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

When it comes to points and miles, it’s easy to get overwhelmed fast, especially when it feels like there’s so much you could be doing. That's why I was so excited to have Devon Gimbel on episode #227, because her approach completely shifts how you think about earning and using points.

Instead of chasing the “perfect” redemption or stressing over every single point, Devon focuses on personal value and building real skill—one 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.

🙈 Stage 1: The Peak of Mount Ignorance

You learn a few things—maybe you get your first travel rewards card or redeem some points—and your confidence goes through the roof. You feel like you've cracked the code. Maybe you’re bragging about a premium credit card without realizing it earns just 1x on dining.

At this stage, you don’t know what you don’t know—and 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 you’ve missed.

😫 Stage 2: The Valley of Despair

Now you know enough to know what you don’t know. And it’s 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 here’s what Devon emphasized—and I totally agree: this phase isn’t a dead end. It’s just the middle of the learning curve. You’re building knowledge, and even if it doesn’t feel like it yet, that knowledge will become skill. You just have to keep going.

💫 Stage 3: The Slope of Enlightenment

This is where things start clicking.

You’ve learned how to optimize your cards, you’re thinking about stacking, using portals like Rakuten, and maybe even earning extra points on expenses through platforms like Plastiq, Melio or Zil Money. You’re evaluating which points matter to you based on your goals. You’re asking the right questions like:

• “Is it worth paying a 2% fee to earn 4x points I’ll use for business class flights?”
• “Should I speculatively transfer Amex points to Hawaiian and then Alaska?”

It still takes work, but the progress is clear—and confidence starts to return.

🤩 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. I’ve 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 that’s okay—it’s part of the process.

The Truth: There’s No Single “Right” Way to Play the Game

The points and miles world is full of advice, tips, and spreadsheets—but in the end, it’s about finding what works for you. It’s 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, you’re not doing it wrong. That’s it. That’s the takeaway.

So stop chasing perfection. Focus on progress. Start where you are, and don’t forget to celebrate the wins—big or small—along the way!

P.S. No matter which stage you’re 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 spend—whether that’s 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 can’t use is wasted effort.
• Be Smart About Processing Fees: For large expenses (taxes, tuition, daycare), run the math on a 1.7–3% fee versus the points value you’ll redeem (ideally 4¢–5¢/pt). Leverage platforms like Plastiq, Melio or Zil Money (coupon code: ATH300) and the right bonus-category cards—but double-check that coding rules haven’t 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 everything—adjust 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 10×–20× promos. Bulk-buy non-perishables or gift cards, then stack further discounts for massive point hauls.
• Don’t Shun Portal Redemptions: If a business-class cash fare makes sense—say a $3,000 roundtrip with no extra fees—booking via your portal at 1.5¢/pt can be a smart, low-stress move, especially if you’ll earn points on that spend.
• Question “No-Card” Vendors: When a supplier says, “We don’t take cards,” investigate alternatives (business payment apps, Venmo business profiles, etc.). You might unlock lucrative ways to earn for payments you already have to make.

Editor’s Note: The content on this page is accurate as of the posting date; however, some of our partner offers may have expired. Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.