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Author: Crysta Butler

Don’t Let a Bonus or Stock Sale Catch You Off Guard at Tax Time

If your income changes during the year because of a bonus, stock sale, retirement distribution, or another large source of income, the tax impact can catch you by surprise if you wait until filing season to sort it out. The amount you owe and when you need to pay it depend on more than the size of the income increase.

Topics Discussed:

  • How the 90% current-year and 100% or 110% prior-year safe harbor rules work
  • When estimated tax payments are due and when payments may differ during the year
  • How a bonus or stock sale can affect estimated tax requirements
  • Why withholding is treated differently from estimated tax payments
  • How retirement-account withholding may fit into year-end tax planning
  • What information to gather before a fall tax-planning conversation with your CPA

Transcript:

Paul Sydlansky, CFP®:
Today I have with me Megan Hubbard, who is a CPA and partner at Mengel Metzger Barr. I’m excited to leverage Megan’s expertise as we talk about some of the common questions we get from clients around taxes.

Megan, thank you so much for joining us today. I appreciate it.

Megan Hubbard, CPA:
Absolutely.

Paul:
I have a list of questions that come up pretty often with clients. Fall is a time when we start looking at projections, taxes, and opportunities for things we may be able to do before year-end.

One topic that often comes up is the two safe harbors, the 90% current-year rule and the 100% or 110% prior-year rule.

Could you explain what those mean and how someone should think about them when they’re planning for the current year?

01:39 | Understanding the Two Safe Harbors

Megan:
Absolutely. When we talk about estimated taxes, there are basically two main safe harbors individuals can use to avoid an underpayment penalty.

The first is the 90% current-year safe harbor. During the year, you need to pay at least 90% of what your total tax liability will ultimately be for that year.

And when we say 90%, we’re talking about 90% of your tax, not 90% of your income. That’s an important distinction.

The challenge with that method is that you need a pretty good idea of what your income and tax liability will be for the year. That isn’t always easy depending on your sources of income.

Do you own a business? Is a lot of your income investment-related, where you aren’t sure exactly where things will end up?

The other option is the 100% or 110% prior-year safe harbor, which is often easier to work with.

Generally, you look at the total tax shown on last year’s tax return, which is a known number, and make sure you’ve paid at least the required amount during the current year through withholding or estimated tax payments.

The reason there are both 100% and 110% thresholds is that the requirement increases for higher-income taxpayers.

The higher-income threshold is based on the prior year’s adjusted gross income. That threshold is $150,000 for most taxpayers and $75,000 if you’re married filing separately.

Paul:
And that $150,000 is an income threshold, correct?

Megan:
Correct.

When you’re determining which safe harbor to use, if you have a client whose income fluctuates quite a bit from year to year, I usually look first at the prior-year safe harbor because we know exactly what that number is.

We know the prior-year tax, so we can determine what needs to be paid to meet that threshold.

03:35 | What the Safe Harbor Actually Does

It’s important to remember what a safe harbor does. It protects you from an estimated tax underpayment penalty.

It doesn’t mean you won’t owe additional tax when you file your return.

If your income increases significantly, you could still have a balance due when you file in April. The safe harbor simply means you prepaid enough during the year to avoid the estimated tax penalty.

There’s also a rule under which there generally isn’t an estimated tax penalty if the amount you owe after withholding and credits is less than $1,000.

Paul:
In a broad sense, what do those penalties look like? Are they based on a percentage of the amount that was underpaid, or is it a fixed dollar amount?

Megan:
It’s a percentage calculation. That’s something your accountant can work through with you.

There are clients who look at that penalty somewhat like paying interest to hold on to the money. There could be situations where someone wants to compare the underpayment penalty with what they could earn by keeping those funds available, but you need to look at the actual numbers and have someone help calculate it.

Paul:
That leads into my next question about estimated taxes.

For many of our clients who are salaried W-2 employees, withholding comes directly from their paycheck. But when someone becomes financially independent, owns a business, or starts receiving income from other sources, estimated taxes may become part of the picture.

Do estimated tax payments need to be equal every quarter? Can they be bunched together? What are the rules around the timing?

Megan:
In most cases, you’re going to be making four estimated tax payments during the year.

The standard deadlines are April 15, June 15, September 15, and January 15 of the following year. They don’t line up exactly with traditional calendar quarters.

Under the standard method of calculating estimates, you take the amount you’re required to pay for the year and divide it into four equal installments.

That doesn’t mean every taxpayer has to make four equal payments.

06:46 | Uneven Income and the Annualized Income Method

If someone’s income isn’t earned evenly throughout the year and there’s a large fluctuation, we can use what’s called the annualized income method.

That allows us to calculate the estimated tax requirement based more closely on when the income was actually earned.

That can be particularly helpful for someone who receives a large bonus, sells a large investment, or has another significant source of income later in the year. We don’t necessarily want to treat that income as though it was earned evenly throughout the entire year.

You also have to consider the cost and benefit of doing those additional calculations and potentially working with a CPA on them.

Some clients prefer the consistency of four equal payments, and that may make sense for them. It’s an individual calculation.

07:42 | When the Income Was Received

You also don’t have to make an estimated payment on the exact day you receive the income.

Under the annualized income method, income received during different portions of the year is associated with the applicable estimated payment period.

Withholding vs. Estimated Tax Payments

Another important distinction is the difference between withholding and estimated tax payments.

When we’re making sure enough tax has been paid during the year, federal withholding from W-2 compensation or a retirement distribution is generally treated as though it was paid evenly throughout the year, regardless of when it was actually withheld.

That can be a useful tax planning tool if you need additional withholding later in the year to address a shortfall.

Paul:
So with RMDs, for example, someone could theoretically wait until December, take the required distribution, and do a large amount of withholding at that point. The IRS may treat that withholding as though it occurred throughout the year.

Megan:
Correct.

That can be a useful planning strategy for retirees.

Let’s say you get to the end of the year and realize a retiree hasn’t had enough federal tax withheld or hasn’t made enough estimated payments.

If that person has a traditional IRA, one option could be to take a taxable IRA distribution in December and have a large amount of federal tax withheld from it.

It doesn’t necessarily have to correct a shortfall. Someone who is already taking an RMD could simply plan to handle withholding as part of that distribution.

10:09 | Consider the Tax Cost of the IRA Distribution

One thing to remember is that this strategy doesn’t reduce your tax. We’re using withholding as a tool for meeting the tax prepayment requirements.

We also need to consider the tax consequences of the IRA distribution itself.

With a traditional IRA, the distribution will normally generate taxable income. We don’t necessarily want to create unnecessary taxable income solely to generate withholding.

Tying the strategy to an RMD or another distribution the client already needs to take may make more sense.

You need to look at the full situation: the estimated tax requirements, taxability of the distributions, the person’s age, and the other factors involved.

Paul:
I think you answered this next question, but I want to ask it directly because we have many clients with executive compensation and company stock, whether that’s RSUs, options, or shares they’ve held for several years.

Let’s say we have a W-2 client earning $250,000 a year. In October, they sell stock and generate another $250,000, with $125,000 representing a long-term capital gain.

Does the tax on that gain need to be paid in that quarter, or could they potentially wait until they file the following April?

Megan:
It depends.

First, if someone sells stock at a gain, that gain is taxable in the year the stock is sold.

Then we look at the estimated tax rules to determine whether that gain creates an additional estimated tax requirement.

The timing matters. If you had a stock sale in April or May, for example, we would look at whether it affects the June payment.

12:49 | Start With the Safe Harbor

But we really want to go back to those safe harbor rules first.

Let’s say you have a very large stock gain, but when you look at your withholding and any estimated payments you’ve already made, you’ve paid enough to meet the applicable prior-year safe harbor.

In that case, you may have already paid in enough for estimated tax purposes.

An additional payment may not be required solely because of the stock sale.

You may still owe additional tax when you file your return, but if you’ve met the applicable safe harbor, you may be able to pay that balance at filing without an estimated tax underpayment penalty.

13:59 | How Rising Compensation Can Affect the Calculation

This is something we see with people who have executive compensation, RSUs, and company stock.

If someone’s salary has increased from the prior year, their withholding may also have increased.

In some cases, that withholding from compensation may already be enough to meet the applicable prior-year safe harbor.

But you also need to think about the following year. If you had a large capital gain this year, your prior-year tax number may be higher next year.

That can change the amount required to meet the safe harbor in the subsequent year.

Paul:
That’s a good point about salary increases.

Someone may think, “I’m making more income,” but they’re also withholding more. For the prior-year safe harbor, we’re focused on the tax number rather than simply looking at the increase in income.

Megan:
Correct.

We’re looking at the prior-year tax and determining whether enough has been paid to cover the applicable percentage of that amount.

The 90% current-year safe harbor is still available. It may come into play when income is lower or more predictable and we have a good idea of what the current-year tax liability will be.

But the prior-year safe harbor is often easier to calculate because we’re starting with a known number.

Paul:
One last question.

This is the time of year when we’re doing tax projections and thinking about potential year-end planning opportunities for clients.

Is there one thing you’d tell someone who is thinking about doing a projection? Is there information they can provide that makes the process more useful?

Megan:
My advice would be to start thinking about year-end planning in the fall.

Here in New York, when the leaves start changing, that’s a good reminder.

A lot of clients wait until December to have these conversations, and by then there’s less time to provide proactive guidance or consider different strategies.

17:23 | What to Bring to a Fall Tax Planning Meeting

I recommend getting into the habit of having a fall planning meeting with your CPA.

Bring things like your current-year pay stub showing year-to-date income and withholding, along with year-to-date investment information.

You can look at where things stand at the end of September, with three months remaining in the year, and ask: Am I on track? Have I paid enough? Do I need to pay more?

Maybe the answer is that you don’t need to make an additional payment.

Then you normally have another touchpoint with your CPA during tax season. At that point, your tax return gives you the prior-year tax number that can be used when planning estimated payments for the coming year.

18:13 | Keep Your CPA Updated When Something Changes

Between those meetings, reach out if something unexpected happens.

Maybe you receive a large bonus that wasn’t anticipated, sell stock, or begin taking distributions from a retirement account.

Proactive communication gives your CPA the information needed to help plan appropriately.

And in some cases, adequate withholding or your prior-year numbers may mean you don’t need to send in a large payment immediately.

Being able to coordinate with a CPA and someone in the financial planning world can be very helpful.

Paul:
My takeaway from that is: when the leaves turn, not when it starts snowing in upstate New York.

Megan:
That’s right.

Paul:
Because it can snow early here, too.

Megan, thank you so much for your time. This was fantastic and really helpful. We appreciate you joining us.

Megan:
Absolutely. Thank you.

Paul:
All right.

 

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 463-8400, Ithaca, NY office at (607) 438-2914, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

Who We Help: When Career Success Brings Financial Complexity

You’ve spent years becoming an expert in your field. That doesn’t leave much time to become an expert in investments, taxes, insurance, and estate planning, too. See how an outside perspective can help answer the financial questions that have been sitting on your list.

Topics Discussed:

  • Balancing financial planning with your career
  • Sorting out complex financial accounts
  • Knowing when you need expertise
  • Questioning whether anything is being missed
  • Getting a fresh financial perspective

Transcript:

You’ve built something real, a family, a career, maybe even your own business. People come to you for answers. But why is money the one area where you still feel like you’re guessing?

You’ve got a 401(k), maybe an old rollover that you’ve been hesitant to figure out what to do with, equity compensation that nobody’s ever really explained to you how it works and the implications. That’s common, even for people who are experts in their own field.

Being busy in one career doesn’t leave you much room to become an expert in investments and tax and insurance and in estate planning. And it’s not just going to happen. You’re not just going to pick up these skills by accident. Nor are you going to have time to become an expert in all these areas as well.

So the question sits usually unspoken. Do you have the right person looking out for you, or are you just kind of guessing on that as well too? Is there something that an outside expert could catch in a few minutes that’s been sitting out there for years?

Whether actually something’s being missed or not, that’s an answerable question. A fresh set of eyes trained on your situation, whether that means reviewing what you already have or helping you build something new, tends to surface the answer really fast.

Sometimes it confirms you’re in good shape. Sometimes it catches something that could compound into something much bigger over the years.

If you’ve built a lot and you want a straight answer on whether or not it’s actually working, reach out. We’re happy to talk.

 

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

Why Private Equity Might Not Be the Best Investment for You

Private equity has been viewed as one of the most sought-after investments in finance. Pension funds, Ivy League endowments, and some of the world’s wealthiest investors have poured billions into it. If these sophisticated investors all want private equity, shouldn’t you?

The answer depends on something most discussions about private equity overlook.

How Private Equity Earned Its Reputation

Investing in private equity simply means investing in companies that aren’t publicly traded.

Instead of buying shares of companies on the stock market, private equity funds invest directly in privately owned businesses, often holding those investments for years before eventually selling them or taking them public.

There are good reasons institutions have invested in private equity for decades.

Private equity has historically offered the potential for attractive long-term returns, access to companies before they reach the public markets, and diversification beyond publicly traded stocks and bonds. Large institutions also have something many individual investors don’t: the ability to commit capital for long periods without worrying about when they’ll need the money back.

Those characteristics helped private equity earn its reputation. But they don’t eliminate the tradeoffs.

More Access Doesn’t Change the Investment

Private equity itself hasn’t fundamentally changed. What’s changed is who can invest.

Private equity firms are increasingly offering products designed for affluent individual investors, and platforms have made those investments more accessible than ever before.

More access gives investors more choices, but it doesn’t change how private equity works. The same tradeoffs that institutions have always understood still exist today.

Looking Beyond the Reputation

One of the biggest differences between private equity and traditional investments isn’t simply the potential return. It’s how the investments are structured.

Higher Fees and More Complex Valuations

Private equity generally costs more than traditional investing. Management fees are common, and many funds also charge performance fees when investments increase in value.

The important part isn’t just how much you’re paying. It’s when you’re paying it.

With publicly traded investments, everyone can see the market price every day. When an investment is sold, everyone knows exactly how much it gained or lost.

Private companies work differently. Because they aren’t publicly traded, their values are estimated periodically until the business is eventually sold. Some private equity funds use those estimated values to calculate performance fees before the investment is actually sold and the gain is known. If those estimates later prove too optimistic, investors may have already paid performance fees on gains that never ultimately materialized.

That doesn’t mean every private equity fund works this way. But it does illustrate why private equity often requires investors to look beyond reported returns and understand how the investment is structured.

Less Liquidity

Another important difference is liquidity.

Public stocks can generally be bought or sold any day the market is open.

Private equity works differently. Many investments limit withdrawals, require investors to commit money for years, or only allow redemptions during certain windows. That may fit well for institutions investing with decades-long time horizons, but for individual investors, especially those approaching retirement or expecting to use their investments for income, flexibility may be much more valuable.

The Real Lesson

Private equity didn’t earn its reputation because it was exclusive. It earned its reputation because it fit the needs of the investors who were using it.

Pension funds, endowments, and other institutions often invest with time horizons measured in decades. They have professional investment staff, extensive resources for evaluating managers, and the ability to leave money invested for long periods without needing immediate access.

Many individual investors have different priorities.

You may value lower costs, greater transparency, easier access to your money, or the simplicity of broadly diversified public investments.

That doesn’t make one approach better than the other; it simply means the investment should fit the investor.

Final Thoughts

Private equity may have a place in some portfolios, and its growing availability gives more investors the opportunity to consider it. But exclusivity was never what made private equity valuable.

What matters is whether it improves your financial plan.

If it helps accomplish something your current portfolio can’t, it may deserve consideration. If a broadly diversified, lower-cost, and more liquid portfolio already meets your needs, adding private equity simply because it’s now available may not improve your outcome.

Before committing capital to any private equity investment, it’s worth having a conversation about how it fits into your overall financial plan. If you’re considering private equity or have questions about an opportunity you’ve been presented with, I’d be happy to discuss whether it makes sense for your specific situation.

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.

What the Growing Federal Deficit Could Mean for Your Retirement

Concerns about the federal deficit have many people nearing retirement wondering how it might affect their financial future. Could taxes rise? Will inflation remain elevated? Could Social Security change?

Those are important questions. But the better question is this: would your retirement plan still work if any of those things happened?

No one knows exactly how Congress will address the country’s fiscal challenges, but understanding the possibilities can help you build a retirement plan that’s prepared for more than one outcome.

How Large Is the Federal Deficit?

According to the Congressional Budget Office, total federal spending in 2026 is projected at $7.4 trillion against revenues of roughly $5.6 trillion — a deficit of $1.8 trillion, or 23.3% above what the government collects. To put that in perspective, the federal government is borrowing one dollar for every four it spends. For retirees, those numbers matter because they influence many of the assumptions that go into a retirement plan, including future tax policy, interest rates, inflation, and Social Security.

According to J.P. Morgan’s “Five Scenarios for the Federal Debt,” federal debt held by the public is projected to rise from roughly 100% of GDP today to 120% by 2036 under the CBO’s baseline and potentially as high as 127.7% if current tax breaks are made permanent and tariff revenues underperform projections.

The Federal Government’s Only Options and Why the Likely Path Matters to You

At its core, the math isn’t complicated. When government spending exceeds income, there are only four ways to close the gap: raise taxes, reduce benefits for current recipients, reduce benefits for future recipients, or borrow the difference.

In practice, not all options are equally likely. Historically, Congress has been reluctant to reduce benefits for current retirees, and raising taxes has also proven politically difficult. Millions of Americans depend on Social Security and Medicare, making major changes challenging regardless of which party is in power. 

That has left borrowing as the path lawmakers usually rely on. But borrowing doesn’t resolve the underlying imbalance and can make the problem worse. As debt levels rise, upward pressure on interest rates, borrowing costs, and inflation follows. J.P. Morgan estimates that rising debt could push long-term Treasury yields up by nearly 90 basis points over the next decade, increasing borrowing costs and creating challenges for both bond portfolios and the broader economy.

None of this tells us exactly what will happen next, but it does explain why retirement plans should account for more than one possible outcome.

The One Number That Touches Your Plan: Social Security

For most retirees, the federal deficit matters only if it eventually affects the income they rely on. That’s where Social Security enters the conversation.

According to the most recent Social Security Trustees’ Report, the Old-Age and Survivors Insurance (OASI) Trust Fund is projected to be depleted in 2032.

The word you’ll hear attached to these projections is insolvency, which can sound alarming if you don’t know what it means in this context. It does not mean Social Security disappears or that checks stop. Instead, it indicates that the trust fund reserves run out, and the program pays benefits from ongoing payroll tax revenue alone at reduced levels, unless Congress acts.

If Congress takes no action before then, incoming payroll tax revenue would still fund a substantial portion of promised benefits, but not all of them. The Trustees estimate that benefits would need to be reduced by approximately 22% across the board to match available revenue.

How We Account for This in Retirement Planning

At LRA, we don’t believe successful retirement planning depends on predicting what Congress will do. We believe in building plans with enough resiliency to withstand a range of outcomes.

Our view is straightforward. Continued borrowing appears more likely than dramatic benefit cuts for current retirees, although no one knows exactly how lawmakers will proceed. Because borrowing can influence inflation, interest rates, and long-term government finances, we believe it’s prudent to account for those possibilities.

That leads us to build plans that remain resilient even if future Social Security benefits are lower than today’s projections.

Given the Trustees’ projection that benefits could be reduced by 22% if the trust fund were depleted without legislative intervention, we have begun incorporating a similar reduction into many client retirement projections. In other words, we often build retirement plans assuming clients may receive less than their currently projected Social Security benefit.

We hope those reductions never occur, but would rather help clients prepare for a more challenging scenario and be pleasantly surprised than build a plan that depends on the most optimistic outcome. If benefits are fully preserved, that creates additional flexibility. If they aren’t, the plan has already accounted for the difference. That is how we build resilience.

Focus on What You Can Control

No one can say with certainty how the federal deficit, national debt, or Social Security funding challenges will ultimately be addressed. What matters is understanding how different outcomes could affect your retirement plan and ensuring you are prepared for them.

Just as an individual can improve their finances only by earning more or spending less, the government faces the same arithmetic. The longer those decisions are deferred, the fewer options remain. A well-designed retirement plan should be flexible enough to adapt to changing tax laws, benefit levels, and economic realities.

If your current retirement projections assume full Social Security benefits and haven’t been reviewed recently, give us a call. We can’t predict the future, but we can build a retirement plan that aims to hold up across a wide range of possible futures.

Sources: 

  1. https://www.cbo.gov/publication/61882
  2. https://am.jpmorgan.com/us/en/asset-management/adv/insights/market-insights/guide-to-the-markets/
  3. https://am.jpmorgan.com/us/en/asset-management/adv/insights/market-insights/market-updates/notes-on-the-week-ahead/five-scenarios-for-the-federal-debt/
  4. https://am.jpmorgan.com/us/en/asset-management/adv/insights/market-insights/market-updates/notes-on-the-week-ahead/five-scenarios-for-the-federal-debt/
  5. https://www.ssa.gov/OACT/TR/2026/

 

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.

More Than Numbers: Why Paul Does This Work

What drives someone to spend their career helping other people with their money? In this video, Paul Sydlansky, CFP®, shares why he became a financial planner and what keeps him doing this work. It’s a closer look at the person behind Lake Road Advisors and what he hopes every client feels.

Topics Discussed:

  • Numbers are just a tool
  • A young couple’s year-long planning process
  • Helping clients through life’s changes
  • Being the first call when decisions get hard
  • Having someone genuinely in your corner

Transcript:

For as long as I can remember, I’ve always liked helping people and at the same time I’ve enjoyed numbers and investing. That’s why becoming a financial planner has been such a natural fit for me. The irony is that the longer I’ve been a planner, the more I realize that the numbers are just a tool. What we’re providing for our clients is security and a plan to help them live the life they want now and in the future.

Early in my career, I worked with a young couple who was really nervous about starting a family, not emotionally but financially. We took this couple through a year-long planning process where we reviewed everything. Their balance sheet, their investments, their cashflow, their insurance, their estate plan and after a full year they finally had the confidence to move forward. Today they have two young children and what stuck out with me through that experience is that this is so much more than investing and numbers.

It’s about helping people feel comfortable to live the life they want and build the life they want for the future. What I love most about being a financial planner is helping clients as life happens, whether that’s good or bad, whether maybe there’s a loss in the family, there’s a new job opportunity or a job loss, a new business opportunity, whatever it may be. Helping people and being that first call, being that resource and that honest opinion when they want to know, “Is this possible? Does this make sense? Are we thinking about this right?” is extremely rewarding.

What I want people to know who work with Lake Road Advisors is simple. It’s that we have their back when times are good and especially when there’s indecision about what the future holds and they’re not sure of which way to turn next. That feeling of having somebody in your corner who knows you, understands what’s important to you and can give you honest feedback and help you plan for the future and genuinely cares about where you’re headed is extremely important to us.

That’s why we’re here.

 

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

If You’re Hacked, Don’t Count on Your Bank to Make You Whole

Most people I talk to assume their bank or brokerage will make them whole if something goes wrong, like a hacked account, a fraudulent wire transfer, or a scam that seemed legitimate. That’s what I used to think, too.

When I left Wall Street to start my financial planning firm in 2016, I never expected cybercrime to become a recurring theme in client conversations. But over the years, I’ve sat with too many people dealing with the fallout of being hacked—lost account access, money wired to the wrong place, and months spent trying to recover funds that may never come back.

You don’t hear about it often because when it happens, people are embarrassed and feel like they should have known better. It’s not exactly something that they share on social media or at the family get-together. 

But given the right circumstances, almost anyone can become a target. Cybercriminals study human behavior for a living. They exploit trust, urgency, and routine. And if you’ve spent years growing your wealth, you’re a more attractive target than you realize. 

The numbers back this up. The IMF reports more than 20,000 cyber incidents in the financial sector over the past two decades. Among family offices worldwide, nearly half have experienced a cyberattack in the last one to two years. Among those managing over $1 billion, that figure climbed to 62%.

The lesson here isn’t that only the ultra-wealthy are at risk. Anyone with savings, investment accounts, or retirement assets has what criminals are looking for.

That’s why cyber hygiene belongs in every financial plan, right alongside insurance, estate planning, and tax strategy. It’s not just an IT problem, but a financial planning issue.

Consider Their Stories Your Wake-Up Call

An industry expert, Mark Hurley, runs a company focused on digital privacy and protection for families. He recently shared a few stories that got my attention.

One family had spent years planning to buy an apartment in Paris. During a trip, one family member used a public charging station and unknowingly compromised a device. Criminals got into their email, monitored their conversations, and learned everything about the upcoming purchase.

When the family arrived in Paris, the criminals locked them out of their email and sent a wire request to their advisor for $2 million. The advisor did everything right—scheduled a verification call and ran through the proper steps. But by then, the criminals had cloned voices using AI, gathered personal details from social media, and redirected the family’s cell communications.

After a lengthy process, the advisor had every reason to believe they were talking to their client.

Unfortunately, they weren’t; they were talking to hackers, and their client’s money was stolen. 

Mark also described a researcher who lost $400,000 from a bank account after accessing financial information on public Wi-Fi while traveling. In another situation, a family lost $360,000 from a checking account through fraudulent transactions.

In both cases, the victims assumed the bank would make them whole, but it didn’t work out that way.

I’m not telling these stories to scare you. These stories are proof points. They show how cybercrime has evolved well beyond phishing emails into sophisticated operations that combine AI, psychology, patience, and careful planning.

The common thread is an assumption that the safeguards around their money were stronger than they actually were. These people weren’t careless; they were simply unaware.

5 Habits That Can Help Protect Your Wealth

You don’t need a computer science degree to protect yourself, but you do need to be diligent with good cyber hygiene habits. 

Mark compares cyber hygiene to locking your front door. A lock won’t stop every criminal, but it makes you a more difficult and much less appealing target. When it comes to cyberattacks on your bank accounts, following these five cyber hygiene habits can be all that’s needed for a hacker to choose to go after someone else. 

1. Use a password manager and unique passwords. 

If you’re using the same password across multiple accounts, one breach can compromise everything. A password manager generates and stores a unique password for every account and will even notify you if you’ve reused a password. Your bank, email, cell phone provider, and investment accounts should each have a different password. If a criminal gets into one, they aren’t able to use the same password to get into the others.

2. Secure your devices. 

Your phone contains access to most of your financial life. Enable automatic updates. Use a strong passcode, not a four-digit PIN. Review your privacy settings. Think of your phone as a digital wallet. You wouldn’t leave your wallet open and unattended on a restaurant table.

3. Use a VPN on public Wi-Fi. 

Airports, hotels, coffee shops, and other popular public networks can expose your information to anyone paying attention. A VPN encrypts your internet traffic, making it much harder for someone else on the network to see what you’re doing. If you’re checking financial accounts while away from home, this is a simple, inexpensive layer of protection.

4. Create a dedicated recovery email. 

Most accounts let you reset a password through email. Set up a separate email address used only for account recovery on your most important accounts. If your everyday email is compromised, this one step can block criminals from reaching your financial accounts.

5. Protect the accounts connected to your money. 

Criminals often don’t start with your bank. They start with your email, social media, or cell phone account, then use that access to work their way in. Enable multi-factor authentication wherever it’s available. Add a security PIN to your cell phone account. These steps make it significantly harder to intercept security codes or impersonate you.

Cyber Hygiene Is Part of the Plan

Most people think of financial planning as investments, taxes, insurance, and estate documents. I’d add cyber hygiene to that list. I like to think of it as wealth protection. It’s not as complicated as it seems, though it does take some effort to set all of this up properly. I think it’s worth it to help safeguard what you’ve spent decades building.

That’s why we’ve partnered with Digital Privacy and Protection (DPP). Protecting what you’ve built doesn’t stop at managing assets—it includes understanding what can threaten them.

If you’d like to go deeper, I’d encourage you to watch our webinar, “The $2 Million Cyberattack That Started at an Airport Charging Station.” It takes a closer look at how modern cybercrime actually works, and what you can do to make yourself a harder target. 

Sources:

  1. https://www.elibrary.imf.org/view/journals/001/2026/062/article-A001-en.xml
  2. https://www.familywealthreport.com/article.php/Cyber-Attacks-Target-The-World%27s-Family-Offices-%E2%80%93-Study?id=204019

 

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.

Suddenly in Charge of the Money? Here’s Where to Start

In a lot of marriages, one person ends up running the money. It’s rarely a formal decision. One partner drifts toward the accounts, the passwords, the whole long-term plan, and over the years, it becomes their lane. That setup can work well for decades. But the part couples rarely get to is making sure both people know where everything lives, so that if one partner ever has to manage alone, the path is already clear.

Fortunately, that clarity is something you can create, and if you’re reading this after a loss, you can build it now. Plenty of people have stepped into this role during a profoundly hard time and come through it with their footing restored. This piece is about where to start and what you can safely leave for later.

Start With Stability

When a client comes to me after suddenly becoming the one in charge of the money, the first thing I tell them is that nothing needs to be solved today. The only goal right now is stability.

I once began working with a successful PR executive a few years after she lost her husband unexpectedly. She was the family’s breadwinner and a respected creative leader, but money at home had always been his domain. He kept much of it in his head, with logins scattered across his devices. Our first job together was simple: get her access to the accounts, locate the key documents, and confirm the bills were covered.

Another client, a corporate attorney, became a widower with two teenagers after his wife’s brief illness. She’d been an accountant before staying home with the kids, and she ran the household finances for years. He felt enormous pressure to figure it all out fast. We did the opposite and slowed down, focusing on cash flow, the next round of expenses, and the handful of people he’d need to call.

In both cases, the priorities were the same: make sure you can reach cash, keep the essential bills current, and gather the important documents and contacts. That’s enough for now. You’re looking for just enough clarity to take the next steps, one at a time.

Build a Clear Picture

Once the immediate situation is steady, you can start assembling the full view. Now that the urgent items are covered, you can turn your attention to the full picture: what you actually have, and what still needs a closer look. Clarity here is what makes everything else feel manageable.

Find Where Everything Is

For some people, this is straightforward: labeled folders, maybe a spreadsheet or two. For others, it’s more of a treasure hunt. Start by pulling together account statements (bank, investment, retirement), any logins or password manager access, and both physical and digital files.

Review the Estate Plan

Next, see what’s already in place: a will, any trusts, and the titling on your accounts. Identify who’s named as executor or trustee, how assets are titled, and what instructions were left. If there is no will or trust, that’s workable too, and it becomes a priority for the next phase, ideally with professional guidance.

Take Inventory of Assets and Liabilities

List what you own: cash accounts, investment accounts, retirement accounts, real estate. I tell clients the hope is that you find more than you expect, and being thorough is how that happens. Old 401(k)s from past jobs are a common and happy surprise. Then list what’s owed, starting with mortgage and credit card statements and any loans, and review recent transactions for recurring payments. If an unfamiliar debt turns up, try not to take it personally. Sometimes one partner carried a financial worry privately to spare the other. You may not be responsible for every debt you find, though there are exceptions for joint accounts, co-signers, and community property states. Either way, the estate itself may need to settle certain debts before assets can be passed on.  

Review Insurance

Insurance can bring real relief. A retired nurse I worked with braced for financial strain after her husband died unexpectedly in his late fifties, then found his life insurance was far more substantial than she’d realized. It gave her room to make calm, deliberate choices. Check the life insurance policies and how to file a claim, any health coverage changes, and your home and auto policies.

Address Taxes

Taxes are the one item that can’t wait. A final return will need to be filed, and your filing status will likely change going forward. This is a good place to lean on a tax professional, who can make the process smoother and help you catch anything easy to miss.

What Can Wait

Grief has a way of creating urgency. As the early fog lifts, many people feel a strong pull to reorganize everything at once: sell the house, simplify the accounts, redo the investments. That impulse is natural. The bigger decisions, though, like restructuring a portfolio or selling property, rarely need to happen right away. What does deserve prompt attention is the procedural work, such as updating beneficiaries, consolidating accounts, and transferring ownership correctly.

Giving yourself time before making those bigger decisions lets you build a plan that fits this chapter of your life with your new income, timeline, and priorities in view.

You Don’t Have to Do This Alone

Managing grief is hard enough on its own. Doing it while making big financial decisions is something no one should have to face without support. As a CFP® professional, I help clients bring order to complex financial situations and steer around the costly missteps that are easy to make when emotions run high.

At LRA, we want both partners to feel informed and prepared long before a crisis. That starts with a shared understanding of where the money is, how it’s handled, and who to call when questions arise. To help make that easier, we put together the SOS Folder Checklist. It’s designed to help your family gather and store the most essential information in one easy-to-find place—everything from account access to key documents and personal wishes. You can download it here.

Whether you’re facing a loss now or want both partners ready for what’s ahead, we’re glad to help. Reach out and schedule a free consultation with us today to get started.

Sources:

  1. https://www.bankrate.com/personal-finance/debt/debt-responsibility-after-spouse-death/ 

 

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.

The Story Behind Lake Road Advisors

Before he founded Lake Road Advisors, Paul Sydlansky, CFP®, spent 13 years at Morgan Stanley. That experience taught him a lot, including what was missing from the way most firms approach financial planning. In this video, he shares the story behind LRA, including what the name means, what he wanted to do differently, and where the firm is headed after 10 years of growth.

Topics Discussed:

  • Why Paul left Morgan Stanley after 13 years
  • What the firm’s name actually means
  • How working inside a big firm shaped LRA’s approach
  • Building a firm focused on planning, not products
  • Ten years of growth with the same mission

Transcript:

I started my career working at Morgan Stanley back in 1999. After 13 years working in institutional equities, by most measures, my career was headed in the right direction. However, my life was changing. I had three kids under three years old, and while financially we were doing well, I was not on the path that I wanted to be. Something needed to change. 

My in- laws introduced me to a cottage on East Lake Road along Keuka Lake in the Finger Lakes region of upstate New York. For me, it was a place that for the first time in a long time, I was able to take a step back and actually be intentional and think about my future rather than just getting caught up in the rat race. The name Lake Road Advisors represents that planning, that intention that we all need to take when we think about our future.

It’s about understanding where we want to be and setting a course to get there. After spending my entire career in a large investment bank, I realized what it was built to do and what it wasn’t. For me, the idea of Lake Road Advisors was to help people figure out a plan, not focus just on investments, but the entire picture, to be a guide and help them get wherever they want to go. After spending the first part of my career in a large investment bank, I knew what it was built to do, who it was built to help, and who it wasn’t. For me, Lake Road Advisors was built not just to talk about investments, but more importantly, your plan, how you’re getting there, how you’re staying on track. It was built to be a partner with our clients to help them achieve those goals, whatever they may be.

We are extremely fortunate to have just crossed our 10-year anniversary. Our clients have grown, our firm has grown, but one thing has remained the same. We are here to help you build a path, be an accountability partner, and ultimately achieve your goals. The mission is simple, and it remains the same today.

 

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

How to Help Your Aging Parents Protect Their Finances Without Overstepping

Your parents have always been sharp. From building a successful career to managing a household budget, they never missed a beat. They managed investments, handled negotiations, and kept every financial detail in order.

Then one day, your mom can’t remember the password she’s used for 20 years. Or your dad’s credit card declines because he forgot to pay the bill.  

It might be nothing. Or it might be the first signal that something has changed.

When it comes to cognitive decline, financial warning signs often appear before a medical diagnosis. And by the time there’s a crisis, the damage can be expensive, emotionally and financially.

Early Financial Warning Signs: What Often Shows Up First

Cognitive decline is usually gradual. In high-functioning adults, it can be subtle. In fact, financial changes are often one of the earliest signs that something isn’t quite right.

That doesn’t mean every late bill or forgotten password signals dementia. Normal aging can include slower processing or occasional word-finding issues. But significant changes in financial judgment, especially when they’re clearly different from your parents’ baseline, deserve attention.

Picture this: Your father, who spent thirty years building a conservative portfolio, suddenly wants to invest in cryptocurrency he heard about on YouTube. Or your mother, meticulous about thank-you notes and thoughtful giving, writes a $10,000 check to a charity she’s never mentioned before.

These aren’t isolated incidents. They’re pattern breaks.

The slip-ups may seem minor at first. The mail may start piling up on the kitchen counter. A utility bill goes unpaid or gets paid twice in the same month. Your parents, who once managed multiple accounts with ease, now seem confused about which credit card they used or what their retirement account is worth. Something that used to be a routine transaction that took minutes now triggers phone calls and visible frustration.

Then you may start to notice subtle changes in judgment and influence. Your dad mentions an unfamiliar new neighbor who’s been giving him investment tips. Your mom gets defensive when you ask about her recent purchase. Tension is creeping into conversations about money that wasn’t there before, and they’ve become reluctant to share information..

Missed payments, rising delinquencies, and declining credit scores can occur years before a formal diagnosis. By the time families realize something’s wrong, damage has often been done—both financial and relational.

Panic won’t help. Paying attention will.

You shouldn’t be waiting for a crisis or dismiss the changes as “just getting older.” When financial habits change in ways that feel out of character, and your parents’ behavior no longer matches the competent, careful people you’ve always known, it’s time to take action. 

Structure, support, and early intervention protect both their assets and their dignity.

The Biggest Risk: Elder Financial Fraud

As cognitive abilities shift, even subtly, vulnerability to fraud increases. Declining executive function makes it harder to evaluate risk, resist pressure, or detect manipulation. And, unfortunately, scammers are skilled at spotting small lapses in judgment. The guardrails that once felt automatic start to weaken, and that’s when the wolves appear.

Older adults are targeted by all kinds of schemes, but scammers use variations of the same playbook. Watch for these: 

  • A government impersonator scam in which someone poses as Medicare or the IRS and demands immediate payment. 
  • Fake prize notifications that require “fees” to collect winnings. 
  • Tech support calls that claim a computer virus has compromised accounts. 
  • High-pressure investment pitches, designed to appear credible and legitimate. 
  • Charity solicitations that tug at the heart and empty the wallet. 
  • The particularly sordid “grandparent” emergency features a panicked voice pretending to be a grandchild saying they’ve been arrested and need money wired immediately.

The tactics are always the same: urgency, secrecy, fear, and pressure to act now.

I always remind families that this can happen to anyone. Intelligent, accomplished people fall victim every day. Your parents’ success doesn’t inoculate them. In fact, it often makes them bigger targets.

On a positive note, simple protections go a long way. Make sure your parents know to never share Social Security numbers, passwords, or account details over the phone, email, or text; no legitimate organization asks for these. They should be using multifactor authentication, keep devices updated, and never wire money or purchase gift cards at someone else’s request, no matter how urgent it sounds. Scammers rely on panic. 

Your best moves are to monitor their statements regularly and keep lines of communication open. Your involvement doesn’t eliminate risk, but it dramatically lowers it. The goal isn’t to strip your parents of autonomy. It’s to build safeguards that protect them without diminishing their dignity.

Build Financial Guardrails Before There’s a Problem

The most effective protection starts while your parents are still fully capable of participating in the decisions, not when there’s a crisis.

One simple safeguard is to designate a trusted contact for investment accounts. This doesn’t give anyone control—it simply allows an advisor to reach out to a named person if there are concerns about unusual activity or well-being. Regulators now view this as a best practice.

From there, take inventory. Accounts, income sources, recurring bills, insurance policies, and estate documents. Many older adults accumulate accounts over the course of decades. Consolidating and simplifying makes oversight easier and reduces the chance that something slips through the cracks. Automatic bill pay and account alerts help too, creating structure without removing independence.

Legal preparation is equally important. A durable financial power of attorney must be established while your parent has full capacity. Waiting too long can mean court involvement, higher costs, and unnecessary stress. Once the documents are in place, financial institutions and agencies such as Social Security should have copies on file.

As responsibilities gradually shift, document conversations and keep siblings informed. Transparency protects relationships as much as assets.

You don’t want to take over overnight, but build a framework early that preserves dignity, reduces risk, and makes any future transition calm instead of chaotic.

Protect Your Finances While Supporting Your Parents

As life expectancy rises, many of my clients find themselves managing two financial responsibilities at once. Couples are building their own future while helping aging parents navigate theirs. With one in five Americans now over 65, many living into their 90s, and long-term care costs climbing steadily, the pressure is both financial and emotional.

A comprehensive plan starts with clarity around your parents’ resources. What assets are liquid? What accounts carry tax consequences? Which income sources are reliable? Smart sequencing matters: use accessible, low-tax assets first while preserving retirement accounts for later care stages.

Second, open communication is essential. Discuss preferred care, living arrangements, and budget realities early. If one sibling provides hands-on support, address compensation or inheritance expectations upfront to avoid future conflict.

And as a reminder, it’s important to protect your own financial plan. Supporting your parents by paying medical bills or bailing them out financially when they’re faced with an unexpected problem, without a plan to do so, can create long-term strain. Consider offering measured, sustainable assistance instead that fits your financial picture. And if you want to help anyway or it can’t be avoided, understanding gift limits and coordinating with a CPA can make your assistance more tax-efficient.

At LRA, we don’t isolate generations. We look at the full picture—parents, children, taxes, care, estate planning, and your goals. Done thoughtfully, you can support those who raised you without compromising your own family’s future.

Where to Start

Protecting your parents’ finances requires thoughtful structure before stress forces rushed decisions. When you recognize early warning signs, build guardrails, and align both generations under one coordinated plan, you reduce risk and preserve dignity—for them and for you.

Many of my clients are doing this work in both directions at once. They’re clarifying their own retirement timeline while stepping in to protect the people who raised them. They have difficult conversations while everyone can still participate. They create frameworks that provide security without stripping independence. They protect the people who raised them while safeguarding the future they’re building for their own families.

If you’re starting to notice subtle changes or simply want to prepare proactively, book a consultation. Together, we can build a strategy that honors your parents’ autonomy, protects their assets, and keeps your own financial plan intact.

 

Lake Road Advisors (LRA) is a virtual wealth management firm headquartered in Corning, NY, with offices in Ithaca, NY, and Vancouver, WA. Founded by Paul Sydlansky, CFP®, in 2016, it serves successful couples planning their next chapter—whether that’s retirement, part-time work, or a less demanding second act. Paul has worked in the financial services industry for 25+ years. Prior to founding Lake Road Advisors, he worked at Morgan Stanley in Manhattan for 13 years, where he was a senior-level manager within the Institutional Equities Department. In 2018, he was named to Investopedia’s Top 100 Financial Advisors list. Paul received a Bachelor’s degree in Economics from Marist College and holds an MBA from New York University Leonard N. Stern School of Business. Paul is a CERTIFIED FINANCIAL PLANNER® and a member of the National Association of Personal Financial Advisors (NAPFA) and the XY Planning Network. They can be reached by phone at the Corning, NY office at (607) 438-2914, Ithaca, NY office at (607) 463-8400, or Vancouver, WA office at (607) 292-2172 or at the firm’s website at https://www.lakeroadadvisors.com/ 

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.