Retirement Questions That Baby Boomers & Gen X Are Asking
Retirement Questions That Baby Boomers & Gen X Are Asking
May 2, 2024

Each generation is currently navigating a unique part of the retirement planning experience. With many baby boomers preparing for the transition into retirement and Generation X starting to think more about their retirement savings, these major life events come with a handful of financial planning questions.

Each generation is currently navigating a unique part of the retirement planning experience. With many baby boomers preparing for the transition into retirement and Generation X starting to think more about their retirement savings, these major life events come with a handful of financial planning questions. In today’s episode, we’ll focus on some of the common questions that these age groups are asking.


While there’s no universal solution to these questions, this episode will provide some important considerations to keep in mind. As Frank and Walter express in this episode, it’s important to address these kinds of questions early on and get a plan in place so that you can step into retirement with confidence.


Be sure to stay tuned until the end of the episode, where Frank answers a listener's question about whether or not to take out a life insurance policy.


Here’s some of what we discuss in this episode:

0:00 – Intro

2:53 – Important considerations 5 years before retirement

7:31 – Downsizing or relocating in retirement

10:15 – Gen Xers seeking professional help

14:03 – Wanting to retire early

17:36 – Getting to know Frank

20:43 – Listener question


Subscribe & follow the show for free on your favorite apps:

Helpful Resources:

Learn more about the T.I.M.E. planning process by clicking here.


You can also schedule a free planning session with Frank Oliver and the team by clicking here.

Get your copy of Frank's book!

January 22, 2026
Why do you need a tax professional? Managing taxes during retirement will be the single most important factor in determining your ultimate lifestyle. In addition to a financial planner and estate planning attorney, a qualified tax professional is an integral part of any planning team.
January 22, 2026
New Rules Are Here. On July 18, 2024, the IRS issued both final regulations under the 2020 SECURE Act and proposed regulations under the SECURE 2.0 Act of 2022. These long-awaited new regulations impact many parts of the required minimum distribution (RMD) rules for retirement accounts. The final regulations are effective for 2026, and the proposed regulations can be used immediately as guidance. Here are the highlights:
December 22, 2025
What is considered investment income? Investment Income: Interest, dividends, capital gains (long and short), annuities (not those in IRAs or company plans), royalty income, passive rental income, other passive activity income. NOT Investment Income: Wages and self-employment income, active trade/business income, distributions from IRAs, Roth IRAs and employer plans, excluded gain from the sale of a principal residence, municipal bond interest, proceeds of life insurance policies, veterans’ benefits, Social Security benefits, gains on the sale of an active interest in a partnership or S corporation.
December 22, 2025
What is a 60-day rollover? What is a 60-day rollover? A 60-day rollover is the distribution of funds from a qualifying retirement account payable to the account owner who then has 60 days to redeposit the funds into another qualifying retirement account.
By Walter Storholt December 4, 2025
You’ve probably heard the saying, “There’s no such thing as a bad question.” But in retirement planning, the way you frame your question often determines the quality of your answer. In this episode, we’ll share some common retirement questions, and how a simple reframing might lead to a more useful answer.
December 1, 2025
It is important for you to take an active role in your retirement planning. Life changes and events happen that require you to update your tax and estate plans. Use the information below to see how your planning might be affected. As you can see, many items require you to take action now.
December 1, 2025
This year...
October 30, 2025
Would you rather have a million dollars today, or a magic penny that doubles every day for 30 days?
October 30, 2025
Planning for Health Savings Account (HSA)Distributions in 5 Easy Steps. A health savings account is a tax-advantaged medical savings account that helps people pay for qualified out-of-pocket medical expenses. What are the withdrawal rules for HSAs? Are there special considerations that must be taken into account?
By Walter Storholt October 30, 2025
Today, Frank tackles a listener’s question about whether splitting money between multiple advisors could be beneficial or just create more confusion.
Show More