A Financial Advisor’s Pre-Retirement Checklist

Retirement is not just a financial milestone. It is a transition that changes how you generate income, pay taxes, manage healthcare, invest your savings, and plan for the future.

Many retirees focus almost entirely on building their retirement accounts, but the years immediately before retirement are often when the most important decisions get made. Choices involving Social Security, Medicare, taxes, pensions, investments, and withdrawal strategies can affect your financial security for decades.

Some of these decisions are irreversible. Others can create unexpected tax consequences or increase financial stress if they are not reviewed carefully.

Before you leave your job, here are 10 critical retirement decisions worth reviewing carefully.

1. Can You Actually Afford to Retire?

Why It Matters

This is the most important retirement question and often the most emotional one.

Many people focus on whether they have “enough” saved, but retirement planning is really about whether your income can sustainably support your lifestyle over a retirement that could last 25 to 30 years.

The biggest risk is not simply running out of money. It is retiring without understanding:

• how your income will work

• how inflation affects spending

• how market declines impact withdrawals

• how taxes reduce retirement income

• how healthcare costs fit into the plan

What to Review

• Your expected monthly retirement expenses

• Guaranteed income sources

• Investment withdrawal strategy

• Inflation assumptions

• Sequence of returns risk

• Emergency reserves

• Expected retirement longevity

Example

A couple retiring at age 62 may initially believe they only need $7,000 per month. But after factoring in healthcare premiums, inflation, travel, taxes, home maintenance, and irregular expenses, their actual spending may be closer to $9,000 monthly.

That difference can significantly impact how sustainable their retirement plan is.

Key Insight

Retirement success is not just about portfolio size. It is about whether your income plan can survive inflation, market volatility, and unexpected expenses over time.

2. When Should You Claim Social Security?

Why It Matters

Social Security is one of the most important retirement income decisions because claiming timing can permanently affect your lifetime benefits.

Many retirees underestimate:

• how much benefits increase by waiting

• the impact on surviving spouses

• how taxes affect benefits

• how working before full retirement age can temporarily reduce payments

What to Review

• Claiming at 62 vs. full retirement age vs. 70

• Spousal benefits

• Survivor benefits

• Earnings limits before full retirement age

• Taxation of benefits

• Longevity expectations

• Coordination with retirement withdrawals

Example

A retiree eligible for $2,200 monthly at full retirement age could receive roughly:

• $1,540 at age 62

• $2,200 at full retirement age

• nearly $2,900 at age 70

That difference can significantly impact lifetime household income, especially for married couples.

Important Note

The best Social Security strategy is not always about maximizing benefits. It is about coordinating benefits with taxes, investments, pensions, and overall retirement income planning.

3. Have You Planned for Healthcare and Medicare Costs?

Why It Matters

Healthcare is one of the biggest retirement expenses and one of the largest sources of financial anxiety for retirees.

People retiring before age 65 often underestimate the cost of private health insurance before Medicare begins. Others make Medicare enrollment mistakes that create lifelong penalties or unexpected coverage gaps.

What to Review

• Healthcare costs before Medicare eligibility

• Medicare enrollment deadlines

• Medicare Part B and Part D coverage

• Medicare Advantage vs. Medigap

• IRMAA surcharges

• Long-term care exposure

• Health Savings Account planning

Example

A retiree who delays Medicare enrollment because they misunderstand employer coverage rules could face permanent premium penalties later.

Similarly, higher-income retirees may unknowingly trigger IRMAA surcharges that significantly increase Medicare premiums.

Key Insight

Healthcare planning is not just about insurance coverage. It is also about tax planning, income management, and preparing for future care needs.

4. Have You Reviewed Your Retirement Tax Strategy?

Why It Matters

One of the biggest surprises retirees face is discovering that retirement does not automatically lower taxes.

Different retirement accounts are taxed differently, and poor withdrawal sequencing can unintentionally push retirees into higher tax brackets.

What to Review

• Roth conversion opportunities

• Future RMD exposure

• Tax diversification

• Capital gains planning

• Social Security taxation

• Medicare IRMAA thresholds

• Withdrawal sequencing

Example

A retiree with large traditional IRA balances may face substantial required minimum distributions later in retirement, even if they do not need the income.

Strategic Roth conversions before RMD age can sometimes reduce future tax exposure and improve long-term flexibility.

Important Note

Many retirees focus on investment returns but overlook lifetime tax efficiency. The way retirement income is structured can be just as important as portfolio performance.

5. Do You Have a Reliable Retirement Income Strategy?

Why It Matters

Retirement changes the financial mindset from accumulation to distribution.

That transition can feel uncomfortable because your paycheck stops and your portfolio becomes the primary income source.

Without a clear strategy, retirees often either overspend too early or become afraid to spend at all.

What to Review

• Which accounts to withdraw from first

• Cash reserve strategy

• Sequence of returns risk

• Dividend income assumptions

• Withdrawal sustainability

• Coordination between income sources

Example

Two retirees with identical portfolios can experience very different outcomes depending on when market declines occur early in retirement.

Large withdrawals during market downturns can permanently damage long-term portfolio sustainability.

Key Insight

A retirement income plan should balance:

• stability

• flexibility

• tax efficiency

• long-term growth potential

6. Is Your Investment Risk Appropriate for Retirement?

Why It Matters

Many people approaching retirement ask the same questions:

• “Am I taking too much risk?”

• “What if there’s another 2008?”

• “Should I move everything to cash?”

The challenge is balancing protection with growth.

Being too aggressive can increase volatility at the wrong time. But being too conservative can create inflation risk and reduce long-term purchasing power.

What to Review

• Current asset allocation

• Portfolio downside risk

• Retirement timeline

• Cash reserves

• Bond allocation

• Inflation protection

• Income needs from investments

Example

A retiree holding overly conservative investments may struggle to maintain purchasing power over a 25-year retirement, especially during periods of elevated inflation.

Important Note

Retirement investing is not about eliminating risk entirely. It is about managing risk appropriately for your goals, income needs, and time horizon.

7. Have You Reviewed Your Pension Options Carefully?

Why It Matters

Pension elections are often irreversible.

For retirees with pensions, decisions involving lump sums, survivor benefits, and payout structures can have major long-term implications for household income and estate planning.

What to Review

• Lump sum vs. monthly pension

• Survivor benefit elections

• Inflation adjustments

• Pension solvency considerations

• Tax implications

• Coordination with Social Security

Example

Choosing the highest monthly pension payout without survivor protection may leave a surviving spouse with significantly reduced household income later.

Key Insight

The best pension decision depends on:

• health

• marital status

• other retirement assets

• legacy goals

• guaranteed income needs

8. Have You Updated Your Estate Plan and Beneficiaries?

Why It Matters

Many retirees assume their estate documents are current when they have not reviewed them in years.

Outdated beneficiary designations and missing legal documents can create unnecessary complications for family members later.

What to Review

• Wills and trusts

• Powers of attorney

• Healthcare directives

• Beneficiary designations

• Transfer-on-death accounts

• Inherited IRA rules

• Estate tax considerations

Example

An outdated IRA beneficiary form can override instructions written in a will.

That mistake can unintentionally direct retirement assets to the wrong person.

Important Note

Estate planning is not just about wealth transfer. It is also about maintaining control, simplifying administration, and protecting family members during difficult situations.

9. Have You Reviewed Your Debt and Spending Plan?

Why It Matters

Retirement spending often changes more than people expect.

Some retirees spend less. Others spend significantly more during the first decade of retirement due to travel, hobbies, home projects, or helping family members financially.

What to Review

• Mortgage payoff decisions

• Credit card debt

• Retirement budget assumptions

• Downsizing considerations

• Support for adult children

• Large one-time expenses

• Lifestyle expectations

Example

A retiree may choose to keep a low-interest mortgage rather than aggressively paying it off in order to preserve liquidity and investment flexibility.

The right decision depends on both financial and emotional factors.

Key Insight

A realistic retirement spending plan should account for both expected and unexpected expenses.

10. What Happens If Something Goes Wrong?

Why It Matters

One of the biggest retirement planning mistakes is assuming everything will go according to plan.

Strong retirement planning includes preparing for uncertainty.

What to Review

• Long-term care exposure

• Widowhood planning

• Emergency reserves

• Market downturn scenarios

• Caregiving costs

• Family health history

• Insurance coverage

Example

A major healthcare event or long-term care need can dramatically change retirement spending and income needs later in life.

Preparing in advance can help reduce financial stress during difficult situations.

Important Note

Retirement planning is not about predicting the future perfectly. It is about building flexibility into the plan.

Common Retirement Mistakes to Avoid

Some of the most common retirement mistakes happen during the transition into retirement itself.

These include:

• Claiming Social Security too early without reviewing alternatives

• Ignoring tax planning opportunities before RMD age

• Underestimating healthcare costs

• Taking too much or too little investment risk

• Failing to stress-test retirement income

• Overlooking beneficiary designations

• Retiring without a coordinated withdrawal strategy

• Assuming retirement spending will remain constant

Final Thoughts

Retirement is one of the biggest financial transitions of your life. The decisions made in the years immediately before retirement can affect your income, taxes, healthcare costs, and financial flexibility for decades.

Many of the most expensive retirement mistakes are preventable with proactive planning and careful coordination.

At Greenbush Financial Group, we believe retirement planning should go beyond investment performance alone. A successful retirement plan coordinates income, taxes, healthcare, investments, estate planning, and long-term risk management into a strategy designed to support both confidence and flexibility throughout retirement.

Before you stop working, make sure you review the decisions that matter most.

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 Section

1. What is the most important financial decision before retirement?

   The most important decision is determining whether your retirement income plan is sustainable. This includes reviewing spending needs, withdrawal strategies, taxes, inflation, and healthcare costs.

2. When should I claim Social Security?

   The right claiming age depends on your health, marital status, income needs, longevity expectations, and overall retirement plan. Claiming early permanently reduces benefits, while delaying can increase lifetime income.

3. How much should I have saved before retirement?

   There is no universal number. Retirement readiness depends on your expected spending, income sources, taxes, healthcare costs, and lifestyle goals.

4. What are the biggest retirement tax mistakes?

   Common mistakes include ignoring Roth conversion opportunities, triggering higher Medicare premiums, poor withdrawal sequencing, and failing to prepare for RMDs.

5. Should I pay off my mortgage before retirement?

   It depends on your cash flow, interest rate, liquidity needs, and personal comfort level. Some retirees prioritize debt elimination, while others prefer maintaining investment flexibility.

6. How do I prepare for healthcare costs in retirement?

   Review Medicare options, estimate out-of-pocket expenses, understand IRMAA rules, and consider how long-term care costs could affect your retirement plan.

7. What happens if the market crashes early in retirement?

   Early retirement market declines can increase sequence of returns risk, especially when withdrawals are occurring simultaneously. Maintaining proper diversification and cash reserves can help reduce this risk.

8. Why is retirement planning more than just investing?

   Retirement planning also involves taxes, healthcare, income coordination, estate planning, Social Security, spending strategy, and risk management decisions that affect long-term financial security.

Claiming Social Security Early or Late: Which Age Is Right for You?

Deciding when to claim Social Security is one of the most important retirement decisions because it directly impacts your lifetime income. Claiming early at 62 reduces your benefit, waiting until full retirement age (67) provides your standard benefit, and delaying to age 70 increases your benefit significantly. At Greenbush Financial Group, our analysis shows that the right decision depends on your life expectancy, income needs, tax strategy, and overall retirement plan.

How Social Security Benefits Change by Age

Your benefit amount is based on your Full Retirement Age (FRA), which is typically 67 for those born in 1960 or later.

Benefit Adjustments by Claiming Age

• Age 62 → ~30% reduction

• Age 67 → 100% of your benefit

• Age 70 → ~24% increase from FRA

Example

If your FRA benefit is $2,000 per month:

At Greenbush Financial Group, we emphasize that this is a permanent decision that affects income for life.

Why This Decision Matters So Much

Social Security is one of the only income sources in retirement that is:

• Guaranteed for life

• Adjusted for inflation

• Not impacted by market performance

This makes it a critical foundation for retirement income planning.

When It May Make Sense to Claim at Age 62

Claiming early provides income sooner, but at a reduced level.

Situations Where Age 62 May Make Sense

• You need income to retire

• Health concerns or shorter life expectancy

• You want to preserve investment assets

• You are concerned about future policy changes

Trade-Off

• Lower monthly income for life.

At Greenbush Financial Group, we typically see this strategy used when income needs outweigh long-term maximization.

When Claiming at Full Retirement Age (67) Makes Sense

Full Retirement Age provides your standard benefit without reductions or credits.

Situations Where Age 67 May Make Sense

• You want a balanced approach

• You are still working into your mid-to-late 60s

• You want to avoid early reduction penalties

• You are unsure about delaying further

Key Advantage

• No reduction, no delay risk.

When It Makes Sense to Delay Until Age 70

Delaying increases your benefit through delayed retirement credits.

Benefits of Waiting

• Higher guaranteed monthly income

• Better inflation-adjusted income over time

• Increased survivor benefits for a spouse

Situations Where Age 70 May Make Sense

• You have longevity in your family

• You do not need income immediately

• You want to maximize lifetime income

• You are concerned about outliving your money

• You have significant Tax Deferred Assets to drawdown

At Greenbush Financial Group, delaying to 70 is often one of the most effective ways to increase guaranteed retirement income.

The Break-Even Analysis: When Do You Come Out Ahead?

A common way to evaluate this decision is through a break-even analysis.

General Insight

• Break-even age is often around 78–82

• If you live beyond this range, delaying may result in higher lifetime income

Important Note

This analysis does not account for:

• Taxes

• Investment returns

• Spousal benefits

• Personal spending needs

How Taxes Impact Your Social Security Decision

Your Social Security benefits may be taxable depending on your income.

Key Considerations

• Up to 85% of benefits can be taxable

• IRA withdrawals can increase taxation

• Claiming earlier may reduce taxable income in some scenarios

Planning Strategy

Coordinate Social Security with retirement withdrawals to manage your tax bracket effectively.

Spousal and Survivor Benefit Considerations

Married couples should evaluate this decision together.

Key Rules

• Spouse can receive up to 50% of the higher earner’s benefit

• Survivor receives the higher of the two benefits

Planning Insight

Delaying benefits for the higher earner can increase survivor income significantly.

At Greenbush Financial Group, spousal coordination is often one of the most impactful strategies.

A Simple Decision Framework

Instead of looking for a one-size-fits-all answer, consider these key questions:

Ask Yourself

• Do I need the income now?

• What is my health and life expectancy?

• Do I have other income sources?

• What is my tax situation?

• Am I planning for a spouse or survivor benefit?

Common Mistakes to Avoid

• Claiming early without a plan

• Ignoring spousal benefits

• Focusing only on break-even analysis

• Not considering taxes

• Making the decision in isolation from your full retirement plan

Final Thoughts

There is no universally “correct” age to claim Social Security. The best decision depends on your financial situation, health, and long-term goals.

At Greenbush Financial Group, our analysis shows that integrating Social Security into a broader retirement income and tax strategy leads to better outcomes than focusing on the decision in isolation.

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 better to take Social Security at 62 or 70?
   It depends on your health, income needs, and life expectancy. Delaying increases lifetime income if you live long enough.
2. How much more do you get by waiting until 70?
   About 8% per year after full retirement age, up to age 70.
3. What is the break-even age for Social Security?
   Typically around age 78 to 82.
4. Can I work while collecting Social Security at 62?
   Yes, but your benefits may be reduced if you exceed income limits before full retirement age.
5. What happens if I delay Social Security past 70?
   There is no additional benefit increase after age 70.