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Welcome to the latest edition of the Healy Wealth Management newsletter, your monthly guide to navigating the financial complexities of life.
Let us know your thoughts. And if there’s something that could benefit a friend or family member, please send it their way.
Many successful families quietly wrestle with an important question: How much should we really share with our children about our finances and our legacy?
In this short video, John and Kathy Healy explore why transparency is not about revealing every number or handing over spreadsheets. It is about giving your family context, clarity, and confidence over time.
· Start with values, intent, and preparation.
· Methodically unfold disclosure gradually.
· Proactively model your family’s legacy.
Saying nothing does not preserve harmony; it shifts risk into the future, when emotions are higher and context is missing.
If you’ve wondered about family meetings, but didn’t know where to start, click on the video below.
Where do you go for a Peekaboo injury?
There is a critical difference between passwords humans create and passwords that are truly random. Humans think in patterns. We capitalize the first letter, add a number at the end, reuse familiar words, and favor the same few symbols. Those passwords look complex, but to modern hacking tools they are highly predictable.
Example of a weak human-created password:
MapleRiver82!
Computers do not guess passwords the way people do. They try combinations at extraordinary speed. Each additional character multiplies the number of possibilities. Expanding from lowercase letters to include uppercase letters, numbers, and symbols increases that search space even more. This is why a truly random 14–16 character password can take centuries to crack, while many human-created passwords fall in minutes or hours once exposed.
This matters most for your email account. Your email password is arguably the most important one you have. It receives password resets, security alerts, confirmations, and documents for banks, brokerages, and tax portals. If someone gets into your email, they often do not need to “hack” anything else. They simply reset it.
So if your email password must be long and strong, why rely on weaker passwords everywhere else? Attackers rarely start with banks. They start with easy sites and move sideways through reused credentials and reset links.
Password managers solve this elegantly. They generate long, truly random, unique passwords for every site and store them securely. You do not have to remember them.
Example of a strong random password:
A7&QZ9Ia9#FQ2LxP
With a password manager, you only remember one master password.
That master password should not be clever. It should be long and memorable. Think passphrase, not password.
Example of a strong master password:
River-Falcon3-Maple.Drift-Compass
It is long. It uses mixed case, numbers, and symbols in non-obvious places. Most importantly, it is memorable to the person who created it and meaningless to everyone else.
The takeaway is simple: humans are bad at randomness. Attackers exploit that at machine speed. Password managers remove human pattern-making from the equation and protect the most important gateways to your financial life. That is not overkill. It is modern financial hygiene.
As part of our risk management oversight for clients, we encourage you to consider using a password manager. Please let us know if you have any questions.
I told my wife she should embrace her mistakes.
She gave me a hug.
1099s are issued in waves, and the timing depends on both IRS rules and the types of investments you own.
If your account holds relatively simple investments, such as individual stocks or bonds, your 1099 Consolidated Tax Statement typically begins arriving in mid-January, starting around January 17.
In our portfolios, options are used only for protective puts and collars. Accordingly, they are reported on Form 1099-B as completed trades and do not delay 1099 delivery.
Accounts that include mutual funds, ETFs, or REITs often receive 1099s in mid-February, beginning around February 14. These investments frequently reclassify income after year-end, which requires additional time to finalize accurate tax reporting.
Accounts holding more complex securities may receive 1099s in late February or early March due to later issuer reporting deadlines.
In some cases, a preliminary 1099 may be available online in mid-February. This draft document is intended for planning only and should not be used to file a tax return.
The IRS requires broker-dealers to furnish most 1099s by February 15, but firms may request a 30-day extension, moving the deadline to March 15. This extension is widely used to improve accuracy and reduce the need for corrected forms. Broker-dealers then file final 1099 data with the IRS by March 31.
Clients enrolled in electronic delivery typically see their 1099s online sooner and receive email notifications when documents are ready. If your forms arrive too late to prepare your return on time, filing an extension is often the most practical approach and does not increase audit risk, provided any estimated taxes are paid by April 15.
Please reach out if you would like help understanding the timing of your documents or coordinating with your tax professional.
The greatest challenge in investing is not markets, recessions, or headlines. It is human nature.
People instinctively understand value when it comes to goods and services. A lower price on groceries, travel, or a new car is an obvious improvement. We make these judgments constantly, based on personal experience. But ownership in a company is different. Most people have little intuition for business value. Valuation is not a precise science; it is a fuzzy art built on uncertain forecasts, changing competition, and an evolving economy.
When value is hard to see, people focus on what is visible. In investing, that visible thing is price.
This is why lower prices on ownership in strong companies do not feel like opportunities. Instead, they feel like warnings. As prices fall, attention shifts away from what actually matters — the company’s long-term ability to earn, reinvest, and grow — and toward the daily noise of markets and news.
Behavioral finance helps explain why this happens. Research shows that people experience losses about twice as intensely as gains. That emotional imbalance makes temporary declines feel permanent and dangerous, even when the underlying businesses remain healthy. Discomfort gets mistaken for risk.
Add to this the recurring belief that “this time is different.”1 Every crisis feels unprecedented in the moment. Yet the companies that drive long-term economic progress have survived wars, inflation, political turmoil, and technological disruption — and continued to compound value.
Because these reactions are hardwired, clear thinking about investing does not arise naturally. It must come either from your disciplined focus on business value or from your continued trust in an advisor who stays focused on it for you.
Successful investing is not about predicting markets. It is about owning great companies, accepting temporary declines, and staying aligned with a sound plan when emotions push hardest in the opposite direction.
In the end, temperament matters more than tactics. But temperament does not come from willpower or optimism. It comes from perspective.
Investors who anchor themselves to price movements will always struggle emotionally, because prices are noisy, volatile, and untethered from day-to-day business reality.
Investors who anchor themselves to intrinsic value experience markets differently. They understand they own companies with durable earning power, not symbols reacting to headlines. When perspective is grounded in value rather than price, patience becomes rational, declines become tolerable, and long-term success becomes far more likely.
1 “This Time Isn’t Different” by Nick Murray (2025)
“It is better to be vaguely right than exactly wrong.”
– Carveth Read
Answer:
The ICU.