I shared my perspective for the piece: one of the most powerful things pre-retirees can do is “test drive” their future plans. As I told Investopedia, “If a client is still working, I suggest they ‘test’ their retirement lifestyle: try volunteering, join new groups, travel for a month, or take a sabbatical if possible. It’s better to discover what needs adjusting before making the leap.” This proactive approach helps uncover what truly brings meaning—and highlights what might need tweaking—before retirement is set in stone. In my experience, the retirees who stay happiest are those entering this new chapter with clear intentions, rich social ties, and “a willingness to reinvent themselves as circumstances change.”

As I emphasized to ThinkAdvisor, this isn’t just an S&P 500 index issue—so-called “value” indexes and even many ETFs marketed as diversified often sneak in allocations to the Magnificent 7 (like Apple), leaving investors much more exposed than they realize. That’s why I strongly advocate for a true portfolio x-ray—not just stacking up ETFs or broad funds, but actually peeking under the hood to see where the real risk lies

As I shared with Money for their article, “When paychecks stop, the first rule is triage: prioritize the essentials.” The top of your list should always be home and health—making sure you maintain shelter, utilities, insurance, and basic medical needs. As I cautioned, “Cut everything nonessential” and, if necessary, consider deferring payments on bills not tied to survival, like credit cards or streaming services. Hits to your credit or non-vital services can be repaired later, but “recovering from lost shelter or insurance is much harder.”

To help seniors and their families avoid financial whiplash, CBS News gathered advice from leading experts—and as I shared in the article, a proactive, multi-pronged approach can go a long way. One key step I recommend is earmarking a dedicated “medical emergency” fund: “There’s no magic number, but I usually advise retirees to earmark a medical ‘shock absorber’ fund, ideally $5,000 to $10,000 set aside specifically for healthcare curveballs.” If you’re still pre-Medicare, contribute as much as you can to a Health Savings Account (HSA)—it’s triple tax-free and rolls into retirement

As families contend with inflation and staggering housing costs, more adult children are drawing on the “Bank of Mom and Dad” for everything from rent to student loans—even vacations—well into their 20s and 30s. And as I shared with The Daily Upside, this extended financial support can add up fast, often derailing even the most diligent retirement plans. “I’ve seen everything from the family phone plan that never dies to parents paying for housing, student loans, or even vacations. Some have delayed retirement, taken on part-time work, or cut back on their own spending or savings.”

As I shared in the article, the impact is twofold. On one hand, those catch-up dollars will now be taxed up front (eliminating the current income-reducing benefit), but, as I explained, “Your money will grow tax-free from that point on, and you won’t owe taxes on withdrawals in retirement.” For savers who expect their tax rate to be higher in the future, this can be a valuable, forced Roth diversification opportunity. Still, anyone counting on the short-term reduction of taxable income from pretax catch-ups will need a new plan.

As I told CNBC for their article, the #1 trap I see is investors buying last year’s winners or trendy ETF flavors, rather than focusing on true diversification and clarity of purpose. “It's easy to think more funds equals more safety, but piling on new ETFs—especially sector, thematic, or leveraged varieties—often leads to costly overlap without adding real protection,” I shared. Instead, I advise clients to look for a clear, evidence-backed strategy and to regularly review their positions for unintentional duplication or style drift. Simplicity, transparency, and alignment with your actual goals almost always win in the long haul.

As I shared with Investopedia, “the truth is, most retirement income—Social Security, pensions, and RMDs from IRAs and 401(k)s—remains taxable, and the order and timing of withdrawals can have a huge effect on your tax bill.” For example, every dollar distributed from pre-tax accounts like a 401(k) or traditional IRA is ordinary income, potentially bumping you into a higher tax bracket if you’re not careful. Sage planning means knowing your bracket not just for this year, but for several years out, particularly as RMDs (Required Minimum Distributions) can act as “bracket-busters” and catch retirees off guard with forced taxable withdrawals.

As I told CNBC for their article, time is of the essence: “Now is the time to work with your advisor or tax preparer to run multi-year tax projections.” That means taking a proactive look at your savings strategy over the next year or two. Should you accelerate pre-tax catch-up contributions before the rule change lands? Is it smart to start embracing Roth sooner, especially if you expect your tax rate to be the same or higher in retirement? These questions become especially critical for high earners who have limited access to Roth IRAs and need to be thoughtful about their tax diversification.

As I told The Daily Upside for their article, the game has changed. “Clients now recognize that taxes aren’t a once-a-year headache. They’re a crucial piece of every wealth and retirement strategy, especially in the face of sweeping tax law changes that create moving targets and new phase-outs.” With Americans paying over $206 billion in capital gains taxes last year, even the best investment returns can be quickly devoured by Uncle Sam if taxes are an afterthought instead of a core part of the plan.

As I shared for this article, the most strategic next step isn’t just about piling up more dollars—it’s about intentionally building out tax flexibility. With nearly all savings trapped in pre-tax IRAs and 401(k)s, early retirees often face what I call the “Retirement Income Jenga Tower”—the challenge of stacking and pulling various withdrawals, Social Security timing, and tax brackets for maximum after-tax income. Too much in pre-tax accounts can lead to unexpectedly high taxes down the line, especially as required minimum distributions kick in, Social Security begins, and Medicare means-testing (IRMAA) becomes a reality.

In today’s markets, many investors react to the latest bout of volatility by playing it “safer,” piling into cash, CDs, or bonds—even as those options lose ground to the rising cost of living. But as I shared with TheStreet, being too conservative may actually be the riskiest move for your long-term financial health. Investors often underestimate just how much market exposure—and, yes, temporary discomfort—they need to reach goals like a secure retirement. Sitting on the sidelines in fear of another bad year ignores the fact that missing decades of growth can do more damage than one bear market ever will.

As I shared with MarketWatch, this turning point is no time for complacency. With the era of high-yield CDs drawing to a close, it’s time to explore alternatives. When working with a client whose CD matured, I opted to move the proceeds into a multi-year guaranteed annuity from a strong insurance company, locking in a rate north of 5%. For money that can afford a bit of a “time-out” and doesn’t need FDIC insurance, these annuities represent a powerful (if under-appreciated) tool—just make sure to due your diligence on the insurer’s financial strength and understand the surrender terms.

As I shared with Investopedia for their article, the most underestimated pitfall isn’t plan selection, but how certain financial moves—like Roth conversions, big IRA withdrawals, or realizing capital gains—can inadvertently push your income over key Medicare thresholds. Since Medicare Part B and D premiums are based on your tax return from two years prior, a poorly-timed maneuver can trigger IRMAA (Income-Related Monthly Adjustment Amount) surcharges that effectively double your premiums.

As I shared with MarketWatch, the instinct to chase higher yield or take on more investment risk can be strong as cash yields shrink—but that’s rarely a wise response. “Don’t take on more risk than you can handle just to make up for shrinking cash yields—stay rooted in your financial plan,” I advised in the piece. For borrowers, reviewing your loan rates is smart, but be realistic—those with fixed-rate loans may not see immediate relief, and big changes won’t happen overnight.

For some, it can work—with careful planning, clear expectations, and a willingness to keep your spending within real-world limits. As I shared with Investopedia, early retirement at age 60 with this amount is “doable for some—but only with strong planning, modest spending, and healthy doses of realism.” The wild cards? Lifestyle, healthcare, inflation, and where you plan to call home.

When the Moneywise team reached out for expert commentary, I shared what I see every day: “Parents are more permissive now and more likely to provide, but I also think the need is greater. I think parents see that and say, ‘I have the ability to help out.’” The reality is that families face a tough choice between letting their kids struggle—or proactively saving and planning to ease that transition into adulthood.