Hey Girlies,
Emily here, writing to you from a half-empty living room littered with boxes and disassembled furniture. (ICYMI, I’m moving!)
I can’t help but think back to the post-college days when I moved cross-country with only a carload of things. Or 4 years later when I moved cross-country again with only 2 carloads of things. I like to think I’m not much of a “stuff” person, but there’s nothing like packing for a move to make you reckon with the reality of our consumer culture. 🛍️
And on that note, I can’t talk about ‘stuff’ and ‘consumer culture’ without mentioning Black Friday/Cyber Monday, and the conflicting relationship I have with it.
While the essence of these “holidays” kind of gives me the ick, I’m also a sucker for a deal. 🤓
Cassidy and I both took advantage this year by getting great deals on purchases we’d been planning for months (plane tickets for me, extra-toasty slippers for Cassidy, the newly minted Minnesotan! ❄️).
Speaking of plane tickets, this week’s podcast episode is a fun one. We’re diving deep into the world of points and miles with our friend Ross Alcorn, CEO and founder of Itinerary Boss. This is a topic many of you have asked for — and it’s something we want to learn about, too.
Enjoy!
On the pod 🎧
Do you ever see all those Instagram influencers flying business class using miles and points and think, “How TF do they do that?”
Well… we sat down with a miles-and-points expert to figure it out.
Ross Alcorn, CEO and Founder of Itinerary Boss, has saved tens of thousands of dollars on travel in 2025 alone — and he’s joining us to help us learn how to do the same.
Welcome to the world of points and miles, where you can turn your regular spending into free (even luxury) travel. ✈️
In this episode, Ross busts some common myths about travel hacking and offers some mindset shifts that are crucial for getting started:
For example:
You don’t need to spend like crazy, run a business, or travel all the time to score free vacations with points and miles.
Don’t be scared of credit card annual fees — they typically pay for themselves.
Points > cash back if offsetting travel costs is your top priority.
In the past, free travel has felt like such a pie-in-the-sky dream (or something you can only get if you spend all your free time chasing deals). But we’re confident Ross’s tips are just what we all need to make it a reality.
Let’s make 2026 the year we master points and miles (or at least learn enough for a free flight somewhere!).
Listen to the episode, let us know what you think, and get back to us with any follow-up questions. Based on how many questions we had for Ross, we’re anticipating we may need to organize a follow-up Q+A episode, too.
More of a reader? Check out the full episode breakdown on our blog.
🎤 Mic drop moment:
“Even if you’re taking a few trips… this is worth your time because there’s ways that you can offset every single flight cost, every single hotel cost.”
Resource roundup 📚
I (Emily) have already read How to Win at Travel by The Points Guy’s Brian Kelly, but it’s in my figurative* TBR stack for a second pass-through. (*I actually have no idea where the book is — packed away in some box to be moved! We’ll reunite soon.). If this week’s episode piques your interest, this book goes wayyyy more in depth. I’m excited to read it again after chatting with Ross.
Speaking of The Points Guy, this episode, where he guests on The Financial Feminist podcast, is a winner. Listen for tons of tactical takeaways.
This guide from Money With Katie helped me (Emily) prioritize the best credit cards when I was ready to break out of the cash back-only philosophy. I don’t follow this strategy precisely, but I do find it really helpful (and have 2 of her recommended cards).
All this points and miles talk going in one ear and out the other? Listen to a previous episode of The Finance Girlies — Inside our wallets: Our favorite credit cards and (simple) reward strategies — for an even more beginner-friendly conversation.
Catchup corner 💬
What we’ve been up to:
E: I just returned from spending the holiday with family. Highlights include: hanging out with my 3 little nephews, going to IKEA 🤪, and getting a beautiful snowfall.
C: I ran my first-ever Turkey Day 5K on Thursday and then had Friendsgiving with a friend who was also spending the day solo. We ran the 5k, cooked a bangin’ meal, and then went to the movies to see Eternity.
What we’ve been reading/watching/listening to:
E: The Secret Life of Mormon Wives (Season 3). I can’t look away.
C: Every morning I wake up, make myself a cup of English Breakfast tea, put one of these YouTube videos on the TV, and read for 30 minutes on the couch before I head into work. It’s been such a grounding way to start the day.
What we’ve been crafting:
E: I’ve been putting together the most low-effort holiday cards/moving announcements ever (trying to keep things as easy as possible!). Instead of paying $100s for fancy holiday cards, I printed lots of copies of a favorite photo from the year, added a cute sticker with our new address, and voila!
C: I spent the long weekend making paper chain garland and crocheted granny square ornaments for my tree.
Biggest travel credit card win (so far):
E: While on vacation in southern Utah, we returned to our parked rental car to find a 12-inch crack across the windshield. The invoice from the rental company was a stunning $780. 🫠 Did we have to pay? Nope — thanks to my Chase Sapphire Preferred card’s free auto rental coverage. 💪
C: I have the Delta SkyMiles Platinum American Express Card, which comes with free upgrades to Comfort+ and First Class. I almost always get a free upgrade to Comfort+ when I fly, but in Jan. 2024, I flew to Mexico for a business trip and got upgraded to first class on both my departing AND returning flights. I’ve never felt so fancy.
Money tip of the week 💸
If this episode inspired you to up your credit card game, make sure you have a solid card that rewards your typical spending habits with bonus points. (Remember, don’t dive into this until you have a budget and are spending within your means.)
To find your next best card, start with a spending audit:
Look at bank and credit card statements from the last three months, and total your spending in various categories (for example, rent, groceries, dining out, entertainment, streaming, travel, gas, Ubers, etc.).
Next, identify your top spending categories.
Research the best credit cards that give you bonus points for those purchase categories. For example, if dining and groceries are some of your top spending areas, consider a card that offers at least 3x points on dining and groceries.
That’s it for this week, girlies.
Love ya, bye!
Emily + Cassidy
