Saving Money and Optimizing is My Kryptonite

Summary

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All the Hacks: Money, Points & Life

Episode: Saving Money and Optimizing is My Kryptonite
Date: June 10, 2026
Host: Chris Hutchins

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Episode Overview

In this candid, solo episode, host Chris Hutchins takes a raw, introspective look at his relentless drive to optimize—which, while unlocking savings and upgrades, also becomes a persistent trap stealing time, mental bandwidth, and, ironically, happiness. Using recent personal examples—booking a family trip to Cabo and crafting thumbnails for the podcast’s YouTube channel—Chris unpacks how the endless pursuit of the “best deal” can sabotage well-being, reveals productivity systems he’s now putting in place, and shares actionable tactics for listeners who want to reclaim time in a world overflowing with “hacks.”

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Key Discussion Points & Insights

The Optimization Trap

• Chris’ Personal Realization:
  He recounts (00:17) how, despite his career as a professional optimizer, he wasted dozens of hours to save marginal amounts of money or points, notably when booking flights to Cabo.

  • “The more I looked into this, the more I realized it's not about the money and it's a trap I keep falling into. I really doubt I'm alone.” (00:20)

• The Irony of Optimization:
  Chris realizes that many optimizers are caught in a loop where the pursuit of perfection or savings yields diminishing returns and unnecessary stress.

  • “It just feels like there is too much. I haven't gotten to exercise like I wanted to...there’s both real reasons and as I dug into it, real reasons that maybe don’t need to be there.” (06:45)

Overcommitted and Under-resourced

• Juggling Too Many Projects:
  • Running the podcast, curating the newsletter (100,000 subscribers), managing an app (Card Tool), being present for family, all with a shrinking support team (from three people to now just himself).
  • Exploring how AI automations often simply create space for more work, not less.
    • “Sometimes these AI tools that make us feel like we can do more...end up giving us more work.” (05:35)
  • Feeling burned out, considering drastic moves like cutting the podcast back—and his process for (thankfully) not acting impulsively.

Case Study #1: The Cabo Flight Booking Saga (14:00–27:00)

• The Downward Spiral:
  • Spent over a month fussing over flights from San Francisco to Cabo.
  • Obsessing over miles vs. dollars, timing, promotions, deal stacking, same-day change hacks, and cardholder discounts—only to find the savings didn’t justify the effort.
  • Missed the optimal fare by waiting too long, further illustrating the trap.
• Memorable Quote:
  • “From April 17 to May 25, I took dozens of hours of my life and tons of mental overhead, all to save money on flights that I kind of felt like at the beginning were maybe $100 too much...someone could probably argue that it was more.” (20:28)

Case Study #2: YouTube Thumbnails Rabbit Hole (27:00–32:00)

• Obsessing Over Perfection:
  • Attempts to DIY high-performing YouTube thumbnails after initial agency successes—even building elaborate prompts for AI generators.
  • Wasted 5–10 hours per week for marginal gains, draining energy that could be spent elsewhere.
• Chris’ Honest Reflection:
  • “If you’re spending 10, 15 hours on something, then somehow the hourly rate (for hiring a thumbnail agency) is actually a little bit more reasonable than it sounded at first.” (25:35)
  • “When I looked at how I was spending my time...they were different tasks, but it was the same move. Like, it was the same thing. I knew the rational answer of what I should do, but I didn’t stop myself.” (27:30)

Root Cause Analysis: The Real Reason Optimization Hurts (32:12–37:00)

• Psychoanalyzing With AI:
  Chris uses Claude/AI with deep personality profiling to dig into his behavior:
  • Not About the Money or Time:
    • “It’s that I can’t stand knowing there was a better way to do something and that I didn’t take it…It almost feels like admitting there was a better way and then I let it go.” (32:38)
  • This perfectionist mindset leads to costly, chronic indecision—“willing to lose money by waiting, because it wasn’t really about the money.”
• Memorable Moment:
  • Realizing he’d spent a month optimizing for a better deal on flights—yet by the end, couldn’t even remember the original price he was trying to beat. (34:27)

The Flip Side of AI Tools

• The “After Automation” Dilemma:
  • New tools give the illusion of clarity and save time—but in reality, they often create more decisions, more points to optimize, more work.
  • “So every time I can build a new skill and build a new tool that will save me time in the future, [it] compounded the time it takes me in the present.” (35:38)

New Systems & Solutions (37:08–end)

Rewiring the Optimization Instinct

• The "Book First Then Optimize" Rule:

  • Book something (seats, tickets, etc.) as soon as it makes sense—then let optimization happen if and only if there’s time, using monitoring/alert tools.
  • “Once I've booked it, it really takes up a lot less space in my head and I don't care about the optimizing as much as I do ahead of time.” (37:10)

• Tools He Recommends:

  • Points Path – Award flight alerts and comparisons overlay in Google Flights.
    • “It's the tool I'm primarily using when I'm booking travel domestically.” (40:58)
  • Autopilot – Monitors cash bookings and automatically rebooks if prices drop.
  • Both have special All the Hacks promo offers for listeners (see website).

The “Star” Productivity System (43:31 onwards)

• Physical To-Do List, with a Twist:

  • Chris adds a conspicuous “star” on tasks that can easily spiral into wasted hours—reminding him to ask: “Could I be outsourcing this? Can I set a strict rule for how much time to spend?”
  • “Every time I see a star, I have to write something next to it, which is how I'm going to not let this go down the rabbit hole.” (44:34)
  • Uses Amy (his wife) as an occasional accountability partner.

• Implementation in Other Life Areas:

  • Back to outsourcing thumbnails to an agency.
  • Building or using simple organizational tools (not over-engineering with AI) for newsletters, business tasks, and more.
  • Recognizing that using judgment and curation (not just automation) is his true “value add.”

How to Avoid Big, Knee-Jerk Changes

• Track Your Actual Time Use:

  • Before making drastic work/life changes, review where the time goes—via browser history, app logs, and analytics tools.
  • “There might be some very small changes I can make that will have huge, huge, huge impact on how I spend my time.” (49:46)

• Lesson:

  • “It only seems like I should be sharing that with you...because it doesn't make sense to try to reinvent the wheel if there's really great advice already here.” (50:13)

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Notable Quotes & Moments

• “It’s easier to pay $100 for convenience than to lose $100...feeling that loss is what's really painful for me.” (32:54)
• “The only person I'm not letting stop [from optimizing endlessly] is me.” (35:41)
• “If I'm going to spend 10 hours on something and I can outsource it for $100, I am willing to do that. Because not only is that valuing my time at $40 an hour, but it's removing this really big piece of mental overhead...” (42:53)
• “Just because you hear something once doesn't mean it sticks.” (50:27)
• “I haven't fixed everything. I don't have all the answers, but I think I've realized that sometimes it seems so easy to make a change that has a huge impact on something in your life...when in reality there's something else you're doing that is getting in the way.” (51:10)

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Timestamps for Key Segments

| Time | Segment | |----------|-------------| | 00:17 | Chris admits optimization trap: “It's not about the money and it's a trap I keep falling into.” | | 06:10 | On overwhelm: “Now I feel like I can build all kinds of tools...But in the short term I feel like I have more work than ever.” | | 13:29 | The Cabo flight booking spiral begins | | 20:28 | Chris’ multi-week effort to save $100–$400 | | 27:36 | YouTube thumbnail rabbit hole described | | 32:38 | “It’s not about money and it’s not about time…” (Root cause) | | 37:08 | “Book first, then optimize” system explained | | 43:31 | The “star” productivity solution | | 49:46 | The value of reviewing real time use before drastic changes | | 50:27 | On re-listening to best advice and episodes | | 51:10 | Meta lesson: “Sometimes the big change isn’t the real answer” |

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Listener Takeaways & Closing Thoughts

• Don’t let perfect be the enemy of good: Book, buy, or ship “good enough”—then optimize only if it’s truly worth it.
• Set boundaries: Use physical or digital cues to spot and interrupt optimization rabbit holes.
• Automate alerts, not actions: Let tools handle background monitoring, but don’t let them justify relentless tweaking.
• Value your time at least as much as your money or points.
• Regularly audit your actual time use before changing your routine or work hours.

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Feedback Invitation

Chris is experimenting with a more raw, conversational podcast style. Listeners are invited to weigh in on format, video, or anything else via [e-mail].

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Summary prepared by All the Hacks Podcast Summarizer – June 2026

Transcript

[Nick Loper]

I almost cut my entire income in

[Sponsor/Ad Voice]

half to save $400 on purpose.

[Nick Loper]

I genuinely thought it was a good idea before I realized what was happening. So let me explain how someone who

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optimizes his money and life for a living ended up doing something that crazy.

[Nick Loper]

Because the more I looked into this, the more I realized it's not about

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the money and it's a trap I keep falling into.

[Nick Loper]

And I really doubt I'm alone. And I think I finally get why I do it. And I want to share the system I'm going to put in place to stop pouring so much time into things that don't matter and get back that

[Sponsor/Ad Voice]

time for the things that do.

[Nick Loper]

If you enjoy this episode, or really any episode we've done in the past, or you want to just keep upgrading

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your money points in life, please do

[Nick Loper]

me a favor and hit follow or subscribe. It really does help out the show. Okay, so before I set the stage, I learned something funny.

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Recording transcripts of everything going on in my life.

[Nick Loper]

And that is that I can have

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an interesting conversation with a friend or

[Nick Loper]

be a guest on another podcast with almost zero prep. And then I sit down and think about recording an episode of my show and my optimization or perfection brain kicks in. And it takes 10, 20, maybe more hours of prep work, writing out notes, trying to script out ideas, organizing stuff. So today I'm not gonna do that. Today is an episode that has some notes. I haven't quite gotten to the point that I will just record with nothing written down. But last week I got on a plane and there was no WI fi. So I pulled out the notes app and I just started sketching some notes and I had a couple LLM conversations to organize those notes and get some feedback that I'm actually going to share. And I put that together and I'm recording this. And so this is much more like a conversation I'll have with a friend,

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which might even actually be a new

[Nick Loper]

format for this podcast in the future than it is a real deep dive

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where I've prepped and scripted and thought through everything.

[Nick Loper]

But I actually think it might be more real and more interesting because of the way I'm doing it. So definitely, please send feedback on, format, on thoughts on anything, anytime. You could do that in a comment on Spotify, YouTube, Apple, you could put it in a review or you can send it to podcastlthehacks.com so let me take you back to why I'm even doing this. And it's because right now I feel like I have no Free time. And I know that might seem crazy because when you hear this podcast, you might think, wow, it's just an hour a week. But with everything that's going on, it feels way more than just a full time job. In addition to the podcast, there's the newsletter that we run, which if you aren't subscribed, I highly suggest doing that because I spent a ton of time in it. It's all thehacks.com email. There's a hundred thousand people right now. And every week I try to curate the best of what's going on. And I've reformatted it a bit recently to really focus on my top picks for the week. I'll make one recommend recommendation. I'll share a little bit of what's going on in my life the last week. Things that just can't make it into the podcast because we prepare and record it more than a couple days in advance. And I started including my take on a lot of these deals and things that are happening. Just trying to make sure that you have one consolidated place every Saturday morning to get a sense of what's happened and what's going on in the world of kind of saving money, travel points, miles and all that. So that's one thing. There is one thing I want to do and I just don't have time for it is I'd love to create a space in the Bay Area somewhere on the peninsula where people who like to tinker and build can come and work out of either during the day and have a desk or on the weekend. And so if you happen to live in that area and that's interesting, go to all the hacks.com builder. You could fill out a quick form to let me know. So that's something. And then I spent a lot of time working on this app called Card

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Tool that I've made for our members.

[Nick Loper]

And we have this whole community of members at all the hacks.com/join and it's maintaining both features for that app, but also curating and making sure we always have the best card offers. So if you go to all the hacks.com cards, you can see the best offers at any given point in time. We don't just show offers that are partner links. Sometimes they're referral links, sometimes they're links we find online. Our goal is to always put the best offers there. So if you're looking for a new card or trying to see what the biggest welcome bonus you can get, you could just go to that site. All the hacks.com cards and you can find the best offers or whether they're links that support the show, support our members, or don't support anyone, I just want to make that easy. So that's a lot of the stuff going on outside of the podcast and just general logistics of life with two young kids. But a couple other things started happening and one is that for a short window of time we stopped having an au pair and Amy, my wife, has decided she's going to take on all of the responsibilities related to the kids during the week, at least until our youngest is kind of in full time kindergarten where there is a full day of schedule and there's a little bit more time to get back. And so the team went from three to two. But then about a month ago my assistant and operations person who was kind of helping make sure everything in this podcast and company runs needed to step away for personal reasons. And so the team in the last recording this on June 1, six months, five months, has gone from three to two to one. And so I'm feeling like things are happening so fast and just trying to stay on top of everything going on is becoming a full time job. And I'm trying to automate a lot of those things and using AI to do it. But it sometimes feels like using lots of AI tools can make your life more efficient, or sometimes it feels like you have even more work. And I think partially I do have more work because I'm taking on more, but also I now feel like I can take on more. So I do. So there's this great post that I'll link to in the show Notes called After Automation. There's also a podcast episode on it by the team at every and it kind of talks about how sometimes these things, these AI tools that make us feel like we can do more and we'll have more free time, end up giving us more work and might end up creating more jobs. And so that's something I've been thinking about a lot because I now feel like I can build all kinds of tools to solve all these problems that

[Sponsor/Ad Voice]

will have long term payoffs.

[Nick Loper]

But in the short term I feel like I have more work than ever. So that's kind of the tee up for where I'm at right now. It just feels like there's so much going on and I imagine that even if there weren't AI tools, even if I weren't running a business, life just always feels like there's so much going on just having a family, having kids, trying to plan the Logistics of the year, the week, summer camps. It always feels busy. And so that is just a lot. And I wanted to get back some free time. You know, there are weeks where I feel like I'm working 60, 70, 80, 90 hours a week. And maybe some of that's unnecessary, but it just felt like a lot. Now, I also know I'm a serial procrastinator, and so sometimes the episodes I'm recording get recorded right at the last minute before they kind of need to be done for editing. I know that I push things off. That is in my nature. And I know that I love to explore and go down rabbit holes, and sometimes that feels like it's part of the job. And so I give myself permission to do it because I think, oh, maybe it'll be interesting content. But I got to a point where right now it just feels like there is too much. I haven't gotten to exercise like I wanted to. Amy's offering to take the kids on the weekends more so I can get caught up. And there's both real reasons and as I dug into it, real reasons that they maybe don't need to be there. So what do you do in a situation like that? And my first instinct was it feels like recording the podcast because I spend so much time preparing is one of those things that if we scaled that back, we would free up time. So I thought, gosh, what do we do? Do I take a month off? Do we take the summer off? Do we make the show every other week instead of every week, do we

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take every third week off?

[Nick Loper]

And as I thought about this, I thought, what if we experimented and took every other week off? That seemed like a path forward that would make sense. Now, as many of you know, or maybe you don't know, the ads on the podcast from our partners, that is the primary source of revenue for this show. Sometimes it's also the links that you guys use to support the show when you open up new cards. But that revenue would probably get cut in half if the show went to every other week, which is a big decision, right? Cutting half the revenue out of the business is a big decision. However, it just felt like there was no time. And if I'm not able to prioritize my health, if I'm not able to prioritize my family, then what is it all for? Now, before I actually made that decision, it felt like a good idea. I wanted to really dig into how I'm spending my time to make sure that I'm not jumping to the wrong decision. And so I looked back and thought hard and looked at my browser history. I looked at how I spent my time. I asked an AI tool to go look at all my transcripts from my days to try to figure out where my time is going. Because unlike a job where you have tons of meetings and you can look at your calendar, I don't really have that. And the more I dug in and the more I asked Amy to kind of share her thoughts, the more I just started laughing at just such a ridiculous, ironic situation of how I'm spending my time relative to the decision I was about to make. And so I'm going to give you a couple examples that are very recent from the last few weeks that maybe feel similar to you guys sometimes, but just go to show how irrational we can be in the pursuit of better outcomes, optimal things, saving money, etc. And so one of them is a trip to Cabo that we are about to take and, and booking the flights for that trip. Now this has actually been a month long process. Now this doesn't mean I've been spending every day for a month on it, but I've been trying to book these flights for the better part of a month. The first record I have of searching for them came in the middle of April. And I first looked at flights and thought, gosh, this just seems expensive, right? I was looking at flights from San Francisco to Cabo and it's a three hour flight. I feel like flights used to be in the 200, $300 range, maybe even 4 or 500. And at the time they were about $700 round trip. Now we were thinking of going in June. June is not, you know, the perfect weather in Cabo. It's hot, right? The spring, the winter can be much better time. So a part of me was like, gosh, why is this expensive now later came to realize, okay, it's kind of the week or two after school gets out, so there's a little bit of demand. We're coming off of this giant conflict in the Middle east that's driving fuel prices up. And so maybe that price was justified, but for me it just seemed so expensive. And it also seems so expensive because when I looked, there were cheaper flights, but you had to change planes, you had to leave at 6am and something held me back from booking these flights. Nonstop flights to cabo were about $350 each way, and for a family of four, $700, that's almost $3,000. Now we had a great deal for where we were staying, so we already had saved so much on that trip in general that maybe you could argue that who cares what the flights are cost? Or maybe you could argue that given the situation we're at in life, given that this is a vacation with the entire family, that we aren't going to get to take that often because of school, because of work. Just stop worrying about it. However, I just couldn't because it just felt like it was way too expensive and there wasn't a great way to optimize it at the start this episode is brought to you by NetSuite. Every business is asking the same question.

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[Nick Loper]

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[Nick Loper]

that's allthehacks.com superhuman this was all happening Right around the time I was creating some skills for different AI tools, just general skill files that could work with Claude or ChatGPT, Codex. And so I was trying to build a framework for here's how I book travel. And the broad idea was if I could actually codify my entire booking process

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into a system that could be repeatable,

[Nick Loper]

then I could actually spend all the time I want on booking flights without it being my time, and I could get the results I want. And so I'm actually working on that skill and might publish it to members to kind of see how it goes and maybe publish it publicly if people get value out of it. So one challenge was instead of just booking the flights, I kept wanting to iterate on this process. Another challenge was that very recently United started offering 10 to 15% off flights if you have a United card. Now I have a United debit card, and in order to get that deal, you have to spend $10,000 on the debit card. And I was kind of in search of a way to spend money on a debit card that would not necessarily come at the opportunity cost of getting a lot more points doing something on a credit card. And so that was kind of holding me off on wanting to do this. Now, my dad happens to have status and a United card, so he was getting that 15% off. But in order to book from his account, I would need to set up the United points pooling feature, which works, but as I learned, takes three days for a new member to join and then takes 24 hours for the points to post. And so if every time it felt like, would it actually be faster to to get the $10,000 of spend on my card so that I got the benefit, how long would it actually take for that to happen? The first attempt I had didn't actually work. There was a purchase that was in a category that was excluded. And so I kind of kept trying to find the optimal way to book this flight and the prices went up and now they were at $500 a person to get to Cabo instead of $350. And the points needed went from 30 something to 40 something. And even after that cardholder discount. Now, don't get me wrong, I have a lot of points, but it just seems so crazy to spend 40 something thousand points to fly one way nonstop to Cabo in economy, when this summer we're flying to Europe in business class nonstop for 75,000 points. And so like, there's just something in my brain that was struggling to make this happen. However, there were Other flights that day that changed planes or left at just ridiculous times and had layovers that were 10, 15,000 points. And so one of the challenges I also had was, well, the nonstop flight was really expensive, but a 6am flight through Houston might have been 15,000 points. And because I have status, we could same day change. So all of a sudden I'm starting to think, well, what if we fly out of other airports? What if we change planes? What if we book an unoptimal flight and then hope that on the day of we can same day change into the direct flight. So I'm going down this rabbit hole that listening to it and repeating it out loud seems so ridiculous. And ultimately we land on a 20,000 point flight that leaves from Oakland Airport, which is further away from us than SFO or San Jose, and changes planes in San Diego. And I'd kind of talked myself into, well, it's on Alaska and I have status, so we can pick premium seats or maybe we'll even get upgraded and maybe we can same day change to the SFO flight if we want. And honestly, at the time, 20,000 points versus 42,000 points times four passengers was saving almost 80,000 points, which I'd probably value at a thousand dollars. And so we ended up booking that flight and I remember Amy saying, wait, 20,000 points? What about the flight that was $350? Couldn't we have booked that? Well, no, now it's $500. Because I waited so long trying to get this deal. And every day I set up alerts for different options that I could get from United or from other options. And I was getting these alerts. And so as they came in I was like, okay, well there's a good deal, but I have to set up these points pool to book it. And now I've got to transfer the points over and they take 24 hours. And finally after these alerts are coming in, I've rebooked us on a United flight that was kind of unoptimal because it, you know, left at a bad time and changed planes, but it was super cheap. And I thought we could same day change to then eventually finding a 30,000 point version of it that left early in the morning and had no seats together to the original flight that we actually wanted that we could have booked for $350. I ended up booking it for 30,000 points plus taxes per person. And the seats are actually not as optimal as they would have been if we had just booked it a month ago because it's kind of Filled up. So we've got two of us sitting together and two random people. So from April 17 to May 25, I took dozens of hours of my life and tons of mental overhead, all to save money on flights that I kind of felt like at the beginning were maybe $100 too much. And at the end of the day, I ended up paying an amount that was not too different from what they were originally. And someone could probably argue that it was more. So we're talking about somewhere between zero and a hundred dollars a person was saved. So maximum 400 for dozens of hours of time. So that seems crazy, right? Like, that just seems, in hindsight, like a waste of time. But in the moment, I was struggling. And I'll talk about why, but I'll give you one more example, because it seemed like that was the worst offender. But I looked at how I spent my time, and there was one other big culprit, and it's all around YouTube. And I'm gonna give you some context around YouTube because I think it's helpful context. Since the beginning of the show, I have recorded the video of all of the interviews we've done. And for the last, let's call it 3ish years, I've recorded the video of all the solo episodes I've done as well. And so we still haven't put out the video for all of the original episodes that we never released on video on YouTube, but we have, going forward, started putting them all out on YouTube. Then when Spotify rolled out video, we put it on Spotify. And then just this past week, Apple had an easy way for us to start rolling out video on Apple Podcasts, and we did that as well. And so video takes a lot more time and energy to create, especially on the editing side. Right. Just recording the video isn't any harder than the audio, other than I might need to turn on some lights and look at the camera and whatnot. But fundamentally, the challenge is in editing and making sure that you know, when the right person's talking, they're on camera, that we get good reactions. The cuts are a little harder because you can see a jump cut that you might not see if you were just listening to the audio because there's nothing to see. I am very, very curious if that effort is worth it. If you're watching this on YouTube, if you're listening to this on Spotify or Apple and the video is there, does it even matter? Because if it doesn't, why am I doing it? You know, it's a tremendous amount of Work. I do it because I think it gives a little bit more of an interesting environment to the episode. It's if you happen to be watching it, you can see the person talking. Sometimes I'm able to do some screen sharing. When there's a guest, you can kind of see a bit more of the interaction. But if it's not important, if people don't enjoy the value of video, especially as we've pushed it out on Apple, which is kind of our biggest platform, you know, I'd love to hear from you. So let me know. Podcast at all the hacks.com very curious. And the other challenge is that YouTube is very different than Spotify or Apple. And this is changing a little bit. But on YouTube, the primary audience is people that aren't subscribers to the show. Even though we have, you know, a hundred thousand subscribers on YouTube, if I look at every single episode, the primary people that are watching it are not subscribers. That means that if you're watching this on YouTube, you should probably click that subscribe button because you're probably not subscribed. But it also means that the way you package on YouTube is so important, and so getting your title and your thumbnail and the first 30 seconds of a video really, really matter. And because of that, you've probably noticed if you've listened for years, that the start of the podcast used to be a bit more podcast style. Hey, welcome to all the hacks. Like, this is what the show's about. You know, excited you're here. For an audience of people who don't yet know the show, don't know me, that's a really weird way to kind of be greeted. If you maybe clicked a video that was talking about how to save money on a trip to Europe, you're like, well, who's this guy? Why do I care about the name of his podcast? Like, I don't even know him. I just want to understand why I could get a better deal flying to Europe this summer. And so packaging really matters. And it matters so much that we've sometimes created thumbnails and titles and ab tested them, and something that I thought would perform better than something else ended up performing a third as good as the other option. And so the difference between a great thumbnail or a great title or a great early opening of an episode could be whether a hundred people watch it or a hundred thousand or a million people watch it. And so when we got started, we started working with a thumbnail agency and title agency. Just because I wanted to work with someone who's thought about this way more than I have. And they charged an amount of money that somehow, even though I understand this still feels high, which was about $400. And so for $400, they would ideate, they would do research, they would come up with design ideas. We would pick a final candidate, or maybe sometimes two to ab test, and then they would produce the final asset and come up with a title to support it. If it sounds crazy to spend that much for one image, you know, it did to me. But also at the same time, the number of hours spent on it could be really high. And so if you're spending 10, 15 hours on something, then somehow the hourly rate is actually a little bit more reasonable than it sounded at first. And I think the worst thing that happened to my thumbnail journey on YouTube was that the first episode we put out was episode 181 with a friend of mine named Kai. And the episode was titled making an easy $3,000 a month from Online Deals. And it was a great episode. And it took off on YouTube like no episode we've ever done before. I think at the time, the best episode had done 10, 20, 30,000 views. And that episode quickly ramped to over a hundred thousand views. Now, in my mind, I thought, wow, thumbnails and titles really do matter. And then the next week we tried. Didn't have a huge impact. And we kept trying. Now, it worked better than the generic thumbnail thumbnails we'd done before. We made that first unique thumbnail, but it didn't do the a hundred thousand well. And so we just kept trying week after week for maybe three, six, nine months. I can't remember exactly how long. And we saw traction, but not as much as I had thought we would based on our early experimenting. And the hypothesis for why that is the case is that YouTube doesn't know what to do with us, because this is not a show about a specific topic. Some weeks we're talking about how to optimize your life. Some weeks we're talking about points and miles. Some weeks we're talking about saving money. Some weeks we're interviewing someone about parenting. So if YouTube sees someone coming to us watching a Points and miles video, and they're like, researching city cards, and so they found our episode All About City, and we try to show them another episode of the show, and we show them an episode about parenting, they're probably not in that mode. And so a lot of the people that find us on YouTube find us for a specific topic. They're not necessarily People who are interested in optimizing all aspects of their lives, like people listening to this show right now probably are like you, because they found us in a different way. They didn't find us knowing what the show was even about. And so YouTube really struggles with shows like that, best I can tell. So we finally made the decision to move to templates for the show. And for a while, I was still having the agency make templates at a lower cost, where those templates didn't have all the research. They weren't trying to tell a story as much as they were just trying to be a consistent design that looked good and cohesive. And ultimately, I ended up taking that templated process over because the team we worked with at Clickables. So if you're interested in YouTube thumbnails, check out Clickables. They're fantastic. They built a template I could use and very quickly change the text, throw an image of the guest on and put up. And the idea was, let's just do that every week. Let's spend an hour on it at most and publish that. Because at the end of the day, no matter how much we worked on thumbnails, it didn't seem to move the needle. However, when I started taking that process over, I couldn't help myself but try to make the best thumbnail. I would look at the episode and think, gosh, I know there's something better than a template. And I would go into ChatGPT and I'd say, come up with some ideas. Or I'd go into Claude and do the same thing. And then when ChatGPT image 2, this new image model, came out, it was so good at creating images, but not just creating images. The thing that it nailed, which made thumbnails feel like something I could do, was you could create a thumbnail and

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use a fake person on it and

[Nick Loper]

then say, hey, could you remove the person and leave everything just as it is? And in the past, I don't know if anyone's tried this. You'd have an AI tool generate a thumbnail or an image of anything. Maybe you're trying to decorate your house. Can you show me what it would look like to put a couch on the wall? And then you say, actually pull the couch out, you know, from the wall a foot, and all of a sudden you got a different couch facing a different direction? So it was so bad at kind of consistently iterating on the same image. And GPT image 2 is so good at that. And so I could come up with an idea, I could Ideate the idea, and then I could create a prompt. I could give it some feedback, tell it to do research on YouTube thumbnails and generate something that was really good.

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Maybe it didn't have me on it

[Nick Loper]

yet, but I could remove the person on it, replace it with me, and end up with a thumbnail that was just like the great thumbnails that I'd been working with the Clickables team to create. And so for the last month, that has been what I've been doing. And so if you look at the thumbnails on YouTube, you'll say, wow, they look better than the templates that I'd done before. And yes, they've probably performed a little bit better, but at the end of the day, they have not performed better to justify the five to 10 hours a week I've spent trying to come up with new systems for prompting these thumbnails. And not just creating them, but for whatever reason, I know that they're better when I ab test them because we can pick the best one. So I've not been making just one, but three. And you might ask, like, why are you wasting all your time on this? And the short answer is, a little bit.

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It's fun.

[Nick Loper]

I just have this desire to try and make the best thing possible. Like, when I create this show, I want it to be the best version of the show. One of the reasons that someone at YouTube told me the show might not be working is because it's too long and it's an hour long instead of 20 minutes. And they're like, why don't you try to explain, you know, the entire city credit card ecosystem in 20 minutes? Or, why don't you try to explain how to book award travel in 20 minutes? And my answer is, well, I don't think I can do a good job in 20 minutes because there's just more information. And leaving it out feels like I'm doing a disservice to people watching and listening. And that's just how my brain works. So I don't know what to tell you, but when I looked at how I was spending my time on thumbnails and I looked at how I was spending my time on flights, they were different tasks, but it was the same move. Like, it was the same thing. I knew the rational answer of what I should do, but I didn't stop myself. And like I said, it's not that I'm doing this because I'm training to be a travel agent or a thumbnail designer. I do feel like I could outsource those things. However, like, sometimes it feels really good to do something yourself. It feels good to learn it and try to hone it and refine your craft at something, even if you don't want to do it professionally. And I love building systems around those things. So building out a flight skill or building out a thumbnail skill, that's fun. But at the end of the day, it was not a good use of time. In fact, when we rewind to the story I said at the beginning, I was currently sitting on this idea of cutting half the revenue of the show, which is significantly more than $400 a week. But I was thinking that it would be the best way to free up my time. When in reality, in just one week, probably last week, I had spent at least 15 hours, maybe even 20 hours on thumbnails and on booking travel for a trip next week. And that is crazy. So there's a really easy way that I could have freed up that time. I could have spent $400 on the thumbnail designer, I could have just booked the original travel. But I didn't. And so that was what led to me to have kind of a really deep conversation with an LLM. I used Claude because I have a folder where my personality profile from this site, deep personality lives. So it not just knows me from just all the interactions I've had, but it also knows the nuances of my psychological profile and trying to figure out why I'm doing this, what am I doing this for and what can I do differently because there's something going on. This episode is brought to you by Green Chef.

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That's code [e-mail] 50allthehacks this episode is brought to you by Upwork. One of the biggest unlocks I found

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running a business is realizing I don't have to do it all by myself.

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I've hired freelancers for years, copywriters, designers, contractors. And what I keep noticing is how

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That's up w o r k.com upwork.com As I started thinking about this, there were really two things that hit me. So first off, I'm going to just share the feedback from the session I had in Claude. I'll just read it because you know, the why of why I do this really helps because what I thought it was at the beginning wasn't really what it was. And it said it's not about money and it's not about time. It's that I can't stand knowing that there was a better way to do something and that I didn't take it. Once I spot that better deal finding a same day change or you know, the points pulling angle booking the easy flight doesn't feel like I'm buying convenience, right? It doesn't feel like I'm just paying $100 to book the flight now so that I buy back my time. It almost feels like admitting that there was a better way to do something and then I let it go. And that might sound like the same thing to some people, but for me it's very different because, you know, it's almost like it's easier to pay a hundred dollars for convenience than to lose a hundred dollars. Like, feeling that loss is what's really painful for me. And the proof is a little bit in the contradiction that I caught myself with on Cabo flights, because I thought back to the what I was thinking in the process. And I remember specifically thinking that I

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was willing to lose money by waiting,

[Nick Loper]

meaning I knew the flight prices might go up, but letting the flight prices go up was not really that painful because it wasn't really about the money. It was about not getting the absolute best deal I could and the moment. And so as those prices creeped up, I actually wasn't upset that the price went up. I was upset that I didn't do the optimal thing when it comes to finding a better deal. And so it was easier for me to just wait until maybe I could spot a deal that was better than the rack rate that I was seeing online so I could feel like I found that deal than it was just accepting that the original price was probably fine and moving on. And a few things made it worse. If you had asked me, prior to researching this episode briefly, what the original price of the ticket was, I genuinely forgot it. Right? I spent a month trying to get a better deal than an original flight

[Sponsor/Ad Voice]

price that I didn't even remember because

[Nick Loper]

the number I was optimizing for wasn't even real. I'd convinced myself sometimes also that this is research for the podcast, right? I could tell a story about saving money on flights, but the real story is that I should have just booked the first flight I found and moved on and saved the time. And sometimes there is a real opportunity to save money on flights. And so I don't want to say that the best answer is to just book the first thing you see, because there are a lot of times, and I'm going through the process of booking a few other trips for the year where five minutes of research might save you 80%, because there actually is a great deal, but it's the final 10% of savings or maybe the lack thereof just for the sport of optimizing. That, I think, is the hard thing. But for me it's even harder because I give myself permission to do some of these things because I say I can talk about it and it's helpful for others, but it might actually be more helpful to share how I've gotten past that. And I stopped doing it because I imagine that there are a lot of people listening that end up in a situation similar to mine. Hopefully not. But I imagine that's the case. And then again, I think AI is making this worse because some of that effort is something that was just me, but now it feels like every time

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I can go build a new skill and build a new tool that will

[Nick Loper]

save me time in the future, but compounded the time it takes me in the present. And one of the craziest things Claude kept calling this, the deepest cut, is that I give everyone else on earth permission to do the thing I don't give myself permission to do. When a friend calls me and it's like I'm trying to book this flight to go on this trip, what should I do? I will often tell them, oh, well, that seems reasonable. Just book this price. I won't tell them, go spend 50 hours doing this. Like, I know it's unreasonable. I might look once to help them get the deal and then let it go. But the only person I'm not letting stop is me. And all the stuff that loses out is stuff that feels less urgent, like exercise, family kind of episodes, things that I could put off because I get stuck down this rabbit hole, things that don't have a deadline. Now, when those things do have a deadline, I end up getting to them. But a flight has a departure date, so it maybe feels more important than a workout does. The thumbnail, it has a published date, has to go out that you need to upload something. And so this is a challenge. And so let me talk about what I'm going to do about it. Because I want to buy back time, because I want to have more time to do things. I don't want to feel like I'm drowning every day. But also, maybe I don't want to cut back on half the podcast because that's not the right answer. And so I don't need to want a better deal less. The instinct for spotting deals and spotting awesome things is one that I've built this entire podcast on. I just need to make not chasing it to the end the path of least resistance. So with flights, I think the answer

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for me and for many people might

[Nick Loper]

be to book something first and then decide whether you want and how much you want to optimize it. Because I found that once I've booked a flight, it just feels so much better. I don't worry even if I know that there was optimal things that I could do to try to drive the price down or go to a different airport or change planes or same day change once I've booked it, it really takes up a lot less space in my head and I don't care about the optimizing as much as I do ahead of time. And so, for example, for this trip that we're taking to Hawaii, there were some decent flights I could book with points and I just went and booked it, which is very unusual. But I've started training myself to just book something. And the good news is if you book something with points, you can cancel it and get back your money. With the US programs internationally, I think there's probably a little bit more to consider because if you're transferring points to a foreign carrier, sometimes those points have higher cancellation fees or sometimes, you know, they expire. So I do think you want to be a little bit more careful with bigger trips, but that's a once a year kind of thing. For regular travel, I'm usually booking out of American, Alaska, United, Delta, that kind of stuff. And for those flights, if you book with points, you can cancel almost up until boarding, maybe even up until takeoff, maybe sometimes after that, and get back

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almost everything that you paid for.

[Nick Loper]

I think United lets you cancel after you've taken the flight if you didn't take it for a fee. If you're booking with cash, you're almost always going to get a full refund. If you're not booking basic economy, maybe in the form of flight credits or oftentimes it's not that much more expensive to pay for a refundable ticket. I'm going to call that the toll that I'm willing to pay now to close the loop to make this easier right when it's, oh, do you want to pay 179 or 229 to book a refundable ticket? I think I'm just going to pay that 229, assuming that 229 is a better deal than what I could get with points. Once I've done that, it just frees up so much mental space. This episode is brought to you by Mercury.

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codes and discounts from all our [e-mail] deals. They're all brands I love and use,

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so please consider supporting those who support us.

[Nick Loper]

There are two really, really fantastic tools once you book a flight to make sure you still get the best deal without having to think about it. So I'll share two of those. One is any awards search tool, but the one that I think has really helped me for all my domestic travel is Points Path. And Points Path is a browser extension that you can run that shows up and overlays on top of Google Flights all of your flight prices in points and looking at multiple ways to book it. So it might look at Alaska and American to see which is cheaper and

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it'll compare it right there right in

[Nick Loper]

front of your Google Flights results and give you the best price. And if you're a pro member you

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can search out further.

[Nick Loper]

You can also set alerts. So once you click that I can

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say hey, alert me if this price goes down.

[Nick Loper]

And the alerts have been so valuable. In fact, it's how I ended up getting the flight that I wanted to Cabo for a much better deal than it originally was. And so if you're interested, I talked to Julian who's the founder of Points Path and if you use all the hacks 15 you can get 15% off a pro plan on Points Path. It's a great tool and it's the tool I'm primarily using when I'm booking travel domestically and I'm not planning a

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big trip where I'm going to spend

[Nick Loper]

tons and tons of points. Most other award search tools also have alerts and you can set those up. But I find that I usually have two modes of travel. It's like I'm planning a really big trip and I want to set alerts to try to find opportunities to go to Europe in the summer and get four seats. Or we're going to Cabo this week and I want to find flights or I have to go to this thing in Chicago and I'm looking for flights and I'm not as flexible. I'm considering cash or points and so I just want to see the best deal and Then I want to set an alert that can alert me when things drop. And it's been fantastic. And then if you're paying with cash, there's an app called Autopilot and I used to work with Sam, who's the founder, so I emailed him and was like, what can we do? And if you go to all the hacks.com autopilot you can sign up for Autopilot. What they do is they monitor all the cash bookings you make and if the fare drops, they will automatically go

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and exchange that flight for a lower priced flight.

[Nick Loper]

So if you book a flight on united and it's 400 bucks and now the flight's $300, they will go in and rebook that flight on United for $100 savings and get you back that $100. And so the way they make money is that they charge a 25% fee on that savings. So they save you $100, they're going to charge you $25. Now if you sign up at all the hacks.com autopilot you will get your first hundred dollars savings free. So if they save you that a hundred dollars, they're not going to charge you 25%. They also have a pro plan that has a bunch of features. I think they also monitor award flights just like Points Path does. And in that case they would just monitor whatever you've booked. So that's great. If you've booked it, you want to get a better deal. Points Path is also great if you book one flight, but maybe there's three flights you want to book and so you can set an alert on all three of them without having to go and create alerts in all of the other tools. Obviously I mentioned the flight booking skills that I'm working on to kind of simplify organizing all that information in one place, but that's a little bit further out and you can't get that today. So my new plan for flights is if I'm paying cash, book something refundable. If I'm doing points, book it with points and just book the best thing for now and later decide whether I want to optimize it if I want. And that'll be driven by looking at award alerts from primarily Points Path if it's for award and Autopilot if it's cash. So that's what I'm focused on right now and I think that's going to work. Now we're a couple weeks into it. I have gone and booked a bunch of trips and I've not thought about it ever since I booked it, and I feel a lot freer, but let's see how that keeps going on thumbnails. I just went back to the thumbnail agency I was working with and said, hey, can you guys take this back over? If I'm going to spend 10 hours on something and I can outsource it for $100, I am willing to do that. Because not only is that valuing my time at $40 an hour, but it's removing this really big piece of mental overhead that is really hard for me right now if I don't outsource it completely. Also, whether I want to outsource my time at $40 an hour is a question, but I don't have the time right now. So because I no longer have a team of three, and I have a team of one, in order to insource this project, I would need to hire someone. And right now, the time it would take to hire someone and ramp them up, you know, I just don't have that this week. Right. I am going down that path and looking for someone. Right. Right now, I think the perfect person for me is someone who's really dialed into AI tools and has gone really deep on building stuff, because I'd like them to be a collaborator in that and someone that's got good writing skills. So if I find that person, great. But until I find that person, right now I'm focused on how I can outsource individual tasks to people that are probably going to do a better job than me because they live and breathe it. And so how do you make this work? Because if I think about how this unfolded, it's not like I sat down and said, I want to spend another six hours booking flights today, because that's a good use of my time. It just kind of happened. And the one thing, I went back and forth with this session in Claude about what to do, and they had all these ideas, and ultimately it came down to finding some thing that I'm already doing that I can attach this new. I don't know, mantra is the right word, but this new philosophy to. And so I thought, okay, do I put a sticky note on my computer? Do I have a reminder go off every two hours during the day? And for me, as much as I love technology, I really enjoy having a piece of paper on my desk that is just a list of the things I'm working on so that I can look at and make sure things don't slip through. Because sometimes, you know, my inbox in one day might add 200 emails. Now, when I sit down in Superhuman to kind of jam through those emails, I can get through it really quickly. But the email is not the best place to know the projects I'm working on that need to get done and when they need to get done. And so I have this piece of paper every day, and I now have a indication, which is literally just a big star that I put on this piece of paper as I run through the list, which is a reminder, is this a task that could take longer than it needs to, that I should not let take that long? And I just put a star on it. And then I have this subtle cue looking down multiple times a day that this is a thing that I should outsource or not go down a rabbit hole for. And for each one of those things, as I make that star, I ask myself, how could I do that? And so instead of waiting until I'm in the moment and realizing, I just look down and I say, oh, I need to book travel to this conference in Chicago. So I'm going back to the Chicago seminars conference. It's now called the Points Travel Festival. I'm speaking this year, and I need to book my travel. And so I put a star book, Chicago seminars travel star. And I write down, like, book first thing. Anytime I see a star, I have to write something next to it, which is how I'm going to not let this go down the rabbit hole. I don't know if this will work. It might not work. Sometimes I just sit down with Amy and I'm like, let's just talk through the star things. And you can, you know, maybe over lunch, I'll say, hey, can you just talk to me for a second, make sure I'm not, you know, wasting too much time? Like, it's good to have an accountability partner. And if you work by yourself, sometimes that disappears. But the star thing works on the system I already have, and I think it's going to help. And so I decided to outsource the thumbnails for other things that are big parts of my life. I'm trying to think how I can systematize them without trying to go build custom software. And so for the newsletter, I didn't try to go build a newsletter bot, but what I did do is try to build a place where anytime I flag something on X or anytime I have an article, I can either forward it or star it or bookmark it some way. And that'll all just get organized into one place. So it's Saving me time. But I'm not trying to build a whole piece of software to run everything. And I did build a little system where when I have all the things that I want to include, I can go in and in a simple kind of markdown file kind of way, star them or move them up and down so they know which section they're in. And then I can sit and draft them and I can write notes and all of that kind of stuff. Like, I'm not outsourcing that to AI because I just feel like judgment is the thing. It's missing, and it's the reason people show up here is that it's not just me letting an AI run things. It's listening to someone who has thought a lot about this. Apply a layer of judgment over what's important, what's interesting, what matters, and what the research I've done is saying, so I'm not going to go and cut out half the episodes of the year, right? Like, that was the idea. That is definitely not what I'm doing. I'm not going to cut the income of the show in half because I can't learn, you know, by instinct, how to spend less time booking flights. I'm going to create a system which is as simple as a to do list with a star and some rules of thumb, which are on flights. Book the first thing that makes sense and then decide how much you want to further optimize it. And I'm going to see how that unfolds and I'll share, I'll come back and let you know. That said, I did decide that in July, I am going to take a week off the podcast. It's around my birthday and I just wanted to experiment. One other thing. If you caught the Derek Sivers episode a few months ago, I realize as I'm trying to take all the lessons I've learned to heart and really kind of level up and evolve in this world of optimizing. I've gotten a tremendous amount of advice from episodes I've done in the past, talking to really smart people. And I've been going back and listening to some of those episodes because just because you hear something once doesn't mean it sticks. And so that happened with the Derek Sivers episode. I listened to it and I was like, wow. Like, even though I recorded this and have listened to it in the past, re listening to it was really valuable. And when I look at the data and the analytics, many of the people listening have not been here for five years. They have not heard every episode. So to the extent I'm finding episodes that when I re listen to it, I get meaningful value out of it, I might replay that episode on the feed because I think it's really valuable. Now, I'm not just going to replay episodes for the sake of filling a week, I'd rather take a week off. But I will replay episodes when I truly believe that it's been long enough since this episode came out and the content within it is worth listening to twice. And so if you see something and you think, oh, I've heard that before, I would encourage you to take it with the direction I just said, which is that it's there for a reason and you might get a lot out of it listening to it again. And I'm not going to do that every week. That's not the goal. But as I go back, listening to the catalog of things I've done, trying to see how I can use those lessons to improve my own life, it only seems like I should be sharing that with you because it doesn't make sense to try to reinvent the wheel. If there's really great advice already here, I will probably try to layer on at the beginning, in the middle or the end, some updated context, some updated feedback, some updated thoughts. But at the end of the day, there are a handful of episodes that are just still so good that I'm going to reshare them as I find them. So I haven't fixed everything. I don't have all the answers, but I think I've realized that sometimes it seems so easy to make a change that has a huge impact on something in your life, whether that's, oh, something's not working. I need to change jobs, I need to move, I need to cut a bunch of my business back, when in reality there's something else you're doing that is getting in the way. And I've tried really hard to find that. Now, part of the reason I was able to find it, just to give people some ideas, is that I was recording everything I do right? All my browser history is there. It turns out when I asked, I can't remember if it's Codex or Claude. What I'm doing on my computer. Turns out that Mac OS was kind of logging somewhere somehow which apps are open during times a day. It's probably for the I forgot screen time app so you can get all of this data to try to recreate where you're spending your time, what you're doing. And by doing that, I've been able to really take an inventory of how I spend my time without having to go and kind of set up my own timecard of how much time did I spend doing X today? How much time did I spend doing Y? Like that is too much lift. And so one great thing is that a lot of these tools make it easy to track how you're spending your time. And I would encourage you to do that before you make any big changes. Because it turns out, as I've learned, that there might be some very small changes I can make that will have huge, huge, huge impact on how I spend my time. So before we wrap, a couple other things. Please email me with feedback if you have thoughts on Video Podcast at all the hacks.com if you have thoughts on this episode how it feels to listen to a more raw and casual conversation than something that's a little bit more prepared, rehearsed and scripted versus something that feels a little bit more prepared and organized and maybe a little bit less raw because it's a little bit kind of written out. Let me know. I really love feedback. Please send it in any way you have and I look forward to sharing, you know, the journey that I'm on that hopefully is helpful to you to hear more about. So that is it for this week. I will see you next week.

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[Nick Loper]

Com.