My Top 5 Mistakes with Points & Miles
All the Hacks: Money, Points & Life
Milestone Benefits Can Shift The Math
Chris shows how milestone awards (plus points, upgrades) materially reduce net cost of status, notably United.
#258: The 5 biggest mistakes Chris has made in his points & miles journey. He dives into the hidden cost of status, the math behind point values, the power of opportunity cost, and why hoarding points quietly destroys value.
Link to Full Show Notes: https://chrishutchins.com/top-5-points-and-miles-mistakes
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Resources Mentioned
Credit Cards
- US Bank Altitude® Reserve Visa Infinite® Card
- Robinhood Gold Card
- The Atmos™ Rewards Visa Summit Card
- Citi® / AAdvantage® Executive World Elite Mastercard®
- Citi® / AAdvantage Business™ World Elite Mastercard®
Award Search Tools
- Gondola (Get $50 here)
- Points Path Chrome Extension
ATH Podcast
- Ep #245: How Much Are Points and Miles Worth in 2025?
- Leave a review: Apple Podcasts | Spotify
- Email for questions, hacks, deals, and feedback: podcast@chrishutchins.com
Full Show Notes
(00:00) Introduction
(00:28) Mistake #1: Not Valuing My Time
(02:09) Setting a Personal Minimum Hourly Rate
(03:51) Step Back and Ask “Is This Worth It?”
(04:23) The Hidden Cost of Mental Overhead
(05:48) Using Daily and Weekly Priorities to Stay Focused
(07:00) Mistake #2: Not Considering the Opportunity Cost
(11:34) Mistake #3: Chasing Status
(16:56) Airline by Airline: The Value of Status in Real Life
(20:52) Reframing the Cost of Status
(24:09) When Milestone Benefits Change the Math
(28:33) Chris’s Status Plan Going Forward
(31:52) How to Decide Whether Status Is Worth Chasing
(32:50) Mistake #4: Overvaluing Points
(34:20) What the Data Actually Shows
(35:43) Why “Retail Value” Is Misleading
(41:22) When Paying Cash Can Be the Better Value
(46:03) Mistake #5: Not Cashing Out Points
(49:27) Chris's Plan for 2026
Connect with Chris
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