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  • Our Approach
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    • Our Videos
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    • Raymond James Resources
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Paige Courtot

Election, AI and Your Money

September 2, 2026 //  by Paige Courtot

Every election cycle, something remarkable happens. Half the country becomes convinced that if their candidates lose, the economy is doomed. The other half becomes convinced that if their candidates win, the market is headed straight up.

Then the election happens. And eventually, the stock market goes back to doing what it has done through Democrats, Republicans, wars, recessions, inflation, scandals, technological revolutions and an impressive number of predictions that turned out to be completely wrong: businesses adapt, earnings grow, the economy evolves and, over time, markets have historically moved higher.

With the 2026 midterm elections approaching—and artificial intelligence seemingly appearing in every investment conversation—I think investors need to hear a simple message:

Vote in the voting booth. Invest according to your financial plan.

Those are two very different activities.

The Market Doesn’t Belong to Either Political Party

We all have political opinions. I certainly do. But your portfolio doesn’t care how you vote.

Historical data makes the point. Fidelity has reported that, looking at SCP 500 returns from 1926 through 2023, average annual stock returns were positive under every major combination of political control: approximately 14.0% with unified Democratic government, 14.5% with unified Republican government, 16.6% with a Democratic president and divided government, and 7.3% with a Republican president and divided government.

That does not mean markets rise every year. They absolutely do not. Bear markets, recessions and major declines have occurred under both parties. The important point is that long-term market growth has not belonged to one party.

Capital Group has illustrated the same idea another way: a hypothetical $1,000 invested in the SCP 500 in 1933 and left invested across Democratic and Republican administrations grew to roughly $21.9 million by the end of 2023.

Think about everything that investor lived through: World War II, Korea, Vietnam, the Cuban Missile Crisis, Watergate, double-digit inflation, the oil embargo, the 1987 crash, the dot-com bubble, 9/11, the Global Financial Crisis, COVID, multiple wars and multiple recessions.

Getting the political forecast right has historically been far less important than remaining invested in the growth of American business.

Midterm Elections Are Especially Interesting

The 2026 election is a midterm, and midterm years have historically produced plenty of investor anxiety.

Fidelity reports that since 1938 the SCP 500 has produced a price gain in the 12 months following a midterm election 95% of the time. Its research also shows average returns of roughly 5% during the second year of a presidential term and approximately 14% during the following 12 months.

Capital Group found that since 1950, the average SCP 500 return during the one year following a midterm election was 15.4%, and its study found no negative one-year post-midterm periods through the period examined.

Schwab found a similar pattern over a shorter history. Since 1974, the SCP 500 averaged approximately 5.7% in the three months following a midterm election and was positive in 11 of 13 periods. Six months after the election, the average was approximately 12.4%, with positive returns in all 13 periods studied.

Why? It may have less to do with who wins than with uncertainty beginning to clear. Before an election, investors are debating taxes, regulations, spending and campaign promises. Afterward, the future may not be clear—but it can become less unclear.

And 2026 Is Already Refusing to Follow the Script

Fidelity reports that the average midterm-year drawdown since 1961 has been about 19%. Yet through its August 2026 review, the SCP 500’s peak-to-trough decline for the year had been about 9%, while the index was up roughly 14% year to date by mid-August.

So even when we know the historical pattern, the market does not have to follow it.

One of my favorite investment strategies: stop trying to predict things you don’t need to predict.

Then There Is AI

If elections are producing anxiety, artificial intelligence is producing something different: FOMO.

Everyone wants to know: What’s the next NVIDIA? Is AI a bubble? Which company will dominate? Should I own more technology?

I am extremely bullish on the importance of AI. That does not mean every AI investment is attractive at every price. Those are two entirely different statements.

AAII asked its members about this in June 2026. About 36.3% said AI-related stocks were in a bubble. Another 51.5% believed at least some AI stocks were too expensive. Only 7.4% said there was no AI-stock bubble.

There is another AI risk investors should understand. The SEC, FINRA and NASAA have warned that AI- generated investment information can be inaccurate, incomplete, misleading or even fabricated. AI can sound incredibly confident while being incredibly wrong. I know a few humans who have that feature too.

Use AI as a copilot—not an oracle.

Use it to summarize, compare scenarios, identify questions and explain complicated concepts. Then verify the information and apply human judgment.

Six Things That May Matter More Than the Election

1.  What Return Are You Actually Keeping?

A 10% portfolio return does not necessarily mean you became 10% wealthier. Taxes matter. Fees matter. Inflation matters. Withdrawals matter.

The IRS’s 3.8% Net Investment Income Tax, for example, can apply to certain investment income once modified adjusted gross income exceeds applicable thresholds. Instead of asking only, “What did my portfolio earn?” ask, “What did I actually keep?”

2.  Are You Managing Taxes—or Just Filing a Tax Return?

Tax planning should happen throughout the year. Can losses be harvested? Should gains intentionally be realized? Does a Roth conversion make sense? Can a Ǫualified Charitable Distribution help accomplish charitable and tax objectives? Should appreciated securities be donated rather than cash?

For 2026, the federal estate and gift tax basic exclusion is $15 million per individual, while the annual gift-tax exclusion is $19,000 per recipient.

Are you trying to pay the least tax this year—or the least tax over your lifetime? Those are not always the same thing.

3. How Much Cash Is Enough?

Cash has important jobs: spending, emergency liquidity and opportunity. It can also prevent forced selling during market declines. But at some point, cash stops being a liquidity strategy and becomes a market- timing strategy.

The Federal Reserve’s longer-run inflation objective remains 2%, so long-term cash holdings also have purchasing-power considerations.

I like to give every dollar of cash a job: spending, emergency, opportunity or near-term purchase. If a large pile is left over labeled “I’m nervous,” that probably deserves a conversation.

4.  What Will You Do When the Market Drops 30%?

Not if markets become volatile—when. I would rather decide what we will do during the next major decline while markets are calm.

Panic is expensive. Preparation is boring. I’ll take boring.

5 Are You Managing Investments—or Managing Wealth?

Your investment portfolio is only one component of your financial life. Taxes, estate planning, insurance, liability protection, retirement income, charitable planning, beneficiary designations, family issues, business interests, lending, long-term care and legacy all matter.

I have seen beautifully managed portfolios attached to outdated estate documents. That is not comprehensive wealth management.

Here is my test: If something happened to you tonight, could your spouse or children find every important account, document, insurance policy and professional they need tomorrow morning?

6. Do You Know When You’ve Won?

Successful investors spend decades accumulating. Eventually, some reach a point where additional wealth is unlikely to meaningfully change their lifestyle. At that point, perhaps the question should change from “How do I maximize my return?” to “What is this money actually for?”

Morningstar’s latest retirement-income research calculated a 3.9% base-case starting withdrawal rate for a 30-year retirement with a 90% probability of funds remaining under its assumptions. That is not a universal rule, but it illustrates how retirement success depends on time horizon, asset allocation, inflation and spending flexibility.

The objective is not simply accumulating the largest possible pile of money. It is creating a financial strategy that supports the life you actually want to live.

Vote for Whoever You Want. Just Don’t Let Your Portfolio Vote.

November will arrive. Someone will win. Someone will lose. Approximately half the country will be happy. The other half will tell us civilization has approximately 15 minutes remaining.

Then Monday morning will come.

Millions of Americans will go to work. Companies will compete. Entrepreneurs will start businesses. Scientists will invent things. AI will continue evolving. Consumers will continue consuming. Businesses will continue trying to increase profits. And investors will continue owning pieces of those businesses.

That is why we are not interested in building financial plans around one election prediction—or around guessing the next AI winner. We would rather build around the things we can actually influence: taxes, diversification, liquidity, risk, retirement income, estate planning and behavior.

36 Years, Thousands of Families—and Plenty of Headlines

At Carver Financial Services, we have been helping individuals and families navigate their financial lives for more than 36 years. Over that time, we have had the privilege of working with thousands of people through some extraordinary markets—and some extraordinarily difficult ones.

We have seen bull markets and bear markets. Recessions and recoveries. The dot-com boom and bust. 9/11. The Global Financial Crisis. COVID. Inflation. Rapidly changing interest rates. Wars, political upheaval, presidential elections, midterm elections and more “once-in-a-lifetime” events than any of us would care to experience in one lifetime.

The headlines have changed. The lesson has not.

You cannot control the markets, Washington or what happens next. You can control how prepared you are.

Our job is not to pretend that we can predict every market move. It is to help our clients navigate the inevitable ups and downs, make thoughtful decisions when the world gets noisy, identify opportunities when they arise and keep their financial strategy aligned with the people and goals that matter most to them.

Technology—including AI—will continue to change how we analyze information and deliver advice. Tax laws will change. Markets will change. Political leadership will change. Life will change. The value of having a thoughtful plan, a disciplined process and people you trust to help navigate those changes remains incredibly important.

Prepare. Don’t Predict.

If the election goes the way you hope, your plan should work. If it does not, your plan should still work. If AI transforms the economy faster than anyone expects, your strategy should be able to adapt. If today’s market leaders disappoint, your financial future should not depend on one stock, one sector or one prediction.

The goal is not to predict Washington or the next NVIDIA. The goal is to build a financial strategy that can succeed across many possible futures.

If you have questions about your investments, taxes, retirement income, estate planning, portfolio risk—or simply whether all the pieces of your financial life are working together—we invite you to reach out to the Carver Financial Services team.

Sometimes the most valuable conversation is not about what the market will do next. It is about what you should do next.

We’re here to help you navigate what comes next.

Past performance does not guarantee future results. The SCP 500 is an unmanaged index and cannot be invested in directly. Historical election-cycle statistics are illustrative and should not be interpreted as forecasts. This material is for educational purposes only and is not intended as individualized investment, tax or legal advice. Investors should consult appropriate professionals regarding their individual circumstances.

Sources:

  • Fidelity Viewpoints, “The Surprising Truth About Midterms and Stocks,” August 2026.
  • Capital Group, historical election-cycle and long-term investing
  • Charles Schwab, historical SCP 500 performance following midterm
  • AAII Sentiment Survey, June 11,
  • SEC / FINRA / NASAA, gov, “Artificial Intelligence (AI) and Investment Fraud: Investor Alert.”
  • Internal Revenue Service, Topic 559, Net Investment Income Tax; Publications 550, 590-A and 590- B; Estate and Gift Tax FAǪs.
  • Federal Reserve, Statement on Longer-Run Goals and Monetary Policy
  • Morningstar, “What’s a Safe Retirement Withdrawal Rate for 2026?” December.

Carver Financial Services manages more than $3.9 Billion in assets as of August 2026 for clients globally. You can contact Randy Carver personally at randy.carver@raymondjames.com or the full team at (440) 974-0808.

Opinions expressed are those of the author/speaker and are not necessarily those of Raymond James. All opinions are as of this date and are subject to change without notice. Investing involves risk and you may incur a profit or loss regardless of strategy selected. Past performance may not be indicative of future results. Prior to making an investment decision, please consult with your financial advisor about your individual situation. Every investor’s situation is unique and you should consider your investment goals, risk tolerance and time horizon before making any investment. The forgoing is not a recommendation to buy or sell any individual security or any combination of securities.

Category: BlogTag: artificial intelligence, business owners, Investing, Media, Randy Carver, retirement planning

1.16.27 – 31th Annual Resource Breakfast

September 2, 2026 //  by Paige Courtot

 

31st Annual Resource Breakfast

Prepare today. Thrive tomorrow | An exclusive morning of insight, strategy, and conversation with world-renowned futurist and AI expert Jonathan Brill — built for investors, business owners, and families navigating a rapidly changing world.

Why attend:
A morning built around three things:

  1. Complimentary breakfast — Arrive at 8:00 AM to a full breakfast and time to connect with other attendees before the program starts.
  2. Practical market & AI insights — A clear-eyed look at where markets, technology, and disruption are heading, and what it means for your plan.
  3. Actionable strategies for the next 5 years — Leave with specific steps to prepare your investments, business, and family for what’s ahead.

Featured Keynote: Jonathan Brill | Business futurist · AI strategist · Bestselling author

Jonathan helps investors, business owners, and families prepare for a rapidly changing world and identify the opportunities created by disruption. Expect a candid, practical session — not a lecture on hype, but a working guide to what’s next.

Schedule:

  • 8:00 AM — Check-in & breakfast: Doors open. Enjoy a complimentary breakfast and time to connect before the program begins.
  • 9:00 AM — Keynote presentation: Jonathan Brill shares market insight, AI strategy, and what to prepare for over the next five years.
  • 10:00 AM — Q&A & closing: Open floor for questions, followed by closing remarks from the Carver Financial Services team.

When:

Saturday, January 16, 2027

8:00 – 9:00 AM Registration & Breakfast | 9:00 – 10:00 AM Presentation

Where:

Mentor Fine Arts Center | 6477 Center St | Mentor, OH 44060

You can register for this free event here.

This event will be recorded for your convenience. 

There is neither a cost nor any obligation to attend this event. You are encouraged to invite family and friends.

Category: EventsTag: AI & disruption, Family wealth planning, Future-proofing your business, Market strategy

Katie Spotz Prepares to Row Across the Pacific — For a Cause Greater Than the Record Books

September 1, 2026 //  by Paige Courtot

 

 

 

 

 

 

 

 

 

 

 

This month, we’re proud to shine our Client Spotlight on Katie Spotz — niece of a valued Carver Financial Services client — whose extraordinary blend of athletic endurance and humanitarian purpose is about to carry her across one of the most daunting stretches of open water on Earth.

Katie is no stranger to pushing the limits of what’s physically possible. A world-record endurance athlete, author, speaker, U.S. Coast Guard veteran, and dedicated clean-water advocate, she has spent her career redefining what one person can accomplish — and who it can help along the way.

A History of Extraordinary Feats

Katie’s resume of accomplishments reads like a list of “impossible” tasks, checked off one by one:

  • Youngest person to row solo across the Atlantic Ocean
  • Swam the entire 325-mile length of the Allegheny River
  • Completed 11 ultramarathons in 11 consecutive days

But what sets Katie apart isn’t just the scale of these challenges — it’s the purpose behind them. Through her endurance feats, she has helped provide lasting access to clean water for more than 50,000 people around the world.

Her Boldest Challenge Yet

Now, Katie is preparing for the most ambitious undertaking of her career. During a launch window from late December 2026 to early January 2027, she will attempt a 10,000-mile solo row across the Pacific Ocean, traveling from Lima, Peru, to Cairns, Australia. She’ll spend approximately eight months alone at sea, without a support boat, relying entirely on her own strength, preparation, and resolve.

If successful, Katie will make history as:

  • The first woman to row solo from South America to Australia
  • The first American woman to row the Pacific Ocean solo
  • A record-setter for the longest nonstop solo ocean row by a woman

Rowing for a Reason

For Katie, this journey has never been about personal glory alone — it’s about the communities she can uplift along the way. Her Row for Water campaign aims to raise $1 million to bring clean-water access to 100,000 people in Fiji, continuing her long-standing mission of turning physical endurance into lasting global impact.

It’s a powerful reminder that resilience, when paired with purpose, can change lives far beyond the finish line.

How You Can Support Katie’s Mission

Katie’s journey across the Pacific will test her physically and mentally in ways few can imagine — but the reward, if she succeeds, extends far beyond personal achievement. It’s an opportunity to bring clean, safe drinking water to tens of thousands of people who need it most.

Donate here to support Katie’s Row for Water – Pacific Edition campaign

We’re honored to know Katie through our client community, and we’ll be following her journey closely as she prepares to set out on this historic row. Stay tuned for updates as her launch window approaches.

Category: Uncategorized

A Nation That Argues With Itself — And Markets That Keep Compounding Anyway

September 1, 2026 //  by Paige Courtot

Every election season, clients ask a version of the same question: “Given everything happening in Washington, shouldn’t we do something different with the portfolio?” It’s a fair question, and it deserves a real answer rather than a reflexive “stay the course.” So here is the thinking behind why we generally don’t recommend reacting to political tension — and the historical record behind it.

America is not a country that lurches. It’s a country that argues, then corrects.

Look at the last sixty years of election results and you don’t see a nation careening from one extreme to another. You see a closely and consistently divided electorate that shifts a few points one way, then a few points back, cycle after cycle. The 2024 election is a recent example of that pattern, not an exception to it: Donald Trump won the popular vote by roughly a point and a half — his best showing in three runs, but still a margin far closer to a coin flip than a mandate. That’s what an evenly divided country producing a modest correction looks like, and it’s the same story told over and over in midterm after midterm, going back generations.

The Constitution was built for exactly this kind of country. We elect a president every four years, but we get to weigh back in two years later on the entire House and a third of the Senate — a built-in mechanism for correcting course without waiting for the next presidential cycle. And on the other end, amending the Constitution itself requires two-thirds of both chambers of Congress plus three-fourths of the states — a bar high enough that no single election, however heated, can permanently rewrite the rules. Frequent small corrections, and near-total protection against permanent extreme ones. That combination is, in our view, one of the most underappreciated reasons the United States has remained investable through genuinely difficult periods.

And “genuinely difficult” is not an exaggeration. Consider what markets have actually lived through:

  • Watergate (1973–74): Amid a presidential resignation, an oil embargo, and double-digit inflation, the S&P 500 fell roughly 50% peak to trough — one of the worst stretches in market history. Investors who stayed invested were rewarded with a +31.6% rebound in 1975 and another +19.2% in 1976.
  • The contested 2000 election: A five-week recount, a Supreme Court decision, and a country split almost exactly down the middle. Markets were volatile through the standoff, but the episode itself was a blip against the larger, unrelated dot-com unwind already underway.
  • The 2008 financial crisis, playing out during a presidential election: The S&P 500 fell 50% in 2008, then rallied 23.5% in 2009.
  • 2016 and 2020, two of the most polarizing elections in modern memory, were followed by

+19.4% (2017) and +16.3%/+26.9% (2020–21) — including a global pandemic and the events of January 6th sitting right in the middle of that second stretch.

None of this means political tension doesn’t matter, or that markets are immune to policy. It means that a diversified, long-term portfolio has repeatedly absorbed shocks — assassinations, resignations, recounts, insurrections, pandemics — that felt existential in the moment and reads, a few years later, as a bump on a longer chart.

There’s also a subtler data point worth knowing: going back nearly a century, average annual stock returns have been strong under every combination of party control — unified Republican government, unified Democratic government, and divided government under presidents of both parties. No single arrangement has a durable monopoly on growth. The market, in other words, is pricing in far more than who sits in the Oval Office.

The takeaway we’d leave you with: your investment plan should be built around your goals, your time horizon, and your risk tolerance — not around the two-year and four-year rhythms of Washington. The country will keep arguing with itself, correcting a bit left, then a bit right, exactly as it’s designed to.

History suggests the more durable move is to let that process play out in the voting booth, and let your portfolio keep compounding through it.

As always, we’re happy to talk through how this thinking applies to your specific situation.


Carver Financial Services manages more than $3.9 Billion in assets as of August 2026 for clients globally. You can contact Randy Carver personally at randy.carver@raymondjames.com or the full team at (440) 974-0808.

Opinions expressed are those of the author/speaker and are not necessarily those of Raymond James. All opinions are as of this date and are subject to change without notice. Investing involves risk and you may incur a profit or loss regardless of strategy selected. Past performance may not be indicative of future results. Prior to making an investment decision, please consult with your financial advisor about your individual situation. Every investor’s situation is unique and you should consider your investment goals, risk tolerance and time horizon before making any investment. The forgoing is not a recommendation to buy or sell any individual security or any combination of securities.

Category: BlogTag: artificial intelligence, business owners, Investing, Media, Randy Carver, retirement planning

Wings & Wheels 2026

August 28, 2026 //  by Paige Courtot

Category: Video

The Retirement Plan Nobody Talks About

August 26, 2026 //  by Paige Courtot

 

“Get the money right, and everything else takes care of itself.”

That’s what most people believe walking into retirement. After more than three decades of sitting across the table from families getting ready for this next chapter, I can tell you it’s not quite true — and the research backs that up.

The Study That Changed How We Think About a Good Life

In 1938, Harvard researchers started tracking a group of young men — some Harvard sophomores, some from Boston’s toughest neighborhoods — and kept following them, decade after decade, through marriages, careers, health scares, retirements, and eventually, old age. It’s still running today, expanded to include spouses and children, and it’s the longest-running study on adult life ever conducted.

Eight decades in, the finding that keeps showing up, no matter how many times researchers re-run the numbers, isn’t about income, career success, or even genetics. It’s this: the quality of a person’s close relationships in their 40s and 50s predicts their health and happiness in their 80s more reliably than their cholesterol does.

Let that sit for a second. Not their account balance. Not their career title. Their relationships.

What Rarely Makes It Into the Plan

Every retirement conversation I’ve ever sat in covers withdrawal rates, tax brackets, Social Security timing, healthcare costs. All of that matters — I wouldn’t be in this business if it didn’t. But most of those conversations skip right past the thing the research says matters just as much: whether there are people in your life who’ll still be there once the job that structured your days for 30-plus years is gone.

Here’s why that catches people off guard. A career doesn’t just pay the bills — it hands you an identity, a schedule, a sense of purpose, and, often without anyone realizing it, most of your social life. The coworkers, the standing lunch, the quick check-ins — a lot of that has a quiet expiration date stamped on it the day you clean out your desk. It’s common for a good number of those relationships to fade within a year or two of retiring, not out of anyone’s fault, just because day-to-day proximity was doing more of the work than anyone gave it credit for.

The Marriage Question Nobody Wants to Ask

There’s a demographic shift worth knowing about here too. Divorce among adults 50 and older — often called “gray divorce” — now accounts for nearly 40% of all divorces in this country, up from under 9% back in 1990. The rate roughly doubled between 1990 and 2010 for that age group, and climbed even faster for those over 65.

Retirement doesn’t cause that shift. What it does is remove the scaffolding — the careers, the packed schedules, the kids at home — that was quietly holding a lot of marriages together without anyone examining them too closely. Suddenly there’s a lot more time at the same breakfast table, with a lot less to distract from whatever wasn’t being talked about.

This Isn’t Just a “Feelings” Issue

If this sounds more like a topic for a therapist than a financial advisor, here’s the data point that changes that: the U.S. Surgeon General’s office found that chronic loneliness carries a health risk comparable to smoking up to 15 cigarettes a day, and raises the risk of dementia in older adults by roughly 50%. That’s not a soft, feel-good statistic. That’s a measurable risk to someone’s health — and it belongs in the same conversation as a withdrawal rate or an estate plan.

What Business Owners in Particular Should Watch For

This shows up especially often with business owners — people who’ve spent 20 or 30 years so wrapped up in running something that the business quietly became their whole identity and most of their social circle. I’ve sat with clients who sold their company for a life-changing number and still couldn’t relax into retirement, because the thing that had structured every one of their days for decades was suddenly just gone. The balance on the statement was never the problem. The blank calendar was.

What Actually Helps

None of this is a reason to dread retirement — it’s the opposite. People are living longer, healthier lives than any generation before them, which means there’s more runway than ever to build something good. A few things worth doing well before the last day of work:

  • Take real stock of who you’d actually call if something went wrong at 2 a.m. If that list is short, that’s worth addressing now, not after the transition.
  • Have an honest conversation with your spouse about what the next 20 years actually look like — not the brochure version.
  • Find something to be part of where you’re the new person again. It keeps you building relationships instead of just maintaining the ones you’ve already got.

Where This Fits Into Your Plan

We build financial plans around the life people actually want to live — income, taxes, healthcare, legacy, all of it. But a plan that only accounts for the money and skips the rest isn’t a complete plan. If part of getting ready for this next chapter means thinking through the relational side of it too, that’s a conversation worth having, right alongside the one about your portfolio.

If you had to guess, right now, whether you’ve got the people side of retirement as buttoned up as the financial side — are you confident in the answer? If not, that’s usually worth a conversation.


Carver Financial Services manages more than $3.8 Billion in assets as of June 2026 for clients globally. You can contact Randy Carver personally at randy.carver@raymondjames.com or the full team at (440) 974-0808.

Any opinions are those of Carver Financial Services and not necessarily those of Raymond James. Expressions of opinion are as of this date and are subject to change without notice. Raymond James and its advisors do not offer tax or legal advice. You should discuss any tax or legal matters with the appropriate professional. Investing involves risk and you may incur a profit or loss regardless of strategy selected, including diversification and asset allocation. Prior to making an investment decision, please consult with your financial advisor about your individual situation.

Category: BlogTag: artificial intelligence, business owners, Investing, Media, Randy Carver, retirement planning

September 2026

August 13, 2026 //  by Paige Courtot

Category: Client Memo

What Documents Do I Need to Keep on File?

August 13, 2026 //  by Paige Courtot

What Documents Do I Need to Keep on File?

Download the Guide

Most people have a filing cabinet, a desk drawer, or a digital folder stuffed with paperwork they’re afraid to throw away — and no real sense of what’s actually necessary to keep. The result is often one of two problems: important documents get shredded too soon, leaving a gap when they’re needed most, or nothing ever gets thrown away, turning recordkeeping into a permanent, disorganized burden.

The truth is that different documents need to be kept for different reasons and different lengths of time. Some protect you in the event of an audit. Some establish eligibility for benefits. Some simply prove that a debt has been paid or a deduction was legitimate. Knowing which is which can save you real time, stress, and risk down the road.

Here’s a breakdown of what to keep, and for how long, organized by category.

Legal Documents

Legal paperwork tends to fall into two buckets: documents you’ll need once and can then archive permanently, and documents tied to a specific life event that you’ll need to produce again later.

  • Citizenship and residency documents. If you’re a U.S. citizen, keep your Social Security card, birth certificate, and passport on file indefinitely. If you’re a foreign national, hold onto everything related to your entry into the U.S. — passport, Green Card, and I-94 — for the same reason.
  • Estate planning documents. Keep a copy of your Will, any Trusts, Powers of Attorney (both general and healthcare), your Living Will, and your beneficiary designations. Store the originals somewhere secure, and give copies to the people who play a role in carrying out your wishes — your agents, Executor(s), and Trustee(s). If something happens to you, the people who need these documents shouldn’t have to search for them.
  • Marriage records. If you’re currently married, keep your marriage certificate. It’s often required for a legal name change, proof of marriage for insurance benefits, or a joint mortgage application. If you signed a prenuptial agreement, store the original somewhere safe as well.
  • Divorce records. Divorce papers should be kept indefinitely. They can affect everything from asset division to future benefit eligibility.
  • Military discharge papers. If you served in the military, your discharge papers may be required to prove eligibility for veterans’ benefits, so they’re worth keeping permanently.
  • Safe deposit box documentation. If you have a safe deposit box, keep the relevant paperwork on file so that access isn’t a barrier for you or your heirs.

Tax Documents

Tax recordkeeping rules are some of the most specific — and most commonly misunderstood.

  • General rule: Keep at least three years of state and federal tax returns, along with supporting documentation such as W-2s, 1099s, and year-end statements from banks and investment accounts.
  • State-specific rules: Some states, including California, require you to keep tax returns for longer than three years. Check your state’s specific requirements.
  • Underreported income: If you believe you may have failed to report income equal to more than 25% of your gross income, keep six years of tax returns on file. This aligns with the IRS’s extended statute of limitations for substantial underreporting.
  • Worthless securities or bad debt: If you’re claiming a loss for worthless securities or a bad debt deduction, keep those records for seven years.
  • W-2s: Keep all your W-2s until you begin collecting Social Security, since they can be used to verify your earnings history.
  • Gifts and inheritances: If you’ve made taxable gifts or received an inheritance, keep every Form 709 you’ve filed, along with any Forms 8971 or 706 you’ve received, in your permanent records.

Healthcare Documents

Healthcare-related recordkeeping is often overlooked until it’s needed — usually at the worst possible time.

  • Medicaid planning. If there’s a chance you’ll apply for Medicaid, particularly to help cover long-term care costs, keep detailed financial statements and transaction records for the previous five years. Medicaid generally applies a five-year look-back period when reviewing applications, and gaps in your records can complicate or delay approval.
  • Health Savings Accounts (HSAs). Keep every medical receipt from the date your HSA was opened. These receipts may be needed to substantiate tax-free withdrawals, even years later.
  • Medical expense deductions. If you’ve written off medical expenses on your tax return, keep those records for as long as you keep your tax returns — generally three years.
  • Medicare. If you’re enrolled in Medicare, keep your Medicare Summary Notices for at least a year, or until any related bill is paid in full. If you’re enrolled in an employer drug plan considered “creditable,” keep the annual Notice of Creditable Coverage your employer provides — you’ll need it if you enroll in Part D later.

Asset and Debt Related Documents

This is often the largest and most complex category, especially for people who own investments, retirement accounts, real estate, or a business.

Investment and bank accounts

  • Keep your most current statements on file, whether paper or electronic.
  • Keep your end-of-year statement until you’ve completed your tax return for that year.
  • If you own investments purchased before 2012 — the year custodians were first required to track cost basis — keep records of what you paid for those non-covered investments. Your 1099 may not report cost basis on older holdings, so your own records may be the only proof you have.

Retirement accounts

  • Keep documentation of any contributions and withdrawals, including IRS Form 5498.
  • If you took a Coronavirus-Related Distribution, retain your withdrawal request and Form 1099-R.
  • If you completed a Roth conversion, keep records showing the conversion.
  • If you made non-deductible traditional IRA contributions, keep Form 8606 until the account has been fully withdrawn, since it’s used to track your cost basis over time.

Small business ownership If you own a business, keep the following as part of your permanent records:

  • Federal EIN, business formation documents, ownership agreements, and business licenses
  • Payroll records, employment tax records, and expense receipts
  • Business asset records, such as purchase and sales invoices, deeds, and titles
  • Records of employee benefits, including retirement plan documents

Debts If you have a mortgage, student loans, or other debt, keep the loan documents until the loan is paid off. Once it’s paid off, keep documentation proving the debt was satisfied in full — this can matter years later if a lender’s records are ever incomplete or disputed.

Property If you own real estate or automobiles, keep deeds, titles, settlement statements, and bills of sale until you decide to sell. Also keep documentation of any capitalized purchase-related fees, since they affect your cost basis.

Home office deductions If you’re self-employed and deduct home office expenses, keep receipts for housing and home office-related costs — utility bills, mortgage statements, and similar documentation — to support the deduction if it’s ever questioned.

Home improvements Keep receipts for home improvements. They can be used to substantiate adjustments to your property’s cost basis when you eventually sell.

Property in multiple states If you own real property in more than one state, keep detailed records — receipts, travel itineraries, and similar documentation — proving which state you lived in for the majority of the year. This is especially important if you’re concerned about state income tax liability or need to establish residency in a particular state.

Other Documents

  • Higher education records. Keep copies of diplomas, transcripts, or certifications proving you completed coursework — these can matter for professional licensing or employment verification well after graduation.
  • Insurance policies. Keep your most current homeowners, disability, and life insurance policies on file, and replace outdated versions as they renew.
  • Employment contracts. If you’re currently employed, keep any signed contracts on file, including non-solicit or non-compete agreements. These can become relevant if you change jobs or start a business later.

Why This Matters

Recordkeeping isn’t just an administrative chore — it’s a form of financial protection. The right documentation can be the difference between a smooth Medicaid application and a five-year scramble to reconstruct financial history. It can determine whether a tax deduction holds up under audit, or whether a family member can settle an estate without unnecessary delay.

At the same time, holding onto everything forever isn’t the goal either. A thoughtful approach — knowing what to keep, for how long, and why — makes it easier to stay organized without being buried in paperwork you’ll never need.

If you’re not sure whether your recordkeeping is where it should be, or if you have questions about how these guidelines apply to your specific situation, we’re happy to help you sort through it.


Any opinions are those of Randy Carver and not necessarily those of Raymond James. Expressions of opinion are as of this date and are subject to change without notice. Raymond James and its advisors do not offer tax or legal advice. You should discuss any tax or legal matters with the appropriate professional. Investing involves risk and you may incur a profit or loss regardless of strategy selected, including diversification and asset allocation. Prior to making an investment decision, please consult with your financial advisor about your individual situation.

Category: Carver University

10.22.26 39th Annual CPE Event

August 8, 2026 //  by Paige Courtot

This year’s program will feature an important OBBA legislative and planning update covering critical changes impacting clients in 2026 and 2027, along with presentations showcasing state-of-the-art technology and advanced AI-driven tools that can identify sophisticated planning opportunities in minutes instead of hours.

Category: Events

5 Important Legal Documents When Your Child Turns 18

July 14, 2026 //  by Paige Courtot

When a child turns 18, they become a legal adult. Parents no longer have automatic access to their medical, educational, or financial information, and they cannot make decisions on their behalf without permission. To help protect your child and prepare for emergencies, consider these five important legal documents:

FERPA Waiver

  • Allows parents to access college education records, including grades, tuition, financial aid, and disciplinary information.
  • Helpful if parents are assisting with college finances or want to stay informed.

HIPAA Waiver

  • Gives parents permission to access their adult child’s medical records and speak with healthcare providers.
  • Does not allow parents to make medical decisions.

Advance Directive (Medical Power of Attorney & Living Will)

  • Names someone to make healthcare decisions if the child is unable to do so.
  • Includes instructions for medical treatment and life-support preferences if the child becomes seriously ill or incapacitated.

Financial Power of Attorney

  • Authorizes a trusted person to manage financial matters if the child is unable to do so.
  • Can include paying bills, managing bank accounts, handling investments, filing taxes, or other financial responsibilities.
  • Authority can be broad or limited, depending on the document.

Simple Will

  • Specifies how the child’s assets should be distributed after death.
  • Helps avoid legal complications and allows an executor to manage both physical and digital assets, such as social media accounts.

Key Takeaway:

Having these documents in place helps ensure parents or another trusted individual can assist an adult child with education, healthcare, finances, and estate matters when needed. An estate planning attorney can help prepare the appropriate documents for your family’s situation.


Any opinions are those of Randy Carver and not necessarily those of Raymond James. Expressions of opinion are as of this date and are subject to change without notice. Raymond James and its advisors do not offer tax or legal advice. You should discuss any tax or legal matters with the appropriate professional. Investing involves risk and you may incur a profit or loss regardless of strategy selected, including diversification and asset allocation. Prior to making an investment decision, please consult with your financial advisor about your individual situation.

Category: Carver University

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