Retirement Savings – Ramp Up to Retirement

What Your Parents’ Retirement Can Teach You About Planning Your Own (Ep. 38)

By Ramp Up to Retirement | September 23, 2026

Your parents’ retirement experience can reveal lessons that are difficult to see while you’re still working. What has changed between their generation and yours, and which financial habits still hold up?

In this episode, Dan Reese, CFP®, explains how retirement planning has changed across generations and what you can learn by asking your parents thoughtful questions. He covers the shift from pensions to personal savings, the healthcare gap before Medicare, longer life expectancies, lifestyle creep, and the possibility of retiring earlier than planned. Dan also shares ways families can talk about money without making the discussion feel intrusive.

Key points:

Why testing your retirement plan against leaving work at 62 can help you prepare for an earlier-than-expected retirement
How the shift from pensions to 401(k)s places more responsibility on your personal retirement savings
Why Medicare premiums, supplemental coverage, and long-term care need separate consideration in retirement
How lifestyle creep can raise the amount of income you’ll eventually need to replace after leaving work
Questions you can ask your parents about retirement without starting with account balances or net worth
And more!

Resources:

Carson Wealth Retirement Readiness Quiz

Connect with Dan Reese CFP®:

Podcast: Play in new window | Download | Embed

Subscribe: Apple Podcasts | RSS | More

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!