Real Randy Jones

What would you do with a windfall?

A business sale. An inheritance. A bonus that lands bigger than expected.

Most people assume they'd handle it well.

But sudden money follows patterns. And the patterns aren't always flattering.

Psychologists call it sudden wealth syndrome: the anxiety, decision paralysis, and relationship pressure that arrive alongside a large sum. It shows up whether the windfall was a complete surprise or something you spent years building toward.

The 5 most common mistakes we see:

• Upgrading your lifestyle before a strategy exists

• Giving to family under emotional pressure

• Attempting to make decisions without professional guidance

• Freezing and making no decisions at all

• Missing the critical deadlines in year one

All five can be managed, but only if you get ahead of the emotions before the decisions start piling up.

The most important thing you can do in the first 90 days? Maybe nothing.

Tell very few people. Then consider building a team of professionals who can offer insights and guidance.

There is rarely a cost to waiting. There is frequently a cost to moving too quickly.

True or false: Americans in March 2026 are applying for fewer mortgages than they were during the Great Recession.

True. And it's not even close.

96 OF THE 100 LOWEST NUMBER OF WEEKLY MORTGAGE APPLICATIONS SINCE 1999 HAVE HAPPENED IN THE LAST 3 YEARS! (according to the Mortgage Bankers Association's Mortgage Application Index)

Yet, unemployment today is a fraction of what it was during the financial crisis.

People aren't staying out of the market because they can't qualify. The market is gridlocked. Here's why.

• Millions of homeowners locked in at 3 percent during the pandemic. Selling means giving that up for another mortgage that may have a higher interest rate. So they're not moving.

• If existing owners aren't selling, inventory can become thin, prices might stay elevated, and buyers wait for something to change.

• Most are waiting for rates to drop. But when they do, demand may pick up, competition returns, and that window closes faster than expected.

Here's the truth about market timing: it almost never works the way people picture it.

The better question isn't "When is the right time to buy?" It's "Am I financially ready to move when the right opportunity comes?"

According to a Fidelity article, for the ‘25-’26 school year, the average published all-in cost at a 4-year public school for out-of-state students is $45,780, and the average private school costs $60,920.

So, because today is 529 Day (it’s 5/29, get it?), it’s a good time to revisit one of the most flexible tools for tackling those numbers.

What 529 plans actually do:

• Tax-free growth and tax-free withdrawals for qualified education expenses. State tax treatment will vary, and so will fees and expenses.

• Use them for college, trade school, K-12 tuition, and apprenticeships. A 529 can even repay up to $10,000 in student loans.

• Whether a 529 qualifies for a state tax deduction will depend on your state of residence, as state tax laws and treatment may vary from federal tax laws.

• Superfund up to $95,000 in a single year by using five years of gift tax exclusions at once. But remember if you make nonqualified distributions, earnings will be subject to income tax and a 10 percent federal penalty tax.

• Minimal impact on financial aid—parent-owned 529s are assessed at a maximum rate of 5.6 percent.

Grandparents, parents, aunts, or uncles can contribute.

And starting in 2026, the K-12 annual withdrawal limit doubles to $20,000.

The best time to start was years ago. The second-best time is now.

Yes, Memorial Day marks the unofficial start of summer. But let's not forget what this day is really about.

Today, we remember those who gave everything. The men and women who served and never came home.

Some of us knew them. Some of us are here because of them.

However you spend today, take a moment to pause. Enjoy the long weekend, but hold space for what it actually means.

To the families carrying that loss: we honor them with you.

Your business is likely your biggest asset, yet many small business owners don’t think of it that way. Check out this recent study that explores owner mindsets and key considerations to ensure your business is working for you.

compass.massmutual.com

Most parents think the last tuition check means game over for college. The data says it's halftime.

50 percent of parents with adult children still provide regular financial support, spending $1,474 a month to do so. That's more than twice what they're putting toward their own retirement.

Here's what "just helping out a little" actually looks like:

• 75 percent of parents aged 45+ are financially supporting at least one adult child, even though over half of those children can meet their own basic needs, according to a 2025 AARP survey.

• 42 percent of supporting parents report financial stress. 9 percent have retired early because of it.

• 47 percent say they've sacrificed their own financial position for the sake of their kids.

• 18 percent say the support could continue indefinitely. They don't see an end in sight.

This isn't about being less generous. It's about being intentional.

Whether your kid just graduated, graduated five years ago, or is still in school, the question is the same: Is your support happening by design or by default?

That's worth a conversation.

Whether you’re renovating a home, considering a business opportunity, or just need extra flexibility with cash flow, there are ways to access funds without selling your investments. Several approaches are available, and understanding liquidity options can help keep long‑term goals in view. Let’s connect.

Think you have to start claiming Social Security at 62?

That's a myth that could cost you.

Fidelity recently broke down this common misconception with the facts behind Social Security:

• Claiming at 62 locks in a permanent 30 percent reduction compared to waiting until full retirement age.

• Waiting from 62 to 70 can increase your monthly benefit by approximately 77 percent.

• If you're divorced after 10+ years of marriage and haven't remarried, you may be entitled to 50 percent of your ex-spouse's benefit, and claiming it doesn't affect theirs at all.

• Benefits are based on your highest 35 earning years, not just what you made before 65. Working past 65 can still improve your calculation.

• Once you claim it, that's your benefit, adjusted only for cost-of-living increases.

The decision of when to claim is one of the most consequential decisions when preparing for retirement.

For a benefit designed to last 20, 30, or more years, the math is worth getting right.

Your retirement outlook probably covers income, investments, and Social Security.

But does it answer this question: if your health changes at 82, who coordinates your care, how is it paid for, and what burden does it place on the people you love?

That's the conversation most families aren't having early enough.

A few numbers that put it in perspective:

• 70 percent of adults who reach 65 will need some form of long-term care.

• A semi-private nursing home room now costs a median of $114,975 per year, and that number is climbing fast.

• Projected out 20 years, nursing home care could approach $186,000 annually.

• Continuing care retirement communities (CCRCs) offer an alternative: move in while independent, with access to assisted living, memory care, and skilled nursing on one campus as needs change.

• A portion of CCRC entrance fees and monthly fees may have tax considerations since they can be classified as a medical expense. Most people don't know this.

The biggest mistake we see? Waiting.

CCRCs require applicants to be healthy enough to live independently. Many have waitlists.

"I'll just stay in my house" feels like the safest option. But it's only safe if you've stress-tested what happens when care needs escalate.

Have you started this conversation with your family or your financial professional?