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- 2 Surprising Stats About High-Earners, the Oscar-Winning Lesson on Money, 5 Auto Insurance Items to Review, And More
2 Surprising Stats About High-Earners, the Oscar-Winning Lesson on Money, 5 Auto Insurance Items to Review, And More
Benjamin Daniel, CFP®
July 05, 2025
Read Time: 4-minutes
Happy Saturday,
Here is this week’s edition of 6-Point Saturday — financial insights to help you make smarter money decisions.
Let’s get into it.
Point #1 — And The Oscar Goes To…
In 1997, at the age of 27, Matt Damon won his first Academy Award for Best Screenplay (Good Will Hunting). After Damon won the Oscar, he went home, sat down on his sofa, and looked at the award…
As he looked at it, he was suddenly overwhelmed by a heartbreaking thought:
“I remember very clearly looking at that award and thinking, ‘Imagine chasing that, not getting it, and then getting it finally in your 80s or your 90s with all of life behind you and realizing what an unbelievable waste of your life.’”
Damon stood on the Oscars stage for eighty-one seconds. That’s 0.0000641% of the four years he spent working on Good Will Hunting. To let 0.0000641% of an experience determine one’s happiness or satisfaction is a heartbreaking waste of one’s life.
“My heart broke,” Damon said. “I imagined another one of me [not getting that award until I was] an old man, and going like, ‘Oh my god, Where did my life go? What have I done?’ And then it’s over.”
Staking our happiness on an event in the future outside of our control is pretty risky.
This mindset shows up in money all the time, too…
It reminds me of my recent post (that I shared in last week’s newsletter as well):
The 4 most dangerous words in personal finance:
"I'll be happy when..."
Happiness isn't just for the finish line.
You can build a life you enjoy along the way.— Money Wisdom (@MoneyWisdom_)
12:28 AM • Jun 27, 2025
The thing about numbers and money is that they’re technically infinite…
That is, we can always reset our income, net worth, or spending goals to a higher level after we’ve hit our previous goals.
To be sure, there’s nothing wrong with having goals.
But delaying your happiness until you’ve hit some arbitrary financial goal that can continually increase is a guaranteed way to live miserably.
Instead of chasing a finish line that keeps moving, design a life you enjoy living along the way.
Point #2 — Auto Insurance Primer
Insurance may not be the most captivating topic, but it’s super important…
Just think of the risks and potential costs:
You injure another individual and are sued for thousands of dollars
An uninsured motorist injures you, and you’re stuck with the medical bills
Auto policies offer all kinds of coverage.
Here are 5 areas to review periodically (at least 1X per year or when your life circumstances change significantly):
Liability
This protects you if you’re liable for property damage or bodily injury to others.
Collision
Collision coverage helps repair or replace your vehicle if it’s damaged by another vehicle or object, regardless of fault.
Comprehensive
Comprehensive coverage helps you repair or replace your vehicle after non-collision events theft, vandalism, natural disasters, etc.
Deductibles
Collision and Comprehensive coverage have deductibles, or amounts you need to pay before insurance kicks in. The higher your Deductible, the lower your monthly premium payment, and vice versa. Consider the size of your Emergency Fund to determine a Deductible amount that’s optimal.
Uninsured/Underinsured
You may not be at fault in an accident, but if the other driver is uninsured or underinsured, that can be very costly for you. Uninsured/Underinsured helps protect your bank account if the other driver doesn’t have enough insurance.
A quick annual review can protect you from unwanted, costly surprises.
Point #3 — 2 Surprising Statistics on High-Earners
Many people feel uncertain whether they’re on track financially…
And that uncertainty creates anxiety.
1 way to lower that?
Look at benchmarks or statistics on how others are doing.
The Wall Street Journal shared an interesting piece this week titled “They’re in the Top 10% of Earners. They Still Don’t Feel Rich. ($)
Some snippets that give perspective [Emphasis mine]:
“American households that make about $250,000 or more are typically considered to be in the top 10% of earners. Many in that bracket realize that the number sounds huge—and by many measures, affluent Americans are indeed thriving. Yet the top-line figures can mask a sense of financial fragility in many high-earning families.
Years of soaring costs for housing, college, insurance and borrowing feel oppressive, even for those with hefty paychecks. They might be sitting on a mountain of home-equity gains, but that doesn’t provide a huge sense of security when companies are getting rid of white-collar workers and it’s the rare employer that offers a guaranteed pension.
It isn’t that families making $250,000 feel poor—many make much more than their parents ever did, or much more than they themselves ever thought they would. It’s just that they don’t feel rich, either.”
2 Statistics:
1. Only 26% of people in the top third of earners—households making about $130,000 or more—said in the three months ending in June that they were better off than a year ago, near the lowest level since the depths of the financial crisis in 2009, according to the Michigan survey. This group is worried about tariffs and higher costs. They’re also increasingly concerned about losing their jobs.
“Even people who are doing pretty well aren’t maybe as satisfied as we might imagine,” said Matt Killingsworth, a senior fellow at the University of Pennsylvania.
2. Killingsworth runs an app that asks tens of thousands of people ongoing questions about their level of happiness. More than a quarter of people whose households earn between $200,000 and $300,000 a year report that they are either “not very satisfied” or “not at all satisfied” with their financial situation, he said.
2 takeaways:
If you're among the highest earners and are feeling pinched, you're not alone.
If you're not among the highest earners, there’s a lesson here. Of course a higher income erases a lot of problems and striving to increase income is virtually always the best lever to pull to improve your financial situation. At the same time, simply assuming more money fixes everything is an illusion. Having realistic expectations about costs (to avoid sticker shock) and leaving breathing room in your spending for the unexpected is key.
Point #4 — Happiness Examined
A few snippets on happiness and money [Emphasis mine] from Let’s Get Happy:
“Midlife misery is common. Happiness through life is U-shaped. When do we hit rock-bottom? Economist David Blanchflower analyzed data from across the developed world and concluded the depth of midlife misery arrives at age 47.2. …
Our relative standing matters. Richard Easterlin is arguably the father of happiness research. He identified a fascinating paradox: Those with more money say they’re happier, and yet a society doesn’t become happier as it grows wealthier. Why not? We care less about our absolute standard of living and more about our standing relative to others.
What matters is what we focus on. One strategy for boosting happiness: Ponder the good things in our life. This is a key reason that those with higher incomes tend to say they’re happier. When surveyed, those further up the income scale think about their good fortune, and that prompts them to say they’re happy.
Happiness comes in two flavors. Eudaimonic happiness is walking out of the office on Friday evening knowing we got a lot accomplished over the past week. Hedonic happiness is seeing friends right afterwards for a couple of beers and a burger. Hedonic happiness tends to be fleeting, while the glow of eudaimonic happiness has the potential to last longer.”
Point #5 — Quotes of the Week
“People are always trying to add more stuff to life. Reduce it to simpler, pure moments.”
“If you don't value your time, don't expect other people to respect it.
Consider pointless meetings. The more you attend, the more you get invited to.
Great work requires long stretches of uninterrupted focus. That means saying no to low-value things and concentrating on the few that matter.”
Point #6 — My Questions of the Week
Instead of thinking: “I’ll be happy after I X”, fill in the blanks:
Today, I’m going to be happy about ______ part of my finances, because ______.
Even what feels like a “small” win counts — no answer is too small.
Reply to let me know! I read all responses.
Thanks for reading — I hope you found a helpful idea or two.
I’ll see you next Saturday with more.
Have a great weekend,
Benjamin Daniel, CFP®
Founder, Money Wisdom
P.S. Want to take control of your money (and stop stressing)? Here are 2 ways I can help:
Financial Health Check: Get your biggest money questions answered, understand where you stand financially, and get a personalized action plan from a CFP® professional. Book a free Intro Call here (or purchase today) to see if you’re a good fit.
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Disclaimer:
This material is not investment or tax advice. No responsibility for loss occasioned to any person or corporate body acting or refraining to act as a result of reading this material can be accepted by the publisher.
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