japan using points and are hoping to fly business class. My oldest son flew business class once (paid for by points), and I think it was the highlight of his trip.

On the flip-side, I also know it can feel like a significant investment of time and overwhelming for some. This is where I think it’s helpful to have an experienced expert who can share simple strategies and tips for the most important things to prioritize to make an impact. Things like spending more than you would otherwise or taking on additional debt are not what I would advise. It’s about being really intentional and strategic.

This year, our approach to earning points has shifted a bit, and we’ve earned 275,000 points by July 1st. I’d love to outline it below and get your thoughts on my strategy. Where else can I optimize? What holes do you see? Or, conversely, am I over-optimizing?

Bilt now offers points on mortgages, as long as your daily spend parallels that cost. For example, if your mortgage is $5,000 (close to our actual scenario) and you spend $3,750 in additional daily spend (75% of your housing cost), you’ll earn 5,000 points plus the additional 3,750 points, for a total of 8,750 points a month. So far in 2026, we have earned 37,000 points here. For context, we use the Bilt Blue Card because we didn’t want to pay another high annual fee on top of our Chase Sapphire Reserve and American Express Platinum.
Once we reach that threshold for Bilt, we’ll move our spending to one of those two cards, as both platforms have exceptionally valuable points and transfer partners, in addition to programs like Points Boost and the Fine Hotel + Resorts Program. So far, we have racked up 93,000 points on Chase (the large majority came through referrals, travel bookings, and Lyft), and 38,000 from American Express, 14,800 of which came from Rakuten.
Because we no longer live in a United hub and are now primarily flying on Delta, we downgraded our United cards and opened a Delta card that had a 85,000 point sign-up bonus if we spent $4,000 in six months. We had to purchase two large items anyway, so we’re on track to earn that 85,000 this month.
I also religiously use Rakuten for any online shopping, so I have another 22,000 points waiting for us during the next Membership Rewards day in August.
In total, that’s 275,000 points, with the other half of the year to go, where we project to earn another 40,000 from Bilt and 40,000 from other spending combined across Rakuten, Chase, and American Express.

I love the intentionality of your approach. Reading through, I was struck by how similarly we’ve set up our systems.

Earning points on your mortgage is major.
Timing the Delta sign-up bonus around purchases you already had planned is such a smart move.
Swapping your United card for Delta given where you live and who you’re flying with is a savvy strategic choice.
You are optimizing purchases by religiously using Rakuten. It’s all paying off.

As to where you could optimize, I’d run a fee audit. Once the sign-up bonuses are earned, it’s helpful to confirm the annual costs are still worth it and to calculate the value you’re getting from each card. On the flip-side, given your Bilt card use, you can also evaluate if you’d get more benefit from upgrading there. I am with you in that I only want to pay for cards with a high annual fee when it’s worth it.

I’d also keep an eye on the redemption side. Points tend to lose value over time, so I’m an earn-and-burn person, meaning I make plans to use my points within a reasonable time frame.

I resonated with what you shared in your write-up about not agonizing over optimal spending. That life is also not for me, but for any large recurring or one-time expenses, it can be impactful to optimize. Much like your choice to prioritize hitting the Delta sign-up bonus.

As far as over-optimizing, I don’t see that. Your approach is dialed in, rather than obsessive.

For someone planning a few trips a year (not 10+), how would you scale down my strategy? What's the "starter kit" version of what my husband and I are doing?

When I think about a “starter kit,” I gravitate toward larger key decisions and habits that can have the most impact:

First, I’d get the Rakuten browser extension so that cash back opportunities are flagged for you automatically when you’re shopping online. Over time, as you see the impact, checking cash back becomes a habit, and you start factoring it into your decision-making.
From there, I’d start with one card in an ecosystem that matches how you already travel or plan to travel. Put your everyday spending on it and pay it off in full each month.
If you can time a sign-up bonus around spending you already have coming, even better.

I read a survey* from your team at Rakuten and The Harris Poll that says nearly half of shoppers (49%) forget to apply rewards when they check out. It’s a missed opportunity, and it got me wondering: What other checkout habits are costing shoppers money every week that are easy to shift/implement?

Beyond forgetting to activate rewards, another common habit that costs shoppers money is checking out without comparing offers. Many shoppers default to the first retailer they find, but the same item may be available for less elsewhere, and Cash Back rates can differ by retailer. Before you complete your purchase, take a minute to check Rakuten to find the best combination of price and Cash Back. It's a simple step that makes a noticeable difference over time.

As a recent example, when I was booking our hotels for our upcoming Italy trip, I saw that the various booking sites offered similar room rates and perks, but the cash back on Expedia vs. Booking.com vs. Orbitz varied significantly. I’m always looking for the best all-in deal.

Let’s talk stacking promotions: I’ll often see a sale on a site like Farm Rio, and then see they have a Rakuten cash-back offer for an additional 15%, so I’m able to pay the lowest cost and get a nice boost in points. How often does that happen across retailers? Is it something more shoppers should be keeping an eye out on? What else is worth knowing about points stacking?

It happens more often than people realize, especially during major shopping moments like back-to-school season, Labor Day, and Black Friday. Retailers frequently run their own sales while Rakuten is simultaneously offering Cash Back, giving shoppers the opportunity to stack both and maximize their savings on the same purchase.

The best part about stacking is that shoppers don’t have to choose between a great sale price and earning rewards. While shoppers often run into restrictions like “cannot be combined with other offers” when using promo codes or coupons, Rakuten Cash Back can be applied on top of a retailer’s own discount or promotional sale, allowing shoppers to save on the sale price while still earning Cash Back.

The key is to check Rakuten before making a purchase, especially during major shopping moments when Cash Back rates are often boosted.

Beyond the obvious (browser extensions, checking before purchases, etc.), what's a Rakuten feature or trick most people don't know about? I have the app on my phone as well, but I’m never quite as good at using it when I’m in a store!

One feature many shoppers don’t take full advantage of is Rakuten’s in-store Cash Back offers, like you mentioned. While most people think of Rakuten for online shopping, the app can also help you discover offers from participating retailers when you’re shopping in person. This is especially helpful for everyday trips to places like CVS, Target, and other retailers where you’re already picking up essentials, as well as those spontaneous small shopping sprees. Before making a purchase, it’s worth checking the app to see if you can earn Cash Back on items you were planning to buy anyway.

Another lesser-known trick (that you’ve also mentioned) is that shoppers don’t have to take their Rakuten rewards as Cash Back. By linking an eligible American Express card that earns Membership Rewards, shoppers can choose to receive their Rakuten earnings as American Express points instead. This allows everyday purchases made through Rakuten to help build up points that can be used toward travel and other rewards.

Our family has earned thousands in cash back using Rakuten over time and I’ve only become a super user in the last few years. After reading through your strategies though, I’m leaning towards switching my cash back for points!

A few months ago I was at the park gushing to a friend about Rakuten, and a woman came up to me and shared that she used Rakuten to book her sister’s bachelorette and it almost paid for her entire portion of the trip. When we use it for big travel purchases, the benefits stack up quickly.

Last fall, Rakuten launched a partnership with Bilt Points, similar to the one they have with American Express’s Membership Rewards. How do you decide which program to use (or do you think the cash-back option is the best one entirely)? I primarily look at having a mix of points in all categories, keeping an eye on transfer partners I might want to use in the next couple months, but I’m not always running the math, which might be leaving some value on the table. Can you share how you’d approach it?

There’s no one-size-fits-all answer. It really depends on what you’re working toward. I always encourage shoppers to start with their end goal.

If you’re planning a trip and know you’ll redeem points through a specific airline or hotel transfer partner, earning American Express Rewards or Bilt Points through Rakuten may help you get more value from those purchases. For example, Bilt points generally hold a higher per point valuation with World of Hyatt and American Airlines. If you don’t have a redemption in mind, Cash Back offers the most flexibility since you can use it however you’d like via PayPal or check. You can get your cash back through PayPal to use that money however you’d like.

It’s also worth taking note of where you already have points. If it’s spread across several programs, it may make sense to concentrate your earnings in the program that will help you reach your next redemption faster, rather than slowly accumulating small balances everywhere.

On the other hand, if you’re close to earning enough points for a flight or hotel stay, directing your Rakuten rewards there can help you get over the finish line sooner. Ultimately, the best strategy is to be intentional!

This newsletter is primarily written for women, and we’re often the ones deploying our household’s purchasing power. Do you find that women are also more diligent when it comes to savings via programs like Rakuten? What's the most common blind spot you see in how women approach reward spending?

Rakuten and The Harris Poll actually released data* earlier this year that shows maximizing rewards has become a priority for shoppers across the board, regardless of gender. When it comes to big purchases, women are slightly more likely to say they strategically maximize rewards, with 78% saying they do so compared to 75% of men. And when asked whether they’re prioritizing rewards more than ever, men and women responded equally, with 74% of both groups saying rewards are playing a bigger role in their shopping decisions.

Regardless, what this tells me is women are being smart, strategic and thoughtful about saving. These small habits add up and over time help to build a financial muscle that influences smart financial decision-making across the board.

Slow travel here means longer stays, fewer flights, more time in one place. Does that change how you'd advise someone to prioritize points, maybe more toward hotel loyalty and long-stay perks, versus airline miles (which is what I’d usually lean towards)?

Slow travel is a great example of how shoppers can rethink the way they maximize rewards. If you’re taking fewer flights and spending more time in one destination, it may make sense to look beyond just airline miles and take advantage of opportunities to earn on hotels, vacation rentals, rental cars, and other travel-related purchases through Rakuten.

Whether you’re booking a longer hotel stay through partners like Expedia, Priceline, or IHG Hotels & Resorts, or planning a road trip with a rental car company like Hertz, there are opportunities to earn Cash Back on travel expenses you’re already planning to make.

That said, the best rewards strategy comes down to your personal travel habits. Rakuten data shows that 43% of shoppers use travel purchases as a way to earn rewards, while 53% use rewards to help fund travel. Whether you’re earning Cash Back to put toward a future getaway or redeeming those rewards to offset the cost of an upcoming trip, Rakuten is a great tool for reaching your travel goals.

Similar to slow travel, I’m also passionate about slow fashion and not spending just to spend. At the same time, there are items we’ll need throughout the year that we can plan for—you once said Memorial Day is a peak time for travel gear and hotel stays to be heavily discounted. Do you have any insights on what might be on the horizon for shoppers or travelers in the coming months?

I always encourage shoppers to be intentional and think ahead about purchases they know they’ll need throughout the year. Labor Day is a great example of a seasonal shopping moment where consumers can find value on items they were already planning to buy. It’s a smart time to shop for back-to-school clothing and refresh fall wardrobes, as well as outdoor furniture as retailers transition out of summer inventory.

For travel specifically, if timing aligns, I try to book during Rakuten’s promotional events like Big Stack and Big Give Week where cash back on travel can be upwards of 10–15%. You can also look out for boosted rates throughout the year. January also tends to be a great time to book travel because post holiday demand drops sharply. For travel to locations during peak times, I try to book further in advance. If I’m more flexible with location and dates, I often look for last minute deals.

Sign up for loyalty programs with travel booking sites so you’re alerted to their promotions and deals. They often run promotions in summer and then another round in the fall on “Travel Tuesday” (after Black Friday/Cyber Monday). A lot of it comes down to getting familiar with pricing so you can watch it over time and grab a great deal.

Anything I didn’t ask that you’d love to cover or any final tips you want to share?

Have fun with it if you can. Points and miles might sound like homework, but this is one of the rare corners of personal finance where the payoff is a trip you get to dream about and enjoy.

Celebrate the wins along the way, whether that's shopping with Rakuten, seeing a sign-up bonus hit your account, or realizing you just flew your family somewhere for close-to-free. And if you want to keep in touch, you can find me on Substack at @thefiscalfemme: Ashley Feinstein Gerstley.

*Survey Methodology: This survey was conducted online within the United States by The Harris Poll on behalf of Rakuten (or Autumn Communications) from Mar 24 - 26, 2026, among 2,098 adults ages 18 and older. The sampling precision of Harris online polls is measured by using a Bayesian credible interval. For this study, the sample data is accurate to within +/- 2.7 percentage points using a 95% confidence level. For complete survey methodology, including weighting variables and subgroup sample sizes, please contact Nora Rabie at nora@autumncommunications.com.

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