All the Hacks: Money, Points & Life

Episode: My Top 5 Mistakes with Points & Miles

Host: Chris Hutchins
Date: December 17, 2025

Episode Overview

In this deeply reflective solo episode, Chris Hutchins reveals his top five mistakes from a decade-plus journey optimizing points, miles, and loyalty statuses. With characteristic candor and data-driven insights, Chris digs into mistakes that even seasoned point hackers still make—how to better value your time, account for opportunity cost, rethink status chasing, challenge point valuations, and embrace the idea of actually cashing your points out. If you’re serious about maximizing travel and rewards for the long-term (and avoiding common—and costly—pitfalls), this episode is brimming with honest evaluation, practical tactics, and an open invitation to reconsider the fundamentals of your points game.

Key Discussion Points and Insights

1. Not Valuing My Time

(00:40 – 10:30)
Chris reflects on how points “optimization” can easily erode time—and peace of mind. He shares how hours spent on trivial deals, endless spreadsheets, and chasing small refunds often come at the expense of family, health, work, or true enjoyment.

• Examples of Time Wasters:

  • “I’ve driven to Costco to check for gold that was out of stock. I’ve sat on hold for an hour to get a small refund for a price drop. I have booked flights, hotels, or even entire vacations I never ended up taking.” (01:33)
  • Obsessive deal-scanning and portal comparisons for trivial cashbacks

• Evaluating Value:

  • Setting a “minimum hourly rate” to decide if a given deal is worth your time: “There was a deal on a crypto app ... took about 10 minutes to do ... $3,000 an hour. That is worth my time. But sometimes, it’s two dollars for a spoiled Amazon Fresh item—do you really want to live-chat for that?” (05:10)

• Mental Overhead:

  • “The whole day I was checking ... and it was so stressful. And the whole savings was probably $10 for the whole thing. Going forward ... how do I get this done now so I don’t have to have it looming over my head.” (09:05)

• Actionable Tactics:

  • Regularly pausing to check if you’re actually creating value or just scratching a curiosity itch (09:54)
  • Set daily/weekly priorities to keep first things first
  • Accept that “entertainment” is a valid reason to pursue hobbyist optimization, but know when to step away.

2. Not Considering Opportunity Cost

(10:30 – 20:50)
Underestimating what you’re giving up by not choosing the highest-return option.

• Opportunity Cost Scenario:

  • Using a United Club Business Card for status (1.5x miles/dollar) versus a US Bank Altitude Reserve (3x points on mobile wallet = 4.5% cashback):
    • “$270,000 spend gets you United status and $5,265 in miles. That same spend on Altitude Reserve ... $12,150 cash back. The United status actually cost $6,885.” (13:45)
  • “It’s okay to ignore this. It’s okay to know I had an opportunity cost, but I really wanted Hyatt Globalist ... Just understand that there is a cost to not using a card that has a better return.” (18:14)

• Key Takeaway:

  • Always factor in what cards and benefits you’re forgoing—and be honest about it.

3. Chasing Status

(20:51 – 55:08)

Chris’s 2024 “Status Audit”

He shares candidly about the myriad airline statuses he earned (some through pure spend, some via generous referrals, and some with actual travel)—and how little value many provided.

• The Breakdown:
  • United Silver (flew 11 times—got real value)
  • Delta Gold (never flew Delta that year)
  • American Executive Platinum (chased for reciprocal Alaska benefits, but then Alaska improved)
  • Alaska Platinum (13 flights, but 11 in First: “If I can upgrade to First for $40 ... it’s worth it for me.” 37:00)
  • Southwest A-List (helpful, but expensive in terms of spend)
  • JetBlue Mosaic (matched, but never flew)

Status Cost Math

• Card spend required for top status: $140k–$420k (varies by airline/program)
  • Most people earn 1x points per dollar unless lucky with bonus categories.
  • Opportunity cost of using a 3% cash-back card can mean spending $2–4k (or more) “for” the status.
    • “To earn top tier status, assuming your opportunity cost is a 3% card ... it’s roughly three to $4,000.” (45:44)

Status Milestones Change the Calculation

Factoring in milestone rewards (like United PlusPoints, Delta Choice Benefits) can shift the equation—sometimes making pursuit of certain statuses almost “free” (justifying the spend, only if you maximize those perks).

• “I started thinking United was the most ridiculous ... But the value of the things you get by hitting that status are the highest, and so it’s actually worth it—if you can get that value.” (52:09)

New Approach

• Drive status only on airlines that truly matter for your travel pattern.
• Sometimes just paying for upgrades/seats is a better deal than chasing status.
• “I'm hoping that next year I don't end up where I did this year, which was I thought I was starting this year without focusing on status, and I ended up getting sucked in. It was fun. I'm going to try next year to not do it.” (55:05)

4. Overvaluing Points

(55:09 – 01:07:55)

Challenge Point Valuation Wisdom

• Transferable points currencies (Chase, Amex, etc.) are often “valued” ~2 cents/point in the rewards media, but the underlying travel partners may only be worth 1.3–1.4 cents per point.
  • “Is flexibility really worth 42% more?" (56:10)

Points ≠ Actual Cash Value

• The real value is what you’d have paid for a trip, not the notional “cash price.”
  • Example: SFO–London one-way in business shows as 4.5cpp, but alternative roundtrip routings, cash fares, points earned, and status earned would mean the real point value is closer to 1.0–1.5cpp (or even less after considering opportunity cost). (01:01:20)
  • “If you bought that $3,000 flight on your credit card, you’d earn points from the spend… bring the value of those points down to 1.04 cents.” (01:04:27)
  • Points for one-way redemptions game the numbers but often don't reflect true preferences—most people book roundtrip.

Special Case: Hotels

• Hilton points are among the worst for value (standard award nights often ~0.5cpp, and you can buy Hilton points for that), while Chase points transferred to Hyatt can yield better (~1.7cpp median).
• When comparing award stays, always include cash-back opportunities and bonus point earnings on cash bookings.

5. Not Cashing Out Points

(1:07:56 – 1:18:00)

Chris calls himself out for hoarding points, reminding listeners that unused points only devalue.

• Most points currencies allow some kind of direct cash-out—often through travel portals (1–2cpp), gift cards (0.5–1cpp), or cash/mortgage statement credits (sometimes 1.1cpp with Amex Schwab).
• “If you have a million points ... that’s worth at least $10,000. I'm still making this mistake. I haven't brought myself to do it.” (1:10:07)

His Plan:

• Keep enough points for 1–2 years' travel; cash out any excess.
• Reevaluate in six to twelve months how this approach feels in practice.

Notable Quotes & Memorable Moments

“Sometimes in this hobby I end up doing things that are not the best use of my time—even though there are things that I’d want to spend my time doing ... I need to start valuing my time.”
— Chris Hutchins (04:25)

“To earn top tier [airline] status, assuming your opportunity cost is a 3% card ... it’s roughly three to $4,000. That’s really expensive, right? You have to really value these statuses.”
— Chris Hutchins (45:44)

“It’s a game. I know it’s fun. Maybe you could find something else fun ... I’m hoping that next year I don’t end up where I did this year, which was I thought I was starting this year without focusing on status, and I ended up getting sucked in.”
— Chris Hutchins (55:05)

“If you bought that $3,000 flight on your credit card, you’d earn points from the spend on that card ... bring the value of those points down to 1.04 cents. But also you’d earn a ton of redeemable miles ... and status.”
— Chris Hutchins (01:04:27)

“Points, sitting in our points account, usually end up being worth less over time. And so my goal is to try this in 2026 ... experiment with cashing them out because I just am accumulating them faster than I'm using them.”
— Chris Hutchins (1:16:08)

Timestamps for Major Segments

| Segment | Timestamp | |-----------------------------------------------|----------------------| | Intro & Overview of Mistakes | 00:00 – 01:27 | | Mistake 1: Not Valuing My Time | 01:28 – 10:29 | | Mistake 2: Not Considering Opportunity Cost | 10:30 – 20:50 | | Mistake 3: Chasing Status | 20:51 – 55:08 | | Mistake 4: Overvaluing Points | 55:09 – 1:07:55 | | Mistake 5: Not Cashing Out Points | 1:07:56 – 1:18:00 | | Final Takeaways and Wrap-Up | 1:18:01 – End |

Tone & Style

Chris’s tone remains warm, confessional, and relatable throughout—never boastful, always honest. He uses real numbers and “spreadsheet logic,” invites listeners to avoid self-judgment, and encourages both healthy skepticism and enjoyment in the hobby.

Summary for Listeners

Whether you’re new to points and miles or a longtime optimizer, this episode is your chance to see behind the curtain—where even the most passionate hackers rethink what really creates value, joy, and true upgrades in life. Chris’s five mistakes (and thoughtful corrective plans) are a masterclass in balancing opportunity, mental energy, status, and reward—all to make your travel hacking journey smarter and, most importantly, happier.