My “Easy Button” Strategy for Free Travel and Credit Card Points

A few weeks ago, I shared that I flew with my kids to Africa and back (in upgraded seats) for mostly FREE using miles from just the last 18 months, and I got a bunch of messages asking some version of:

“Okay, but HOW do you have that many miles in 18 months?”

Yes, I fly a lot for keynotes… BUT a huge chunk of my travel strategy has absolutely nothing to do with getting on a plane and flying to get those miles. 

I do not have a spreadsheet with 17 credit cards. I’m not constantly opening and closing accounts. I don’t spend Sunday afternoons researching transfer partners. And I most definitely don’t want to spend 45 minutes figuring out how to squeeze an extra 0.7 cents of value out of a point.

AND, I didn’t want to leave easy moey on the table either.

Essentially, I wanted the Lazy Girl version. I knew I needed an easy Efficient Advisor-esqe plan. 

If you’re a busy financial advisor who loves a good vacation but does not need another hobby, welcome. This is my strategy.

My rule: simple beats optimized

Could I squeeze more value out of my spending if I became a full-fledged credit card hacker?

Absolutely.

Do I want to?

Absolutely not.

My goal is to have a handful of cards that give me benefits I will actually use, put the right expenses on them, automate or link whatever I can, and then move on with my life.

I’m looking for the 80/20.

Here’s what that looks like for me.

#1: I use a tool called SkyKey because I don't want to watch and see if my flights go down in price

One of my favorite “easy buttons” is SkyKey. Once you book a flight—whether you paid in cash or miles—SkyKey continually monitors it for a better price. If the fare drops, they can help rebook it at the lower rate so you get the savings back, and they keep 20% of what they save you.

And listen, I will pay someone 20% ALL DAY EVERY DAY to find money I was never going to take the time to find myself. 😂 I am absolutely not going back and checking the price of flights I've already booked every few days.

I bet at least once every other week I get an email from them saying they saved me $10 here, $120 there, or that they rebooked one of my rewards flights for fewer points. Those little savings add up—and every single time I think, “Yep. I never would have caught that.”

And sometimes the savings aren't so little. SkyKey recently saved me $1,440 on my flights to South Africa. Even after their fee, that's a whole lot of money back in my pocket for essentially zero additional effort on my part.

THIS is exactly what I mean by my Easy Button strategy. I don't need to maximize every single dollar or point myself. I want systems that quietly do the work for me in the background.

Check out SkyKey Here! (I get $10 when you register and add a flight -- and I'll be donating that to St. Jude!)

#2: I picked a single airline and I maximized the benefits with a credit card

I currently have both the Delta SkyMiles Platinum American Express Card and the Delta SkyMiles Reserve American Express Card because you get a free ticket every year without having to do anything. That's my style. 

Free Companion Tickets Every Year: I wanted to find cards where I applied once and got a huge benefit on autopilot. I keep both of these cards year after year because of the annual Companion Certificate after renewal. Basically a FREE ticket every year to anywhere in the US and a few closer international options (Mexico, Dominican Republic, etc). So I have both cards so I get two companion passes. It's that simple. The free ticket kicks in after you’ve owned the card for year. 

Instead of playing the “how do I maximize every single point?” game, I know I have a built-in travel benefit every year that I can plan around. I buy my ticket and get one of my sons for free. Twice a year. And no, you can’t use them at the same time, but that’s where miles come in. I’ll discuss that below. 

But this is my kind of credit card strategy: get two free plane tickets each year without having to think about it.

The Delta SkyMiles Platinum Amex is up first. The annual fee is $195/year---but hear me out. The Delta Platinum also currently comes with benefits like a companion certificate after renewal, TakeOff 15 on eligible Delta award travel, up to $120 per year in Resy statement credits, up to $120 per year in Uber credits, and up to $150 in Delta Stays credits at a wide variety of hotels. Enrollment is required for some benefits and, of course, terms apply.

But I get way more than my $195 fee back just using these benefits. And, I hooked them up through the Amex website so it just happens automatically and I don’t have to think about it. 

My Delta SkyMiles Platinum Amex referral link

The Delta Skymiles Reserve Amex has a higher annual fee ($650 right now), but it also comes with way beefier benefits. The current benefits include an annual companion certificate after renewal that can be used for eligible First Class, Delta Premium Select, Delta Comfort or Main Cabin travel, plus up to $240 annually in Resy statement credits, up to $120 annually in rideshare statement credits, up to $200 in Delta Stays credits, and Delta Sky Club access subject to the card's current visit limits and terms.

My Delta SkyMiles Reserve Amex referral link

I have both.

If I were married, I would also look at whether it made sense for each spouse to hold their own eligible card rather than simply adding someone as an authorized user. Why? Because separate qualifying accounts can potentially mean separate annual companion certificates. So 4 free flights a year. 

Again: Lazy Girl Math.

I’m not trying to win the Points Olympics. I want benefits that are easy to understand and that I know I’ll use.

And because I naturally spend a lot through my business, I put all of my business expenses on my Delta card and let the miles accumulate in the background.

And, depending on the card, you get a TON of Delta Skymiles when you sign up so… I do it like this. 

Buy my ticket.
Get my son Cameron’s ticket for free (companion pass).
Use those intro miles to pay for Parker’s ticket (also free). 

#3: Then I connect all the little “set it and forget it” mileage earners for that same airline 

This is my favorite category because it requires almost no ongoing effort.

Uber:
For example, you can link your Delta SkyMiles account to your Uber account and earn miles on eligible Uber rides and qualifying Uber Eats orders. So you get miles from the Delta side AND the statement credits from Amex. It’s a double dip!

You set it up once.

Then you take an Uber.

Miles show up.

THIS IS MY LOVE LANGUAGE.

See Delta's current Uber and SkyMiles partnership

SkyMiles Dining:
I do the same thing with SkyMiles Dining. Register your cards– they don’t even have to be Delta cards–go eat at participating restaurants, and earn miles. I don't plan my life around which restaurants participate. If I happen to eat somewhere that does? Surprise miles!!! Again, I’m not getting on and looking stuff up and working around it. I just naturally let it happen.
(I'll address it below, but I use my Marriott card at restaurants and get the double dip of points/miles from both!) 

SkyMiles Shopping:
Then there is SkyMiles shopping where you can earn additional miles when shopping online with participating retailers. My rule here is the same: I'm not buying something just to get miles. But if I'm already buying the thing, why not get the miles? It includes places like Home Depot. I recently did a renovation project and ordered all of the things for store pickup… just did it through their portal instead. Do I remember to do it every time… nope! But when I do, I get easy miles. 

Sign up for free SkyMiles Shopping with ANY credit card HERE!

I don't change my life to earn points. I make the things I'm already doing earn me points.

Miles: And then, of course, I earn miles on purchases. 

I use my Delta reserve for my business. So I’m earning 8k-10k miles per month just on my spending. You get the big introductory offer when you sign up and then after year one I just buy one ticket, use the companion pass for a son, use miles for the other son and my finance if he’s coming with us!

#4: I picked a single hotel brand and I maximized the benefits with a credit card

Next up: my Marriott Bonvoy Boundless card.

I love Marriott points because I enjoy staying somewhere fabulous without paying the fabulous-hotel price. And like the companion pass, I get one free night every single year without doing anything. So, for the very reasonable $95 a year... worst case scenario is one free room! Again, I don't have to think about a thing. 

 Right now, the Boundless earns 3X points on the first $6,000 in combined annual spending at grocery stores, gas stations and dining, so those are easy categories for me to remember. 

That's it. I literally wrote Gas, Grocery, Dining on the card in a Sharpie marker. 

Gas. Groceries. Dining. Marriott. Done.

My Marriott Bonvoy credit card referral link

And just like the Delta cards, you get a bunch of free points and/or free nights when you sign up! Depending on your level of fancy, you can instantly get a few nights for free. 

Once I have the Marriott points, I like saving them for trips where hotel prices make me want to cry. Hello, bougie hotel I would never pay cash for... including Ritz Carlton’s.

Like I mentioned above... I have my Marriott Boundless card linked to my Delta Skymiles Dining… so I get miles AND Marriott points when I eat at those restaurants. Double Dip! 

FINALLY: When you use Marriott points to book the rooms, you get a 5th night free. They go really far and I only had to learn ONE hotel system. Are there better ones? Maybe, but this works for me! 

So to recap: free nights, lots of points when you sign up, get 5th night free when you use your points. No brainer. Easy to understand, cheap to hold! 

#5: Everything else? Chase Freedom Unlimited.

This is where I refuse to overcomplicate things. All my personal expenses go here that aren’t Gas, Groceries or Dining. 

If an expense doesn't have an obvious home somewhere else, I use my Chase Freedom Unlimited.

It currently earns at least 1.5% points back on purchases, with higher earning rates in certain categories. I then convert these points to airlines or hotels. Often I use these to supplement the Marriott rewards. 

I don't have to stand at the register wondering which of my 13 cards gets 2.4 points instead of 1.8 points on whatever I'm buying.

It's my catch-all. And then I transfer those points to Marriott to get my 5th night free. Stupid simple. 

My Chase Freedom Unlimited referral link

The entire Lazy Girl system:

If I had to boil my strategy down, it's ridiculously simple:

1. Pick an airline you actually use and concentrate on all the program offers.
2. Look for cards with annual benefits you know you'll use that require very little effort year over year.
3. Link the passive programs like Uber, dining and shopping so miles accumulate without you thinking about it.
4. Give your other cards specific jobs based on categories that are easy to remember.
5. Have one catch-all card for everything else.
6. Use points for the travel experiences that feel expensive or special enough to make the points worthwhile.
7. Don't spend three hours trying to save $37.

That last one might be the most important.

I'm a business owner. I'm a mom. I travel a lot. I have approximately 4,972 other things I could be doing.

I don't need credit card points to become another part-time job.

I just want to occasionally look at my account and think:

Oh, cool. I guess we're going to Africa.

And THAT is my kind of financial system.

One final note: This is simply what I do—not individualized financial advice or a recommendation that any particular card is right for you. Credit cards have annual fees, eligibility requirements and terms that change, and carrying a balance can quickly wipe out the value of rewards. I pay attention to the benefits I actually use and choose cards accordingly. Some of the links above are referral links, which means I may receive a referral bonus if you apply and are approved (which I would really appreciate since I use them a lot for me and my kiddos!)