So we had a meetup last week that was so awesome! Probably one of the best ones we’ve ever run. We were outside at the Forest Lake Lakeside Memorial Park near where I live. The gazebo was packed, and so many rad people showed up. A friend of mine, Joe Saul-Sehy, who’s the host and founder of The Stacking Benjamins Podcast was there and helped lead an activity with the group that got everybody talking, arguing, and laughing all at the same time lol! It kinda stuck with me afterward, and I wanted to get my thoughts out, learn more, and share. So it’s the whole reason this post exists.
The activity started with one simple question tossed out to the room:
“What’s something you spent a ridiculous amount of time optimizing for almost zero benefit?“
This got the group lit up. Some people were practically raising their hands to confess lol! For example, somebody spends so much time comparing gas station apps to save a few bucks a month. Kinda like my Mother-in-Law who’d sometimes drive across town chasing a five cent per gallon discount on gas and probably burned more gas getting there! Or, the person that has researched credit card reward categories for six weeks and still hadn’t picked one. All of this was kinda funny, but it also totally hit a nerve, because all of us in that room, myself included, have absolutely done something like this in our lives at some point.
So this question has been rattling around in my head and I wanna dig into it.
The Trap of Feeling Productive While Going Nowhere
Here’s the thing about over optimizing your money. It feels like discipline. It feels responsible. You tell yourself you’re being totally good with your money by squeezing every last cent out of every single decision. But a lot of the time, you’re just avoiding the harder part, which is actually deciding something and moving on with your life. It can be so hard, but make the decision and move the F on!
I mean, I’ve said this before and I’ll be straight with you. I’m not really a spreadsheet guy. Never have been. I know plenty of folks in this community who build these massive, spreadsheets that are tracking every category of spending down to the penny, and hey, if that floats your boat, go for it. That’s just never been my style. I’d typically rather do quick gut check math and get on with my day than build a whole tracking system to save four bucks a month. And actually, the research kinda backs up why that approach might actually serve us better!
Economist Herbert Simon coined a term back in the 1950s called “satisficing.” It’s a crazy mashup of “satisfy” and “suffice,” and the idea is simple. Instead of chasing the mythical perfect option, you find something that’s good enough and you go with it! The whole point was that gathering more and more and more information to land on a perfect answer can end up actually costing you more, in time and energy, than that perfect answer is even worth. Like, I take my time so seriously. We have a finite amount of it, and I’m always concerned I’m wasting time.
Psychologist Barry Schwartz built on this in his book The Paradox of Choice. He split people into two camps. Maximizers and Satisficers. Maximizers typically won’t settle for anything less than the absolute best option, so they continue to research, compare, and agonize over every decision. Satisficers, on the other hand, tend to find something that checks the boxes, or most of the boxes, and keeps moving. So here’s the part that should make every over-analyzer in the FI community chill for a sec. The research on this suggests satisficers tend to actually be happier! Maximizers burn so much more time and energy chasing perfect, and they’re more likely to second guess themselves even after they’ve made the call.
There’s a job market study that captures this perfectly. Maximizers landed jobs paying about 20 percent more on average than satisficers did. Sounds rad, right? It’s a bigger paycheck, no argument there. But the maximizers often reported feeling worse about their choice. They couldn’t seem to shake the feeling that a better offer was always out there somewhere, just out of reach.
That right there is the f’n trap. More optimizing does not always guarantee a better outcome. It just guarantees more of your time gets eaten up.
Real Scenarios Worth Arguing About
So back to our meetup. Joe laid out a handful of real world scenarios and had everybody get up and move to one of three areas. The areas were labeled “worth optimizing,” “good enough as is,” or “never do this.” Keep in mind here, there are no right answers, just total gut reactions, and man, did it spark some debate. It was SO FUN!
So let’s try some of these on for yourself. Would you drive fifteen minutes out of your way to save a quarter a gallon on gas? Or, have you spent, like, six weeks researching a new TV before you ever pull the trigger. This is me! I will research and learn so much before making the decision when it comes to buying technology like a tv, or camera. I mean get this. Would you spend months on reddit and YouTube cross-referencing guitar pickup reviews, tone samples, and wiring diagrams to shave twenty bucks off a set of pickups you could’ve just bought on Amazon and be done with it?
That’s a real thing that happens. We disappear into a rabbit hole of comparing models for weeks straight, debating tone and capacitor values like it’s a f’n doctoral thesis, all to save less than the cost of a decent lunch. Meanwhile I could’ve press the buy now button, bought the set that sounded good enough to our own ears, plugged in, and BOOM you could’ve been jamming the same week.
Would you take a connecting flight to save two hundred bucks? What if it adds four extra hours onto a trip? No way! Is it a family of four? Okay, now the big one…would you continue working five extra years past the point where you could already retire, just to pad out a bigger safety cushion? Just to feel more secure.
Obviously, none of these have a right answer. That’s kind of the whole point, right? What counts as smart optimizing for one person is a total waste of life for somebody else, depending on what your time is actually worth to you, what time of life you’re in, and what you genuinely care about.
From what I found, a good gut check that can work pretty well is to ask yourself what your time is roughly worth per hour, then ask if the time you’re about to burn chasing a savings is worth more than the savings itself. If you’re spending three hours shopping around to save eight bucks on car insurance, you basically just paid yourself less than minimum wage for that research! If saving four cents a gallon means driving fifteen minutes each way, you’re burning gas and burning your own life to chase pennies you’ll never even notice missing.
On the flip side though, some decisions absolutely deserve real time and attention. Things like a mortgage rate, or a major insurance policy totally makes sense. You are saving hundreds or thousands of dollars. Where your retirement dollars are actually going? Those choices carry enough weight over enough years that digging in pays for itself many times over.
Questions Worth Asking Yourself
If you want to figure out where you actually land on this, skip the vague “am I being smart with money” question and get specific instead. These came straight out of our small group breakouts that night, and they hit different when you sit with them for a minute.
- Where in your life are you currently optimizing something that honestly does not matter anymore?
- What is something you have made peace with as good enough, and you’re genuinely fine with that?
- What is something you refuse to settle on, because it truly has to be better?
- What is eating up your time for basically zero return, and needs to get cut this week?
- Where are you already putting in the right amount of effort, even though some part of you knows you could squeeze out a little more?
- Where do you actually need to lean in harder, because the payoff there is real?
Sit with those honestly for a minute and you’ll probably find at least one thing you’ve been guarding way too closely that stopped mattering years ago.
The Bigger Question Behind All of This
There was one more question from that night that also stuck with me. If your salary jumped 25 percent tomorrow, how long before that new number just felt normal?
C’mon now, please be honest with yourself. Probably not very long, right? That’s kinda how this game works. We always chase the next optimization, we hit it, and the satisfaction fades out in about a week. Then we’re off chasing the next percentage point, the next basis point, the next few cents a gallon, and the cycle just keeps going and going.
At some point you’ve got to ask yourself the question, “what you’re actually optimizing for?” Are we optimizing for more money, or is it for more life? Because those are NOT always the same goal, and chasing one too hard can quietly cost you the other.
I tend to think about this every time I catch myself falling down a reddit rabbit hole over something that, if I’m totally honest, it does not matter nearly as much as I’m treating it. The goal was never to squeeze every possible penny out of every decision. The goal was to build a life that actually feels free. Sometimes the most financially responsible move you can make is just closing the tab, making the call, and going and enjoying your night with the people you love.
Good enough can be a real strategy! It’s true. Don’t consider it being lazy. It can be a real strategy that is, backed by actual research, that frees you up to spend your limited time on what’s genuinely worth optimizing and everything else on just living your life.
Horns up my friends 🤘