My Top 5 Mistakes with Points & Miles

All the Hacks: Money, Points & Life

Chris Hutchins

Society & Culture, Investing, Self-improvement, Places & Travel, Business, Education

4.7 • 1.4K Ratings

🗓️ 17 December 2025

⏱️ 59 minutes

🔗️ Recording | iTunes | RSS

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Summary

#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 Partner Deals Superhuman: Free month of the fastest and best email with code ALLTHEHACKS DeleteMe: 20% off removing your personal info from the web LMNT: Free sample pack of my favorite electrolyte drink mix Gelt: Skip the waitlist on personalized tax guidance to maximize your wealth NetSuite: Free KPI checklist to upgrade your business performance For all the deals, discounts and promo codes from our partners, go to: chrishutchins.com/deals Resources Mentioned Chris' Presentation Slides 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: [email protected] 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 Newsletter | Membership | X | Instagram | LinkedIn 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. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	We all love the thrill of optimizing our points and miles, but even the most experienced of us,
0:05.9	myself included, slip up. So in this episode, I'm going to share my top five mistakes I've made
0:11.2	in my points and miles journey. And some of these I realized way too late, and a few of them I'm
0:16.0	even still making today. I'm going to go deep on most of them, looking at the numbers, the
0:20.7	tradeoffs,
0:21.3	and what I would do differently so you can avoid falling into the same traps and focus on
0:26.6	what actually moves the needle. Not every mistake needs a spreadsheet to explain, but in
0:31.5	this case, most of mine do. Also, there are timestamps in the show notes. So if at any point
0:36.5	in time, you want to jump to the next mistake, go back to one, skip around, click the timestamps to jump around. And if you're new here, I'm Chris Hutchins. And if you want to keep upgrading your money, points in life, click follow or subscribe. So before I jump in, you should know that I actually put this whole thing together as a talk that I gave at the Chicago Seminars Conference last week, which is an amazing Points of Miles event.
0:58.8	There are slides that went along with that talk.
1:01.4	If you're watching on YouTube or Spotify, you should be able to see the video and look at the slides.
1:06.1	If not, I'll put a link in the show notes so you can click and follow along.
1:10.0	You shouldn't need the slides.
1:11.6	This could stand on its own all by itself, but in case you're interested, they are there.
1:16.0	So let's get into it. So the first mistake that I've made in this game is to just not value my time.
1:23.0	And it's very apparent in lots of cases. So here are some examples of how I spent my time. I've
1:29.0	driven to Costco to check for gold that was out of stock. I've sat on hold for an hour to get a
1:35.2	small refund for a price drop. I have booked flights, hotels, or even entire vacations I never
1:41.7	ended up taking. I have compared cashback portals for really small
1:46.1	purchases that I probably sometimes even returned. I've endlessly scrolled through blogs,
1:52.2	emails, slacks, WhatsApp, websites to try to find the latest deals. And I've built dozens of
1:58.4	spreadsheets to optimize just about everything when it comes to my
	...

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