đ The 4-Step Framework to Become an Expert in Points & Miles

Points and miles can feel overwhelming fastâbut it doesnât have to be that way. Thatâs why I was excited to have Devon Gimbel on episode #227. Her 4-step framework simplifies everything, focusing on *real skills* over chasing perfection.
Instead of chasing the âperfectâ redemption or stressing over every single point, Devon focuses on personal value and building real skillâone step at a time.
To help navigate the learning process, Devon uses a 4 step framework (based on the Dunning-Kruger curve) that mirrors how we actually grow and learn in this space. Understanding these stages can help you recognize where you are and how to move forward.
đ Stage 1: The Peak of Mount Ignorance
You learn a few thingsâmaybe you get your first travel rewards card or redeem some pointsâand your confidence goes through the roof. You feel like you've cracked the code. Maybe youâre bragging about a premium credit card without realizing it earns just 1x on dining.
At this stage, you donât know what you donât knowâand it feels great.
This is where many people are when they first fall down the points rabbit hole. But that initial boost can be misleading, because as soon as you learn a bit more, you start to realize how much youâve missed.
đŤ Stage 2: The Valley of Despair
Now you know enough to know what you donât know. And itâs brutal.
You start to see mistakes in your past redemptions, you realize you missed bonuses, used the wrong cards, or redeemed points for poor value. The natural response? Doubt. Frustration. Sometimes paralysis.
But hereâs what Devon emphasizedâand I totally agree: this phase isnât a dead end. Itâs just the middle of the learning curve. Youâre building knowledge, and even if it doesnât feel like it yet, that knowledge will become skill. You just have to keep going.
đŤ Stage 3: The Slope of Enlightenment
This is where things start clicking.
Youâve learned how to optimize your cards, youâre thinking about stacking, using portals like Rakuten, and maybe even earning extra points on expenses through platforms like Plastiq, Melio or Zil Money. Youâre evaluating which points matter to you based on your goals. Youâre asking the right questions like:
- âIs it worth paying a 2% fee to earn 4x points Iâll use for business class flights?â
- âShould I speculatively transfer Amex points to Hawaiian and then Alaska?â
It still takes work, but the progress is clearâand confidence starts to return.
𤊠Stage 4: Unconscious Competence
Eventually, the strategies become second nature.
You instinctively know which card to use. You know which airlines are best for family travel. You can sit down and book an award flight without stress. You might even help friends book their trips just to sharpen your skills.
But even at this stage, the learning never really stops. Iâve been deep in this game for years, and we want to plan a trip to Asia for four, but I know I'll have to relearn when schedules open, which airlines release award seats, and how to track it all. And thatâs okayâitâs part of the process.
The Truth: Thereâs No Single âRightâ Way to Play the Game
The points and miles world is full of advice, tips, and spreadsheetsâbut in the end, itâs about finding what works for you. Itâs about creating amazing experiences, making travel more accessible, and feeling good about how you're using what you earn.
If you love how you're using your points, youâre not doing it wrong. Thatâs it. Thatâs the takeaway.
So stop chasing perfection. Focus on progress. Start where you are, and donât forget to celebrate the winsâbig or smallâalong the way!
P.S. No matter which stage youâre in, here are some high-impact tactics (which we also discuss in the episode) to help you maximize points and miles:
- Prioritize Your Highest-Yield Opportunities: Focus on cards and bonuses that deliver the biggest return for your actual spendâwhether thatâs welcome offers or bonus categories on everyday and business purchases.
- Choose the Right Points Currency: Pick currencies that align with your travel goals. Earning extra points in a program you canât use is wasted effort.
- Be Smart About Processing Fees: For large expenses (taxes, tuition, daycare), run the math on a 1.7â3% fee versus the points value youâll redeem (ideally 4¢â5¢/pt). Leverage platforms like Plastiq, Melio or Zil Money (coupon code: ATH300) and the right bonus-category cardsâbut double-check that coding rules havenât changed.
- Leverage Major Spend Categories: Look beyond the obvious: insurance premiums, home renovations, or other big costs can be routed through payment services to rack up thousands of points each year.
- Scale Award Travel for Families: Flexibility is everythingâadjust dates, airports, or even split your party. Target airlines with reliable award space for groups (Emirates fifth-freedom routes, Condor via Alaska, Singapore from the West Coast), and set alerts to snag seats when they pop up.
- Stack Shopping Portal Bonuses: Use portals like Rakuten ($40 bonus here) or Savewise (20% off with ALLTHEHACKS20) during 10Ăâ20Ă promos. Bulk-buy non-perishables or gift cards, then stack further discounts for massive point hauls.
- Donât Shun Portal Redemptions: If a business-class cash fare makes senseâsay a $3,000 roundtrip with no extra feesâbooking via your portal at 1.5¢/pt can be a smart, low-stress move, especially if youâll earn points on that spend.
- Question âNo-Cardâ Vendors: When a supplier says, âWe donât take cards,â investigate alternatives (business payment apps, Venmo business profiles, etc.). You might unlock lucrative ways to earn for payments you already have to make.
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