Retirement Income – Ramp Up to Retirement

Roth vs. Pre-Tax 401(k): Choosing When to Pay Taxes for Retirement (Ep. 37)

By Ramp Up to Retirement | September 9, 2026

Choosing between Roth and pre-tax retirement savings can feel simple until taxes, healthcare costs, income changes, and future withdrawals enter the picture.

In this episode, Dan Reese, CFP®, explains how Roth and pre-tax 401(k) contributions affect when you pay taxes and why the more appropriate choice may change throughout your career. He covers why lower-income years may favor Roth contributions, when pre-tax savings may become useful, and how Roth assets can provide added flexibility in retirement.

Dan also explores employer matches, Roth IRAs, contribution limits, healthcare subsidies, Medicare premiums, inherited accounts, and the value of reviewing your savings strategy as your income and circumstances change.

Key points:

How Roth and pre-tax 401(k) contributions determine when taxes are paid on your retirement savings
Why lower tax rates early in a career can make Roth contributions worth considering for younger savers
How promotions, career changes, business income and changing household income can affect your savings choice
How Roth savings may provide flexibility when managing taxable income, healthcare-related costs and tax brackets during retirement
How Roth IRAs and Roth 401(k)s differ, and what to know about employer matching contributions
And more!

Resources:

Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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When Should You Claim Social Security? (Ep. 36)

By Ramp Up to Retirement | August 26, 2026

When should you claim Social Security, at 62, full retirement age, or 70?

The answer can affect more than your first monthly payment, including your future income, taxes, portfolio withdrawals, and the benefit available to a surviving spouse.

In this episode, Dan Reese, CFP®, explains how Social Security benefits differ when claimed at age 62, full retirement age, or age 70. He examines break-even calculations, annual cost-of-living adjustments, life expectancy, earnings limits, and household claiming decisions. Dan also explains how delaying benefits may create room for Roth conversions, change portfolio withdrawals, and support a surviving spouse.

Key points:

How claiming at 62, 67, or 70 can produce significantly different monthly Social Security payments
Why cost-of-living increases compound differently when your starting Social Security benefit is higher
When health, longevity, income needs, and other retirement resources may influence your claiming age
How delaying Social Security may create additional time for Roth conversions and lower taxable income
Why couples should consider survivor income before either spouse begins receiving Social Security
And more!

This is not intended to provide specific legal, tax, or other professional advice. For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Converting from a traditional IRA to a Roth IRA is a taxable event.

Resources:

Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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Do Roth Conversions Still Make Sense After Tax Law Changes? (Ep. 35)

By Ramp Up to Retirement | August 12, 2026

If you’re approaching retirement with a large traditional IRA, deciding whether to convert to a Roth account can affect your future taxes, Medicare costs, and what your heirs receive.

How do taxes, Medicare costs, retirement income, and estate planning all connect when making this decision? The right decision depends on your situation, not just what tax rates are doing.

In this episode, Dan Reese, CFP®, explains how recent tax law changes have shifted the reasons people may evaluate Roth conversions as part of their retirement planning. He shares how Roth conversions can affect retirement taxes, future required distributions, and the assets passed to heirs. Dan also explains how reviewing your current financial picture, evaluating different tax-bracket scenarios, and coordinating with financial and tax professionals can help clarify the potential trade-offs.

Key points:

How Roth conversions can affect retirement taxes, Medicare premiums, and future financial decisions
Why recent tax law changes changed the reasons many people consider Roth conversions
How inherited retirement accounts can create tax concerns for the next generation
Why spreading conversions across multiple years may help manage tax brackets
How financial planning connects taxes, income, investments, and estate decisions
And more!

This information is not intended to provide specific legal, tax, or other professional advice. For a comprehensive review of your personal situation, always consult with a tax or legal advisor. Converting from a traditional IRA to a Roth IRA is a taxable event.

Resources:

Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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How to Know If Your Financial Advisor Is Really Helping You Plan for Retirement (Ep. 34)

By Ramp Up to Retirement | July 22, 2026

Are you getting financial advice, or are you simply getting investment updates?

Many people build strong relationships with their financial advisor, but that doesn’t always mean every part of their retirement plan is being addressed. Knowing what questions to ask can make a meaningful difference before small planning gaps become bigger problems.

In this episode, Dan Reese, CFP®, explains how to evaluate whether your financial plan is covering the areas that matter most. He shares the 3-lane planning framework, covering investments, retirement income, and tax planning, and discusses how Social Security, Medicare, estate planning, and long-term tax decisions work together. Dan also explains why planning performance often matters just as much as investment performance when preparing for retirement.

Key takeaways:

How fiduciary advice differs from investment-focused conversations and why that distinction matters
Why retirement income, tax planning, and investments should work together instead of separately
Questions to ask when evaluating whether your advisor is addressing your complete financial plan
How Social Security and Roth conversion decisions can influence lifetime retirement taxes
Why planning performance may have a greater financial impact than investment returns alone
And more!

Converting from a traditional IRA to a Roth IRA is a taxable event.

Resources:

Connect with Dan Reese CFP®:

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Tax-Focused Estate Planning Before Retirement (Ep. 33)

By Ramp Up to Retirement | July 8, 2026

Estate planning is often treated as a task to complete later, but many of the biggest financial decisions begin long before legal documents are signed.

How can tax planning, retirement income planning, and investment decisions work together to support your long-term goals while potentially improving how assets are transferred?

In this episode, Dan Reese explains why estate planning is much more than wills and legal paperwork. He shares how investment planning, retirement income planning, and tax planning all influence one another through what he calls the three lanes of the financial highway. Dan also explores how Roth conversions, beneficiary designations, charitable giving, and account positioning can affect taxes during retirement and for future generations.

Throughout the conversation, he emphasizes creating a coordinated strategy while there may still be more planning flexibility.

Key takeaways:

How investment, retirement income, and tax planning work together instead of as separate decisions
Why estate planning begins with strategy before legal documents are created and updated
How Roth conversions may influence taxes paid by both retirees and future beneficiaries
Why beneficiary designations and asset location can change long term tax outcomes
How coordinated planning may uncover opportunities across multiple financial decisions
And more!

Resources:

Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

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You’ve Retired. Now What? The Hardest Financial Shift You’ll Ever Make (Ep. 16)

By Ramp Up to Retirement | August 27, 2025

Most people think the hard part is saving for retirement, but the real challenge begins when the paychecks stop.

Dan Reese walks through the crucial mental and financial shift from accumulation to decumulation and why so many retirees get it wrong. From tax surprises and market volatility to emotional roadblocks and overlooked estate planning, Dan breaks down the common pitfalls and shares what it takes to create a truly sustainable income plan.

You’ll learn how to map out long-term tax liabilities, balance guaranteed vs. variable income, and build financial confidence in retirement.

What to expect in this episode:

The #1 mistake retirees make when “flipping the switch”
How market downturns affect withdrawals differently from contributions
Why tax surprises can be more common (and dangerous) in retirement
How to align spending, legacy goals, and income with confidence
And more!