Most people think about taxes once a year, when it's time to file their return. But tax preparation and tax planning are two very different things. Tax preparation looks backward. Tax planning looks forward. And when you're approaching retirement, that distinction can have a major impact on how much of your money you actually get to keep.

In this episode, Kevin shares a story from earlier in his career that changed the way he thought about taxes and financial advice. Then he breaks down some of the biggest tax-planning opportunities retirees and those approaching retirement should be thinking about throughout the year, not just during tax season.

We'll discuss capital gain and tax-loss harvesting, Social Security taxation, ACA premium tax credits, Medicare IRMAA surcharges, charitable giving strategies, qualified charitable distributions, Roth conversions, inherited IRAs, and more.

More importantly, we'll look at how all of these decisions interact.

Because good retirement tax planning isn't simply about paying the least amount of tax this year. It's about making intentional decisions today that could help you better manage your lifetime tax bill.

If you're approaching retirement with significant savings and wondering whether you're being proactive enough about taxes, this episode will give you a framework for what to be thinking about before year-end.

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⛳ PFR Nation (Who This Is For)

If you're over 50, have saved seven figures (or multiple seven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place.

-Kevin

Connect with me here:

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This is for general education purposes only and should not be considered as tax, legal or investment advice.

Thousands of retirees relocate every year looking for lower taxes, a lower cost of living, better weather, or to be closer to family.

In this episode, Kevin sits down with estate planning attorney and financial advisor Ryan Smith to discuss the estate planning issues that many retirees overlook after relocating. From wills and trusts to powers of attorney, healthcare directives, probate laws, and beneficiary designations, they explain what should be reviewed when you establish residency in a new state.

While this conversation focuses on retirees relocating during retirement, the same planning considerations will apply to just about any retiree.

In this episode, you'll learn:

Why moving to another state can impact your estate plan

Which legal documents should be reviewed after relocating

Tennessee-specific estate planning considerations

Common mistakes retirees make when changing residency

Practical steps to protect your family and your legacy

Making life easier for your fiduciary relationships and beneficiaries

Whether you're moving for family, lower taxes, or a better retirement lifestyle, this episode will help you avoid costly planning mistakes before they're discovered when it's too late.

Connect with Ryan Smith here:

Next Frontier Estate Planning

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👍 If you found this helpful: Hit Like, subscribe, and I’ll see you next week with more retirement planning content designed for people over 50 who want to make work optional.

Are you interested in learning more about working with me on your retirement plan? You can start with visiting my firm's website at https://imaginefinancialsecurity.com/

Or, you can fill out our Retirement Readiness Questionnaire:https://imaginefinancialsecurity.com/retirement-readiness-questionnaire/

-Kevin

This is for general education purposes only and should not be considered as tax, legal or investment advice.

Connect with me here:

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Will Social Security really be cut by more than 20%?Should you claim early before the rules change? Or is the media exaggerating what's actually happening?

In this episode, I will break down the latest Social Security Trustees Report, explain what the 2032 Trust Fund projection actually means, and discuss the newly introduced PROMISE Act designed to begin addressing the program's long-term funding shortfall.

You'll learn:

What the Social Security Trust Fund actually is

Why the Trust Fund is projected to be depleted around 2032

Why Social Security isn't expected to "go bankrupt"

Whether claiming benefits early is a smart strategy

How a potential 22% benefit reduction could affect a retirement plan

What the new PROMISE Act does (and doesn't do)

The most likely changes Congress could make to strengthen Social Security

Practical planning steps you can take today without overreacting to the headlines

If you're approaching retirement or already retired, this episode will help you separate fact from fear and make more informed decisions about one of the most important income sources in your retirement plan.

⁠⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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-Kevin

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This is for general education purposes only and should not be considered as tax, legal or investment advice.

Planning for retirement isn't just about building an investment portfolio. For many people, the hardest part of retirement is feeling that loss of identity their careers provided.

I'm very excited to have Sandy Vecchi on for this episode to discuss one of the most overlooked aspects of retirement planning: purpose, identity, and building a meaningful "third act."

After spending decades in financial services, Sandy discovered that many retirees struggle not because they risk running out of money, but because they lose the structure, relationships, and identity that work once provided. Following a deeply personal family health crisis in her retirement, she completely redefined what retirement could look like and now helps others do the same.

In this episode you'll learn:

• Why retirement is an identity transition, not just a financial one
• The "honeymoon phase" many retirees experience
• How to discover purpose after leaving your career
• Why financial independence creates freedom, but not fulfillment
• The biggest regrets people have later in life
• Practical ways to prepare emotionally before retirement
• How to build a meaningful legacy beyond money

If you're within a few years of retirement, or have already retired, this conversation may change how you think about your next chapter.

If you enjoyed this episode, please like, subscribe, and share it with someone preparing for retirement.

📌 Connect with Sandy Vecchi:

Website:  https://www.sandyvecchi.com/
YouTube:  https://www.youtube.com/@sandyvecchi9814
LinkedIn:  https://www.linkedin.com/in/sandy-vecchi-mba-a2a528378/

Instagram:  https://www.instagram.com/sandyvecchispeaking

***This is for general education purposes only and should not be considered as tax, legal or investment advice***

What if the smartest retirement move isn't retiring at all?In this episode, I walk through a case study of a 59-year-old professional with more than $3 million saved who could retire tomorrow, but isn't sure he should.Instead of asking whether he can retire, we explore a different question:What if he simply stopped saving for retirement?By redirecting tens of thousands of dollars each year toward travel, family, hobbies, and experiences while continuing to work a few more years, he may actually improve both his financial confidence and his quality of life.In this episode we discuss:• What "coasting to retirement" really means• When saving more stops meaningfully improving your retirement• How delaying retirement changes your odds of success• How many high-income professionals oversave• How to know if you've already "won the game"• The emotional side of retirement planning

Every retirement plan is different, but if you're approaching retirement with $1 million, $2 million, or more saved, this may be one of the most important mindset shifts you'll ever hear.

⛳ PFR Nation (Who This Is For)If you're over 50, have saved seven figures (or multiple seven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the community!

-Kevin

Connect with me here:

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This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

Retirement planning looks very different when you're single.Whether you're divorced, widowed, or intentionally single, the financial decisions you face in retirement aren't the same as they are for married couples.

In this video, I’ll discuss the unique retirement planningchallenges facing single retirees, including Social Security claiming strategies, Roth conversions, tax brackets, Medicare IRMAA surcharges, estate planning, long-term care, investment strategy, housing decisions, and whyretirement spending may look different when you're planning for one instead of two.

Topics Covered:

• How retirement planning changes when you're single
• Social Security strategies for single retirees
• Roth conversions and tax planning
• Medicare IRMAA and RMD planning
• Estate planning essentials
• Housing and Continuing Care Retirement Communities (CCRCs)
• Long-term care considerations
• Retirement spending for single retirees
• Advantages of retiring single

Whether you're already retired or preparing for retirement,understanding these differences can help you better prepare as you plan for and execute a successful retirement.

⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

-Kevin

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This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

In this Retirement Q&A episode, I answer four of thequestions I received recently from retirees and people preparing for retirement.

We'll cover:

• Is the 4% Rule still the best safe withdrawal rate?
• What is the best investment allocation during retirement?
• Are the new Trump Accounts actually worth using?
• What do retirees regret most at the end of life?

If you're within 10 years of retirement or already retired,this episode will help you make smarter financial decisions as you prepare for and execute your retirement.

⬇️ Resources Mentioned

Retirement Manifesto: The Regret We Get Wrong:

https://www.theretirementmanifesto.com/the-regret-we-get-wrong/?fbclid=IwY2xjawSzaDpleHRuA2FlbQIxMABicmlkETF2N205R3M1UzM0ZGZMYUdUc3J0YwZhcHBfaWQQMjIyMDM5MTc4ODIwMDg5MgABHmlG7eBoSF4Xx8iY2T14aNEAsHcdJXiZ683hqbVHRknuOrZntYuEtrs6NMNR_aem_mu0XSSVgTO14CfX4Nj12cA

• Trump Accounts Deep Dive (Episode #123)

https://open.spotify.com/episode/1GxHxa1rasICkIrlLOb8J9?si=AJQ8RMcDQr-BOcgs2vzVHQ

⁠Areyou interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

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****Most advice for retirees suggests to delay SocialSecurity as long as possible. But is that always the right move?

In this episode, we'll discuss five real-world situations where claiming Social Security earlier may actually be the better decision.

You'll learn:

✔️ How longevity impacts yourclaiming strategy

✔️ Why Social Security break-evencalculators may be incomplete

✔️ The hidden impact claimingdecisions can have on your investment portfolio

✔️ How Social Security affectslegacy planning and leaving money to your children

✔️ Spousal and survivor benefitconsiderations

✔️ Why many retirees strugglepsychologically with spending their nest egg

✔️ How claiming benefits earlycan help manage sequence of returns risk during market downturns

The reality is that Social Security claiming decisionsshould never be made in isolation. They should be coordinated with your retirement income plan, tax strategy, investment portfolio, legacy and lifestyle goals.

If you're approaching retirement and wondering whether toclaim Social Security at 62, Full Retirement Age, or 70, this episode will help you understand the tradeoffs and make a more informed decision. Hope it helps.

-Kevin

Connect with me here:

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This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

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Many retirees spend decades worrying about whetherthey'll have enough money.

But what happens when you've already solved the incomeproblem?

In this case study, we examine a 65-year-old retiree witha $1.9 million portfolio, an $85,000 pension, and Social Security benefits thatcover nearly all of her retirement spending needs.

We discuss:

• Why retirement planning changeswhen income is already covered
• How pensions affect investmentstrategy
• Roth conversion opportunitiesbefore required minimum distributions begin
• Lifetime gifting strategies foradult children
• Charitable planning usingQualified Charitable Distributions (QCDs)
• Creating a tax-efficient legacy

If you've accumulated significant retirement assets andwant to optimize retirement, this episode is for you.

The big question isn't whether you can retire.

It's what to do next after you've already won theretirement income game.

Connect with me here:

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***This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

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 Are you underestimating your retirement expenses?

One of the biggest mistakes I see pre-retirees make isn't poor investing, claiming Social Security incorrectly, or even tax planning mistakes. It's failing to accurately estimate what retirement will actually cost.

After 18 years helping people plan for and execute retirement, I've noticed the same retirement expenses catch people by surprise over and over again.

In this episode, I break down the 7 retirement expenses most retirees underestimate, including:

✅ Travel and the "Go-Go Years" of retirement

✅ Home repairs, renovations, and aging-in-place upgrades

✅ Retirement tax planning opportunities and tax surprises

✅ Financial support for adult children and grandchildren

✅ Hiring help for tasks you used to do yourself

✅ Vehicle replacement costs

✅ Healthcare, Medicare, and long-term care expenses

If you're within 5-10 years of retirement, already retired, or trying to determine how much money you need to retire comfortably, this episode will help you build a more realistic retirement budget and avoid costly planning mistakes.

• Why most retirees underestimate expenses
• My own experience underestimating costs
• The expensive "Go-Go Years" of retirement
• Home repairs and renovations
• Tax surprises in retirement
• Adult children still on the payroll
• Paying others to do things you used to do yourself
• Vehicle replacement costs
• Healthcare and long-term care expenses
• Why retirement spending isn't linear

This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.