The Malcolm On Money Guide to Restricted Stock Units

If you work in a high-earning occupation like technology or healthcare, you have probably found yourself sitting through your fair share of sales pitches for life insurance, wondering how you got there. And when those sales pitches are concealed behind buzz phrases such as “family banking” or “7702 plans,” you are right to be skeptical and keep your hand on your wallet.  

In most cases, you are better off buying inexpensive term coverage to protect against any income gaps for financial dependents and then investing the difference that would’ve gone toward a lifetime of monthly premiums into a low-cost index fund instead. However, for the right person with a long enough time horizon, a life insurance retirement plan (LIRP) can make sense. 

The capital markets have a way of making us feel like we should always be “doing something.” When stocks are plunging, doing nothing feels irresponsible. And when they rip higher, doing nothing conjures up a feeling that you’ll miss out on the next opportunity.  

That itch to act is human, and it’s gotten stronger in the age of push alerts, app badges, and celebratory screen flourishes after each trade. Regulators have warned that these “digital engagement” tricks can prompt people to trade more than they otherwise would, and research has tied push notifications to a measurable spike in trading within minutes. But all this constant activity amounts to nothing more than “tinkering.” 

Cash feels good. It’s certain. It’s liquid. It lets you sleep at night. But like keeping all your plants in the shade, too much “safety” can stunt growth. The question isn’t whether cash has a role in your broader financial strategy—it absolutely does. The question is where the line sits between prudent reserves and a drag on your long-term plan. 

As a general rule of thumb, it is a good idea to cap the amount you park in cash to just one full year of essential living expenses. This is because most white-collar professionals who are laid off don’t go a full 12 months without earning an income, and keeping significantly more than that on the sidelines exposes you to inflation risk without commensurate benefit. 

Building a portfolio of rental real estate has long been a favored strategy for families intent on creating generational wealth—often from scratch. Yet, parents who plan to pass their rental properties to their children sometimes overlook a fundamental question: Do your children actually want to inherit the properties you've spent decades managing? 

All too often, parents spend significant portions of their lives building and managing real estate portfolios and dealing with the inevitable headaches such as tenants, maintenance issues, and regulatory requirements—only to have their children inherit and quickly sell the properties in the end. It's a scenario that happens more frequently than many parents realize, rendering their lifetime of hard work and financial discipline effectively moot. 

Whether it’s due to uncertainty around tariffs or productivity gains brought on by advancements in artificial intelligence, a growing number of companies—including hyperscalers such as Microsoft and others—are making tough decisions to trim overhead. Whether the layoff notice comes with a generous severance or merely a handshake and well wishes, the fallout can be both emotionally and financially disorienting. 

While tech titans like Microsoft have long been known for offering competitive exit packages—including a few months’ salary, extended COBRA coverage, and stock vesting acceleration—those perks don’t erase the uncertainty that follows. These offers often emerge with little warning, and for employees who hadn’t planned on leaving the company anytime soon, the challenge is not just deciding what to do next but determining how to navigate a financial transition they didn’t ask for. 

Whether transforming the way we purchase and listen to music with Apple Music and the iPod, reshaping global communication with the iPhone, or redefining wearables with the Apple Watch, Apple Inc. has long been at the forefront of major tech trends. But with Microsoft, Alphabet, and Meta all sprinting ahead with the development of advanced large language models capable of handling complex reasoning, the spotlight is on artificial intelligence (AI) and Apple’s absence from the leaderboard.

Yet by focusing solely on AI, Apple risks overlooking a far more immediate and strategic opportunity in financial technology. Unlike its rivals, Apple already commands an extraordinary level of consumer trust, a fiercely loyal user base, and a well-established fintech infrastructure—making it uniquely positioned to expand deeper into financial services.

One of the most vital steps in estate planning is correctly designating beneficiaries for your assets. These designations often override what’s written in your will, meaning they dictate who receives funds from retirement accounts, life insurance policies, and certain financial accounts. And planning for the eventual transfer of your wealth to your heirs is an essential part of ensuring your financial legacy is handled according to your intentions. 

However, many individuals place an inordinate share of their focus on accumulating assets and selecting beneficiaries, without fully equipping their heirs with clear guidance on how to manage the assets once they inherit them. Missteps—such as misunderstanding tax obligations or ignoring the nuances of retirement account rules—can lead to a significant erosion of the overall gift you intended to leave for your loved ones.

For opportunistic investors, employer stock purchase plans (ESPPs) become more attractive in a bear market. This is because stocks are bought at an additional “discount” on top of the price cut that is inherently built into the plan. 

ESPPs are employer-sponsored investment plans that allow employees to purchase company stock at a discounted price—typically 15%. However, when a stock is in bear market territory, it means that the company’s stock price is down 20% or more from its 52-week high. This indicates that at a minimum, you could feasibly buy the stock at a 35% discount with respect to its recent trading range. 

Investors often chase the next big thing, focusing on the latest headlines and quarterly earnings beats. But the most resilient portfolios—the ones that weather market shocks and grow meaningfully over decades—aren’t built on speculation. They’re built on conviction.

At the core of these portfolios lies what may be best described as “anchor investments,” which are a small handful of high-conviction stocks that act as the ballast of a long-term investment strategy. An anchor investment isn’t just a company you happen to like. It’s a stock you understand deeply, believe in fundamentally, and would be comfortable holding through several periods of volatility and uncertainty.

While in the middle of your career and possibly raising a family—likely in your 30s, 40s or 50s—it can be challenging to plan for the days when full-time employment is an option for you rather than a requirement. Nevertheless, it is important to keep in mind that the decisions you make during your pre-retirement years directly affect when you can retire and the lifestyle you will enjoy in those years.

The closer you get to your desired retirement date, the less of your overall net worth you should have concentrated in the stock of your employer. Your company stock is likely a significant portion of your overall investment portfolio, and thus your retirement plan. And the more volatile that stock is, the tougher it becomes to incorporate those shares into a retirement income plan.