Retirement shouldn’t be about spreadsheets. It should be about pickleball at 10am on a Tuesday.

But enjoying that freedom starts with knowing the answer to one question:

Am I ready to retire?

It is one of the most common questions we hear from clients and is also one of the hardest to answer with a simple yes or no.

Closely followed by two others:

• Will I run out of money?

• What kind of returns should I realistically expect?

These questions come up whether you are five years from retirement or already there. They also tend to show up together, because retirement planning is not just about hitting a number. It is about understanding risk, income, and how your money needs to function once your paycheck stops.

In this client Q&A, we break down how to think about retirement readiness, how much risk makes sense, and how to set realistic expectations for investment returns without guessing or chasing what someone else is doing.

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Q: Am I On Track for Retirement?

This is a big question, and it is a loaded one. Am I Ready to Retire?

There are a lot of moving parts, which is why blanket rules and online calculators often miss the mark.

That said, there is a simple way to get a back-of-the-napkin answer that gets you most of the way there.

Start With Your Lifestyle, Not a Formula

You will often hear that people spend less in retirement. In reality, that is not always true.

What we typically see is this:

• Early retirement spending is often the same or higher

• Travel increases

• Deferred experiences finally happen

• Time, not money, becomes the constraint

Because of that, a good starting point is your current spending, not what someone says you should spend in retirement.

Look at what you actually spend on:

• Housing

• Food

• Travel

• Utilities

• Transportation

• Entertainment

• Insurance

• Everything that supports the life you want

It is usually best to look at this over a full year, since some months are naturally higher than others. December might look very different than April. Summer might be more expensive than winter. What matters is the average.

Savings contributions are different. If you are actively saving into a 401(k), Roth IRA, or HSA, those contributions can usually be removed from your retirement spending estimate.

What remains is a realistic picture of what it costs to live your life.

Identify Income That Comes In Automatically

Once you know what you spend, the next step is to identify income that comes in without you working.

Start with the basics:

• Social Security

• Pension income, if applicable

• Rental income or other passive income streams

Add up everything that shows up consistently without you having to lift a finger.

At this point, you should have two numbers:

1. What you spend

2. What comes in automatically

If income exceeds spending, you are already in a strong position. If there is a gap, that gap needs to be filled by your investment portfolio.

Using the 4 Percent Rule as a Reality Check

This is where retirement accounts come into play.

IRAs, 401(k)s, brokerage accounts, and other invested assets are typically used to fill the gap between spending and guaranteed income.

A commonly used guideline here is the 4 percent rule.

The idea is simple:

• Take the total value of your investment assets

• Multiply by 4 percent

• That is a reasonable annual withdrawal amount that historically has kept pace with inflation

This is not perfect math. It is not a guarantee. But it does get you close enough to answer the question: Am I ready to retire?

For example:

• $1,000,000 x 4 percent = $40,000 per year

• Combine that with Social Security and other income

• Compare it to your annual spending

If the numbers line up, you are likely on track.

If they do not, something has to change:

• Save more

• Spend less

• Work longer

• Adjust expectations

There is no judgment in that. It is simply math.

Q: Will I Run Out of Money?

This is the biggest fear most people have going into retirement. And it is not one that disappears just because someone explains it to you.

In many cases, the fear only fades once you actually live through retirement and see that the plan works.

Why This Fear Exists

When you are working, income feels unlimited. You may change jobs, get raises, or work longer if needed.

When you retire, that changes.

Your income is no longer tied to your effort, and that psychological shift is significant. You are moving from accumulation to distribution, and that transition can be uncomfortable.

Expenses can still be unpredictable. Medical costs, inflation, and market volatility all add uncertainty.

That is why risk management matters so much in retirement.

The Risk Most Retirees Take Without Realizing It

One of the most common mistakes we see is retirees taking more risk than they actually need to.

Often this happens because:

• Friends are doing it

• Headlines are loud

• Recent returns look impressive

• The market has been strong

• FOMO

When you are working, market swings matter less. If the market drops 30 percent and you are still earning a paycheck, you are not forced to sell investments at a bad time.

In retirement, that changes.

If you need to pull income from your portfolio and the market is down, you may be forced to sell at exactly the wrong moment. That can permanently damage a retirement plan.

Sometimes, when the game is already won, you do not need to keep playing aggressively. You may not need to dominate. You may simply need to avoid losing.

That shift in mindset is critical.

Playing to Win vs Playing Not to Lose

This is where retirement planning becomes personal.

If your biggest fear is running out of money, then your portfolio should reflect that. That often means being more conservative than you were during your working years.

If your biggest goal is maximizing growth and you have more flexibility, you may be able to take more risk.

Neither approach is inherently right or wrong. What matters is that your investment strategy matches:

• Your goals

• Your income needs

• Your tolerance for volatility

• Your actual situation, not someone else’s

Old rules like “your age equals your bond allocation” are outdated. Retirement planning today needs to be far more individualized.

Q: What Returns Should I Expect?

This is another question that we get when someone asks “Am I Ready to Retire?” is “What Returns should I expect” This often gets oversimplified.

Returns depend entirely on what you are invested in.

Stocks

For a diversified stock portfolio, long-term expectations in the range of 8 to 12 percent are reasonable. That comes with volatility, sometimes significant volatility.

Fixed Income

Fixed income investments like bonds, CDs, and Treasuries are designed for stability and income, not growth.

In recent years, expected returns here have been much lower, often in the 3 to 5 percent range.

The trade-off is reduced volatility and more predictable cash flow.

Why Comparisons Matter

One of the biggest mistakes investors make is comparing apples to oranges.

Stocks should be compared to stocks. Bonds should be compared to bonds.

If an equity-heavy portfolio is averaging 5 percent over a long period, that may be a red flag. If a conservative, income-focused portfolio is doing the same, it may be completely appropriate.

Context matters.

Understanding Alternative Investments and Liquidity

Alternatives include investments that are not traditional stocks, bonds, ETFs, or cash. Examples include:

• Private equity

• Private credit

• Real estate

The biggest thing you give up with alternatives is liquidity.

If you own a publicly traded stock, you can sell it and have cash quickly.

With alternatives:

• Money may be locked up for years

• Access may be limited to quarterly windows

• Redemptions may be capped or delayed

Because of that, you should expect higher returns in exchange for giving up liquidity.

As a general guideline:

• Private equity often targets higher returns than public markets

• Private credit should pay more than traditional fixed income

• If an illiquid investment offers the same return as a liquid one, the liquid option usually makes more sense

Liquidity is flexibility, and flexibility matters in retirement.

Why Most Advisors Focus on Diversification, Not Beating the Market

Data consistently shows that most active managers do not outperform the market over long periods.

That does not mean advisors have no value. It means their value lies in:

• Portfolio construction

• Risk management

• Behavioral coaching

• Planning integration

The goal is not to win every year. The goal is to build a portfolio that supports your life and holds up across different market environments.

Am I Ready To Retire? The Bottom Line

Retirement readiness is not about a single number or a perfect return. When you ask yourself “Am I ready to retire?” remember:

It is about alignment.

• Does your income support your lifestyle?

• Does your risk match your goals?

• Are your expectations realistic?

• Is your portfolio built for the phase of life you are in?

If you can answer those questions honestly, you are already ahead of most people.

And if you cannot, that is where thoughtful planning comes in.

If you have questions about your own situation, we are always happy to talk through it with you one-on-one. Schedule a call today!

Retirement planning is one of the most important financial transitions you will ever navigate. It is also one of the most misunderstood. People spend decades saving money in different accounts, following rules, avoiding mistakes, and trying to do “the right thing,” but once retirement approaches, a new wave of questions always shows up.

When should I take money out?
Should I convert to a Roth?
Will I be penalized?
How much will taxes take?
How do I actually get paid when I retire?

These are not small questions. They are real concerns for real people who want to retire confidently, avoid surprises, and feel like the years of hard work were worth it.

In this extended Q&A guide, we break down the most common questions we hear from clients who are planning for retirement. Everything is based directly on real conversations, real scenarios, and real planning strategies that actually work.

Grab a coffee, settle in, and let’s dive in.

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Retirement Questions We Hear Most Often from Clients

Q: What exactly is a Roth conversion, and when does it make sense?

A:  Roth conversion is the process of taking money from an account that grows tax deferred, like a traditional IRA or traditional 401k, and moving it into a Roth IRA. After it moves, the money grows tax free.

To convert it, you pay ordinary income tax on whatever amount you move over. There is no penalty, but the conversion itself counts as taxable income.

So when does it make sense?

For many people, the sweet spot tends to be around the mid fifties to early sixties. That time period is often ideal for three reasons.

First, you have a long time horizon before age 73 or 75, which is when Required Minimum Distributions begin. Once RMDs begin, the government forces you to take out a percentage of your IRA each year, whether you need the money or not. This can push people into higher tax brackets later in life.

Second, in these years you are often in control of your income. You might have retired early, switched careers, slowed down, or otherwise entered a stage where your taxable income is lower than it will be in your seventies. Lower income means lower tax cost for the conversion.

Third, Medicare has not begun yet. Once you turn 65, your Medicare premiums can increase based on your income. This is called IRMAA, which stands for Income Related Monthly Adjustment Amount. A big Roth conversion after age 65 can cause a spike in your premiums two years later due to the Medicare lookback rule. Doing conversions before you hit Medicare avoids a lot of that stress.

For someone in their mid fifties to early sixties who has not yet started Medicare and who has a window of lower income, a Roth conversion can be incredibly smart.

Q: Why do people get surprised by taxes in retirement?

A: There is a common belief that you will be in a lower tax bracket when you retire. It sounds reasonable. You are no longer working. You are not earning a full salary. Your expenses might be lower.

But for a lot of people, that is not what actually happens.

People often enter retirement with seven figure IRAs, real estate income, Social Security, pensions, interest income, and dividends. Once RMDs begin at 73 or 75, they are required to pull out a large chunk of money each year and pay taxes on it. Combined with other sources of income, this sometimes pushes retirees into the same or even higher tax brackets than they were in during their working years.

This is the opposite of what many people were told when they first started contributing to their IRAs decades ago. Back then, the message was simple. Save pre tax money now, enjoy a deduction today, and pay lower taxes in retirement.

For many high income professionals, business owners, and diligent savers with strong investment portfolios, that message simply did not play out as promised.

This is why Roth conversions have become such a powerful planning strategy. They help you control the tax impact before RMDs begin. This gives you more freedom later.

Q: How do Roth conversions affect Medicare?

A: This is a very common retirement question and a very important one.  Medicare premiums are influenced by your income. The higher your income, the more you pay. This is what IRMAA refers to.

Here is the catch. Medicare looks back two years at your income. That means if you do a Roth conversion at age 67, Medicare will look back to your income from age 65 and adjust your premiums.

Clients are often surprised by this. They retire, believe their income will drop, and then suddenly their Medicare premiums jump by two hundred or three hundred dollars a month. That adds up quickly.

This is why doing conversions before 65 can be very helpful. It completely avoids IRMAA and ensures you do not get surprised once Medicare starts.

For people already on Medicare, conversions may still make sense, but it depends heavily on your cash flow, tolerance for temporarily higher premiums, and long term goals. It requires thoughtful planning and precise math.

Q: Can a poorly timed Roth conversion push me into a higher tax bracket?

A: Absolutely. This is one of the biggest risks.

If you are in the 32 percent bracket, for example, and you convert too much, you may cross into the 35 percent bracket. That means the portion of your conversion that crosses the line gets taxed at a higher rate. That is usually not ideal.

The goal with Roth conversions is to fill your tax bracket, not blow past it. Think of it like carefully filling a bucket of water. You want to stop right before it spills over the edge.

This is why end of year planning is so important. By November or December, you know your income for the year. You know where your tax bracket will land. At that point, you can decide exactly how much room you have left to convert without going into a higher bracket.

That kind of intentional planning can save thousands of dollars.

Q: Should I contribute to a Roth 401k or a traditional 401k?

A: This is another very common retirement question.

Most employers now offer a Roth option inside their 401k, although some still do not. The main difference is this:

A traditional 401k uses pre tax dollars. This lowers your taxable income for the year. The money grows tax deferred. You pay taxes when you take it out later in life.

A Roth 401k uses after tax dollars. You do not get a deduction this year. The money grows tax free. Withdrawals are tax free in retirement.

So which one is better?

For many people, especially younger individuals or anyone in their thirties, forties, or even early fifties, the Roth 401k is incredibly attractive. You are likely in a lower tax bracket right now than you will be later in life. You also get decades of tax free growth.

For high income earners, the Roth 401k is also powerful because there are no income limits. Even if you earn too much to contribute to a traditional Roth IRA, you can still contribute to a Roth 401k through your employer plan. The contribution limits are much higher as well.

The only time a traditional 401k may make more sense is when cash flow is very tight. Because Roth contributions are after tax, they can slightly reduce take home pay compared to traditional contributions. If that reduction causes stress or prevents someone from saving at all, then a traditional 401k is the better fit.

You can also split your contributions. Many people do a 50 50 split so they can enjoy some tax savings now while also building tax free money for later.

Q: If I retire, how do I actually get my money?

A: This might be the most common question we hear from new retirees. For decades, clients have received a paycheck on a set schedule. Money shows up in the bank account like clockwork. Bills get paid. Life stays predictable.

Once you retire, the paycheck stops. That is understandably unsettling.

So how do you replace it?

Here is how we coach clients through this transition.

We recreate the paycheck.

We set up an automatic ACH transfer from your investment accounts to your bank account. You choose how often you want to be paid. Weekly, twice a month, monthly. You choose the amount. It might be five thousand dollars. It might be twenty thousand dollars. Whatever fits your lifestyle and plan.

The money flows in on a schedule that feels familiar. Your bills get covered. Your life continues smoothly.

Behind the scenes, the investments fund this income stream. Sometimes the money comes from interest on bonds or private credit. Sometimes it comes from dividends. Other times we sell a small portion of investments that have grown well.

This is where a diversified portfolio becomes very important. Markets rise and fall. Some investments might be down while others are up. A diversified strategy gives us choices. If stocks are down, we can pull from income producing investments instead of selling at a low. If stocks are up, we might trim gains.

Once retirees experience this system, the anxiety usually fades. The predictability of the paycheck returns. The only difference is that you are now the one paying yourself from your own money.

It is empowering once you become comfortable with it.

Q: What if I want six months of income upfront instead of monthly payments?

A: Some people believe they would prefer to take several months of income at once. Maybe ten thousand dollars a month feels uncomfortable, so they want sixty thousand dollars all at once.

What we have consistently seen is that this approach creates more stress, not less.

Large withdrawals make bank balances rise and fall dramatically. People begin worrying about calling for more money. They wonder if it is a good time in the market. They hesitate because the number in their investment account drops. They wait too long. Then they need another large withdrawal. Then they worry again. The cycle repeats.

A regular monthly income smooths all of that out. It recreates the working life rhythm people are used to. It keeps anxiety lower. It keeps planning simple.

There is no need to constantly ask for money, question timing, or wonder whether you are making a mistake. The system runs automatically.

Q: What role does diversification play in retirement income?

A: Diversification is the quiet workhorse of a good retirement plan. You want assets that move in different ways so you are not forced to pull money from something that is temporarily down.

When the market is strong, you may use gains from equities to fund your monthly income. When the market is weak or volatile, you may rely more on interest from bonds, CDs, private credit, or dividend paying investments.

Diversification protects you from making the worst possible mistake, which is selling something at a loss just to free up cash for living expenses. A well built portfolio gives you options at any point in time.

It keeps your long term plan intact even when short term conditions are unpredictable.

Q: How do I know how much I can safely take out in retirement?

A: This is one of the biggest fears retirees face. No matter how much money someone has, the thought is often the same.

Will I run out?
Will we be okay?
Will our lifestyle hold up?

This is incredibly common and completely normal.

The goal of retirement planning is to run the numbers ahead of time. We assess income sources, pension amounts, Social Security timing, investment balances, medical costs, spending patterns, and inflation. We create scenarios for normal markets, good markets, and difficult markets.

When clients see the full picture, confidence increases. The fear begins to fade. They understand how their income gets funded, why it is sustainable, and what guardrails are in place.

Retirement becomes less about worry and more about living.

Q: Is retirement income planning really that personal?

A: Yes. Retirement planning is not one size fits all. It is shaped by your income, your tax bracket, your assets, your health, your values, your spending habits, and your vision for life after work.

Two people with the exact same portfolio balance can have completely different answers to every question on this list.

This is why running the numbers matters. This is why understanding RMDs, Roth conversions, income timing, tax brackets, and Medicare impacts is so important.

Guidance based on general rules is helpful, but guidance based on your exact situation is powerful.

Q: What is the most important takeaway from all of this?

A: Retirement planning is all about timing and strategy. Small decisions made years before retirement can have a massive impact later. It is good to start asking your retiement questiosns as early as possible.

Knowing when to convert, when to save, how to file, when to claim Social Security, and how to structure your income matters more than most people realize.

With the right plan, retirement becomes clear, predictable, and surprisingly simple. Without a plan, retirement becomes a maze of questions, penalties, tax bills, and surprises that could have been avoided.

A good plan builds confidence. A great plan builds freedom.

Final Thoughts

These are the retirement questions people ask us every day. They are real concerns from hardworking people who simply want to retire with clarity.

If you have similar questions and want to run your own numbers, explore scenarios, or create a retirement income plan that actually fits your life, reach out to us today. We help people walk into retirement with confidence, not confusion.

And as always, if this guide was helpful, feel free to share it with someone who might benefit.