2026 Bear Market Retirement Planning: How to Avoid Running Out of Money

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.

How Does Depreciation Work for Rental Properties?

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.

What Causes the Price of Gold to Go Up and Down?

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.

Is the Market About To Stage A Huge 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.

Should You Invest Your HSA Account?

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.

“Sell in May and Go Away” is Dead

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.

What’s a Target Date Fund and Should I Invest in It?

If you've logged into your 401(k) or IRA recently, there's a good chance you've seen investment options labeled something like “2050 Target Date Fund” or “2065 Retirement Fund.” But what exactly is a target date fund, and is it the right choice for your retirement savings?

This article breaks down how target date funds work, their pros and cons, and when they make sense within a broader financial plan.

What Is a Target Date Fund?

A target date fund is a type of investment fund that automatically adjusts its asset allocation based on your expected retirement year—your target date.

For example, a “2060 Target Date Fund” is designed for someone retiring around the year 2060. The fund starts out heavily invested in stocks to maximize growth. Over time, it gradually becomes more conservative, shifting toward bonds and cash equivalents as the retirement year approaches. This automatic reallocation is called the glide path.

Target date funds are often considered a “set-it-and-forget-it” option for retirement investors but understanding how they work may help determine whether they are a suitable option for your savings.

How the Glide Path Works

The glide path is the fund’s built-in schedule for reducing investment risk over time. Here's a simplified example of how the asset allocation might shift as retirement nears: 

This gradual transition helps reduce the impact of market volatility as you get closer to drawing income from the portfolio.  The example above may be a glide path associated with a “2065 Target Date Fund”.

Benefits of Target Date Funds

Simplicity: Target date funds are professionally managed, removing the need to select and monitor individual investments.

Diversification: These funds typically include a mix of U.S. and international stocks, bonds, and sometimes alternative investments, offering broad market exposure.

Automatic rebalancing: The fund rebalances its portfolio over time, keeping it aligned with its risk-reduction strategy without requiring action from the investor.

Good default option: Many 401(k) plans use target date funds as the default investment for participants who don’t actively choose their own allocation.

Potential Drawbacks to Consider

One-size-fits-all: These funds assume that all investors retiring in the same year have similar goals and risk tolerances, which isn’t always the case.

Higher fees: Some target date funds—especially those with actively managed components—can carry higher expense ratios compared to index-based options.

Misaligned risk profile: Some glide paths become too conservative too early, while others remain aggressive longer than ideal. The right fit depends on your personal retirement income plan.

Tax inefficiency in taxable accounts: Frequent rebalancing may create taxable events when held in non-retirement accounts. They are generally best suited for IRAs or 401(k)s.

When Target Date Funds Make Sense

Target date funds can be a solid choice if you:

• Are early in your career and want a simple, broadly diversified investment

• Don’t want to actively manage your retirement portfolio

• Prefer to avoid emotional or reactive investment decisions

• Are not yet working with a financial advisor

They are especially useful as a default option when you’re getting started or want to automate long-term investing with minimal oversight.

When to Consider Alternatives

You may want to explore other investment options if you:

• Have substantial assets and want a more customized portfolio

• Are implementing tax planning strategies like Roth conversions or asset location

• Have other income sources in retirement that affect your risk tolerance

• Want more control over your asset mix and withdrawal strategy

• Have a lower risk tolerance than where the target date fund would allocate your investments

In these cases, building a personalized portfolio may better align with your goals and offer more flexibility.

Final Thoughts

Target date funds can offer convenience, professional management, and a clear path toward a retirement-ready portfolio. For many investors—especially those early in their careers—they can be a smart, efficient way to begin building long-term wealth.

However, as your financial picture grows more complex, it may be worth reevaluating whether a one-size-fits-all fund still fits your personal strategy. A custom portfolio tailored to your income needs, tax situation, and risk tolerance may offer more precise control over your retirement outcome.

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.

Frequently Asked Questions (FAQs)

What is a target date fund?
A target date fund is a diversified investment designed to automatically adjust its mix of stocks, bonds, and other assets as you approach a specific retirement year. It aims to provide growth in the early years and gradually reduce risk as the target date gets closer.

How does a target date fund’s glide path work?
The glide path is the fund’s schedule for shifting from aggressive investments, like stocks, to more conservative holdings, such as bonds and cash equivalents. This gradual transition helps reduce volatility as you near retirement while still pursuing growth early on.

How do I choose the right target date fund?
Most investors select the fund closest to their expected retirement year. However, personal factors such as risk tolerance, savings rate, and income goals should also be considered when choosing a fund.

What are the main benefits of target date funds?
Target date funds offer automatic diversification and rebalancing, making them a convenient “set-it-and-forget-it” option. They can simplify retirement investing for those who prefer not to manage asset allocation themselves.

What are the potential drawbacks of target date funds?
One downside is that investors have little control over the fund’s specific holdings or risk adjustments. Glide paths also vary by provider, meaning some funds may remain more aggressive or conservative than expected.

Are target date funds a good choice for everyone?
They can be a strong fit for investors who want a hands-off approach, but those with complex financial goals or multiple investment accounts may benefit from a more customized strategy. Reviewing the fund’s allocation and costs before investing is essential.

Advantages of Using A Bond Ladder Instead of ETFs or Mutual Funds

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

When it comes to investing, one of the biggest challenges is dealing with interest rate uncertainty. Rates go up, rates go down, and bond prices fluctuate with those changes. For investors who want predictable income and a way to smooth out the risks of rising and falling interest rates, a bond ladder can be a powerful strategy.

In this article, we’ll walk through:

• What a bond ladder is and how it works

• How a bond ladder helps hedge against interest rate fluctuations

• The different types of bond ladders (equal-weighted, barbell, middle-loaded)

• Why some investors prefer an individual bond ladder over bond mutual funds or ETFs

What Is a Bond Ladder?

A bond ladder is a portfolio of individual bonds with staggered maturity dates. For example, you might buy bonds maturing in 1 year, 2 years, 3 years, 4 years, and 5 years. When the 1-year bond matures, you reinvest the proceeds into a new 5-year bond, keeping the “ladder” in place.

This structure offers two key benefits:

1. Hedging Interest Rate Risk: Since a portion of your ladder matures every year (or at regular intervals), you always have an opportunity to reinvest at the prevailing interest rate—whether rates go up or down.

2. Consistent Income and Liquidity: The maturing bonds provide cash flow that can be reinvested or used for spending needs.

In short, a bond ladder helps smooth out the effects of interest rate fluctuations while still generating steady income.

Types of Bond Ladders and How They Work

There isn’t just one way to build a bond ladder. The structure you choose depends on your investment goals, risk tolerance, and views on interest rates. Here are three common approaches:

1. Equal-Weighted Bond Ladder

• How it works: Bonds are spread evenly across maturity dates (e.g., equal amounts in 1, 2, 3, 4, and 5-year maturities).

• Why use it: This is the most straightforward approach. It balances risk and return by spreading exposure across time horizons, making it a good fit for investors who want predictability.

2. Barbell Strategy

• How it works: Bonds are concentrated at the short and long ends of the maturity spectrum, with little or nothing in the middle. For example, you might own 1-year and 10-year bonds, but nothing in between.

• Why use it: Short-term bonds provide liquidity and flexibility, while long-term bonds lock in higher yields. This strategy can be appealing when you expect interest rates to change significantly in the future.

3. Middle-Loaded Ladder

• How it works: Bonds are concentrated in intermediate maturities (e.g., 3–7 years).

• Why use it: Provides a balance between short-term reinvestment risk and long-term interest rate exposure. This can be attractive if you think the current yield curve makes mid-range maturities the “sweet spot” for returns.

Bond ladders can also vary by duration.  Some investors create 5-year ladders, 10-year ladders, or 20-year ladders. 

Why Build a Bond Ladder Instead of Using a Mutual Fund or ETF?

You might wonder: why not just buy a bond fund and let the professionals handle it? There are several reasons why individual investors prefer building their own bond ladders:

• Predictable Cash Flow: With a ladder, you know exactly when each bond will mature and what it will pay. Bond funds and ETFs fluctuate daily, and there are no set maturity dates.

• Control Over Holdings: You decide the maturity schedule, the credit quality, and the exact bonds in your ladder. In a fund, you’re subject to the manager’s decisions.

• Reduced Interest Rate Risk: In a bond ladder, if you hold bonds to maturity, you get your principal back regardless of market fluctuations. Bond funds never truly “mature,” so you’re always exposed to price swings.

• Potentially Lower Costs: By buying individual bonds and holding them, you avoid ongoing expense ratios charged by mutual funds and ETFs.

In short, a bond ladder offers clarity, predictability, and control that pooled investment vehicles can’t always match.

Why You Need Significant Capital for a Bond Ladder

While bond ladders offer many advantages, they aren’t practical for every investor. Building a well-diversified ladder requires a substantial amount of money for a few reasons:

• Minimum Purchase Amounts: Many individual bonds trade in $1,000 or $5,000 increments. To build a ladder with multiple rungs across different maturities, you need enough capital to meet those minimums. When investing in short-term U.S. treasuries, sometimes the purchase minimum is $250,000.

• Diversification Needs: A proper ladder spreads risk across multiple issuers and maturities. Doing this with small amounts of money is difficult, leaving you concentrated in just a few bonds.

• Transaction Costs: Buying and selling individual bonds often involves markups or commissions, which can eat into returns if the investment amount is too small.

• Income Needs: If you’re using the ladder to generate income, small investments may not produce meaningful cash flow compared to what’s achievable with funds or ETFs.

For these reasons, investors with smaller portfolios often turn to bond mutual funds or ETFs. These vehicles pool money from many investors, allowing even modest contributions to achieve diversification, professional management, and steady income without the large upfront commitment required by a ladder

Final Thoughts

A bond ladder can be an excellent strategy for investors looking to hedge interest rate risk, generate predictable income, and maintain flexibility. Whether you choose an equal-weighted ladder for balance, a barbell strategy for flexibility and yield, or a middle-loaded approach to target the sweet spot of the curve, the right structure depends on your unique goals.

And while bond mutual funds and ETFs may be convenient, an individual bond ladder provides unmatched control, transparency, and reliability.

If you’re considering adding a bond ladder to your portfolio, the key is aligning it with your financial objectives, income needs, and risk tolerance. Done correctly, it’s a time-tested way to bring stability and consistency to your investment plan.

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 is a bond ladder and how does it work?
A bond ladder is a portfolio of individual bonds with staggered maturity dates, such as 1-, 2-, 3-, 4-, and 5-year terms. As each bond matures, the proceeds are reinvested into a new long-term bond, creating a cycle that provides steady income and helps manage interest rate risk.

How does a bond ladder help protect against interest rate changes?
Because bonds mature at regular intervals, you continually reinvest at current market rates. This means when interest rates rise, maturing bonds can be rolled into higher-yielding ones; when rates fall, the longer-term bonds in the ladder continue to earn higher fixed rates.

What are the different types of bond ladders?
Common structures include equal-weighted ladders (evenly spread maturities), barbell strategies (short- and long-term maturities), and middle-loaded ladders (focused on intermediate terms). Each structure balances risk, return, and flexibility differently.

Why might investors choose a bond ladder over a bond mutual fund or ETF?
An individual bond ladder offers predictable maturity dates, control over holdings, and stable cash flow if bonds are held to maturity. In contrast, bond funds and ETFs fluctuate in value and have no set maturity, which can expose investors to ongoing price volatility.

Who is a bond ladder best suited for?
Bond ladders typically work best for investors with larger portfolios who want predictable income and can meet minimum bond purchase requirements. Smaller investors may prefer bond funds or ETFs for diversification and lower entry costs. We advise consulting with your personal investment advisor.

What are the key advantages of using a bond ladder in a portfolio?
A bond ladder provides consistent income, reduces interest rate risk, and enhances liquidity through regular maturities. It also allows investors to match cash flow needs with future expenses while maintaining control over credit quality and investment duration.