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Modern Money

It’s not what you think. I’m not going to tell you how to trade meme stocks, buy crypto or create to sell NFTs (Non-Fungible Tokens.)

Most of us have our monthly expenses set-up on autopay, either via our bank bill pay system or through each company individually. As one popular personal finance author put it, automating your finances is “set it and forget it” and “your money management is now on auto-pilot.”

Why Your Money Shouldn’t Be on Autopilot

It can be hijacked.

Last July, my husband and I rented a car from a reputable company at Boston Logan Airport. It was literally bumper-to-bumper traffic from the moment we left the rental garage all the way to tunnel entrance where it finally started to break up. We lost GPS navigation, so we actually had to read signs and I didn’t notice the engine light come on. By the time we emerged from the tunnel, the warning became loud and more frequent giving me just enough time to cross lanes and coast to the side of the road after the engine cut out. The rental company did get us an Uber to a regional airport for a replacement rental and towed the car back to Boston. I can’t imagine the car dying in the chaotic tunnels.

Eight months later, I was checking our credit card statement on the app and noticed another charge from the same rental car company in Boston for almost $400. I verified with my husband that he hadn’t charged this. Then I called them.

It was for labor and a part that only needs to be replaced over time on the vehicle that died on the highway. Not only was the work done 5 months after the incident, they also didn’t notify me until I called about the charge that was even later. I was able to get half of it refunded on the call but the absurdity of it made me research how to get the rest back. I replied to the e-mail containing the invoice with dates and times of the events as I still had the digital receipt in my e-mail and threatened a claim with the BBB. Other than an automated reply, I received no response. Before following up, I checked the CC app again and the remaining refund had been discreetly given.

For Those Still Writing Checks

Like many of you, I rarely write checks other than to service people who don’t accept secure electronic forms of payment. When I have to mail the check, I mail it inside the post office because I have had more pieces of mail stolen in the last year than ever before. This includes my Mom’s birthday card and a response to the State with a lot of personal information to support our tax return. For both of these, I bought / verified postage and literally gave the envelopes to the mail clerk and it still did not arrive at the intended destination.

Mail theft has significantly increased since 2020 along with check washing. Check Washing and Check Theft Scams | American Bankers Association ( Each time I do mail a check, I review my checking account transactions via the app daily to make sure the check clears and no other nefarious activity occurs.

Modern Money

Modern money is using financial technology to improve and securely automate recurring, established transactions allowing us to focus on the important, strategic financials decisions we must make – career, marriage, house, family, investing, retirement, legacy.

If you don’t ever elevate your thinking and planning for the impact of these financial choices along with the actual execution, you’ll continue to live paycheck to paycheck for the rest of your life. As of May 2024, this was 66.2% of the US population including 48% earning over $100,000 and 36% earning over $200,000. Their money is being hijacked by their inattention to, denial of, or inability to change their cost of living. Paycheck to Paycheck Statistics (

Financial Technology Considerations

Automated payments

  • Through your bank bill pay system – everything is all in one place, but everything is also tied to one bank.
  • Through each individual company – more personal control to optimize returns. I set it up this way to pay some via credit card for higher returns but with enough transacted directly from our checking account to qualify for a higher interest rate.
  • Can be adjusted as needed – especially through each individual company. For example, I need to adjust more transacted from our checking account to qualify for an even higher interest rate that wasn’t offered before, much higher than a high-yield savings or Money Market account.
  • Late fees and missed payments are eliminated.
  • Those paid via credit card will need to be updated when the card expires or is stolen.
  • Review the notifications sent via e-mail (or text) and the invoice/statement in the app or online if the amount differs from what is expected.
  • Debt payments such as a mortgage or car payment are routinely automated but should be evaluated frequently especially when an influx of money is received such as a raise, bonus, new job. The more you can pay against the principal, the less interest you will pay over the course of the loan.
  • Zelle and Venmo are increasingly being accepted by service providers but should be used with caution. What Is Zelle? How It Works and Example (
  • Quickbooks payment – again use with caution. Sometimes I have and haven’t used depending on how it was presented and set-up. Is It Safe To Pay Someone Through Quickbooks Online? (

Credit cards

  • Set-up notifications for statements, payment due dates and transactions if needed.

One of our credit cards was hijacked and didn’t notify us of unauthorized transactions that took much longer to resolve. However, the card offers 4% cash back on dining and 3% cash back at grocery stores which isn’t offered on other cards. So, I set-up automated notifications on the app every time it is used.

  • Review your credit card transactions and statements. This is extremely quick to do via the app.
  • Cards vary greatly on rewards, perks, security and annual costs offered. Research to determine what best suits your needs which will change over time, then adjust accordingly.

Automated investments (other than 401k, IRA, Roth)

  • Most of the larger brokerage firms offer this (Vanguard, Schwab, Fidelity, etc.)
  • It can be tricky finding where and how to set-up these automated transactions on the brokerage website. The menus aren’t always obvious, and the instructions aren’t always straightforward. So, I have used a YouTube tutorial to confirm.
  • The most important step is to set-up the transfer from your bank account to your brokerage account on a day of the month that is several days before the funds are set to automatically invest. This allows time for the funds to settle in the brokerage account.
  • The number of investment choices are limited but it enables dollar-cost averaging investing. Dollar-Cost Averaging (DCA) Explained With Examples and Considerations (
  • The amounts invested can be changed as needed. Sometimes we invest more, especially if the market is down and other times less or not at all if we are planning large house projects.
  • Newer FinTech apps like WeBull, SoFi can be experimented with but suggest smaller amounts until fully vetted. We invested in Lending Club for awhile with great returns but the concept wasn’t sustainable. It took several years to liquidate our account. WeBull automated investing works well but has complicated and unpredictable tax document reporting.

Automating your finances isn’t a one-time fix, it’s staying one step ahead.

Featured Image – Photography credit Cary Wauters – near our house.


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