Questions We Hear Most

Retirement, taxes, and investing raise a lot of questions. Here are answers to some of the most common ones.

Retirement, Investing & Planning

How we think about retirement income, taxes, investing, and estate planning, and what goes into a plan built around you.”

  • A Roth conversion can be a useful planning tool in the right circumstances, but it creates taxable income in the year of conversion. We would evaluate today’s tax cost against potential future benefits and consider other income, tax brackets, Medicare implications, required distributions, and estate goals.

  • We prefer to ask, “How can we manage taxes over your entire retirement?” Paying the least tax possible this year is not necessarily the same as having an effective long-term tax strategy. Sometimes intentionally recognizing income today may create greater flexibility later. That is why we believe tax planning and retirement planning belong in the same conversation.

  • That period can present planning opportunities for some people, but conversions should not be automatic. We would model the potential tax cost and evaluate how a conversion interacts with the rest of the plan.

  • It depends heavily on what you are leaving them. Traditional IRAs, Roth accounts, taxable investments, real estate, insurance, and trust assets can have very different tax and estate consequences. We believe the estate attorney, tax professional, and financial advisor should be working from the same overall plan.

  • The purpose of your portfolio may begin changing. During your working years, the emphasis is often on accumulation. In retirement, the portfolio may also need to provide income, maintain liquidity, manage risk, address inflation, and potentially provide assets for a surviving spouse or heirs. That transition deserves careful planning.

  • Taxes should be part of the investment conversation. The type of investment matters, but so does where it is held. Taxable accounts, traditional retirement accounts, and Roth accounts are treated differently. Coordinating those accounts may create planning opportunities.

  • Sometimes they may be appropriate, and sometimes they may not. We do not believe the conversation should begin with the product. It should begin with the problem you are trying to solve. If guaranteed income, longevity risk, principal protection, or another objective is important, an annuity may be worth evaluating alongside other alternatives. Guarantees are subject to the claims-paying ability of the issuing insurance company.

  • We do not think the answer should come from a rule of thumb. We want to understand what retirement looks like to you, what it will cost, what reliable income you will have, what assets will support you, what taxes may look like, how the plan responds during difficult markets, and what happens if you or your spouse lives into your 90s. Only then can we begin evaluating whether your resources reasonably support the retirement you envision.

  • The answer is not automatically age 62, Full Retirement Age, or age 70. We consider life expectancy, marital status, other income, taxes, employment, survivor benefits, cash flow, health considerations and the role Social Security plays within your overall retirement plan.

  • We believe it should be part of the conversation. Your financial plan may help you accumulate and preserve assets, while your estate plan helps determine what happens to those assets if you become incapacitated or after your death. Beneficiary designations, trusts, wills, powers of attorney, taxes, and investment accounts should be coordinated.

  • For us, retirement planning is not simply about accumulating the most money. It is about helping you understand what your resources may allow you to do, identifying the risks that could affect your plan, and creating a strategy designed around the life you worked so hard to build.

For educational purposes only. This material is not individualized investment, tax or legal advice. Individual circumstances vary. Investing involves risk, including possible loss of principal.

Tax Basics

General answers to common tax questions. Your situation may differ, so check with a tax professional before making decisions.

  • Most people who earn income during the year may need to file a tax return. Whether you are required to file depends on factors such as your income, filing status, age, and type of income. Even if you aren’t required to file, you may want to file if taxes were withheld from your paycheck and you may be entitled to a refund.

  • Common documents include your W-2s, 1099s, Social Security information, mortgage interest statements, student loan interest statements, and records of deductible expenses or tax credits. The documents you need depend on your individual situation.

  • A tax credit is often preferable to a tax deduction, but it can depend on the eligibility requirements of each deduction and credit. Tax credits reduce your tax liability dollar-for-dollar, while tax deductions lower your taxable income. For example, if you prepare your taxes and have a total tax bill of $10,000, a $1,000 tax credit would reduce your bill by that amount.

    If you have a $1,000 tax deduction and earned $50,000 in taxable income, your income tax liability wouldn’t decrease by $1,000. Instead, your taxable income would now be $49,000. So, a $1,000 tax deduction can save anywhere from $0 to $370, depending on your tax bracket. Compare this to the $1,000 tax reduction you could get from a $1,000 tax credit.

  • The taxes withheld from your paycheck are generally payments toward your eventual tax bill, not necessarily the exact amount you will owe. If too little was withheld during the year, you may owe additional tax when you file. If too much was withheld, you may receive a refund.

  • In 2026, the Standard Deduction comes to $16,100 for Single taxpayers and $32,200 for Married Filing Jointly taxpayers. For taxpayers age 65 and over, the standard deduction is $18,150 for Single filers and $35,500 for Married Filing Jointly filers. You should calculate your itemized deductions and compare them to the Standard Deduction each year to get the most out of the tax savings available to you.

  • Your refund depends on the difference between the taxes you paid or had withheld and your final tax liability, along with any applicable deductions and credits. Changes in your income, withholding, filing status, dependents, or tax credits can cause your refund to be different from previous years.

  • Common possibilities include the standard deduction, charitable contributions, certain education expenses, retirement contributions, child-related credits, and certain business expenses. Eligibility depends on your specific circumstances, and not every deduction or credit applies to everyone.

  • Generally, yes. Income from freelancing, gig work, consulting, online sales, or other side work may need to be reported on your tax return. Self-employed individuals may also have additional tax obligations, including self-employment tax and potentially estimated tax payments.

  • Each year, the IRS lets you deduct unreimbursed expenses for qualifying medical expenses. The qualified expenses should exceed 7.5% of your adjusted gross income (AGI). Qualifying expenses can include:

    • Preventative care

    • Medical treatments

    • Surgeries

    • Dental and vision care

    • Psychologist and psychiatrist visits

    • Prescription medications

    • Prescription appliances (such as glasses or contacts, false teeth, or hearing aids)

    • Travel expenses paid to receive this medical care (mileage, bus fare, and parking fees)

    How much you can actually deduct depends on several factors. It’s primarily dependent on your income and whether you itemize your deductions or take the standard deduction.

    For example, if your income is $100,000 and you itemize your deductions, you can deduct any unreimbursed medical expenses in excess of 7.5% of your income. That means you could deduct any unreimbursed expenses that exceed $7,500 (7.5% of $100,000). So, if you had $10,000 in unreimbursed qualifying medical expenses, you can include $2,500 ($10,000 - $7,500) in your itemized deductions.

  • If you owe taxes but can’t pay the full amount, you may have options such as an IRS payment plan or other collection alternatives, depending on your circumstances. Filing your return on time can still be important even if you cannot immediately pay the full amount.

  • The tax code provides several ways to control your tax bill through tax adjustments, deductions, and credits. Tax deductions allow you to reduce your taxable income, and tax credits allow you to directly reduce your tax liability.

    When you earn income from a job, you can often reduce your taxable income by contributing to an employer-sponsored retirement plan such as a 401(k) or your own individual retirement account (IRA). You may also have a high-deductible health plan through your employer with access to a health savings account (HSA) or flexible spending account (FSA).

    All of these accounts allow you to contribute pretax dollars to invest or hold in cash for saving or for certain expenses. As a result, these contributions lower your taxable income and save you money on your tax bill.

    If you have dependents, you may qualify for the Child Tax Credit, a partially refundable credit meant to lower the cost of raising a child. This credit, worth up to $2,200 for each qualifying child for 2025, lowers your tax bill dollar for dollar. And there’s the Child and Dependent Care Credit that can provide a credit of up to $2,100 in 2025 for qualifying expenses for taking care of your dependents so that you can work or look for work.