One Shot to Get It Right

"A deer has to be taken with one shot. I try to tell people that but they don't listen." - Michael Vronsky

Five Decisions You Only Get to Make Once

Most financial decisions can be revisited. A portfolio gets rebalanced next quarter. A budget gets adjusted next month. Fine.

A handful of decisions don't work that way. You retire once. You help your parents as they age, once. You receive an inheritance, or you don't. You sell a business once, or you put an estate strategy in place that has to hold up long after you're not around to explain it.

Here's what those moments have in common: by the time they arrive, most of the meaningful choices have already been made. What looks like a single decision is usually the last visible step of a process that started years, sometimes a decade, earlier.

That gap — between when the decision happens and when the preparing for it should have started — is the whole idea running through everything below. The families who navigate these five moments well aren't necessarily the ones with the most assets. They're the ones who started asking questions and organizing their paperwork long before anyone forced their hand. The families who struggle are usually the ones who treated the life event as the starting gun instead of the finish line.

AI deserves a mention here, since it now answers financial questions faster than any of us can type them. It's genuinely useful for some of that — explaining how a Roth conversion works, estimating long-term care costs in your state.¹ But weighing that information against your family's specific circumstances and values? Noticing the thing you didn't think to ask about? Information is turning into a commodity. Judgment, applied to your particular life, is not. Nor will it be, anytime soon.

How Early Should You Start Preparing for Retirement?

Most people picture retirement as something that unfolds gradually and then wraps up on a specific date. In practice, the decade before retirement does most of the work, and the decisions made in that window can shape everything that follows.

Here's a number that surprises most people who haven't seen it: 46 percent of retirees in EBRI's 2026 Retirement Confidence Survey left the workforce earlier than they'd planned.² Not "considered." Left.

The reasons overlap, since many gave more than one:²

• 41 percent cited a health problem or disability
• 35 percent cited changes at their employer — a layoff, a restructuring
• 36 percent said they simply felt they could afford to

Preparing for retirement "someday" assumes you get to pick the day. For nearly half of retirees, that assumption was wrong. Sometimes by circumstance, sometimes by choice, but almost never on schedule. My father worked until he was 70, and even that was his own decision, made on his own timeline — the kind of flexibility that isn't an accident. It's the point of preparing early. Flexibility, not account size, is usually what decides whether an unexpected exit becomes a crisis or a minor detour.

Flexibility shows up most clearly in how your money gets taxed. Look at how U.S. households actually hold their retirement savings:³

• Roughly 33 percent own a traditional, tax-deferred IRA
• About 28 percent own a Roth
• Only 17 percent own both

A household sitting almost entirely in tax-deferred accounts has its full withdrawal taxed as ordinary income. Once required minimum distributions kick in, the choices narrow fast. Your tax, legal, or accounting professional can help you sort out how this applies to you specifically.

There's also a quieter risk hiding in the years right around retirement.

Research on sequence of returns risk shows that the market return an investor gets in their very first year of retirement can explain nearly 14 percent of how a 30-year income strategy ultimately performs — more than any other single year.⁴ Two retirees with identical savings and identical long-term average returns can land in very different places, purely because of which years the market happened to dip around their retirement date. This is why retirement income is a different discipline than retirement savings. Saving asks how much you'll have. Income asks how you'll draw on it without being at the mercy of the year you happened to stop working.

Past performance does not guarantee future results. The return and principal value of financial markets will fluctuate as market conditions change.

"The decision may happen once. Preparing for it often starts years earlier."

"When Should You Talk to Your Parents About Their Finances?

Every family eventually hits some version of this — the parent who used to have everything under control starts needing help managing it. The families who handle it well almost never wait for a crisis to start the conversation.

More than half of Americans in their forties (54 percent) are currently sandwiched between a parent 65 or older and a child they're still supporting, financially or otherwise.⁵ That's not a rare overlap. It's close to the median experience of that entire decade of life — which means the conversation about aging parents rarely shows up alone. It shows up while you're also funding your own retirement accounts, and maybe a kid's education.

Behavioral finance has a name for why families still put this off. When a topic feels uncomfortable, or the information involved might force action we'd rather skip, we go looking for reasons to wait. Researchers call it the ostrich effect, and conversations about a parent's finances and health sit right in the middle of it.⁶

The irony is that avoiding it doesn't prevent the conversation. It just moves it to a moment with far fewer good options.

Framing matters enormously here. Raise the subject as a question about your parent's competence and it lands as an accusation, even when you don't mean it that way. Reframe it around your own preparations instead — mention that your financial professional recently walked you through updating your own estate documents — and you open a door instead of triggering defensiveness.

There's a financial angle too. Caregivers report averaging around $7,200 a year out of pocket,⁷ which can be a real, unplanned drain on a family's finances.

What Should You Do When You Receive an Inheritance?

Most people treat inheritance as a financial question. It's usually an emotional event with financial decisions attached, and treating it as purely financial is where the trouble starts.

Cerulli Associates has put real numbers on the scale of what's coming:⁸

• $124 trillion is expected to change hands in the U.S. through 2048
• $105 trillion of that goes directly to heirs
• Baby boomers and older generations account for 81 percent of the transfer
• More than half the total dollar volume comes from households that are currently high or ultra-high net worth — just 2 percent of all households

What surprises people is how often that money doesn't last, or doesn't end up used the way anyone intended. A landmark Ohio State study of baby boomers found recipients save, on average, only about half of what they inherit. More than a third — 34.9 percent — ended up with no more wealth than before, or less. Even among people who inherited $100,000 or more, nearly one in five had spent or lost all of it within two years.⁹

That's not a financial-literacy problem. It's what happens when you receive a large sum during one of life's more emotionally loaded moments and make decisions before the emotional weight has had time to settle.

The better approach is almost boringly simple:

1. Pause before acting
2. Understand exactly what you've inherited — a brokerage account and a piece of real estate are not the same animal
3. Ask your tax, legal, or accounting professional about the tax implications, and loop in your financial professional
4. Update your own financial strategy, if it needs it
5. Only then make intentional decisions about the money

"An inheritance often arrives during one of life's most emotional seasons."

How Do You Prepare for a Business Sale or Stock Windfall?

This isn't only about founders selling a business. It applies just as much to an executive ten years into a company, or an early employee sitting on equity. In every case, wealth that took a decade or more to build can go liquid in weeks.

I know this one from the inside. I started and sold a food business myself — sushi, produced fresh daily and delivered to corporate cafeterias, not a restaurant — and the sale itself wasn't the hard part. Staying in it years longer than I should have, past the point where I knew things weren't working, was the hard part. Leaving would have meant admitting I'd been wrong, in public, and I put that off longer than made sense. Preparation isn't just spreadsheets. Sometimes it's deciding in advance what your exit line actually is, so you're not negotiating it with yourself in real time.

The Exit Planning Institute's 2023 survey of privately held U.S. businesses backs this up at scale:¹⁰

• Roughly 80 percent of a typical owner's net worth is tied up in the business itself
• 73 percent of privately held U.S. companies are preparing to transition ownership within the next decade — a wave worth an estimated $14 trillion
• Nearly half expect to exit within five years
• Yet 78 percent of owners still have no formal transition team in place

The wealth is scheduled to move. The infrastructure to move it well, mostly isn't.

The decisions that matter most are almost always easier to make before a liquidity event than after one:

• Managing concentration risk gradually, if permitted
• Structuring the transaction to help manage taxes, if permitted
• Gifting shares to family before a valuation event, if permitted
• Deciding in advance how a windfall will or won't change your lifestyle

Once the money lands, some of those options simply aren't available anymore, and you're left working with whatever's already been decided. The real mindset shift is moving from accumulation to stewardship — deciding what the money is for, now.

"Information can tell you what's possible. Preparation helps determine what's right for your family."

Is a Will Enough to Protect Your Legacy?

Estate planning gets discussed like a paperwork problem — get the will done, name the beneficiaries, move on. The documents matter. They also play a smaller role than most people assume in whether a legacy actually holds together once you're gone.

The paperwork gap is real, and it's getting worse. Only 24 percent of Americans currently have a will, down from 33 percent in 2022. Of the people without one, 43 percent say they just haven't gotten around to it.¹¹

But even the families who do have documents in place often haven't done the harder work behind them.¹²

A trust can help here, but it comes with its own tangle of tax rules and regulations — worth working through with a professional who actually knows that terrain before you move forward.

Estate management, done well, is an ongoing practice, not a one-time signing:

• Review beneficiary designations after every major life event. An outdated form naming an ex-spouse or a relative who's passed can send assets somewhere entirely different from what the will says.
• Talk with your adult children — not necessarily about exact dollar figures, but about the values and reasoning behind the major decisions.
• Organize the practical details. Account locations, contacts, digital access. So a hard season doesn't turn into a scavenger hunt for basic information on top of everything else.

Preparation, Not Prediction

Run through all five of these and the same uncomfortable truth shows up each time: the decision itself rarely announces when it's coming. Retirement gets moved up. A parent's decline accelerates faster than anyone expected. An inheritance arrives in a year that's already full of change. An acquisition offer shows up before the business is ready for it. None of that is a reason to guess at timing. It's the reason to build flexibility long before you need it.

AI can answer questions about all five of these instantly, and that's a real help for getting oriented. What it can't do is sit across the table, understand what your family actually values, and help you sort through the dozen technical decisions that hinge on your specific situation. That's where an ongoing relationship with a financial professional earns its keep — not by reacting in the moment, but by making sure the years leading up to it were spent getting ready for it.

The biggest financial decisions rarely become important on the day they happen. They become important years earlier. I'm glad to help my clients use those years well, whichever of these five moments they're currently sitting in front of.

A few questions I'd expect:

What's the best age to start retirement conversations with a financial professional? Most of what shapes retirement outcomes — Social Security timing, income sequencing — gets decided years before retirement. Starting earlier just means more options stay open.

What is sequence of returns risk, and why does it matter so much? It's the outsized effect that investment returns in the first several years of retirement have on the whole plan. A portfolio's performance in year one alone can explain nearly 14 percent of how a 30-year retirement strategy plays out — more than any other single year. That's why the years right around retirement deserve extra attention.⁴

When should families start talking to aging parents about finances? While the parent is healthy and fully able to participate in the decision — not after a health event has already taken the options off the table.

What should someone do first after receiving an inheritance? Pause. Then figure out exactly what you've received — brokerage accounts, retirement accounts, and real estate are very different animals. Your tax, legal, and accounting professional can help; so can I.

How much wealth is expected to transfer between generations? Cerulli projects $124 trillion in the U.S. through 2048 — $105 trillion to heirs, the rest to charity.⁸

What is concentration risk, and why does it matter for business owners and executives? Having an outsized share of your net worth riding on one asset — a private business, a single company's stock. For the average owner, that's about 80 percent of their net worth.¹⁰

How far in advance should a business owner start preparing for a sale? Years, not months. Some of the tools that help most lose their effectiveness the moment a deal is imminent or signed.

What estate documents matter most? A will, updated beneficiaries, and powers of attorney are the foundation — but documents alone don't guarantee a smooth transition. Talking to your family about the values behind the decisions matters just as much as the paperwork.

Can AI replace the guidance of a financial professional for any of this? It's a strong tool for gathering information fast. It doesn't know your family's history, values, or goals, and it can't weigh trade-offs the way someone who knows your whole financial picture can. Use it as a starting point for questions, not the final word on decisions.

¹ To qualify for the tax-free and penalty-free withdrawal of earnings, Roth IRA distributions must meet a 5-year holding requirement and occur after age 59½. Tax-free and penalty-free withdrawals can also be taken under certain other circumstances, such as the owner's death. The original Roth IRA owner is not required to take minimum annual withdrawals.
² EBRI, 2026. 
³ Investment Company Institute Research Perspective, 2026.
⁴ RetirementResearcher.com, 2026.
⁵ Pew Research Center, 2026.
⁶ TheDecisionLab.com, 2026.
⁷ AARP, 2026.
⁸ Cerulli Associates, 2026.
⁹ News.OSU.EDU, 2026.
¹⁰ Exit-Planning-Institute.org, 2026.
¹¹ Caring.com, 2026.
¹² NewsRoom.BankOfAmerica.com, 2026.

This content is intended for general informational purposes only and does not constitute legal, tax, or financial advice. Rules, figures, and projections referenced are subject to change and should be discussed with your own financial, tax, and legal advisors.