In this episode of Sixty Plus Uncensored, host Seb Frey talks with Chris Kampitsis and Ben Soccodato, partners and financial planners with the SKG team at Barnum Financial Group. Chris and Ben work primarily with retirees and pre-retirees across the country, including many corporate executives navigating retirement, career transitions, and the financial pressure of supporting both aging parents and adult children at the same time. Together, Seb, Chris, and Ben talk about what it actually means to be part of the so-called “sandwich generation” well into your sixties and seventies, how to catch up financially if retirement planning has been neglected, how much of a portfolio should realistically stay in stocks later in life, and the tax questions that come up around inheriting or selling a long-held home.
Before getting into the specifics, it’s worth noting that this conversation reflects the general views and approach of two financial professionals speaking broadly, not individualized advice for any particular reader. Financial planning decisions, especially around taxes, Social Security timing, and real estate, depend heavily on a person’s specific circumstances, and anyone facing these decisions should work directly with a qualified, licensed advisor or tax professional familiar with their full financial picture.
The Sandwich Generation Is Bigger Than People Think
Chris and Ben’s practice has spent the last two decades focused largely on corporate executives who have separated from Fortune 500 companies, whether by choice or through workforce reductions. That specialty, they note, overlaps heavily with a group many people assume is limited to those in their fifties: the so-called sandwich generation, adults simultaneously supporting aging parents and their own children. Seb points out that this group is actually broader than commonly assumed, since many people in their sixties and even seventies still have parents in their nineties who need care, alongside adult children in their forties or fifties who may still need financial support.
Chris and Ben describe encountering a wide range of financial situations in this group, from corporate executives with substantial liquid assets to families whose primary or only significant asset is home equity. Both circumstances require very different planning approaches, and the two are candid that helping someone build financial literacy and a workable plan matters regardless of their starting point, not just for clients with complex portfolios.
For families balancing the needs of aging parents with their own retirement goals, The Family Meeting Guide to Emergency Planning: Essential Paperwork for Aging Parents offers a practical starting point for getting important financial and care decisions organized before a crisis occurs.
Catching Up When Retirement Planning Has Been Neglected
Asked what a 60-year-old should do if they haven’t planned adequately while supporting both parents and children, Ben’s starting point is always a clear-eyed cash flow assessment: understanding current spending versus income, identifying which expenses, like a mortgage or a child’s education costs, are likely to disappear over time, and evaluating what assets like 401(k)s, IRAs, brokerage accounts, Social Security, and any pension or deferred compensation will actually provide.
Chris raises a point he considers essential to these conversations: you can borrow for college, but you cannot borrow for retirement. Many people carry an emotional commitment to fully funding their children’s education because their own parents did the same for them, without accounting for how dramatically college costs have risen relative to inflation. He emphasizes the importance of realistic, sometimes difficult conversations about what’s actually sustainable, rather than assuming a goal like full tuition coverage is automatically the right priority.
From there, Chris and Ben describe a fairly standard sequence of financial fundamentals: establishing an emergency fund before anything else, since an unexpected expense without one often forces people into costly borrowing; making sure not to leave free money on the table in the form of unclaimed employer 401(k) matches, HSA matches, or deferred compensation matches; and only after those basics are covered, considering additional investment vehicles like brokerage accounts or backdoor Roth IRAs.
Debt: Not All Bad, But Rate Matters
On the question of consumer debt, Ben’s guidance centers on interest rate rather than debt in general. A zero-percent promotional financing arrangement, paired with a real repayment plan, is generally fine in his view; a credit card balance accumulating at 20 percent or more interest is a serious problem that needs to be addressed directly, since very few investments will consistently outpace that kind of interest cost.
Chris adds nuance to the broader debt conversation, distinguishing between debt used for discretionary purchases and debt that builds equity or future earning power, such as financing a home rather than renting indefinitely, or borrowing to invest in a business with returns that exceed the interest paid. The pair generally caution against an all-or-nothing approach to eliminating debt before retirement, noting that some clients focus so heavily on entering retirement debt-free that they end up under-saved as a result. A more balanced approach, addressing both debt reduction and consistent saving simultaneously, tends to produce better outcomes than prioritizing one exclusively.
Rethinking How Conservative a Portfolio Should Be in Your 60s
One of the more pointed pieces of guidance in this conversation concerns investment allocation for people in their sixties. Ben pushes back directly on the common assumption that retirement should trigger a shift toward heavily conservative investments. He points to target-date retirement funds, which often land around a 50/50 split between stocks and bonds by the target retirement year, as an allocation he considers too conservative for many people in their sixties today, given that a 60-year-old may realistically have another 30 years of life ahead, along with inflation, healthcare costs, and potentially ongoing support for parents or children to plan for.
Chris frames this in terms of risk: longevity, the risk of outliving one’s savings, is, in his view, a far greater threat to most retirees than short-term stock market volatility. Ben and Chris describe using a blended investment approach that combines broad market exposure through low-cost index funds and ETFs, some degree of sector-based or trend-informed investing, and a smaller, carefully sized allocation toward individual growth stocks or transformational long-term themes, such as artificial intelligence, which they see as having significant long-term expansionary potential. They’re careful to note that specific stock recommendations can become outdated within weeks and decline to name particular picks as durable advice, but they do describe conviction in the broader long-term case for AI and related technology as an investment theme.
Importantly, Chris emphasizes that pursuing long-term growth investments only makes sense alongside a plan for market downturns. He and Ben describe recommending a “volatility buffer,” roughly two to four years of anticipated living expenses held in more stable, lower-volatility investments, so that a client is never forced to sell growth investments during a market downturn simply to cover near-term living costs. This buffer is typically a relatively small percentage of a larger portfolio, freeing the majority of assets to remain invested for long-term growth.
Investment decisions later in life are rarely as simple as becoming more conservative, which is why Low-Risk Investment Strategies for Retirement can be helpful for understanding how stability, growth, and risk may fit together in a retirement portfolio.
Social Security Timing Is Genuinely Individual
Asked when someone should start claiming Social Security, Ben is direct that the right answer depends heavily on individual circumstances, and he outlines several of the major factors that go into the decision: whether a spouse’s benefit will be based on the primary earner’s record, since claiming early reduces that benefit for both people for life; the age gap between spouses, since the higher of two spousal benefits continues for the survivor after one spouse passes away; whether the person plans to continue working, since earnings above a certain threshold before full retirement age can temporarily reduce Social Security benefits; and personal or family health history and life expectancy, which weighs heavily in favor of claiming earlier for some people and delaying as long as possible for others. Ben notes that current policy trends don’t suggest imminent structural changes to Social Security, though this is, by nature, an evolving area worth monitoring rather than something to assume will remain fixed indefinitely.
What to Do With an Inherited Home
Seb raises a scenario common among his own real estate clients: inheriting a parent’s home, which in most cases benefits from a “step-up” in cost basis that can significantly reduce or eliminate capital gains tax on a later sale, compared to selling one’s own long-held primary residence, which can trigger substantial capital gains tax in high-appreciation markets.
Chris’s first piece of advice is structural: families doing estate planning, particularly when placing property into a trust, should make sure the plan is set up correctly to preserve that step-up in cost basis for beneficiaries, something worth confirming directly with an estate attorney. His broader advice for anyone receiving or anticipating an inheritance is to have a financial plan in place beforehand, so that decisions aren’t made reactively or emotionally in the immediate aftermath of a loss. He also cautions people not to overestimate what an inheritance can realistically provide as ongoing income, referencing the commonly cited 4 percent withdrawal guideline as a rough starting point (a million dollars, under this rule of thumb, might support roughly $40,000 a year in supplemental income, adjusted for inflation) rather than treating a windfall as a permanent solution to every financial pressure at once. It’s worth noting that the 4 percent rule is a general historical guideline, not a guarantee, and its suitability varies by individual circumstances.
The Tax Complexity of Downsizing a Long-Held Home
For homeowners looking to downsize out of a long-held primary residence with significant appreciation, Ben outlines the basics: a married couple generally qualifies for an exclusion on the first $500,000 of capital gain on a primary residence, and the cost basis can often be increased by documented home improvements made over the years, which a tax advisor can help calculate accurately alongside selling costs.
He and Chris are clear that a 1031 exchange, commonly used to defer capital gains tax on investment real estate, does not apply to a personal residence; that mechanism is reserved for business or investment property being exchanged for other business or investment property. They acknowledge that some more complex planning strategies exist for people looking to reduce or defer taxes on a primary residence sale, such as converting a longtime home into a rental property to qualify it as investment property before initiating a 1031 exchange, but they caution that these approaches carry real trade-offs and complexity. Chris specifically flags one risk: some deferral strategies convert what would have been long-term capital gains into ordinary income taxed differently down the road, meaning the tax bill may be spread out rather than genuinely reduced. Both emphasize that most of their clients, especially later in life, tend to prefer simplicity over aggressive tax optimization strategies that require ongoing management, like maintaining rental properties or juggling multiple residences to qualify for tax exclusions.
For homeowners weighing whether selling a longtime residence makes financial sense, The Financial Benefits of Downsizing in Retirement explores how downsizing can affect housing costs, home equity, and the broader retirement budget.
Long-Term Care and Insurance: It Depends
On the question of whether people in their sixties and seventies should carry life insurance or long-term care insurance, Chris and Ben are candid that there’s no universal answer. Chris notes that the traditional insurance marketplace generally isn’t the ideal entry point at that age, though there are specific circumstances, such as needing to create liquidity to cover estate taxes without selling a piece of property meant for a particular heir, where a policy held inside a trust can make real sense.
On long-term care specifically, both acknowledge that the traditional standalone long-term care insurance market has become difficult, with claims costs running higher than insurers originally projected and many major insurers exiting the space entirely. As a result, hybrid life insurance and long-term care policies, which allow a policyholder to draw down a life insurance benefit for care costs if needed, without requiring a full separate long-term care claim, have become a more common and flexible option than traditional standalone policies. Ben describes these hybrid products as functioning almost like a “Swiss Army knife” within a broader financial plan, though as with any insurance decision, the right choice depends heavily on individual health, family history, and overall financial picture, and is worth discussing directly with a licensed insurance professional.
Insurance needs can change significantly later in life, and The Best Types of Insurance for Older Adults offers a broader look at the coverage options that may be worth considering as health, care, and financial priorities evolve.
What Working With a Financial Planner Actually Looks Like
For readers curious about the process itself, Chris and Ben describe a fairly structured but not overwhelming onboarding process: an initial 20 to 30 minute call to understand a prospective client’s situation and priorities, followed by secure document upload, then a roughly one-hour Zoom meeting where the planners walk through initial projections and flag specific opportunities, whether in tax strategy, portfolio structure, or estate planning. From there, clients decide whether to move forward with a formal proposal, a process Ben estimates takes a total of around two to three hours of a client’s direct time before a decision is made.
Ongoing engagement varies by complexity: straightforward situations might warrant semiannual check-ins, while more complex financial pictures typically involve quarterly meetings, with a full plan update at least annually to reflect life changes like new grandchildren, relocation, or shifting priorities. Compensation is generally structured as an advisory fee based on assets under management, though the firm also offers tax preparation and insurance brokerage services that may involve separate fee structures depending on what a client chooses to use.
The Bigger Picture: Why AI and Longevity Come Up in a Financial Conversation
Toward the end of the conversation, Seb and the two planners touch on a broader theme that ties much of this planning together: the possibility that many people alive today, especially those currently in their sixties, will live considerably longer than they originally expected, and that emerging technology, particularly artificial intelligence, could meaningfully reshape both the economy and the healthcare landscape they’ll be navigating along the way. Seb, speaking from his own vantage point in Silicon Valley, describes seeing AI adoption accelerate broadly across industries rather than producing the kind of mass unemployment some fear, and suggests that the productivity gains associated with this shift could be substantial enough to influence asset values, including real estate and equities, for years to come.
Chris connects this directly back to the investment conversation, comparing the current period to prior transformational technology waves, such as the rise of railroads or the early internet, and suggesting that if corporate earnings continue to expand alongside these technological shifts, stock valuations may reasonably follow. He offers a pointed piece of framing for anyone anxious about AI’s disruptive potential: rather than avoiding exposure to the companies driving that disruption, it may make more financial sense to be invested in them. None of this amounts to a specific prediction, and both planners are careful throughout the conversation to avoid treating any particular company or sector as a guaranteed outcome, but the broader point, that longevity planning and technological change are increasingly intertwined, is one they clearly see as central to how people in their sixties and beyond should be thinking about their financial future.
Finding Balance Across Generations
What comes through clearly in this conversation is that financial planning for people supporting both aging parents and grown children, while also planning for their own increasingly long retirement, requires more nuance than either extreme, overly conservative caution or aggressive tax avoidance, typically provides. Chris and Ben’s recurring theme is realistic assessment: understanding what a household can actually sustain, building in a genuine buffer against market downturns rather than assuming markets will always cooperate, and making major decisions, whether about Social Security timing, an inherited property, or a home sale, with a full financial picture in view rather than reacting to any single event in isolation. For anyone navigating these overlapping pressures, the conversation offers a useful framework for the kinds of questions worth asking, even though the right answers will ultimately depend on working through the specifics with a qualified professional.