The ‘How Do You Know’ Questions of Retirement Planning
The ‘How Do You Know’ Questions of Retirement Planning
September 17, 2024
September 17, 2024

Were you ever the kid growing up that had to ask, “how do you know?” or “why?” about anything and everything? Turns out, having that inquisitive nature is something that can be extremely valuable to us as we plan out our finances and our retirements, and in today’s show, we’ll dive into some of those questions that you should be asking as you approach your retirement.

Having answers to these critical questions will help you achieve effective retirement planning. From understanding how much income you'll need to navigating the complexities of Social Security benefits, Frank talks through the different strategies and advice that can help people make informed decisions. Tune in for a blend of financial wisdom and personal stories, including a discussion on recent wildfires and a fun debate on camping versus beach vacations.



Here’s what we discuss in this episode:

0:00 – Intro

4:19 – Knowing how much income you need to retire. 

7:55 – How to know when you are financially ready to retire.

9:22 – What about annuities?

11:51 – When to start taking social security benefits.

15:10 – Camping or the beach?

17:21 – Mailbag


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!

By Walter Storholt April 17, 2025
Are HSAs good tax-advantaged accounts? Can you really accumulate funds over the years and use them tax-free in retirement? This is what listener Beth is wondering. She maxes out her HSA every year without touching it. We’ll discuss whether this strategy could be a smart move or if there are potential pitfalls to consider.
April 10, 2025
Tax season is here and it’s the perfect time to start planning for 2025 and beyond. In this episode, Frank dives into the key tax changes for 2025 that could impact your retirement strategy. From increased 401(k) contribution limits to standard deduction increases, Frank breaks down actionable strategies that could help maximize your tax savings this year and beyond.
By Walter Storholt April 3, 2025
Today’s topic comes from a question from Janice, who was recently laid off at 53 and is considering a career change into real estate. But to make it work, she may need to tap into her IRA to make ends meet. Could this put her long-term financial security at risk?
By Walter Storholt March 27, 2025
April Fool’s Day is all about jokes and pranks, but when it comes to retirement planning, getting fooled can cost you real money. Today, we’re uncovering the beliefs that can fool retirees and pre-retirees into making bad financial moves. We’ll cover some of the most common myths that can damage your retirement plans and explain why they might not make much sense for you.
March 24, 2025
Using a Tax Refund to Fund an IRA
March 24, 2025
Top 10 IRA Rollover Mistakes
March 20, 2025
Many retirees and pre-retirees dream of owning a vacation home that they can visit throughout the year. But if you decide to make this move, how should you go about financing a second property? That’s the question one of our listeners, Ted, asked Frank this week.
By Walter Storholt March 13, 2025
We've got a great listener question for you today! This week, Barry shares that he has a life insurance policy through his job, as well as a whole life policy he purchased several years ago. Now, he’s wondering- does he really need both, or should he consider canceling one?
By Walter Storholt March 6, 2025
Social Security claiming strategies can vary greatly depending on family dynamics. This episode explores how different family situations, such as those with a stay-at-home spouse or a blended family, could impact when and how to claim Social Security benefits to help maximize your retirement income.
February 25, 2025
Retirement accounts and divorce
Show More