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

June 27, 2025
Are You Leaving Your Employer? You Have Six Options For Your Employer Plan Retirement Funds
June 27, 2025
Can IRAs be used to benefit a charity? IRAs can be a great source of funds to provide a benefit fora favorite charity, but using these funds can create a number of traps that must be avoided in order to maximize benefits to both the charity and other IRA beneficiaries. 
By Walter Storholt June 19, 2025
Trusts are often touted as smart estate planning tools, but could they actually reduce taxes for your heirs? In this listener mailbag episode, Frank responds to a question from Roger, who asks whether setting up a trust could help his children save on taxes when inheriting investment accounts.
June 12, 2025
If you've recently been pre-approved for a mortgage, you might be surprised by how much house you technically can buy. But qualifying for a certain loan amount doesn’t always mean it aligns with your financial goals. In today’s episode, Frank answers a listener’s question about whether it might make sense to buy at the top of your budget, or to consider a more measured approach.
By Walter Storholt June 5, 2025
If you’ve switched jobs in the past few years, chances are you’ve got an old 401k sitting somewhere, collecting dust and possibly fees. Today, Frank answers a listener’s question about what to do with old 401ks, when a rollover might make sense, and how to avoid common pitfalls when making the switch.
May 29, 2025
When do multiple beneficiaries exist? Multiple beneficiaries exist when an individual names more than one beneficiary for their IRA. When should you name more than one beneficiary? When you want your IRA assets to go to more than one person or entity without having to incur additional fees or paperwork by maintaining separate accounts for each beneficiary.
May 29, 2025
If I miss the 60-day deadline for completing an IRA rollover, is there any way to save the rollover amount from tax? Failing to complete a 60-day rollover on time can cause the rollover amount to be taxed as income and perhaps subject to a 10% early withdrawal penalty. However, the deadline may have been missed due to reasons that are not the taxpayer’s fault. Fortunately, for such cases, the IRS has created an easy, low-cost way to fix late rollover errors. Revenue Procedure 2016-47 enables individuals to self-certify that they are eligible for a waiver of the 60-day deadline and complete a late rollover
By Walter Storholt May 29, 2025
Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and worries for the economy amidst recent news. What if you’ve had 2025 marked on the calendar for a while as the year you plan to retire? Is this a bad time to do it?
May 22, 2025
Market volatility has a way of shaking confidence. It's easy to feel uncertain, but reacting without a plan could do more harm than the drop itself. In this special mailbag episode, Frank tackles timely listener questions about navigating today’s uncertain market.
May 15, 2025
When the market is volatile, it's easy to feel like you're the only one who's ever felt this anxious. But some of the greatest investors in history have lived through chaos, and they left behind wisdom that still applies today. In this episode, Frank turns to voices like Warren Buffett, Benjamin Graham, and Jack Bogle to remind us how to stay grounded when everything feels uncertain.
Show More