Retirement Road Map

Hosted by Derek Gregoire, Keith Ellis, and Matthew Peck

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Episodes

124

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Aug 2026

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About the show

Welcome to the Retirement Road Map by SHP Financial—a podcast empowering today's retirees and pre-retirees to make well-informed financial decisions that will help you spend more time living and dreaming, than worrying and wondering. Join SHP Financial Co-Founders Derek Gregoire, Keith Ellis, and Matthew Peck, CFP® CIMA®, as they share actionable financial strategies and insights, as well as interview top thought leaders in the world of finance, accounting, and estate planning. The SHP trademarked Retirement Road Map is a holistic planning process that focuses on the 5 key areas of retirement planning: Income planning, investment planning, tax planning, health care planning, and legacy planning. The Retirement Road Map is your guide to financial freedom and will prepare you for the retirement you've always dreamed of and deserve!

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August 26, 2026Episode 11033 min

110: The Benefits Of Your Tax & Financial Planning Teams Working Together with Lauren Bakken, CPA

Retirement isn't only about leaving your career behind. It's also about knowing what you're retiring to and making sure the financial decisions you make along the way support the life you want to create. And when taxes, investments, estate planning, and retirement income begin overlapping, trying to navigate everything on your own can become complicated quickly. In this episode, SHP Financial Lead Advisor Laura Russo sits down with recently retired CPA, Lauren Bakken, to discuss the lessons Lauren learned throughout her career serving individuals and small business owners. Lauren shares her own transition into retirement, why she believes your CPA, financial advisor, and attorney should be working together. In this podcast interview, you'll learn: How meaningful work and purpose can make retirement more fulfilling. The importance of understanding the tax consequences before taking retirement distributions. How your CPA, financial advisor, and attorney can work together. Why minimizing taxes isn't always the best financial decision. How small business owners can better prepare themselves for retirement. Why both spouses should understand the family's financial picture. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

August 12, 2026Episode 10924 min

109: Retirement Income Strategies That Create Confidence and Peace Of Mind with Chris Willis, CFP®, CTS™

One of the most common questions that we hear from our clients isn't whether they've saved enough; it's whether their savings can actually provide the income they need to live the retirement they've envisioned. Building wealth during your working years is one challenge, but turning those assets into a reliable paycheck is where a comprehensive retirement plan becomes essential. In this episode, Keith Ellis Jr. is joined by Certified Financial Planner (CFP®) and Certified Tax Specialist (CTS™), Chris Willis, to discuss how retirement income planning goes far beyond simply withdrawing money from an investment portfolio. They explain how understanding your expenses is the foundation of every retirement plan, how different income strategies can fit different personalities and goals, and why no single approach works for every retiree. They also break down the strengths and tradeoffs of guaranteed income, dividend-focused investing, and SHP's bucket strategy for generating retirement income. You'll also learn how income planning fits into SHP's comprehensive retirement strategy that includes investments, taxes, healthcare, and estate planning. In this podcast interview, you'll learn: Why retirement income planning begins with understanding your lifestyle expenses. How guaranteed income, dividend investing, and bucket strategies each serve different goals. Why there's no one-size-fits-all approach to generating retirement income. How balancing safety, income, and growth creates a more resilient retirement plan. Why tax planning should influence your retirement income strategy. How a personalized retirement plan can help you retire with greater confidence. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

July 29, 2026Episode 10829 min

108: The Biggest Regrets For Retirees (And How to Avoid Them) with Kyle Britton

Retirement is often viewed as a financial milestone, but many retirees discover that their biggest challenges have little to do with money. Many wish they had retired sooner, spent more confidently, prepared for the emotional transition away from work, or started important planning conversations with their families earlier. The good news is that these lessons don't have to be learned the hard way. In this episode, Keith Ellis Jr. is joined by Kyle Britton to share insights gathered directly from retired clients who reflected on what they would do differently if they could start retirement over again. Together, they discuss the most common regrets they've heard from retirees, including delaying retirement, underspending despite having enough savings, losing a sense of purpose after leaving work, and overlooking important tax, estate, and legacy-planning opportunities. They also discuss why retirement planning extends far beyond investments, how a comprehensive retirement plan helps pre-retirees make more confident decisions, the value of gifting assets during your lifetime, and why having meaningful conversations with family can help preserve both wealth and relationships for future generations. In this podcast interview, you'll learn: Why many retirees wish they had stopped working sooner. How a comprehensive retirement plan creates confidence to enjoy your money. Why purpose and routine are essential after leaving your career. How proactive tax planning can preserve more wealth for your family. Why gifting during your lifetime may benefit both you and your heirs. How healthcare and legacy planning shape long-term retirement success. Why open family conversations can prevent future estate conflicts. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

July 10, 202637 min

Matt's Markets on the Move Q2: July 2026

Join SHP Financial Co-Founder Matt Peck, CFP ® , CIMA ® , and Lead Advisor, Laura Russo as they discuss current market trends and their potential impact on your financial future.

July 8, 2026Episode 10738 min

107: A Guide to Making Smarter Decisions When Claiming Social Security Benefits with Alina Osokhovska, CFP®

Many retirees assume the biggest Social Security decision is simply choosing the right age to claim benefits. But the reality is far more complex. Your Social Security strategy can affect your retirement income, taxes, spouse, survivor benefits, and long-term financial security, making it one of the most important decisions you'll make during retirement. In this episode, Matthew Peck is joined by SHP's Head Certified Financial Planner, Alina Osokhovska to explain how Social Security really works and why the best claiming strategy depends on your unique financial situation. They discuss the different types of Social Security benefits, the key ages every retiree should understand, and how factors like taxes, market conditions, longevity, and spousal planning influence when claiming benefits makes the most sense. They also discuss how SHP's Retirement Road Map evaluates multiple claiming strategies, recent changes under the Social Security Fairness Act, how working in retirement can affect benefits, why Social Security remains an important part of a comprehensive retirement plan, and why making an informed decision is far more valuable than making a rushed one. In this podcast interview, you'll learn: Why the best Social Security claiming age depends on your complete financial plan. How spousal and survivor benefits can significantly affect retirement income. Why taxes should play a major role in your claiming strategy. How longevity and market conditions influence when to begin benefits. What recent Social Security law changes mean for retirees. How working before full retirement age may affect your benefits. Why personalized planning leads to better Social Security decisions. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

June 24, 2026Episode 10624 min

106: How Proper Retirement Planning Is About More Than Money with Mike Guthrie

The average person spends most of their life preparing for retirement, only to discover that having enough money is just one piece of the puzzle. Once the paychecks stop and the daily routine disappears, retirees often face a different challenge: finding purpose, fulfillment, and confidence in how they spend their time. In this episode, Keith Ellis Jr. is joined by Mike Guthrie to explore what a successful retirement success really means by going deeper than portfolios and income planning. They talk about the emotional and lifestyle transitions that come with leaving a career behind, why purpose and structure remain important in retirement, and how retirees can create meaningful experiences with new hobbies, deeper family connections, and charitable work. They also discuss the role financial planning plays in creating the freedom to pursue the things that matter most, why confidence is essential when transitioning from saving to spending, and how SHP Financial's Retirement Road Map process helps retirees align their finances with their goals, values, and lifestyle. In this podcast interview, you'll learn: Why retirement planning should focus on purpose as well as finances. How structure and routine contribute to a more fulfilling retirement. Why intellectual engagement and lifelong learning can improve retirement satisfaction. How health and fitness impact both quality of life and financial well-being. Why strong family relationships and social connections are essential in retirement. How confidence helps retirees transition from saving money to spending it. Why a holistic retirement plan creates greater freedom and flexibility. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

June 3, 2026Episode 10525 min

105: Why Investors Make Bad Decisions During Market Volatility with Mark Kenney, CFP®, CTS™

Market volatility can cause even the most disciplined investors to second-guess their decisions. When headlines dominate the news cycle and emotions begin to take over, many retirees risk making short-term financial moves that can negatively impact their long-term retirement goals. Without a comprehensive plan in place, fear and uncertainty can lead investors away from the strategies designed to protect their lifestyle and future financial security. In this episode, Keith Ellis Jr. is once again joined by one of SHP Financial's Certified Financial Planner, Mark Kenney, to discuss the role behavioral finance plays in retirement planning and why emotions often drive poor financial decisions during uncertain markets. Together, they break down the psychological tendencies that can lead investors to react impulsively, explain why long-term planning matters more than short-term market movements, and share real-world examples of how proper financial planning can help retirees stay confident during periods of volatility. They also discuss the importance of having different investment "buckets" for safety, income, and growth, how tax planning impacts retirement success, and why open conversations around money and legacy planning can help families better prepare future generations. Mark and Keith explain how having a holistic retirement roadmap can help retirees navigate uncertainty, make smarter financial decisions, and maintain confidence in both their plan and their future. In this podcast interview, you'll learn: Why emotional investing decisions can negatively impact long-term retirement success. How behavioral finance influences the way investors react during market volatility. Why having separate buckets for safety, income, and growth can reduce financial stress. How staying invested during downturns can improve long-term portfolio performance. Why tax planning should be part of a comprehensive retirement strategy. How conversations around legacy planning can help families prepare future generations. Why confidence and clarity are critical components of a successful retirement plan. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

May 20, 2026Episode 10443 min

104: The Difference Between Having a Plan or Just a Portfolio with Nick Nelson

One of the biggest misconceptions investors have about retirement planning is that a healthy portfolio with large balances guarantees retirement success. But without a comprehensive plan that accounts for the income, taxes, investments, healthcare, and legacy goals, retirees can still face unnecessary risks and uncertainty down the road. In this episode, SHP co-founder Matthew Peck is joined by SHP's Vice President of Advisory Solutions, Nick Nelson, to break down the key differences between having a portfolio and having a complete retirement plan. Nick explains why successful retirement planning goes far beyond investment performance and requires coordination across every area of your financial life. Together, they discuss how income planning serves as the foundation of retirement, why investment strategies must evolve during the distribution phase, and how factors like taxes, inflation, healthcare costs, and legacy planning can impact long-term financial success. They also explain how proactive planning and working with a trusted advisor can help retirees navigate uncertainty with greater confidence and peace of mind. In this podcast interview, you'll learn: Why a retirement portfolio alone may not provide the confidence needed for long-term financial success. How income planning serves as the foundation for every other area of retirement planning. Why investment strategies should change when transitioning from accumulation to distribution. How inflation, taxes, and RMDs can significantly impact your retirement income over time. The role healthcare and long-term care planning play in protecting your retirement assets. Why legacy planning goes beyond estate documents and helps define the impact you leave behind. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

May 6, 2026Episode 10331 min

103: The Retirement Planning Mistakes That Could Cost You Thousands in Taxes with Alina Osokhovska

Without a comprehensive financial plan that accounts for taxes, income strategies, and long-term goals, it's easy to overlook opportunities that could significantly impact your financial future. The reality is that even strong investment returns can be undermined by inefficient planning, leading to unnecessary taxes, missed opportunities, and less control in retirement. In this episode, Derek Gregoire is joined by Alina Osokhovska, Certified Financial Planner™, to explore the true role of financial planning and why it goes far beyond portfolio management. With deep expertise in tax strategies and long-term planning, Alina shares how thoughtful, proactive planning can help clients align their investments with their goals while navigating an ever-changing financial landscape. Together, they break down the different types of tax-advantaged accounts, including pre-tax, Roth, and after-tax strategies, and explain how each can play a role in building a more efficient retirement plan. They also discuss the importance of tax diversification, how accounts like 401(k)s, IRAs, 529 plans, and HSAs fit into a broader strategy, and why ongoing planning is essential to adapt to changes in tax laws and personal circumstances. In this podcast interview, you'll learn: Why financial planning goes far beyond investments and serves as the foundation for reaching your long-term goals. How pre-tax, Roth, and after-tax accounts differ and how each impacts your taxes in retirement. Why tax diversification is critical to maintaining flexibility and minimizing unnecessary taxes over time. How inefficient tax planning can reduce your retirement income just as much as market losses. The role of accounts like 401(k)s, 529 plans, and HSAs within a comprehensive financial strategy. Why financial planning is an ongoing process that must adapt to changes in tax laws, income, and personal goals. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube

April 22, 2026Episode 10238 min

102: How to Maximize Your 401(k) and Avoid Common Mistakes in Retirement with Raphael Hanna

For many people, investing money into a 401(k) is the foundation of their retirement. Unfortunately, most investors don't fully understand how these plans work or how to take full advantage of them. From contribution limits to employer matches and tax strategies, small decisions made today can have a significant impact on your long-term financial future. Without a clear understanding, it's easy to miss opportunities and make costly mistakes that could affect your income in retirement. In this episode, SHP co-founder Matthew Peck is once again joined by SHP's Raphael Hanna to break down the fundamentals of 401(k) planning. With years of experience helping clients navigate retirement strategies, Raphael shares practical insights into how these plans function and how to approach them with a long-term perspective. Together, they walk through the key components of a 401(k), including how to determine your contribution amount, how employer matching and vesting schedules work, and the differences between pre-tax and Roth contributions. They highlight common pitfalls to avoid and how proactive planning can help you maximize your retirement savings, giving you greater confidence as you approach retirement. In this podcast interview, you'll learn: The importance of fully understanding your 401(k) as it has replaced traditional pensions for many people. How to determine the right contribution amount based on your income, expenses, and long-term goals. How employer matching and vesting schedules work and why leaving early could mean losing valuable benefits. The key differences between pre-tax and Roth 401(k) contributions and how each impacts your taxes over time. Why tax diversification across pre-tax, Roth, and after-tax accounts can provide more flexibility in retirement. What to consider when rolling over a 401(k) or using in-service distributions to gain more control over your investments. Want the Full Show Notes? To get access to the full show notes, including audio, transcripts, and links to all the resources mentioned, visit SHPfinancial.com/podcast Connect With Us on Social Facebook LinkedIn YouTube