 I recently watched Jay Kelly on Netflix, where George Clooney plays a fictional movie star who dedicates his life to his craft and succeeds by every external measure. The catch? He later admits to choosing his career over his family, only to realize he’s missed many of life’s most meaningful moments and relationships.
I don’t generally sit down to watch a movie looking for financial metaphors, that would be weird. But every so often, a story brushes up against a question I already spend time thinking about. In this case, Jay Kelly’s story happened to remind me of the FIRE movement. Whether it’s Coast, Lean, or Fat FIRE, the core philosophy is the same: front-load sacrifice in your early years to buy freedom later. The math is sound. Saving aggressively from an early age is essentially the equivalent of a financial superpower. The appeal is also undeniable. Who doesn’t want the freedom to do whatever they want in their 40s? I’ve always joked that my dream job is retirement, and FIRE is a good mechanism for getting me there. But the FIRE movement raises a complicated set of questions. What are the movement’s disciples missing by deferring their lives in their 20s and 30s? And how do we find the "goldilocks" zone between saving responsibly for the future and actually living along the way?
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 Budgeting may easily be the least sexy habit in personal finance. And to be honest, it can really suck. It’s tedious, it’s boring, and it often confronts us with truths we’d rather keep in the background.
In my line of work, I routinely hear clients say: “Well, we tried tracking our spending, but life just got in the way and we couldn’t keep it consistent. If things ever get tight, we’ll hunker down then.” But that’s just kicking the can down a road paved with hidden stress. Eventually, a "surprise" expense or heavy financial decision reveals that we weren't as prepared as originally thought. We avoid facing the discomfort for the sake of "ignorant bliss," but as with any bad habit, the cost of that clarity-avoidance compounds.  When you hear the word advertisement, what comes to mind?
A TV commercial? Maybe a billboard on the highway or a bus? The painfully unskippable 30 seconds before a YouTube video? For decades, advertising announced itself. And over time, we learned how to ignore it. Popups, sponsored news content, promoted websites. We’ve become increasingly attuned by filtering out the noise. But of course, every time we adapt to a new style of advertisement, a more effective one takes its place. Today, social media has essentially erased the boundary between content and advertisement, making it increasingly difficult to spot an ad six inches from our face. One moment we’re watching a humor-filled reel. The next, we're being pitched products by an influencer in their messy (but familiar) bedroom. We don’t brace ourselves for a sales pitch because it doesn’t feel like one. After all, who expects an ad from someone who looks like a friend? Ads have never been this well camouflaged, and the numbers prove it's working: social media advertising hit $276 billion in 2025 and shows no signs of slowing down¹. Companies are following the returns, and those returns are staggering. In this article, I want to unpack why social media ads are so profitable for companies, how they’re getting increasingly invasive, and what we can actually do about it.  You're reading this just after Black Friday and Cyber Monday, the unofficial Olympic Games if impulse spending. Billions of dollars flew across checkout pages in a 96-hour sprint, and retailers everywhere are still high-fiving their data scientists. The party isn’t over, however, as it’s time to gear up for the next round: holiday shopping, Secret Santa pressure, and the constant drip of “last chance” year-end deals.
Somewhere in the last decade, online shopping has transformed from a convenient alternative to purchasing goods to a finely engineered behavioral machine designed to get you to overspend. The digital economy depends on our wallets, and it’s increasingly turning to addiction science to extract more of our hard-earned dollars. Just look at the numbers: this year, Americans are expected to take on $55 billion in post-holiday debt, with the average shopper dropping $300–$340 on Black Friday and Cyber Monday alone¹. And that’s before the December avalanche even begins. Consumer debt is one of the biggest obstacles to long-term financial well-being, so it’s worth understanding what we're up against. What makes online shopping so exhilarating? What is that irresistible feeling we get right before clicking purchase? Why does that impulse make it so difficult to stop? By analyzing this unconscious pressure, we can gain the tools to combat it and reclaim our spending decisions.  There are two versions of you.
There’s the one who genuinely wants to get ready for bed early, read before bed, and wake up feeling rested. And then there’s the version of you who lies in bed scrolling on your phone till 11pm. You know, the who had a long day and “deserves to relax”. You know which version you want to be. But you also know which version usually wins. That’s present bias: the magnetic pull of right-now comfort, even when it pushes the person you want to become one more day into the future.  It’s a quiet Sunday afternoon and you’re scrolling through the Lululemon website. The new Scuba Oversized Full-Zip Hoodie jacket catches your eye. It’s sleek and looks extremely comfortable. $148.
You hover for a moment. It’s not outrageous... but it’s enough to give you pause. The price is just a bit too much to stomach. Then, right beneath the price, a soft gray line appears: “Or 4 payments of $37 with Afterpay. Interest-free.” Your mentality shifts. That $148 doesn’t feel like $148 anymore. It feels like $37, a number small enough to slide past your internal budget filter. The hesitation fades. You’re not deciding whether to spend $148; you’re deciding whether to part with $37 today. And that’s easy. Click. Add to Cart.  In the 1970s, CEOs were paid well, but not obscenely so (around 36 times as much as the average worker)¹. Compensation was high, but it wasn’t outrageous. Pay packages were opaque, boardrooms benchmarked internally, and the public wasn’t aware of the numbers.
By 1993, however, CEO pay was beginning to balloon, averaging about 131 times as much as the average worker². That year, in an attempt to stop the rise in executive pay, federal securities regulators required firms to begin disclosing this information publicly³. The idea was that once executive compensation was public, boards would be reluctant to give executives outrageous salaries and benefits out of fear of stoking outrage. What happened next was the complete opposite.  This past summer, my wife and I decided to take a trip to Europe. She had never been before, so I was especially excited. While browsing for plane tickets, I spotted what I thought was a steal: a round-trip flight for $617 per person. Score!
But then came United’s dreaded Basic Economy warning. No flexibility, no checked bags, no real seat selection. I couldn’t stomach the restrictions, so I upgraded to the much more ~luxurious~ ‘standard economy’. The squeeze didn’t stop there. Next, I found myself agreeing to pay extra just to sit next to my wife on both legs of the journey. A couple clicks later, I looked at my cart, only to find that the cost had ballooned to $986 per person. What on earth happened?  Mental accounting is one of my favorite concepts in money psychology. It’s the act of automatically assigning different values to our dollars based on context. Traditional economics tells us that a dollar is a dollar. But if you’re human, you know that’s not how it feels.¹
You don’t have to look far to see this concept in action; the proof is in our daily spending quirks. If you’re anything like me, you’ll pat yourself on the back for skipping a 50-cent coffee upgrade… then think nothing of dropping $20 on a ballpark beer that sells for $3 at the grocery store. We grumble at paying a $3 ATM fee, then happily tack on $12 for an app at dinner. We’ll wait in a long line at Costco to save $5 in gas, but pay a premium to board a flight slightly before anyone else. 
If you had to guess, how much money would you say you spend on monthly subscriptions?
...It’s hard to remember without looking at a statement, right? For reference, my household spends $133/month on subscriptions before counting gym memberships, Wi-Fi, or cell phone bills. My point is: the subscription model is so seamlessly woven into our daily lives that it feels normal. Streaming platforms, fitness apps, software tools, meal kits, medical products, even toothbrushes! Behind the convenience lies a system that exploits human psychology. And the financial consequences may be more damaging than you realize. At The New Diligence, I like to explore how subtle behavioral patterns shape financial behavior. Few systems illustrate this better than the modern subscription economy. |
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