The Closer You Get to Retirement, the More Expensive Mistakes Become

Retirement planning becomes more complex as income, taxes, Social Security, healthcare, and withdrawals begin working together. Learn the signs that professional coordination may help reduce costly mistakes.

Many people successfully manage their finances for decades while saving for retirement. But as retirement approaches, decisions around taxes, Social Security, healthcare, withdrawals, and income planning become more interconnected and harder to reverse. The question is not whether someone is smart enough to manage retirement alone. The question is whether the complexity of retirement planning has reached the point where professional coordination could improve outcomes. At Greenbush Financial Group, we often find that retirees seek guidance not because they lack discipline, but because retirement introduces decisions that can affect income, taxes, and financial confidence for decades.

Retirement Planning Changes Once Paychecks Stop

Many successful professionals and disciplined investors manage their finances perfectly well during their working years.

Saving for retirement is often relatively straightforward:

  • Earn income

  • Contribute to retirement accounts

  • Invest consistently

  • Avoid major mistakes

Retirement changes the equation.

Now the questions become:

  • Which accounts should income come from first?

  • When should Social Security begin?

  • How do Roth conversions fit into the plan?

  • How much cash should be kept available?

  • How do withdrawals affect taxes?

  • What happens if markets decline early in retirement?

  • Would a surviving spouse still be financially secure?

This is why many people who comfortably handled accumulation planning begin questioning whether retirement distribution planning requires additional coordination.

Hiring a financial advisor is not about intelligence.

It is about complexity.

Retirement Planning Is More Than Investment Management

One of the biggest misconceptions about financial advisors is that their role is simply picking investments.

For retirees and pre-retirees, the larger value often comes from coordinating multiple moving parts together.

Retirement Planning Often Involves:

  • Income withdrawal sequencing

  • Social Security timing

  • Roth conversion analysis

  • Medicare IRMAA planning

  • Tax-efficient withdrawals

  • Required Minimum Distribution (RMD) planning

  • Survivor planning

  • Estate coordination

  • Long-term care considerations

  • Investment allocation

  • Sequence-of-returns risk management

As retirement approaches, these decisions begin affecting one another.

That complexity is often what pushes people toward seeking professional guidance.

Some People May Not Need a Financial Advisor

This is important to acknowledge honestly.

Not every retiree needs ongoing financial advisory services.

Some households may have:

  • Simple financial situations

  • Strong financial knowledge

  • Minimal tax complexity

  • Pension income covering most expenses

  • Small withdrawal needs

  • Comfort managing investments independently

For disciplined retirees with straightforward situations, DIY retirement planning may work perfectly well.

The question is not:
“Can someone manage their own finances?”

The better question is:
“Has retirement planning become complex enough that coordination mistakes could become expensive?”

Why Retirement Mistakes Become More Expensive Later

During working years, mistakes are often easier to recover from because future earnings continue.

Retirement changes that dynamic.

Once paychecks stop:

  • Tax mistakes can compound

  • Poor withdrawal timing becomes harder to reverse

  • Market declines may affect withdrawals

  • Social Security decisions become permanent

  • Healthcare costs become more important

  • Sequence risk matters more

The closer someone gets to retirement, the fewer opportunities there may be to correct major planning errors later.

7 Signs Retirement Planning May Be Becoming Too Complex to Handle Alone

1. You’re Unsure How to Create Retirement Income

Many retirees know how to save.

Far fewer know how to create sustainable retirement income.

Questions often include:

  • Which account should I withdraw from first?

  • How much cash should I keep?

  • Should I delay Social Security?

  • How do taxes affect withdrawals?

If retirement income feels improvised instead of coordinated, that may indicate planning complexity has increased.

2. You Have Large IRA Balances

Large pre-tax retirement accounts can create future tax issues many retirees underestimate.

Potential concerns include:

  • Large RMDs later

  • Higher Medicare premiums

  • Widow’s tax trap

  • Increased Social Security taxation

This is where Roth conversion planning often becomes important.

The challenge is not just reducing taxes this year.

It is coordinating taxes across decades.

3. One Spouse Handles Most Financial Decisions

This is extremely common.

Often one spouse manages:

  • Investments

  • Taxes

  • Bills

  • Account access

  • Financial planning

That system may work well until a health issue or death creates a sudden transition.

Many couples seek financial guidance because they want:

  • Shared understanding

  • Organized planning

  • Continuity for the surviving spouse

Good retirement planning should work for both spouses, not just the financially engaged one.

4. You’re Concerned About Market Volatility Near Retirement

Market declines feel different once retirement approaches.

During working years, paychecks continue.

Near retirement, people often worry:

  • “What happens if the market drops right after I retire?”

  • “How much risk should I still take?”

  • “Should I move more to cash?”

These concerns are reasonable.

A strong retirement plan balances:

  • Growth

  • Income

  • Cash reserves

  • Withdrawal flexibility

  • Emotional comfort

Not just investment returns.

5. You’re Unsure About Social Security Timing

Social Security decisions can permanently affect:

  • Household income

  • Survivor benefits

  • Taxes

  • Withdrawal needs

Many retirees underestimate how much claiming timing affects long-term outcomes.

Especially for married couples, survivor planning becomes critical.

6. Your Financial Life Has Become More Complicated

Complexity often increases because of:

  • Business sales

  • Inheritances

  • Multiple investment accounts

  • Real estate holdings

  • Pension decisions

  • Stock compensation

  • Widow/widower concerns

  • Blended families

At a certain point, coordination becomes more valuable than simply managing investments independently.

7. You’re Worried You May Be Missing Something Important

This may be the most common reason retirees seek help.

Not because they feel incapable.

But because retirement decisions become interconnected.

Many retirees quietly wonder:

  • “Am I withdrawing efficiently?”

  • “Could I lower taxes long term?”

  • “What happens if one of us dies?”

  • “Are we taking too much risk?”

  • “Could one mistake hurt us later?”

Those are reasonable questions.

A Simple Retirement Situation vs. A More Complex One

Example #1: Simpler Retirement Scenario

A retiree may have:

  • Pension income

  • Social Security

  • Small IRA balances

  • Minimal taxes

  • Stable spending needs

This household may require relatively little ongoing planning complexity.

Example #2: More Complex Retirement Scenario

A married couple has:

  • $2 million invested

  • Large IRAs

  • Brokerage accounts

  • Deferred compensation

  • Rental property

  • Delayed Social Security decisions

  • Roth conversion opportunities

  • Widow planning concerns

Now retirement planning involves:

  • Tax coordination

  • Withdrawal sequencing

  • Survivor planning

  • Medicare considerations

  • Estate organization

At this stage, the value of coordination may increase significantly.

What Good Financial Advisors Actually Help With

A good retirement-focused advisor should help coordinate:

  • Taxes

  • Retirement income

  • Investment allocation

  • Withdrawal strategy

  • Long-term planning

  • Estate coordination

  • Survivor preparation

The value is often not “beating the market.”

The value is reducing costly mistakes and improving long-term decision coordination.

Not All Advisors Provide the Same Value

This is important.

Retirees should understand that advisors vary significantly.

Some primarily focus on:

  • Investment products

  • Asset gathering

  • Insurance sales

Others focus on comprehensive retirement planning.

Important Questions to Ask

Before hiring someone, retirees should understand:

  • Are they acting as a fiduciary?

  • How are they compensated?

  • Do they provide tax-aware planning?

  • Do they coordinate retirement income strategy?

  • How do they communicate during market volatility?

  • Do they help with survivor planning?

  • Will both spouses understand the plan?

A good advisor relationship should create clarity, not confusion.

Common Mistakes Retirees Make When Hiring Advisors

1. Focusing Only on Investment Returns

Retirement planning is broader than portfolio performance alone.

2. Hiring Someone Without Understanding Fees

Transparency matters.

Retirees should clearly understand:

  • Advisory fees

  • Product commissions

  • Insurance incentives

  • Planning costs

3. Assuming All Advisors Coordinate Taxes

Many do not.

Tax planning often becomes one of the most valuable retirement planning areas.

4. Waiting Until a Crisis Happens

Some retirees delay planning until:

  • A spouse dies

  • Markets decline

  • RMDs begin

  • Taxes spike

  • Health changes occur

Planning is often easier before pressure builds.

Questions to Ask Yourself Before Hiring an Advisor

Consider questions like:

  • Is retirement planning becoming emotionally stressful?

  • Am I confident about withdrawal strategy?

  • Do I understand future tax exposure?

  • Would my spouse know what to do without me?

  • Am I coordinating Social Security properly?

  • Do I have a plan for market downturns?

  • Are estate documents and beneficiaries organized?

The answers may help clarify whether professional coordination could add value.

Final Thoughts

Many people successfully manage their finances during their working years.

But retirement planning often becomes more interconnected and more difficult to reverse once income, taxes, Social Security, healthcare, and withdrawals all begin interacting simultaneously.

At Greenbush Financial Group, we often find that retirees seek guidance not because they want to give up control, but because they want greater clarity and confidence as retirement decisions become more complex.

Hiring a financial advisor is not automatically necessary for everyone.

But for some retirees, especially those approaching major retirement decisions, thoughtful coordination may help reduce costly mistakes and improve long-term financial flexibility.

The goal is not dependency.

The goal is making informed decisions during one of the most financially important transitions of life.

Rob Mangold

About Rob……...

Hi, I’m Rob Mangold. I’m the Chief Operating Officer at Greenbush Financial Group and a contributor to the Money Smart Board blog. We created the blog to provide strategies that will help our readers personally, professionally, and financially. Our blog is meant to be a resource. If there are questions that you need answered, please feel free to join in on the discussion or contact me directly.

FAQ

  1. When should someone hire a financial advisor before retirement?
    Many people consider hiring an advisor within 5-10 years of retirement, especially when decisions around taxes, withdrawals, Social Security, and healthcare become more complex.
  2. Do all retirees need a financial advisor?
    No. Some retirees with simple financial situations and strong financial knowledge may manage retirement successfully on their own.
  3. What is the difference between investment management and retirement planning?
    Investment management focuses primarily on portfolios. Retirement planning coordinates income, taxes, withdrawals, Social Security, healthcare, estate planning, and long-term sustainability.
  4. Why does retirement planning become more complicated?
    Because decisions become interconnected. Withdrawals, taxes, Social Security, Medicare premiums, and market performance can all affect one another.
  5. What are signs retirement planning may be too complex to handle alone?
    Common signs include large IRA balances, uncertainty around withdrawals, tax concerns, widow planning issues, and anxiety about market volatility.
  6. Should DIY investors feel pressured to hire an advisor?
    No. Many successful DIY investors continue managing their finances independently. The question is whether retirement complexity has reached a level where coordination may improve outcomes.
  7. What should retirees look for in a financial advisor?
    Retirees should evaluate fiduciary responsibility, fee transparency, retirement income planning experience, tax coordination, communication style, and survivor planning expertise.
  8. What is the biggest mistake retirees make before hiring an advisor?
    One of the biggest mistakes is assuming retirement planning is only about investments instead of coordinating taxes, income, healthcare, and long-term financial decisions together.
Read More

The Inflation Problem Conservative Retirees Often Underestimate

Many retirees prioritize safety after leaving work, but being too conservative can create risks of its own. Learn how inflation, longevity, and portfolio growth affect long-term retirement income.

Many retirees become more conservative after leaving work, and that instinct is understandable. But avoiding too much market risk can create other risks that are easier to overlook, including inflation erosion, reduced long-term income growth, and the possibility of running out of money later in retirement. A retirement portfolio should not only protect against market declines but also support spending needs over decades. At Greenbush Financial Group, we often help retirees balance safety, growth, and income without taking unnecessary risk.

Many Retirees Focus on One Risk While Overlooking Another

Most retirees worry about losing money in the market.

That concern is completely reasonable.

Once paychecks stop, market declines often feel more emotional because withdrawals may now be coming directly from investment accounts.

As a result, many retirees react by moving heavily into:

  • Cash

  • CDs

  • Savings accounts

  • Short-term bonds

  • Extremely conservative portfolios

At first, this can feel safer.

Balances may fluctuate less. Monthly statements may feel calmer. Market headlines may feel less threatening.

But there is another risk retirees sometimes underestimate:

The risk of becoming too conservative for too long.

Because retirement is not usually a 5-year plan.

For many households, retirement may need to last:

  • 20 years

  • 30 years

  • Or longer

And over long periods of time, inflation can quietly become one of the biggest financial pressures retirees face.

The Hidden Risk: Losing Purchasing Power Over Time

One of the biggest challenges in retirement is that expenses rarely stay flat forever.

Even moderate inflation can slowly increase the cost of:

  • Healthcare

  • Insurance

  • Property taxes

  • Utilities

  • Food

  • Travel

  • Long-term care

Example

Suppose a retiree needs:

  • $80,000 per year today

If inflation averages 3% annually, that same lifestyle could require roughly:

  • $145,000 annually in 20 years

That does not mean spending suddenly doubles overnight.

It means purchasing power slowly erodes over time.

And portfolios that are too conservative may struggle to keep pace.

Why Too Much Cash Can Become a Retirement Problem

Cash plays an important role in retirement.

But many retirees unintentionally turn short-term safety into a long-term strategy.

That can create problems.

The Challenge With Excess Cash

Cash and low-yield investments may provide stability, but they often generate returns that struggle to outpace inflation over longer periods.

Over time, retirees may face:

  • Reduced purchasing power

  • Greater withdrawal pressure

  • Lower portfolio growth

  • Increased longevity risk

This becomes especially important later in retirement when:

  • Healthcare costs rise

  • Inflation compounds

  • One spouse may eventually live alone

  • Required withdrawals increase

The Difference Between Volatility Risk and Purchasing-Power Risk

Most retirees understand volatility risk.

That is the risk of market declines.

But retirement planning also involves purchasing-power risk.

That is the risk that your money loses real spending power over time because growth fails to keep up with inflation.

Both Risks Matter

An overly aggressive portfolio can create uncomfortable volatility.

But an overly conservative portfolio may quietly lose ground for years.

Retirement planning is often about balancing these risks rather than eliminating one entirely.

Why Retirees Still Need Some Growth

One of the biggest retirement misconceptions is:

“Once I retire, I should stop investing for growth.”

In reality, many retirees still need a portion of their portfolio invested for long-term growth because retirement may last decades.

Growth investments may help:

  • Offset inflation

  • Support future withdrawals

  • Reduce longevity risk

  • Maintain purchasing power

  • Improve portfolio sustainability

This does not mean retirees should become aggressive investors.

It means retirement portfolios usually need balance.

A Real-World Example: Conservative vs Balanced Retirement Strategies

Let’s compare two retirees.

Both retire at age 65 with:

  • $1.5 million invested

  • Spending needs of $75,000 annually

  • No pension

  • Moderate Social Security income

Retiree #1: Extremely Conservative

This retiree keeps:

  • 80% in cash and CDs

  • 20% in short-term bonds

The portfolio experiences very little volatility.

But over time:

  • Inflation reduces purchasing power

  • Withdrawals slowly increase

  • Portfolio growth struggles to keep pace

  • Future flexibility declines

Initially, this strategy feels emotionally comfortable.

But the long-term pressure builds quietly.

Retiree #2: Balanced Retirement Allocation

This retiree keeps:

  • Cash reserves for near-term spending

  • Bonds for stability

  • A diversified stock allocation for long-term growth

The portfolio experiences more short-term fluctuations.

But it also maintains greater long-term growth potential to help offset:

  • Inflation

  • Rising healthcare costs

  • Longer retirement timelines

The goal is not maximizing returns.

The goal is balancing stability and sustainability.

Why Fear Often Drives Overly Conservative Decisions

Many retirees become more conservative after:

  • Major market declines

  • Retirement timing stress

  • Watching account balances fluctuate

  • Financial news headlines

  • Economic uncertainty

These reactions are understandable.

Retirement changes how risk feels emotionally.

But investment decisions driven entirely by fear can sometimes create new risks that are less obvious initially.

Important Note

The answer is not ignoring risk.

The answer is understanding that retirement includes multiple risks:

  • Market risk

  • Inflation risk

  • Longevity risk

  • Tax risk

  • Healthcare cost risk

Strong retirement planning considers all of them together.

Sequence Risk Still Matters

Some retirees hear that they should maintain growth investments and assume they should remain heavily invested aggressively.

That can also create problems.

This is where sequence-of-returns risk becomes important.

What Is Sequence Risk?

Sequence risk occurs when poor market returns happen early in retirement while withdrawals are occurring simultaneously.

This can permanently damage long-term portfolio sustainability.

That is why retirement portfolios should balance:

  • Growth potential

  • Stability

  • Cash reserves

  • Withdrawal flexibility

Not simply maximize stock exposure.

The Role of Cash Reserves in a Balanced Retirement Plan

Cash is still important.

The issue is not holding cash.

The issue is relying too heavily on cash for too long.

Many retirees benefit from maintaining:

  • 12–24 months of planned withdrawals in cash or short-term reserves

This may help cover spending needs during market declines without forcing investment sales at poor times.

Key Insight

Cash works best as a stability tool, not a complete long-term retirement strategy.

What About CDs and Bonds?

CDs and bonds can absolutely play an important role in retirement income planning.

But relying exclusively on conservative fixed-income investments can become more difficult when:

  • Inflation rises

  • Interest rates change

  • Spending needs increase

  • Retirement lasts longer than expected

The challenge is that many retirees need portfolios to do two things simultaneously:

  1. Provide stability

  2. Maintain long-term purchasing power

That often requires diversification across multiple asset types.

How Conservative Portfolios Can Increase Withdrawal Pressure

This is one of the least understood retirement risks.

If portfolio growth remains too low for too long:

  • Withdrawals may consume a larger percentage of assets

  • Future income flexibility may shrink

  • Spending adjustments may become necessary later

Ironically, some retirees become more conservative specifically because they fear running out of money.

But insufficient growth can sometimes increase that risk over longer periods.

The Goal Is Not Aggressive Investing

This is important.

A balanced retirement strategy should not feel like speculation.

The goal is not chasing returns.

The goal is building a portfolio designed for:

  • Reliable income

  • Long-term sustainability

  • Inflation protection

  • Emotional comfort

  • Flexibility during downturns

The right allocation depends on factors such as:

  • Age

  • Spending needs

  • Guaranteed income

  • Health

  • Risk tolerance

  • Legacy goals

  • Withdrawal rates

There is no universal retirement portfolio.

Questions Retirees Should Ask

Important retirement planning questions include:

  • How much cash is appropriate for my situation?

  • Could inflation pressure my spending later?

  • Am I too conservative for a 25–30 year retirement?

  • What happens if healthcare costs rise significantly?

  • How would my spouse manage if I died first?

  • Is my withdrawal strategy sustainable?

  • Do I have enough growth potential built into the plan?

These questions are often more valuable than trying to predict short-term market movements.

Common Mistakes Conservative Retirees Make

1. Moving Entirely to Cash After Retirement

This may feel safer emotionally but can increase long-term purchasing-power risk.

2. Ignoring Inflation

Even moderate inflation compounds significantly over decades.

3. Assuming Conservative Means “Risk-Free”

Every retirement strategy involves tradeoffs.

Low volatility does not eliminate long-term retirement risk.

4. Separating Safety and Growth Incorrectly

Many retirees benefit from separating:

  • Short-term spending reserves from:

  • Long-term growth assets

This creates flexibility during volatility.

5. Reacting Emotionally After Market Declines

Emotional investment decisions can permanently alter long-term retirement outcomes.

Final Thoughts

Wanting safety in retirement is completely understandable.

Most retirees are not trying to maximize returns. They are trying to protect the life they worked decades to build.

But retirement planning is not just about avoiding market declines.

It is also about protecting future purchasing power, maintaining flexibility, and creating income that can last through decades of changing expenses and inflation.

At Greenbush Financial Group, we often help retirees balance multiple retirement risks at once rather than focusing on only one type of fear or uncertainty.

The goal is not taking unnecessary risk.

The goal is making sure your retirement plan protects you from both short-term volatility and long-term erosion.

Rob Mangold

About Rob……...

Hi, I’m Rob Mangold. I’m the Chief Operating Officer at Greenbush Financial Group and a contributor to the Money Smart Board blog. We created the blog to provide strategies that will help our readers personally, professionally, and financially. Our blog is meant to be a resource. If there are questions that you need answered, please feel free to join in on the discussion or contact me directly.

FAQ

  1. Can being too conservative in retirement be risky?
    Yes. Holding too much cash or low-growth investments for long periods may increase inflation risk and reduce long-term purchasing power.
  2. Why do retirees still need growth investments?
    Many retirements last 20-30 years or longer. Growth investments may help offset inflation and support long-term income sustainability.
  3. How much cash should retirees keep?
    Many retirees benefit from holding 12-24 months of planned withdrawals in cash or short-term reserves, depending on risk tolerance and spending needs.
  4. Is cash bad in retirement?
    No. Cash plays an important role for stability and near-term spending. Problems usually arise when retirees rely too heavily on cash long-term.
  5. What is purchasing-power risk?
    Purchasing-power risk is the risk that inflation gradually reduces the real value of your money over time.
  6. What is sequence-of-returns risk?
    Sequence risk occurs when poor market returns happen early in retirement while withdrawals are occurring simultaneously.
  7. Should retirees avoid the stock market completely?
    Not necessarily. Many retirees benefit from maintaining some diversified growth exposure while balancing stability and income needs.
  8. What is the biggest mistake overly conservative retirees make?
    One of the biggest mistakes is focusing only on avoiding short-term market volatility while underestimating long-term inflation and longevity risks.
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2026 Bear Market Retirement Planning: How to Avoid Running Out of Money

Retiring in a down market increases sequence of returns risk, which can reduce how long your savings last. The most effective strategies include maintaining a cash reserve, using a bucket income approach, reducing withdrawals, and delaying Social Security. Tax planning and portfolio rebalancing can also improve long-term outcomes. Greenbush Financial Group emphasizes flexibility and disciplined decision-making to help retirees protect income during market volatility.

Retiring during a market downturn can significantly impact how long your retirement savings last due to sequence of returns risk. When withdrawals begin during a declining market, losses can compound and reduce long-term portfolio sustainability. At Greenbush Financial Group, our analysis shows that implementing the right withdrawal, allocation, and income strategies can help protect your retirement plan even in volatile markets.

Why Retiring in a Down Market Is Risky

The primary concern is not just market losses, but when those losses occur.

Sequence of Returns Risk Explained

Sequence risk refers to the timing of market returns relative to your withdrawals.

  • Negative returns early in retirement can permanently reduce your portfolio

  • Withdrawals during downturns lock in losses

  • Recovery becomes more difficult over time

Example

Two retirees with identical portfolios and average returns can have very different outcomes depending on whether market losses occur early or later in retirement.

At Greenbush Financial Group, this is one of the most important risks we plan for when building retirement income strategies.

Strategy 1: Build a Cash Reserve Before Retirement

One of the most effective ways to protect your portfolio is to avoid selling investments during a downturn.

Recommended Approach

  • Maintain 1–3 years of living expenses in cash or short-term investments

  • Use this reserve instead of withdrawing from stocks during market declines

Why It Works

  • Gives your portfolio time to recover

  • Reduces the need to sell assets at depressed prices

  • Provides psychological comfort during volatility

Strategy 2: Use a Bucket Strategy for Income

Segmenting your portfolio into different “buckets” can help manage risk.

Example Structure

Short-Term Bucket (0–3 years)

  • Cash, money markets, short-term bonds

  • Used for immediate income needs

Mid-Term Bucket (3–10 years)

  • Bonds, conservative investments

  • Provides stability and income

Long-Term Bucket (10+ years)

  • Stocks and growth assets

  • Designed to outpace inflation

At Greenbush Financial Group, we often use this framework to align investments with time horizons and reduce sequence risk.

Strategy 3: Reduce Withdrawals During Down Markets

Flexibility is critical when markets are volatile.

Key Adjustments

  • Temporarily reduce discretionary spending

  • Delay large purchases

  • Pause inflation increases on withdrawals

Example

Instead of withdrawing $60,000 during a downturn, reducing withdrawals to $50,000 can significantly improve long-term sustainability.

Strategy 4: Delay Social Security If Possible

Social Security provides a guaranteed, inflation-adjusted income stream.

Why Delaying Helps

  • Increases your monthly benefit

  • Reduces reliance on portfolio withdrawals early

  • Provides more stable income later in retirement

Planning Insight

Using portfolio assets early while delaying Social Security can sometimes improve long-term outcomes. 

Strategy 5: Rebalance and Stay Invested

Market downturns can create opportunities to rebalance your portfolio.

Key Principles

  • Avoid panic selling

  • Rebalance to maintain target allocation

  • Take advantage of lower asset prices

At Greenbush Financial Group, maintaining discipline during downturns is often the difference between success and failure in retirement planning.

Strategy 6: Consider Part-Time Income or Flexible Retirement

Even a small amount of income can reduce pressure on your portfolio.

Benefits

  • Reduces withdrawal rate

  • Allows more time for investments to recover

  • Provides flexibility in spending

Example

Earning $10,000–$20,000 per year can significantly extend portfolio longevity.

Strategy 7: Tax Planning During Market Downturns

Down markets can create tax planning opportunities.

Strategies

  • Harvest capital losses to offset gains

  • Convert IRA funds to Roth at lower market values

  • Manage taxable income to stay in lower tax brackets

At Greenbush Financial Group, we often see that downturns can be an ideal time to implement tax-efficient strategies.

Common Mistakes to Avoid

  • Selling investments out of fear

  • Maintaining rigid withdrawal strategies

  • Ignoring tax planning opportunities

  • Failing to adjust spending

  • Overreacting to short-term market movements

A Real-World Scenario

Scenario

  • Retiree with $1,000,000 portfolio

  • Market declines 20% in first year

  • Withdraws $50,000 annually

Without Adjustments

  • Portfolio drops significantly

  • Recovery becomes difficult

With Strategic Adjustments

  • Uses cash reserve instead of selling stocks

  • Reduces withdrawals temporarily

  • Rebalances portfolio

  • Delays Social Security

Result

  • Improved long-term sustainability

  • Reduced sequence risk impact

Final Thoughts

Retiring during a down market does not mean your plan will fail, but it usually does require adjustments. The key is managing withdrawals, maintaining flexibility, and staying disciplined with your investment strategy.

At Greenbush Financial Group, our analysis shows that retirees who proactively adapt their strategy during downturns are far more likely to preserve their wealth and maintain sustainable income throughout retirement.

Rob Mangold

About Rob……...

Hi, I’m Rob Mangold. I’m the Chief Operating Officer at Greenbush Financial Group and a contributor to the Money Smart Board blog. We created the blog to provide strategies that will help our readers personally, professionally, and financially. Our blog is meant to be a resource. If there are questions that you need answered, please feel free to join in on the discussion or contact me directly.

  1. Is it a bad idea to retire in a down market?
    Not necessarily, but it increases sequence of returns risk and requires careful planning.
  2. How much cash and short-term fixed income should I have in retirement?
    Typically 1 to 3 years of living expenses.
  3. Should I stop withdrawals during a downturn?
    Not entirely, but reducing withdrawals can improve long-term outcomes.
  4. Can a market downturn ruin my retirement plan?
    It can if not managed properly, especially in the early years of retirement.
  5. What is the best strategy during a market downturn?
    Maintain a cash reserve, adjust withdrawals, stay invested, and focus on long-term planning.
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How Does Depreciation Work for Rental Properties?

Rental property depreciation allows investors to reduce taxable income by spreading the cost of a property over 27.5 years. This article explains how depreciation works, how it offsets rental income, and how improvements are treated. It also covers what happens when a property is fully depreciated and how depreciation recapture impacts taxes when selling. Understanding these rules can help investors maximize tax efficiency and avoid costly surprises.

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

Depreciation is one of the most important tax benefits of owning rental property. It allows property owners to offset part of the cost of owning the property against the rental income they receive, which can significantly reduce taxes in the early years of ownership.

In this article, we’ll cover:

  • What depreciation is and how it works

  • The 27.5-year depreciation rule for rental properties

  • How depreciation can offset rental income

  • How improvements are depreciated

  • What happens when depreciation runs out

  • What depreciation recapture is when you sell the property

What Is Depreciation?

Depreciation is a tax deduction that allows rental property owners to recover the cost of a property over time. Even though real estate often increases in value, the IRS allows you to treat the property as if it is wearing out over time and deduct a portion of its value each year.

This deduction can be used to offset rental income, which may reduce how much tax you owe on the income the property generates.

The 27.5-Year Depreciation Rule

Residential rental properties are typically depreciated over 27.5 years.

This means you take the purchase price of the property (excluding land value) and divide it by 27.5 to determine your annual depreciation deduction.

Example:

So, if you purchased a rental property for $300,000, you can depreciate roughly $11,000 per year.

How Depreciation Offsets Rental Income

Depreciation is considered a non-cash expense, meaning you don’t actually write a check for it, but you still get the tax deduction.

Example Scenario:

  • Rental income: $11,000 per year

  • Depreciation: $11,000 per year

In this example, the depreciation deduction offsets the rental income, which may result in little to no taxable rental income for that year.

This is one of the reasons rental real estate can be a very tax-efficient investment.

Depreciation on Improvements

Many rental property owners make improvements to their property, such as:

  • New roof

  • New furnace or heating system

  • Kitchen renovation

  • Bathroom remodel

  • Flooring

  • Additions

These are called capital improvements, and each improvement typically has its own depreciation schedule separate from the original property purchase.

For example:

  • Appliances: Often 5-year depreciation

  • Carpeting: Often 5–7 years

  • Roof: Often 27.5 years

  • HVAC systems: Often 15–27.5 years depending on classification

There are also situations where bonus depreciation or Section 179 may allow you to deduct a larger portion of the improvement cost upfront.

This is an area where working with a knowledgeable tax professional is very important, because depreciation schedules vary depending on the type of improvement.

What Happens When a Property Is Fully Depreciated?

After 27.5 years, the property is considered fully depreciated.

This means:

  • You no longer receive the annual depreciation deduction

  • More of your rental income becomes taxable

  • Your tax liability on rental income may increase

However, you still own the property and still collect rental income — you just don’t get the depreciation tax benefit anymore.

What Is Depreciation Recapture?

Depreciation is a great tax benefit while you own the property, but when you sell the property, the IRS requires something called depreciation recapture.

When you sell a rental property:

  1. You pay capital gains tax on the profit from the sale

  2. You also pay tax on all the depreciation you took over the years

  3. Depreciation recapture is taxed at a flat 25% federal tax rate

Example:

So in this example, when the property is sold, the owner would owe:

  • Capital gains tax on the profit plus

  • $50,000 in depreciation recapture tax

This surprises many real estate investors if they are not prepared for it.

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

Frequently Asked Questions (FAQs)

  1. How long do you depreciate a rental property?
    Residential rental property is depreciated over 27.5 years.
  2. What happens if I don't take depreciation?
    The IRS assumes you took it anyway, and you may still have to pay depreciation recapture when you sell.
  3. Can I depreciate renovations on my rental property?
    Yes, but renovations and improvements typically have their own depreciation schedules.
  4. What is bonus depreciation?
    Bonus depreciation allows you to deduct a large portion of certain improvements upfront instead of spreading the deduction over many years.
  5. Do I have to pay depreciation back when I sell the property?
    When you sell the property, you may be subject to depreciation recapture, which taxes the total depreciation amount taken by 25%.
  6. What happens after 27.5 years of depreciation?
    The property is fully depreciated and you no longer receive the annual depreciation deduction.
  7. Does depreciation reduce my capital gains when I sell?
    No. Depreciation actually lowers your cost basis, which can increase your taxable gain and trigger depreciation recapture.
  8. Can depreciation create a loss on paper?
    Yes. Depreciation can sometimes create a taxable loss even if the property is producing positive cash flow.
  9. Should I work with a CPA if I own rental property?
    It's highly recommended. Depreciation, improvements, and recapture rules are complex, and a knowledgeable CPA can help you maximize tax benefits and avoid costly mistakes.
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What Causes the Price of Gold to Go Up and Down?

Gold prices are influenced by several key factors, including interest rates, inflation, and the strength of the U.S. dollar. While gold is often viewed as a safe haven, it can be highly volatile and may not perform as well as stocks over the long term. This article explains what causes gold to rise and fall, how it compares to other commodities, and how it can be used for diversification. Understanding these drivers can help investors make more informed decisions about including gold in their portfolio.

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

Over the last few years, gold has experienced a significant rally, followed by periods of sharp volatility—including some recent price declines that have caught investors’ attention. As a result, we’ve been having more frequent conversations with clients about what actually causes gold prices to rise and fall, and whether a recent dip represents an opportunity or a warning sign.

In this article, we’re going to walk through the same conversations we’ve been having with clients and explain the major variables that impact the price of gold. Specifically, you’ll learn:

  • Why gold is often viewed as a safe haven

  • How the value of the U.S. dollar affects gold prices

  • Why interest rates play a major role in gold movements

  • Whether gold is a good long-term investment

  • How gold compares to other commodities like silver, copper, and platinum

  • How gold can fit into a diversified portfolio

Gold as a Safe Haven

Gold is often referred to as a “safe haven” asset. What that means is when there is volatility in the global economy—or sometimes in the U.S. stock market—investors may sell riskier assets like stocks and move money into gold in an attempt to protect their principal.

In certain periods in history, this strategy has worked well. When markets become unpredictable, gold can hold its value or even increase while stocks are falling.

However, investors need to be careful with the idea of gold as a safe haven. While gold is sometimes viewed as a “safer” asset than stocks, it is still a very volatile asset class. It is not unusual for gold to move more than 10% in a short period of time. That’s a big difference compared to bonds, which are also considered conservative investments but typically experience much smaller price swings over short time periods.

So while gold can sometimes be a successful safe haven during global volatility, investors must remember that gold itself can be volatile. It should be viewed as a portfolio diversifier, not a guaranteed protection strategy.

Inverse Relationship to the Value of the Dollar

Historically, gold has had an inverse relationship with the value of the U.S. dollar.

In simple terms:

  • When the dollar goes down, gold tends to go up

  • When the dollar goes up, gold tends to go down

Why does this happen?

If paper currency is losing value (purchasing power), investors often move money into physical assets like gold to preserve wealth. Gold is viewed as a store of value that cannot be printed or created like paper money.

On the flip side, when the dollar is strengthening and purchasing power is increasing, investors may feel less need to hold gold, which can lead to falling gold prices.

So historically speaking, movements in the dollar are one of the biggest drivers of gold prices.

Interest Rate Fluctuations

Interest rates are another major factor that influences gold prices, largely because of their relationship with the value of the dollar.

Typically:

  • When the Federal Reserve lowers interest rates, the dollar often weakens, and gold may rise

  • When the Federal Reserve raises interest rates, the dollar often strengthens, and gold may fall

One of the primary reasons attributed to gold's rapid appreciation over the last year was due to interest rates coming down, which weakened the dollar and pushed gold prices higher.

Looking forward, if inflation continues to cool and interest rates decline later into 2026 (outside of the recent Iran events), gold could recover much of what was lost in recent weeks. However, investors must also be aware of long-term inflation risks. If inflation rises again and the Federal Reserve is forced to increase interest rates, that could strengthen the dollar and become a major headwind for gold prices.

In many ways, rising interest rates can be one of the biggest enemies of gold.

Gold as a Long-Term Investment

When we look at long-term annualized returns, gold has not historically been a great long-term investment compared to stocks. Over 20- and 30-year periods, the S&P 500 has outperformed gold.

However, that does not mean gold has no place in a portfolio.

Gold can be useful for:

  • Diversification

  • Protection during market volatility

  • Hedging against a declining dollar

  • Hedging against certain inflationary environments

Gold tends to have lower correlation to stocks and bonds, which means it doesn’t always move in the same direction as traditional investments. Because of that, gold can be a useful component within a diversified portfolio, but investors should be cautious about allocating too much to gold due to its volatility and lower long-term expected returns compared to equities.

Gold Compared to Other Commodities

Clients will often ask: why gold instead of silver, platinum, or copper?

The main reason is predictability.

Gold is primarily viewed as a store of wealth. Its price is largely influenced by:

  • The value of the dollar

  • Interest rates

  • Inflation

  • Global uncertainty

  • Central bank policies

However, other metals like silver, platinum, and copper have significant industrial uses. That means their prices are influenced not just by currency and global events, but also by:

  • Manufacturing demand

  • Technology demand

  • Construction activity

  • Supply chain issues

More variables typically mean more unpredictable price movements.

There are years when gold performs very well and other metals do not, and there are also years where metals like copper or silver outperform gold. In investment management, we often give extra weight to assets that are easier to analyze and understand.

Special Disclosure

This article is meant to educate investors on the price fluctuations in gold based on our experience in investment management over the past number of years. This is not a recommendation to buy or sell gold or any other commodity. Every investor’s situation is different, and decisions should be made based on your individual financial plan, time horizon, and risk tolerance.

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

Frequently Asked Questions About Gold

  1. Why does gold go up when the market goes down?
    Gold is often viewed as a safe haven, so investors sometimes move money into gold during stock market volatility.
  2. What is the biggest factor that affects gold prices?
    The value of the U.S. dollar and interest rates are two of the biggest drivers of gold prices.
  3. Does gold go up when inflation rises?
    Often it does, because gold is viewed as a store of value when purchasing power declines.
  4. Why does gold fall when interest rates rise?
    Rising interest rates typically strengthen the dollar, which historically puts downward pressure on gold.
  5. Is gold a good long-term investment?
    Historically, stocks have outperformed gold over long periods, but gold can still be useful for diversification.
  6. Is gold safer than stocks?
    Not necessarily, gold is still a very volatile asset class.
  7. Why not invest in silver or copper instead of gold?
    Those metals have industrial uses, which makes their prices more unpredictable compared to gold.
  8. How much gold should be in a portfolio?
    It depends on the investor, but many diversified portfolios only allocate a small percentage to gold (under 15%).
  9. What causes gold to drop quickly?
    A rising dollar, rising interest rates, or reduced global uncertainty can all cause gold prices to fall.
  10. Is a drop in gold a buying opportunity?
    It depends on the reason for the drop. Investors should look at interest rates, the dollar, and global conditions before making a decision.
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Is the Market About To Stage A Huge Rally?

The recent stock market pullback has been driven by rising oil prices, inflation concerns, and geopolitical tension involving Iran. As oil surged and uncertainty increased, markets reacted with increased volatility.

However, history shows that declines tied to geopolitical events are often temporary. This raises a key question for investors: is this a warning sign, or a setup for a potential market rally?

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

If the recent market volatility has made you uneasy, you’re not alone. Over the last few weeks, markets have reacted to rising oil prices, inflation concerns, and geopolitical tension in Iran. When volatility returns after a relatively calm period, it can feel like something is seriously wrong, but history tells us this is a normal part of investing, and specifically in this case, the market could be poised to rally in the coming weeks.

In this article, we’ll cover:

  • Forces at work in the market that have created the recent selloff

  • Whether the market may be near a bottom

  • What assets classes are performing well YTD in 2026

  • Charts to guide us as to where the market could go from here

What’s Causing the Market Sell-Off?

The recent market pullback hasn’t been caused by just one issue, but rather a combination of global events and economic pressures.

The biggest driver has been the conflict involving Iran, which has pushed oil prices significantly higher. At the start of the year, oil was around $57 per barrel, and as of March 23, 2026, oil has risen to roughly $90 per barrel. When oil prices rise that quickly:

  • The cost of transporting goods increases

  • The cost of producing goods increases

  • Inflation fears begin to rise

  • The Federal Reserve becomes less likely to cut interest rates

This is why markets have reacted negatively in the short term.

However, based on analyst expectations, there is a high probability that the Iran conflict will be resolved in the reasonably near future. If that happens, oil prices could fall, transportation costs could decline, and inflation fears could ease, which could put the Federal Reserve back on a path toward lowering interest rates.

And that combination has historically been very positive for markets.

It’s also important to remember that we’ve seen this movie before. Recent geopolitical events involving Greenland and Venezuela caused short-term market drops, but the markets recovered very quickly once those situations stabilized. Geopolitical events tend to create temporary volatility, not permanent declines.

An Interesting Trend in 2026: Value vs. Growth

One of the most interesting trends this year has been the difference between large cap growth and large cap value.

As of last week:

  • Large cap growth is down about 7.9% year-to-date

  • Large cap value is up about 2.2% year-to-date

This shouldn’t be a huge surprise. Large cap value includes sectors like energy, which have performed very well due to rising oil prices. Meanwhile, many large cap growth and technology companies, including several of the “Magnificent Seven” stocks, have pulled back this year.

This is a great real-world reminder of why diversification matters.

When one part of the market struggles, another part of the market may be doing well. A properly diversified portfolio helps smooth out the ride when unexpected events occur.

Remember: Volatility Is Normal

The chart below is a great reminder that selloffs and market volatility are normal even during good years for the stock market.

The chart shows two things going back to 1980:

  • The gray bars show the S&P 500 return for the full year

  • The red dots show the largest drop that occurred at some point during that year

For example:

  • In 2025, the market finished up 16%, but at one point during the year, it dropped by 19%

  • In 2024, the market finished up 23%, but had an 8% correction during the year

When you look at the last 45 years, a clear pattern emerges:

Most years the market finishes positive, but most years also have a signification correction at some point during the year.

This is the price of admission for investing. You don’t get the long-term returns of the market without experiencing volatility along the way.

Emotions and Panic Are the Enemy of Good Investment Decisions

The media and the markets will give investors something to worry about every single day.

Some of those concerns are legitimate. Many are not. The key is determining whether a current event represents a temporary disruption or a permanent change to the global economy.

Right now, the concern is Iran, oil prices, and inflation. A few months from now, it will likely be something else. That has always been the case, and it will continue to be the case.

One thing investors cannot forget is that we are currently in a massive wave of innovation and growth driven by artificial intelligence, automation, and robotics. These trends will likely have a much larger long-term impact on markets than most short-term geopolitical events.

This doesn’t mean markets won’t fall. They will.
It doesn’t mean volatility won’t happen. It will.
It doesn’t mean corrections won’t occur. They will.

But it does mean that panic-driven decisions are often the biggest mistake investors make.

Is the Market Close to the Bottom?

No one can consistently predict the exact bottom of a market correction. However, market declines driven by geopolitical events and oil shocks have historically recovered relatively quickly once the situation stabilizes.  The Iran conflict is not likely be to any different.

If the Iran conflict cools down, and:

  • Oil prices fall

  • Transportation costs fall

  • Inflation fears ease

Then the current market pullback could reverse faster than many investors expect.

Market pullbacks often create opportunities that weren’t available when markets were at all-time highs just a few months ago.

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

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Should You Invest Your HSA Account?

Health Savings Accounts can be more than just a tool for current medical expenses. This article explains when it makes sense to invest your HSA, when to keep funds in cash, and how to use an HSA as a long-term retirement strategy. Learn about tax advantages, contribution limits for 2026, and how to transfer funds to investment-friendly HSA providers. Discover how to maximize tax-free growth for future healthcare costs.

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

Health Savings Accounts (HSAs) are a valuable tool that allow individuals to use pre-tax dollars to pay for qualified medical expenses. But there is also a more advanced planning strategy that many people are not aware of — using an HSA as a long-term investment account for future healthcare costs, especially in retirement when healthcare expenses are typically at their highest.

So the question becomes: If you’re not planning to spend your HSA money this year, should you invest it so it grows over time?

In this article, we’ll cover:

  • When it makes sense to invest your HSA

  • When you should keep HSA funds in cash

  • What to do if your employer HSA doesn’t allow investing

  • How HSA transfers work

  • The tax advantages of investing an HSA

  • 2026 HSA contribution limits

  • Frequently asked questions about investing HSAs

The Long-Term HSA Strategy

Many people use their HSA to pay for current medical expenses. But another strategy is to:

  • Contribute to an HSA each year

  • Do NOT spend the HSA

  • Pay current medical expenses out-of-pocket

  • Allow the HSA to grow over time

  • Use the HSA later in retirement for healthcare expenses

This strategy can be powerful because:

  • Contributions are pre-tax

  • Growth is tax-deferred

  • Withdrawals are tax-free for qualified medical expenses

This makes the HSA one of the only accounts that can be tax-free on the way in and tax-free on the way out when used correctly.

Should You Invest Your HSA?

In general, if the money in your HSA is not going to be used within the next year, it can often make sense to invest those funds so they can grow over time.

This is especially true for individuals who:

  • Are 10+ years away from retirement

  • Can afford to pay current medical expenses out-of-pocket

  • Want to build a retirement healthcare fund

By investing the HSA, you are not only getting the tax deduction on the contribution, but you are also getting tax-free growth on the investments if used for qualified medical expenses later.

When You Should NOT Invest Your HSA

If you are using your HSA for current or short-term medical expenses, it usually makes sense to keep that portion in cash or a money market account.

A common strategy is to split the HSA into two buckets:

  • Short-term medical expenses → Keep in cash

  • Long-term retirement healthcare → Invest for growth

This way, you maintain stability for current expenses while still allowing long-term funds to grow.

What If Your Employer’s HSA Doesn’t Allow Investing?

This is a very common issue. Some employer HSA providers only allow cash or money market accounts and do not offer investment options.

Many people don’t realize this, but you are allowed to have more than one HSA account, and you are allowed to transfer money between HSA accounts with no taxes or penalties.

How to Get the Best of Both Worlds

You can:

  1. Contribute to your employer’s HSA through payroll

  2. Then transfer money to a self-directed HSA (such as Fidelity, Schwab, HealthEquity, etc.)

  3. Invest the money in the self-directed HSA

This strategy allows you to take advantage of the tax benefits of payroll contributions while still having access to investment options.

Why Contribute to Your Employer’s HSA First?

There are two major advantages:

1. Payroll Deduction Convenience

Contributions go directly from your paycheck into the HSA.

2. FICA Tax Savings

If contributions are made through payroll deductions:

  • You avoid federal tax

  • You avoid state tax

  • You avoid FICA tax (Social Security and Medicare tax)

If you contribute to an HSA on your own outside of payroll, you still avoid federal and state tax, but you do NOT avoid FICA tax.

That FICA savings alone can be an additional 7.65% tax savings on contributions.

2026 HSA Contribution Limits

HSA contribution limits typically increase each year with inflation. For 2026, the limits are:

These limits include both employee and employer contributions combined.

A Blended Strategy

Some individuals use a combination approach:

  • Use part of the HSA for current medical expenses

  • Invest the remainder for retirement healthcare

In these cases, it is usually a good idea to:

  • Keep enough in cash to cover your deductible and expected medical costs

  • Invest the remaining balance for long-term growth

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

Frequently Asked Questions (FAQs)

  1. Should I invest my HSA or keep it in cash?
    If you need the money within a year, keep it in cash. If it's long-term money, investing may make sense.
  2. What can I invest in inside an HSA?
    Many HSAs allow investments in mutual funds, ETFs, and sometimes individual stocks.
  3. Can I lose money in an invested HSA?
    Yes. If invested in the market, the value can go up or down.
  4. Can I move my HSA to another provider?
    Yes, you can transfer HSA funds between providers with no taxes or penalties.
  5. Why should I use my employer HSA first?
    Payroll contributions avoid FICA tax.
  6. Can I have two HSA accounts?
    Yes, as long as total contributions do not exceed annual limits.
  7. Is an HSA better than a 401(k)?
    For medical expenses, an HSA can be more tax-efficient because it can be tax-free on both contributions and withdrawals.
  8. When should I stop investing my HSA?
    Typically when you are getting closer to needing the funds for medical expenses.
  9. Can I reimburse myself years later from my HSA?
    Yes, as long as you kept receipts and the expense occurred after the HSA was opened.
  10. What is the biggest advantage of investing an HSA?
    Tax-free growth and tax-free withdrawals for medical expenses in retirement.
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“Sell in May and Go Away” is Dead

“Sell in May and Go Away” sounds clever, but the data tells a different story. Since 2020, investors who followed this rule would have missed out on strong summer gains. We break down why discipline and staying invested consistently beat market timing.

By Michael Ruger, CFP®
Partner and Chief Investment Officer at Greenbush Financial Group

One of the most well-known Wall Street adages is the “Sell in May and go away” strategy. The idea is simple: sell your stock holdings in May, avoid the typically slower summer months, and then re-enter the market in the fall when trading activity and returns supposedly pick back up. On the surface, this strategy sounds appealing—who wouldn’t want to avoid risk and still capture the best gains of the year?

But here’s the problem: if you had followed this strategy over the past six years, you would have missed out on some very strong returns. In fact, staying on the sidelines from June through August would have cost you real money.

In this article, we’ll cover:

  • A look at the actual S&P 500 returns from June–August over the past few years

  • Why investors would have been “right” only 1 out of 6 times

  • The real risk of following catchy headlines instead of hard data.

  • Why discipline through volatility has historically paid off.

What the Data Really Says

Below is a breakdown of the S&P 500 Index returns from June through August for each year since 2020.

When we look at the data:

  • Five out of six years, the June – August months produced positive returns.

  • The average return over this period was 6.91%.

  • Investors would have only been correct in sitting out one year (2022), when the S&P fell by –3.37%.

Put simply, investors who followed the Sell In May and Go Away strategy for the past 6 years cost themselves about 7% PER YEAR in investment returns. 

Why the Temptation is Strong

It’s easy to see how investors get drawn into these types of strategies. A headline or article points out that summer months are historically weaker, or that volatility spikes during this period. On paper, it can sound logical: avoid risk, re-enter later, and come out ahead.

But as the table shows, the reality doesn’t line up with the theory. By relying on the “Sell in May” strategy, investors risk leaving money on the table. That’s the danger of market timing—you need to be right not once, but twice (when to sell, and when to buy back in).

Volatility vs. Discipline

There’s no denying that the summer months often bring more volatility to the stock market. Thinner trading volumes and seasonal economic patterns can cause choppier price action. But investors who have had the discipline to ride through those bumps have been rewarded.

The past six years make this clear: while the S&P 500 had its ups and downs from June to August, the overall trend was solidly positive. That’s why sticking to a long-term investment plan often beats trying to time the market.

About Michael……...

Hi, I’m Michael Ruger. I’m the managing partner of Greenbush Financial Group and the creator of the nationally recognized Money Smart Board blog . I created the blog because there are a lot of events in life that require important financial decisions. The goal is to help our readers avoid big financial missteps, discover financial solutions that they were not aware of, and to optimize their financial future.

Frequently Asked Questions (FAQs)

What does “Sell in May and go away” mean in investing?
“Sell in May and go away” is a market adage suggesting that investors should sell their stock holdings in May, avoid the summer months when returns are thought to be weaker, and reinvest in the fall. The strategy is based on historical seasonal trends but often oversimplifies how markets actually perform.

Has the “Sell in May” strategy worked in recent years?
Recent data shows that this strategy has largely underperformed. Over the past several years, the S&P 500 has delivered positive returns during the summer months more often than not, meaning investors who exited in May would have missed out on gains.

Why can following seasonal market sayings be risky?
Relying on old adages or headlines instead of data can lead to missed opportunities or poorly timed decisions. Markets are influenced by a range of factors—economic trends, interest rates, and company performance—not just the calendar.

What’s the downside of sitting out of the market during the summer?
Missing even a few strong market days can significantly reduce long-term investment returns. Staying invested allows you to participate in rebounds and compounding growth that can happen unexpectedly throughout the year.

Why is discipline so important for investors?
A disciplined, long-term investment approach helps smooth out volatility and avoid emotional decision-making. Sticking with a consistent strategy based on goals and time horizon has historically produced better outcomes than trying to time the market.

What’s a more effective alternative to timing seasonal trends?
Instead of trying to predict short-term market movements, investors can focus on maintaining a diversified portfolio aligned with their risk tolerance and financial objectives. This approach emphasizes consistency and adaptability rather than reacting to temporary patterns.

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