I’m Oversharing – For a Reason
When we got into points and miles, we had a lot of questions and a lot of anxiety about it. There was sort of a “this is too good to be true” feel to all of it. It was very difficult to wrap my head completely around. What I was hoping for was someone to lay out how much they spent, how many points they earned and how they used those points to save them money on their vacations.
I watched a lot of YouTube videos, listened to podcasts, and read a lot of blogs. The YouTube videos seemed to be dominated by Gen Y single men flying first class on Emirates, podcasts were dominated by people who knew everything about the hobby and seemed to be speaking directly to other people who knew everything about the hobby, and the blogs I read tended to be about very specific topics in points and miles.
I stopped watching YouTube, in general, because I just didn’t need to see some Instagram wannabe flying first class to Doha or Abu Dhabi (cool, you showered on a plane – you know it’s easier to do in a hotel, right?). Podcasts have become a great resource for me, and I routinely listen to Frequent Miler on the Air, Miles to Memories, and Miles to Go because they have a lot of great and timely information about the hobby. Sometimes, for beginners though, they can get a little in the weeds. As far as blogs are concerned, I pretty much use them by googling a topic and seeing what pops up.
The thing, for me, that was missing was what I’m hoping to accomplish on this page. I needed this question answered “What can I reasonably expect to accomplish by putting all of this effort into earning points and miles and can I use it to take the trips that I want to take?”
This is Very Personal Information
One of the reasons why you don’t see these posts, is that I’m sure people are hesitant to put all of their spending online for people to read. Hell, I’m hesitant about it. When I first started to do this, I was honestly shocked by how much we were charging every month, and we have been following a budget for at least a decade. If I was shocked by our spending, am I being judged by others about it? But that was precisely what I needed to read in the beginning in order for me to understand how people were taking these great vacations. I needed someone to lay out how they earned their points and how they used those points.
This is About More than Saving Money
My goal with this blog, in general, was to try to be as transparent as possible and hopefully encourage the next group of budget minded travel hackers to take the next step. Especially those families who want to take great vacations and develop priceless memories with their kids. Those memories sometimes can’t be accomplished without stepping away from our normal lives and having an adventure together. My favorite times with my kids are when we are on a trip somewhere and those are memories that we will have for a lifetime. If we waited until we can afford those trips, we might’ve just missed their childhood. So if you can take those trips without destroying your budget or going into debt, that’s about as important a life hack as you can possibly have.
So hopefully the tone of this page is correct – this isn’t meant to be a flex. I’m not trying to brag here. We are a fairly normal middle class family and what we’re able to accomplish is definitely within reach for a lot of people and hopefully our experiences can help them understand how to do it.
Monthly Point Checks
The monthly point check posts are intended to provide an update on what we are focusing on at any given time. It’s a more in-depth look into what we were thinking and what we hoped to accomplish at that time. Most of what we’ve done is time-sensitive because we were taking advantage of deals that were available at that time, so not everything applies to today, but the strategies are what’s important.
Points checks from 2025
Points check December 2025
As 2025 came to a close, we looked back at what turned out to be a fairly hectic year of travel. In March, we went to Portugal and Spain, to hike…
Points Check November 2025
November is the beginning of the holiday season and apparently, the beginning of the winter season for those of us who live in the Midwest. On the weekend after Thanksgiving, we…
Points Check October 2025
There wasn’t much going on for us in October. We were recovering from our trip to Nice and Dublin. For me, it was literal recovery. I had finished my first ultramarathon…
Points Check September 2025
September was a fun month. We took a trip with our friends Bill and Theresa to Nice, France, to compete in the UTMB Nice Côte d’Azur ultramarathons. Obviously, that wasn’t the…
Points Check August 2025
August was a month when we spent considerable time preparing for our trip to Nice, France, at the end of September. Unlike most trips, this didn’t mean finalizing trip details or…
Points Check July 2025
July was a fun month. Jenn and I took separate vacations. While Jenn and Emma went on a girls’ trip to Munich and Dublin with Jenn’s sister and our niece, I…
Points Check June 2025
We’re getting ready to embark on another European adventure, although this time we will be on separate vacations. Jenn is visiting Munich and Dublin with our daughter, her sister, and our…
Points Check May 2025
May wasn’t terribly exciting, but Jenn did join me on a business trip to San Antonio. While I’m not a huge fan of being in Texas during the warmer months, I…
Points Check April 2025
April was about the only breather we could take for a while. March consisted of a trip to Spain and Portugal to do a week on the Camino de Santiago. In…
Points Check March 2025
Oh, that’s an ugly chart. For several months, the value of our points and miles has been tanking. There is a very good reason for this. We have been planning a…
Points Check February 2025
Looking forward to the Camino We’ve spent a good deal of time in February planning our spring break trip to Portugal and Spain as well as booking some parts of a…
Points Check January 2025
January was the start of a pretty big year for us. Just two years ago, I was in the middle of planning our first trip to Europe. I honestly couldn’t believe…
Points checks from 2024
Points Check December 2024
December is always a month to get together with family and friends to celebrate the holidays. For a lot of people there is holiday travel, but this has always been a…
Points Check November 2024
November was a pretty good month for us. Why? Well we were in Italy for a couple weeks of it. Italy is a magical place where climate, landscape, food, culture and…
Points Check October 2024
Much of our time in October was spent preparing for our trip to Italy. Our trip included our good friends Bill and Theresa and Jenn’s Parents. None of them had been…
Points Check September 2024
September was a fairly normal month for us. No traveling this month other than Jenn and I did spend a night in fabulous Cedar Rapids, Iowa at the luxurious Residence Inn.…
Points Check August 2024
We’ve been making preparations to go with our friends Bill and Theresa as well as Jenn’s parents to Italy. We will be visiting Florence, Cinque Terre, Venice and Rome on this…
Points Check July 2024
It seemed that July just flew by. I started July off in Montana with old friends celebrating our friend Mat’s wedding. Then a couple of weeks later we were hooking up…
Points Check June 2024
Wow, another big month of accumulating points as we continue to collect Membership Reward points from the three American Express cards that we signed up for this year. Last month Jenn…
Points Check May 2024
May was a pretty big month for us as far as points are concerned. We booked our return trip home from Rome and had a huge bonus hit from American Express.…
Points Check April 2024
April had us recovering from our trip to Costa Rica, and had us planning a camping trip to Canada. Believe it or not, I’m 49 years old, love travel, live only…
Points Check March 2024
March was a pretty exciting month. We took a spring break trip to Costa Rica and had the opportunity to see just how beautiful that country is. We stayed in an…
Points Check February 2024
We’re inching closer every day to our spring break Costa Rican adventure. Honestly, this is a trip that I probably wouldn’t have dared to do a year ago. When we first…
Points Check January 2024
Well, it’s 2024 and Jenn has already managed to go on a trip to Playa Del Carmen without me (I’m not bitter at all). She had some fun soaking up the…
Points checks from 2023
Year End Review 2023
2023 was a huge year for us in points and miles. We went on our first major trips that were funded by points – a couple’s trip to Cabo San Lucas…
Points Check December 2023
That’s a wrap for 2023 and it was a great year for us. We went on our first international trip as a family and primarily used points and miles that we…
Points Check November 2023
A 65,000 AAdvantage mile bonus on my Citibusiness AAdvantage Platinum Select card put us over the $11,000 in value mark for our points and miles for the first time.
Points Check October 2023
October was a pretty dull month for us as far as accumulating points. Jenn signed up for a credit card and I continued to work toward a sign-up bonus but we…
Points Check September 2023
Our point values actually when up this month for the first time since May. It feels good to go in the right direction for the first time in a while. We…
Points Check August 2023
Looking at the chart above, it makes me a little nervous. My points are slipping away! No not really, we’ve been doing what we’re supposed to do with points, we’ve been…
Points Check July 2023
So we did it! We took our first trip outside of the continent. For the kids, it was the first time they had left the country. As I expected, it was…
Points Check June 2023
So it’s about that time. The flights, trains, buses, hotels and Airbnbs are all booked. Our passports are in our hands. In some respects, this is crazy. I’ve always wanted to…
Points Check May 2023
May was another monster month for picking up bonus points with sign up bonuses awarded on 3 separate cards. We now sit over $10,000 in value.
Points Check April 2023
Whew, what a hell of a month! It feels like we were absolutely raking in points. The total value of our points rose by around $3,400. We actually accumulated 3 bonuses…
Points Check March 2023
March was a month where we didn’t finish any of our spending requirements to hit bonuses, but we did apply for a few cards. Jenn’s focus has been on diversifying our…
Points Check February 2023
Only 5 months after redeeming almost all of our points booking our trip to Europe, we had managed to acquire enough points to almost be back to where we were. That…
Points Check January 2023
Jenn gets the Chase Sapphire Preferred, a card that does not prefer me. We begin to rebuild our points after booking all our travel to Europe.
Points checks from 2022
Year End Review 2022
2022 was the year that we got into travel hacking. It was out of a bit of desperation that we started looking into it as a way to reduce the expense…
Points Check December 2022
Shortly after Jenn signed up for the Chase Ink Unlimited card, they changed their sign up bonus. It had been $750 back after spending $7,500 within 3 months. The new offer…
Points Check November 2022
After we finished all of the travel plans and bookings for Europe, we no longer had a clear goal to work toward. We did, however, learn that because we had points…
Points Check October 2022
We finally booked our trip to Europe! I’ll go into greater detail about how we booked this in a different post, but Jenn booked 2 tickets from Chicago to Zurich from…
Points Check September 2022
In September, Jenn referred me to the Marriott Bonvoy Boundless card, and there was something odd about the offer that was sent me. If I applied for the card without a…
Points Check August 2022
By this time, we felt pretty confident that we had accumulated enough points to pay for the flights to Europe and now we were trying to figure out how to reduce…
Points Check July 2022
There wasn’t much going on for us in the miles and points space during July. We did take an amazing camping trip to Chatfield State Park outside of Denver and Cheyenne…
Points Check June 2022
When I booked our flight and Airbnb for Cabo San Lucas, I left 2 days off the calendar. We had 6 days between flights and the last 4 days were locked…
Points Check May 2022
By this time, we had been able to increase our spending on credit cards to virtually all of our spending except for our home loan and automobiles. Most utilities, insurance companies,…
Points Check April 2022
Jenn is a residential house cleaner and owns her own business. That’s a huge bonus when trying to accumulate points. Why? Because if you own a business, you have access to…
Points Check March 2022
We didn’t have any new credit card applications in March. We did, however, take a spring break trip to Biloxi, MS and spent a night in New Orleans on the way…
Points Check February 2022
During January 2022, I did a ton of research on points and miles and I began to figure things out. First of all, I started to do all of this to…
Points Check January 2022
When we got started in points and miles, I really wanted to find real world examples of people who were doing this and had done it for a while. Mostly I…
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