Retirement Toolbox

Retirement Toolbox

Welcome to Retirement Toolbox, the podcast designed to help you build a strong financial foundation and navigate retirement with clarity and confidence. Hosted by Scott Searles, financial advisor and founder of Skybox Financial Group, this show offers straightforward, practical insights to help you protect what you’ve earned, grow your wealth for the future, and reduce your lifetime tax burden. Whether you’re approaching retirement or already enjoying it, tune in for education on income planning, tax-smart strategies, investment decisions, and more. Subscribe now and never miss an episode! For more information, visit https://www.skyboxfinancialgroup.com or call 888-742-0111.

Episodes

August 28, 2025 7 mins

The kids may be heading back to class, but it’s a perfect time for adults to crack open the books too, especially when it comes to retirement. In this episode, Scott puts listeners to the test with a series of essential retirement planning questions every retiree should know.

 

Here are your pop-quiz questions:

✏️ At what age can you receive full Social Security benefits if born after 1960? ✏️ What is the IRA contribution limit fo...

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Big tax law changes always bring big rumors. But before you assume Social Security is now tax-free or that you’re getting a $40K deduction just for breathing, let’s set the record straight on what this new bill didn’t actually do. In this episode, Scott busts the biggest myths surrounding the recent “Big Beautiful Bill,” breaking down the fine print behind headline-grabbing claims.

 

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

...

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You’ve probably heard about the “Big Beautiful Bill,” but what does it actually mean for your retirement plan? In this episode, Scott breaks down the real implications of the new legislation, beyond the headlines and political noise. He walks you through what changed, what didn’t, and the planning opportunities that smart retirees should be acting on now, while the tax rules are favorable.

Here’s some of what we discuss in this epi...

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Tax season is here, but filing your 2024 return is just one piece of the puzzle. Now is also the perfect time to take advantage of new tax rules for 2025—before the year gets away from you. With higher standard deductions, increased retirement contribution limits, and updated HSA rules, there are plenty of opportunities to lower your tax bill and boost your savings. In this episode, we’ll break down the key changes and how you can ...

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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 fool retirees and pre-retirees into making bad financial moves.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

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Presidents aren’t just leaders of a nation. They’re decision-makers who navigate uncertainty, make tough calls, and plan for the future. Today, we’re looking at how the leadership lessons of some of America’s greatest presidents can help you build a smarter, more secure retirement plan.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

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The day President Trump took office, he announced plans to implement a 25 percent tariff on goods from Mexico and Canada. Additional tariff conversations have exploded since that day. How might this impact your personal finances and the economy? Today, we’ll explain a bit of the backstory of tariffs and discuss these new tariffs.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https://5p7b1g...

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Brrr, it’s cold out there! Winter has a lot of people thinking about warmer weather. For some, that just means an annual vacation down south. But for certain retirees, they choose to live elsewhere through the brunt of winter, becoming “snowbirds.” Is snowbird life for you? Let’s talk about what motivates people to take up temporary residence elsewhere, where they go, and if it’s worthwhile.

 

Show Notes & Info:

Schedule A Call...

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February 6, 2025 27 mins

Financial mistakes can happen at any age, but they can have a particularly significant impact in your 60s. This episode offers five common financial blunders to avoid during this pivotal decade.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

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Have you already given up on some of your resolutions for the new year? Well, replace them with a few of the actionable ideas we cover on this episode to help you save smarter, invest better and plan for the future you deserve.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

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Did you know most Americans retire earlier than planned, often due to unexpected health issues, job changes, or financial surprises? These challenges can force people out of work early, leaving them unprepared for decades of retirement. In this episode, we’ll explore recent research highlighting the importance of planning for early retirement, even if it’s not in your current plans.

 

Show Notes & Info:

Schedule A Call With Sco...

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Everyone loves a good game show. Whether it’s spinning the big wheel or hitting the buzzer with all the right answers. But what happens when people turn their retirement planning into a game? Spoiler alert: it’s not always a win! In this episode, we tackle the risky moves people make when they treat their finances like a game of chance.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https:/...

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Imagine you could read your financial advisor’s mind before you even walked through the door for the first time. What would they want you to know? In this episode, we bring you the game-changing insights financial pros wish every saver and investor understood.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

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Social Security is the backbone of retirement for millions of Americans, but big changes may be coming. On this episode, we dive into the recently released proposal to raise the full retirement age to 69 and what it means for your benefits, your future, and your financial security.

Read the full report: https://www.cbo.gov/system/files/2024-09/60516-Full-Retirement-Age.pdf

 

Show Notes & Info:

Schedule A Call With Scott: talkwi...

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The financial landscape is changing rapidly, and if you’re focused on retirement, these shifts can’t be ignored. In today’s episode, we break down the trends that will define the rest of 2024 and what they mean for your retirement plan.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

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Ever wonder how your financial advisor really gets paid—and what that means for you? Whether it’s a fee, a commission, or a salary, the way your advisor earns money could be influencing the advice they give you. In today’s episode, we’re talking about the different pay structures of financial advisors, revealing the benefits, the potential biases, and what you need to know to make sure your money is truly working for you. If you’re...

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With National Financial Planning Month upon us, we’re sitting down with a seasoned financial planner, Scott Searles, to uncover the strategies and steps that go into building a personalized financial plan. From that first phone call to implementing a strategy that aligns with your goals, this discussion will offer valuable insights for anyone looking to understand what it looks like to go through the planning process with a real fi...

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Remember when you were a kid, always asking 'How do you know?' about everything, like why the sky is blue or where the sun goes at night? That curiosity doesn't go away as we get older; it just turns into different questions, like the ones we face when planning for retirement. Today, we’re digging into the 'How Do You Knows' of retirement planning.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Tool...

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Today, we're diving into the history of the Social Security Act, signed in 1935, which has become a crucial part of American retirement planning. We'll explore how this program started, how it's helped millions of retirees, and what challenges it faces as it turns 89. What can we expect for the future of Social Security? Let’s find out.

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https:/...

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Are you telling yourself financial lies? Discover the top lies people often tell themselves about money and retirement. Some of these could be severely holding you back, so stay tuned!

 

Show Notes & Info:

Schedule A Call With Scott: talkwithscott.net

Tax-Free Toolkit: https://5p7b1gdm.pages.infusionsoft.net/

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