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What Beats Willpower, Windfall Decisions, RSUs Explained, and More

From losing money to $150,000+ profit in 6 months...

Author

Benjamin Daniel, CFP®
August 30, 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.

Table of Contents*

*Clickable in the online version. 

Point #1 — What Beats Willpower

“John Henry Patterson was born in Dayton, Ohio, in 1844. He spent his childhood doing chores on the family farm and working shifts at his father’s sawmill. After attending college at Dartmouth, Patterson returned to Ohio and opened a small supply store for coal miners.

It seemed like a good opportunity. The store faced little competition and enjoyed a steady stream of customers, but—for some reason—Patterson's shop still struggled to make money.

Eventually, he learned why: His employees were stealing from him.

“In the next 6 months, Patterson’s business went from losing money to making $5,000 in profit—the equivalent of more than $150,000 today.”

In the mid-1800s, employee theft was a common problem. Receipts were kept in an open drawer and could easily be altered or discarded. There were no video cameras to review behavior and no software to track transactions. Unless you were willing to hover over your employees every minute of the day, or to manage all transactions yourself, it was difficult to prevent theft.

As Patterson mulled over his predicament, he came across an advertisement for a new invention called Ritty’s Incorruptible Cashier. Designed by fellow Dayton resident James Ritty, it was the first cash register. The machine automatically locked the cash and receipts inside after each transaction. Patterson bought two for fifty dollars each.

Employee theft at his store vanished overnight. In the next six months, Patterson’s business went from losing money to making $5,000 in profit—the equivalent of more than $150,000 today.

Patterson was so impressed with the machine that he changed businesses. He bought the rights to Ritty’s invention and opened the National Cash Register Company. Ten years later, National Cash Register had over one thousand employees and was on its way to becoming one of the most successful businesses in America.”

First, a great decision by Patterson to stay open-minded, and flexible to business opportunity.

The main lesson here, though: He found a way to automate good behavior.

This applies to our finances, too.

Every day, we face enormous temptation and pressure: We’re inundated with advertisements, peer pressure, and societal expectations…

Each can easily separate us from our money. From good financial decisions.

And relying on willpower is a recipe for failure.

The key is to get out in front of these temptations…

One of the best ways to act preemptively is to, like Patterson, automate as much as we can. Setting up regular:

  • Contributions to employer retirement accounts

  • Savings to an Emergency Fund

  • Transfers for short-term savings goals (vacation, wedding)

Automating your finances makes following timeless principles like this:

…Feel effortless.

Because streamlining your money routine puts good behavior on autopilot.

The less you rely on willpower, the fewer financial regrets you’ll have—And the more progress you’ll make.

Point #2 — The Most Common Financial Regret

A recent survey by Debt.com revealed that nearly 80% of Americans have at least one financial regret.

The most common one?

Overspending on credit cards.

“Topping the list again: credit card overspending (24%) — an uptick from last year’s 21%.”

A more detailed breakdown:

“Among the group who cited credit card debt as their top regret, 40% said they have between $5,001 and $15,000, compared with 28% with a smaller $500 to $5,000 in debt, 22% with $15,001 to $30,000 in debt, and 11% who said they hold $30,001 to $50,000 in credit card balances.”

How do you tackle credit card debt? 2 proven strategies:

“There are several strategies to manage and pay down credit card debt, with two of the most common being the ‘avalanche’ or the ‘snowball’ method. The avalanche method involves paying off the card with the highest interest rate first to avoid the balance from compounding further, while the snowball method calls for paying off whichever card has the smallest total balance first to gain a sense of momentum, which can help make paying down debt feel easier.”

"Both strategies work. Don't overthink it—simply pick the one that appeals most to you and get started," CFP Benjamin Daniel told Investopedia. "Bonus step: Set up a scheduled payment to pay your cards soon after you get paid. Automation beats willpower every time."

Point #3 — How to Handle a “Windfall” Lump Sum

First, this individual is doing a lot right:

  • High income ($300k + $70k RSUs) in a MCOL (Medium Cost of Living) area

  • No high-interest credit card debt

  • Fully funding 401k, Roth and HSA

That is excellent.

As far as what to do with the $115k, he should first check with his tax professional about any estimated taxes.

Then he needs to be sure to have a solid Stability Fund (Emergency Fund). Since he’s single, he should target 6-months worth of living expenses.

Next, the interest rates on the debt are relatively in line with what you could expect to earn in a moderate risk-tolerance portfolio.

As such, any gains you’d make by investing “would” be offset by any debt interest payments.

A hybrid approach makes sense here. For example, take half to attack the highest-rate debt and put the rest toward starting a brokerage account.

Paying off the debt “guarantees” an increase to his net worth versus investing it all and exposing it to market volatility. And investing the rest helps reduce his concentration risk, aka, a significant amount of his net worth ($300k) in company stock options & RSUs.

Point #4 — RSUs (Restricted Stock Units) Explained

But what are RSUs exactly?

RSU stands for Restricted Stock Units and these are equity compensation awards from employers meant to incentivize performance.

For many higher earners, RSUs can make up a large part of total compensation. So, understanding how they’re taxed and managed is key.

A few of the specifics:

  • They come with what’s called a “Vesting Period,” or a set period of time or performance-based period to get ownership rights.

  • Unlike stock options, RSUs don’t require you to buy the shares—They automatically convert into shares at vesting.

  • RSUs are taxed immediately upon vesting, based on the fair market value on the day of vesting. If you hold the stock after vesting (rather than immediately selling), standard capital gains tax rules apply and your cost basis (the amount you subtract from your selling price) is the fair market value on your vesting date.

Bottom line: RSUs require careful planning, especially for taxes and the decision of whether to hold or sell the shares after vesting.

Point #5 — Quotes of the Week

Continuing the “automation over willpower” theme, which of these is your favorite?

Point #6 — My Question of the Week

What’s one part of your finances you could automate—whether to make life easier (regular bill payments) or more exciting (saving for a vacation, dream home, new vehicle, etc.)?

Reply to let me know! I read every response.

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:

  1. 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 to see if you’re a good fit.

  2. Financial Coaching: If you’d like some accountability in getting your finances into shape, engage in financial coaching. Build the habits & systems to help you start building wealth, pay off debt, and feel confident about achieving your goals. Reply to this email and say “Coaching” to join the waitlist.

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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