🤦‍♂️ My 5 Biggest Points & Miles Mistakes

Even after years of playing the points and miles game, I've realized I'm making some costly mistakes. So here's the complete breakdown of the trade-offs and what I'm changing going forward so you can learn from them.

I share these mistakes on Ep #258 or you can also watch the video below. 

🕐 Mistake #1: Not Valuing My Time

I've spent countless hours on activities with terrible returns: driving to Costco for out-of-stock gold, sitting on hold for small refunds, booking trips I never took, comparing cash back portals for purchases I returned, and building endless spreadsheets. The opportunity cost? Time with my family, growing my business, exercising, or literally anything else.

My New Rules

• Set a minimum hourly rate (at least what you'd earn driving for Uber)
• Pause regularly to ask: "Is this actually valuable right now?"
• Consider mental overhead, not just time (e.g. constantly checking gold prices or monitoring gift card sales)
• Keep daily priorities visible so you can check whether you're spending time on what matters

🎯 Mistake #2: Not Considering Opportunity Cost

Right now, I'm sitting on millions of points that are devaluing over time.

Here's the math that hurts: if I cashed them out into dollars, I'd have money to invest that would grow with the market. Meanwhile, my points are likely devaluing, and I'm earning new points faster than I can use them.

What I'm Doing Differently

Every time I choose between points and cash, I now ask:

• How quickly am I earning new points?
• What's my actual redemption rate?
• What could this cash earn if invested?
• Am I hoarding points because I enjoy seeing the balance grow?

I'm not abandoning points, but I need to be more thoughtful about choosing points over cash, especially when earning rates are similar.

🏆 Mistake #3: Chasing Status That Doesn't Matter

I've chased airline and hotel status that wasn't worth the effort. If you take United Silver status, the benefits include Premier Access, free checked bags, upgrades, economy plus at check-in and better award availability. But I already have access to TSA PreCheck and CLEAR (so faster security doesn't matter), I rarely check bags, upgrade availability doesn't exist for silver and most economy plus seats are gone at check-in.

A typical status run calculation only looks at cost per mile, but that's incomplete. You need to factor in time cost (travel time, time away from family or work), opportunity cost (what else could you do with that money?) and whether you'll actually use the perks.

My New Status Strategy

• Only chase status for airlines and hotels I actually use frequently
• Evaluate the real value of benefits for how I travel, not theoretical value
• Consider if I can get similar benefits through credit cards (Priority Pass, hotel elite status through cards)
• Be honest about whether I'm chasing status because it's useful or because I enjoy the game

💰 Mistake #4: Not Properly Valuing My Points

I thought my points were worth way more than they actually are because I wasn't doing the math correctly. A hotel costs $2,000 cash or 120,000 points. Simple math says 1.67 cents per point. However, if I'm paying cash, I'd earn 10x points from Hilton's loyalty program and 14x points for putting the hotel on a Hilton Aspire, which almost cuts the value of the points in half.

Here's the real killer: Hilton points are worth ~0.5 cents each and you can often buy them for that price directly from Hilton. So if a hotel costs $2,000 or 120,000 points, you're not getting 1.67 cents per point in value—you could have bought those 120,000 points for $600. Your stay only "cost" $600 in opportunity cost, not $2,000.

After running this math on multiple bookings, my "2 cents per point" average is probably closer to 1.5–1.6 cents. 

What I'm Doing Differently

• Consider points earned on cash bookings (this significantly reduces the effective cost of paying cash)
• Factor in cash back alternatives (a 2% cash back card gives me $32 on a $1,600 purchase)
• Remember you can buy some points (if award availability requires standard awards, buying points might be cheaper than you think)
• Track my actual redemption values (I'm keeping a spreadsheet of actual bookings to see what I'm really averaging)

Welcome bonuses are still incredibly lucrative, and 5x points categories still beat 5% cash back, but I need to understand the true value to make better trade-offs.

💳 Mistake #5: Not Cashing Out My Points

I'm sitting on millions of points, accumulating them faster than I'm using them, while they lose value over time. Almost every points program has ways to convert points to cash: travel portal bookings get you 1-2 cents per point, the Schwab Platinum lets you cash out Amex points at 1.1 cents each, Chase's Pay Yourself Back reimburses certain purchases at 1.25 cents per point, and the Amex Business Platinum 35% rebate makes points worth 1.54 cents each when you book flights with your chosen airline.

If I have 1 million points, that's worth at least $10,000 in cash (at 1 cent per point). That $10,000 could be invested, earning returns, growing over time. Instead, it's sitting as points that are probably devaluing year over year.

My 2026 Plan

I'm committing to keeping enough points for two years of travel (this gives me flexibility to book award travel when I find good availability) and cashing out or using everything else.

Everything beyond two years of expected usage should either be:

• Converted to cash
• Used for travel portal bookings

I know this sounds scary. I've said this before and haven't done it. But the more I analyze my actual point values (Mistake #4), the more I realize that 1.54 cents per point through the Amex 35% rebate might be pretty close to my average redemption value anyway.

Money in your bank account grows over time. Points in your account usually decrease in value over time. I'm earning points faster than I'm using them, and I need to accept that hoarding them isn't optimal.

🎯 Moving Forward

All these mistakes have cost me time, money, and at times, peace of mind. At the end of the day, I'm not abandoning points because I love this game too much, but 2026 is the year I start making decisions based on real math instead of the thrill of seeing balances grow.