In partnership with
Trust This.
By Joseph E. Seagle, Esq.
👋 Happy Friday! Today is National Retro Day. If you know how to use a rotary dial phone, congratulations! This is your day.
❗Situation Awareness: On March 11 at 6:00 pm EDST, join the livestream on our YouTube channel to ask me anything. If you have questions you'd like me to answer, go ahead and e-mail them to [email protected], and we’ll get to them that evening.
1 big thing: CBO: Medicare Part A and Social Security lost 12 years in the past year
Florida’s future retirees — especially business owners, physicians, dentists, lawyers, and practice professionals — are staring at a fiscal reality shift. The Congressional Budget Office projects that the Social Security retirement trust fund could be depleted by 2032 and that Medicare Part A could be depleted by around 2040. This is much earlier than projected in the CBO’s previous reports. If Congress does nothing, benefits would not disappear — but they would be automatically reduced to match incoming revenue.
For Floridians planning to retire before 2040, this is not abstract policy chatter. It’s math.
What this could mean for your retirement income
If the Social Security trust fund runs dry, current law requires benefits to be cut to the level payroll taxes can support — historically estimated at roughly 75–80% of promised benefits. Depletion of the Medicare Hospital Insurance trust fund would trigger payment constraints that could result in reduced reimbursements to healthcare providers, higher premiums, or coverage redesign.
For high earners and practice owners, there’s a double exposure:
You may receive less than projected.
You may pay more in taxes or premiums to stabilize the system.
One way to help right the ship — for Social Security at least — would be to remove the cap on earnings that are subject to the Social Security Tax which currently sits at $184,500.00 (Medicare taxes already apply to all wage income, regardless of how much you earn in a given year, so such a tactic won't work to save that program.)
So you may end up paying more Social Security Taxes on wage income in future years before retirement if you’re currently enjoying the existing maximum cap.
Florida’s retiree-heavy economy amplifies the impact. Healthcare access, insurance pricing, and even real estate demand could feel second-order effects.
What to do now—legally and financially
Stress-test your retirement plan assuming Social Security pays 75% of scheduled benefits. If your plan fails under that assumption, it isn’t conservative enough.
Increase control over taxable income in retirement. Roth conversions, strategic use of LLCs, installment sales, and trust planning can help smooth income and potentially manage Medicare premium thresholds.
Build healthcare flexibility. Health Savings Accounts (HSAs), long-term care planning, and private insurance modeling should be revisited. Medicare may continue to exist — but expect higher out-of-pocket exposure.
Protect assets proactively. Florida homestead protections, properly structured multi-member LLCs, and exempt assets (life insurance and certain retirement accounts) matter more when public safety nets weaken.
Delay reliance. If possible, plan for optional work or phased retirement income through consulting, real estate cash flow, or private lending. Diversified income reduces political risk.
Consider and investigate retiring to another country, where the costs of living and healthcare are lower, stretching reduced Social Security payments and Medicare coverage more cost-effectively.
Bottom line for Florida professionals
Social Security and Medicare are unlikely to vanish — but they are unlikely to remain untouched. Retirement planning before 2040 must assume benefit pressure, not stability.
The smartest move is not panic. It’s preparation.
The federal government’s imbalance creates uncertainty. Your job is to create certainty inside your own balance sheet — before Washington decides it for you.
Go deeper: Congressional Budget Office
2. Federal deficit forecast jumps sharply
The nonpartisan Congressional Budget Office (CBO) has updated its official long-term budget projections, and the numbers are sobering. Under current law, the U.S. is projected to run persistent, large deficits over the next decade — with annual shortfalls rising from roughly $1.9 trillion today to about $3.1 trillion by 2036. Over the same window, federal debt held by the public climbs from roughly 100% of GDP to ~120% of GDP.
$36T → ~$52T? Clarifying the Figures
Media coverage (Forbes) has highlighted a potential increase in the cumulative 10-year deficit projection — and that’s where the $36 trillion vs. $52 trillion framing comes in. Recent analyses tied to House Republican briefings point to the CBO baseline where gross federal debt by 2035 could be around $59 trillion — up from a roughly $36 trillion baseline level under earlier forecasts. This isn’t a literal overnight increase in the actual balance, but rather a revision in projected totals when current law is assumed to continue, and new legislation is baked in.
Drivers Behind the Widening Gap
Spending pressures are concentrated in mandatory programs like Social Security, Medicare, and Medicaid, plus rapidly growing net interest costs as debt grows. Further increases in defense and homeland security spending are also adding up, as the Boomer and X Generations leave the workforce (reducing tax revenue) and move into retirement (increasing Medicare and Social Security expenditures). Revenues aren’t keeping pace with these cost drivers — even assuming historical revenue shares of GDP.
The extended debt projections also reflect policy choices such as tax provisions, defense spending levels, and tariff revenues; small shifts in these assumptions can tilt the totals substantially over a decade.
Why It Matters — Big Picture for Business
For entrepreneurs, investors, and licensed professionals in Florida and beyond, this signal matters at three levels:
Vision: Sky-high projected deficits and debt levels — the highest in peacetime history — could constrain future fiscal flexibility and limit government support in downturns.
Traction: Continuous deficits may eventually pressure interest rates upward, add to inflationary expectations, and complicate capital budgeting decisions for businesses.
People / Process / Data: Firms should integrate tax and fiscal risk scenarios into strategic planning, especially as rising net interest costs crowd out discretionary public spending on infrastructure or workforce development.
Takeaway for Strategic Planners
The CBO baseline underscores that without policy changes, deficits and debt will expand significantly — reshaping economic conditions that influence borrowing costs, Federal Reserve strategy, and long-range investment climates. Keeping an eye on how Congress and the White House respond will be crucial to navigating the macro backdrop over the next decade.
This week on an “Ask Joe” episode of the Trust This podcast, I focus on FinCEN’s Residential Real Estate Reporting Rule -- the spirit and intent as well as the black-letter law. I explain when transfers to land trusts must be reported, and when they’re exempt. There’s already some bad information circulating on the Internet, so I dispel the myths -- helping viewers understand the pitfalls for estate planners, real estate lawyers, title agents, and real estate investors alike.
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3. Land Trusts and the FinCEN Residential Real Estate Reporting Rule
FinCEN’s new Residential Real Estate Reporting Rule (effective March 1, 2026) targets non-financed transfers of residential real property to entities and trusts. Many investors using Florida land trusts are asking: Does moving property into a trust now trigger federal reporting?
The short answer: It depends on intent and whether beneficial ownership changes.
The rule in plain English:
A transfer is generally reportable when residential real property (1-4 family residential property or vacant land where such will be constructed) is transferred —without bank financing — to a legal entity or trust, and there is a meaningful change in ownership or control.
What is not the trigger:
It’s not simply whether there is a written contract.
It’s not whether the trust has a third-party trustee.
It’s not whether the structure is called a “grantor trust,” which is specifically exempted from reporting.
What does matter:
FinCEN is focused on substance. If control of the property moves to a new person in a non-financed transaction, reporting is likely required.
Likely not reportable:
Individual deeds property into their own revocable land trust.
The individual remains sole beneficiary
Or assigns their interest in the trust to an entity that the individual still controls (Wyoming LLC, Family limited partnership, etc.) for asset protection layering purposes.
No consideration is paid.
No sale or transaction for any valuable consideration with an unrelated party is involved.
That looks like classic estate planning, asset protection, or probate avoidance.
Potentially reportable:
Property is deeded to a trust or LLC as part of a cash sale.
Beneficial interests are assigned to a buyer in connection with a transaction.
The trust is functioning as a conduit to transfer ownership.
FinCEN’s anti-evasion posture means short-term “layering” structures designed to obscure a buyer carry risk.
Key takeaway:
The compliance question isn’t “Is there a contract?”
The question is “Did beneficial ownership of residential real property change in a non-financed transfer to an entity or trust?”
For investors and trustees, documenting intent and ensuring consistency between form and substance will be critical going forward.
Reporting parties (title agents and lawyers) need to be aware of the pitfalls of accidentally facilitating an illegal “structured transaction.”
Go deeper at AspireLegal.com, and watch the latest episode of the Trust This podcast on YouTube.
4. Freedom “from” vs. Freedom “to” and which one drives entrepreneurs
This is the scene that greeted me when I woke up Monday morning in Asheville. Knowing I had to drive down to Greenville, SC that day for a CLE made for an anxious morning. Fortunately, the wind gusts blew the snow off the driveway and roads by early afternoon, and the drive south was uneventful.
Small business owners often talk about wanting “more freedom.” More time. More money. Less stress. But in entrepreneurship and leadership, freedom has two very different meanings — and confusing them can stall your growth.
Dan Sullivan draws a powerful distinction: the external freedom from versus the internal freedom to. Understanding both is essential if you want real traction in your business.
Freedom FROM: The Foundation of Enterprise
In America, historically we’ve had structural freedom from — from government censorship, from financial and official corruption that destroys meritocracy, from unelected dictatorial authoritarians, from arbitrary seizure of property, from government-imposed restrictions on speech and thought.
That external freedom is the legal soil where entrepreneurship grows.
But here’s the hard truth for small business management:
External freedom doesn’t guarantee business growth.
A stable market doesn’t create vision.
Opportunity doesn’t create execution.
Plenty of people live in freedom. Few build something meaningful with it.
Freedom TO: The Entrepreneurial Operating System of the Mind
Internal freedom to is different. It’s psychological and strategic.
It’s the freedom to:
Set a bold Vision.
Choose your Rocks (90-day priorities) with discipline.
Hold yourself and your leadership team accountable.
Make decisions without waiting for permission.
This is mindset work. And it’s where most businesses stall. If your leadership team lacks internal freedom, you’ll see:
Indecision disguised as “analysis.”
Busywork instead of traction.
Conflict avoidance instead of accountability.
EOS teaches that clarity creates confidence. When your Vision is clear, and your accountability chart is strong, your team gains the freedom to act.
Why This Matters for Business Growth
Freedom FROM gives you opportunity.
Freedom TO creates results.
Entrepreneurs who scale understand that mindset, focus, and disciplined execution turn liberty into legacy. They don’t just avoid restrictions—they proactively build systems, culture, and accountability.
The bottom line: You already have more external freedom than most humans in history. The question is whether you’re exercising your internal freedom to lead boldly.
If you want stronger team alignment, sharper focus, and real traction, start by strengthening your internal freedom TO decide, commit, and execute. That’s where sustainable business growth begins.
We hope you found this helpful — any feedback is appreciated and can be shared by hitting reply or using the feedback feature below.
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