The phrase "sell in May and go away" was born in 19th-century London, where wealthy financiers traditionally fled the city for the countryside in summer, leaving thinner trading volumes behind. The full original adage, charmingly, ended with "and come back on St. Leger's Day," referring to a horse race in September. As investment advice goes, it has all the rigor of a weather rhyme.

And yet, every spring, the phrase returns like clockwork. So let us look at what the data actually says.

The Inconvenient Numbers

According to JPMorgan's trading desk, over the past ten years the S&P 500 has averaged a 1.5% return in May, 1.9% in June, and 3.4% in July. These are not weak months. They are perfectly ordinary, sometimes excellent, months. LPL Financial's analysis of returns over the past twelve years shows the May-through-October stretch has averaged a 5.1% gain, more than double the long-run average of 2.1% going back to 1950.

The long-arc comparison is even less kind to the strategy. According to research cited by Money magazine, $1,000 invested in the S&P 500 from 1976 to 2025 using a strict "sell in May, buy back in November" strategy would have grown to about $46,000. The same $1,000 invested using a simple buy-and-hold approach over the same period would have ended at roughly $295,000. That gap is not a rounding error. That is a retirement.

The Real Risk: Missing the Best Days

Here is what makes "sell in May" particularly costly. JPMorgan Asset Management research shows that a $10,000 investment in the S&P 500 grew to roughly $75,000 over twenty years. But if you happened to be out of the market for just the ten best trading days in that stretch, you ended up closer to $34,000. Miss the twenty best days and you are down near $21,000.

The kicker: many of those best days tend to cluster around periods of volatility, including the so-called "weak" months of May through October. The investor who sits out summer to avoid the dips often misses the rebounds too.

What Smart Investors Actually Do in May

The good news is that the impulse behind "sell in May" is not entirely wrong. Spring is a perfectly reasonable time to review a portfolio. The mistake is exiting it.

• Rebalance, do not retreat. If the recent rally has pushed your equity allocation above your target, trim back to target. Selling everything is not rebalancing.
• Harvest gains tax-strategically. Long-term capital gains rates remain favorable. If you have a position you have been meaning to trim, May is as good a month as any.
• Top up dry powder. If your emergency fund slipped during tax season or vacation planning, refill it now while HYSA rates are still attractive.
• Continue automatic contributions. Dollar-cost averaging is unbothered by seasonality. Your 401(k) does not check the calendar before buying shares.

The Bottom Line

If you take only one thing from this article, take this: time in the market beats timing the market. "Sell in May" is a catchy phrase, not a strategy. It belongs in the same drawer as "buy the dip" and "this time is different": comforting clichés that rarely survive contact with data.

Roll up to a graduation party this month and you will hear two phrases on repeat: "We are so proud" and "We saved too much for college." For a long time, the second one carried a real problem. Money in a 529 plan that did not get spent on qualified education expenses faced the dreaded combo of income tax plus a 10% penalty on earnings if you wanted to pull it out for anything else.

Then SECURE 2.0 changed the rules. Quietly. In your favor.

The Provision That Solves the Overfunded 529 Problem

Section 126 of the SECURE 2.0 Act, which took effect January 1, 2024, allows unused 529 plan funds to be rolled over directly into a Roth IRA in the beneficiary's name: tax-free, penalty-free. For families whose child earned a scholarship, picked a less expensive school, or finished early, this is the cleanest exit ramp the IRS has ever offered.

Source: SECURE 2.0 Act, Section 126, and IRS guidance current as of May 2026.

The Quiet Advantage Most People Miss

Here is the part that financial professionals get genuinely excited about. Regular Roth IRA contributions are subject to income phase-outs ($153,000 to $168,000 for single filers in 2026, $242,000 to $252,000 for married couples filing jointly). If your kid grows up to be a software engineer in San Francisco, those numbers may put a direct Roth contribution out of reach.

The 529-to-Roth rollover, however, is generally interpreted as exempt from the Roth IRA income limits, though final IRS guidance is still pending. Under the current consensus reading among major custodians (Schwab, Fidelity, Vanguard), this makes the rollover one of the few legitimate ways for a high earner to get Roth dollars into their retirement account without the backdoor maneuver.

How It Actually Works: A Quick Example

Imagine Sarah's parents opened a 529 for her in 2008. She is graduating in May 2026 with $30,000 left in the account. Sarah's parents cannot roll the money into their Roth IRA. The rollover only flows into Sarah's Roth IRA, in her name.

In 2026, Sarah works a summer job and earns $9,000. Because her earned income exceeds the annual Roth contribution limit of $7,500, her family can roll $7,500 from the 529 into her Roth IRA this year. They can repeat the move each year until they hit the $35,000 lifetime cap, which would take approximately five years. After that, the 529 still has remaining funds for graduate school, certifications, or a future beneficiary change.

The Fine Print That Trips People Up

• The 529 must have been open for at least 15 years. Changing the beneficiary may restart this clock; ask your plan administrator.
• The funds being rolled over must have been contributed at least 5 years before the rollover. Last year's contributions are not eligible.
• Annual rollovers count toward the beneficiary's total Roth contribution limit. If Sarah already put $2,000 into her Roth from her summer job, only $5,500 of 529 money can roll over that year.
• The rollover must be a direct trustee-to-trustee transfer. Do not have the check sent to a personal account.
• State tax treatment varies. A few states may treat the rollover as a non-qualified withdrawal at the state level and recapture previous deductions. Worth a phone call before pulling the trigger.

Is This for Your Family?

The 529-to-Roth rollover is a fit for families with a mature, overfunded 529 account and a beneficiary who is working, earning income, and not in immediate need of the funds for additional education. It is not a fit if the account is newer than 15 years, the beneficiary has no earned income, or the parents are hoping to redirect funds to themselves. The Roth IRA must be in the beneficiary's name. Always.

If any of this sounds like your situation, this is a worthwhile fifteen-minute conversation. The window for these rollovers is open. Use it deliberately.

The 2026 Atlantic hurricane season officially opens on June 1 and runs through November 30. Most coastal families spend the next two weeks thinking about plywood, generators, and bottled water. They spend far less time thinking about the part that often does the real damage: their financial paperwork.

And this year, there is an extra wrinkle. CBS News recently reported that FEMA's Disaster Relief Fund has dropped into its Immediate Needs Funding threshold, meaning the agency is now restricted to spending on the most urgent life-safety needs. Reimbursements and longer-term recovery projects are being delayed. Translation: if disaster strikes, the federal cavalry may move slower than usual. Personal preparedness matters more than it has in years.

The Five-Step Financial Hurricane Kit

This is not a comprehensive disaster plan. It is the part most families skip.

1. Stress-test your emergency fund. The standard advice is 3 to 6 months of essential expenses. If you live in a high-risk zone, lean toward the upper end. Disaster cash needs to be liquid: a high-yield savings account, not a CD that locks for a year.

2. Keep physical cash on hand. When the power goes out, ATMs stop working and card readers go dark. FEMA recommends keeping a small amount of cash in small bills (singles, fives, tens) in a waterproof container. This is the most boring $500 you will ever stash. It is also the one that will buy you gas and groceries when the rest of the system is offline.

3. Digitize and waterproof your documents. Driver's licenses, passports, birth certificates, insurance policies, mortgage papers, vehicle titles, recent tax returns, and a list of account numbers should be scanned and stored in a secure cloud folder (password-protected). Physical copies belong in a waterproof, fireproof container. After a storm, the difference between "I have the policy number" and "I will be back when I find it" is sometimes weeks of waiting.

4. Review your insurance NOW. The single most expensive lesson coastal homeowners learn is that standard homeowner's insurance does not cover flooding. Flood insurance is purchased separately through the National Flood Insurance Program or a private insurer, and most policies have a 30-day waiting period before coverage takes effect. A flood policy you buy on June 5 likely will not cover a storm that arrives on June 20. According to NOAA's National Centers for Environmental Information, Hurricane Katrina caused approximately $201 billion in damage (inflation-adjusted), making it the costliest U.S. tropical cyclone on record. Hurricane Harvey ranks second at roughly $160 billion. The uninsured share of those losses was staggering.

5. Conduct a home inventory. Walk through your home with your phone. Take video of every room, every closet, every drawer. Open the garage. Open the safe. Save the video to the cloud. When you file a claim later, "I had three televisions" is a much weaker argument than "Here is the video, taken last week, of the three televisions."

The Step Everyone Forgets

Set up automatic payments and direct deposit for as many recurring bills and income streams as possible. If you have to evacuate, the last thing you want is a missed mortgage payment, a lapsed utility bill, or a delayed insurance premium. Automation keeps your financial life running while you focus on your physical safety.

If You Are Already in a High-Risk Area

• Pull and review your homeowner's policy declaration page this week.
• Get a flood insurance quote even if you have not had one before. Flood maps have changed in many regions.
• Confirm your deductible amounts. Hurricane deductibles are often a percentage of the home's insured value, not a flat dollar amount. A 5% deductible on a $400,000 home is a $20,000 out-of-pocket hit.
• Add your insurance agent and adjuster contacts to your phone now. Storm-week phone trees are no fun.

Preparation is not pessimism. It is the simplest form of optimism: a belief that your future self is worth a little planning today.