Sestito Financial

06/17/2026

Most people assume that a spouse's unused estate tax exemption passes to the surviving spouse automatically.

It doesn't.

Claiming it REQUIRES A FILING WITH THE IRS within 9 months of a spouse's death.

The IRS doesn't send a reminder. The deadline just passes.

A six-month extension is available, bringing the total window to 15 months. But the clock starts the day your spouse dies, not the day you think to ask about it.

This is exactly the kind of detail that gets lost in the fog of grief and estate administration.

It's also exactly the kind of thing we watch for on behalf of the families we work with. We also help families by working with their tax, legal, and accounting professionals to make certain that paperwork is completed in a timely manner.

06/15/2026

Father's Day is at the end of this week. Before the dinner and the gifts, there's something worth talking about.

Most men will show up for everyone around them without being asked. But when it comes to their own health, the appointments get pushed off longer than they should. 💚

The CDC reports that women are 33 percent more likely than men to visit the doctor and twice as likely to seek preventive care.

If there is a man in your life worth celebrating on Sunday, ask when he last had a checkup.

That conversation might matter more than any gift.

06/11/2026

True or false: Setting up a trust means your estate will avoid probate.

False. And it's one of the most common estate misunderstandings wealth strategists see. ⚖️

A trust doesn't protect anything the day you sign it. It has to be set up, meaning your assets need to be physically transferred into it:

▪️ Real estate titling may need to be addressed.

▪️ Bank and investment accounts need to be retitled in the name of the trust.

▪️ Insurance policies may need to be updated if the trust will be involved.

Overlooking these steps leaves the trust as an empty legal container.

Your estate may still go through probate. Creditors may still have access. The protections you prepared for may not apply.

The paperwork gets done, life moves on, so don’t let the trust get lost in the shuffle.

It happens more than most people realize. 📋

It's worth a conversation to make sure what you've built is actually doing what you intended. A trust involves a complex set of tax rules and regulations. Before moving forward, consider working with a professional who can guide you through the trust activation process.

06/10/2026

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.

06/07/2026

Some days on the calendar mean more than others. Today is one of them. 💙

If someone you love has faced a cancer diagnosis, you know the journey doesn't end when treatment does. The fear doesn't just disappear. The follow-up appointments keep coming. And somewhere in the middle of all of it, there are these unexpected moments of pure gratitude that are hard to put into words.

Cancer doesn't just touch one person. It's the spouse who rearranged their whole life. The kids who grew up faster than they should have. The friends who showed up and kept showing up.

Behind every survivor is a family that went through it too.

Today is for all of them.

06/05/2026

Markets continued their upward climb in May, supported by strong technology performance, positive economic data, and ongoing diplomatic efforts in the Middle East. The Nasdaq gained 8.36%, the S&P 500 rose 5.15%, and Canada’s S&P/TSX Composite added 2.37%, while investors welcomed better-than-expected job growth and upbeat corporate earnings. With the Fed's next meeting scheduled for June, attention is turning to updated economic projections and what they may signal about the broader economy. From \$24 billion spent on Father's Day to the popularity of dining out and special outings, this month's by-the-numbers highlights how families celebrate the dads in their lives.

Monthly Market Insights | June 2026 U.S. and Canadian Markets Stocks pushed higher in May, fueled by big tech names, positive economic news, and ongoing diplomatic efforts in the Middle East. The Nasdaq Composite, which rose 15.29 percent in April, tacked on another 8.36 percent. The Standard & Poor...

06/04/2026

If you've watched a parent or grandparent navigate this disease, you already know.

It changes everything, and not just for them.

Families are often so focused on the day-to-day of caregiving that the legal and financial side quietly falls behind.

▪️ Who has the authority to make decisions if something changes?
▪️ Is there a long-term care plan?
▪️ Does anyone know where the documents are?

A power of attorney, a healthcare directive, a conversation about what care actually looks like.

These are so much easier to put in place when everyone is healthy and clearheaded than after a diagnosis.

If you have aging parents, this month is as good a time as any to start that conversation. We're happy to be part of it. 💙

06/02/2026

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. 👇

1️⃣ 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.

2️⃣ If existing owners aren't selling, inventory can become thin, prices might stay elevated, and buyers wait for something to change.

3️⃣ 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?" 📋

05/29/2026

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.

05/28/2026

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.