• Define Financial
• The Total Retirement System

Happy New Year, and welcome back to the show. Believe it or not, and it’s still a little hard for me to wrap my head around, this marks the ninth year of hosting this podcast.

So before we officially kick off 2026, I just want to pause for a moment and say thank you. Thank you for listening, for the thoughtful emails, for the candid feedback, and for sharing the show with friends and family. If you can’t tell already, educating and helping people make better financial decisions is something I am genuinely passionate about, and your continued support means more than you know.

Now, as I’ve done in the past, I’m kicking things off this year by dedicating an episode to pulling back the curtain on what my firm actually does, how we do it, and why we approach retirement planning the way we do.

And I’m doing this for two reasons.

1.) First, getting finances in order continues to sit near the top of most New Year’s resolution lists. And if hiring a professional or rethinking your current advisor relationship is something you’re considering this year, we would genuinely welcome the opportunity to have a conversation and see if there’s a good mutual fit.

2.) Second, I believe there’s real educational value in understanding what a thoughtful, proven retirement planning process should look like, regardless of whether you choose to work with us, another advisor, or navigate retirement on your own. So today, I’m walking you through the exact framework my team and I implement for every client.

It’s built around 7 core questions that I think every retiree should answer, and a 4-step process that, when implemented properly and in the right order, can dramatically improve retirement clarity, confidence, and success.

Welcome to another episode of the Stay Wealthy Retirement Show. I’m your host, Taylor Schulte, and every week, I tackle the most important financial topics to help you stay wealthy in retirement. And now, on to the episode.

The 7 Questions That Shape a Confident Retirement

After working with hundreds of retirement savers over the past two decades, I’ve noticed a consistent pattern that’s hard to ignore. The people who thrive in retirement don’t necessarily have the largest portfolios. They have something far more important. A clear, coordinated process connecting every single piece of their financial life.

Now, it’s important to acknowledge that, yes, many people approach retirement with very real financial hardship. Some have battled bad savings habits, some have made glaring mistakes, others have been hit by life events outside their control, and some simply never had the income or opportunity to save enough.

Regardless of the cause, it creates a challenging and often stressful reality, and it’s not something I want to completely gloss over or dismiss. But in my experience, for diligent savers who have built healthy retirement portfolios, the biggest threat to a confident retirement usually isn’t the size of the nest egg. It’s how disconnected the decisions around that money have become.

Investment strategies built at different times for different reasons, but never optimized to work together. Taxes handled reactively. Income decisions revisited year by year. Estate documents drafted once and then forgotten about. Each decision is made in isolation, and in retirement, isolation is expensive. A Roth conversion can spike Medicare premiums. A Social Security decision can impact taxes for decades. Investment risk can affect income and spending confidence. Healthcare decisions can delay retirement altogether.

When you step back and recognize how interconnected these decisions are, especially in retirement, it helps to explain why my team and I stopped thinking and communicating in terms of plans, and started thinking in terms of systems.

At Define Financial, everything we do for our clients is built around what we call the total retirement system. And this isn’t a new idea or a recent shift in how we work. In fact, it’s the exact internal process we built from scratch and have implemented since day one to guide the comprehensive retirement planning work that we do for our clients.

As the firm has grown and evolved over the years and as we’ve grown as professionals, we’ve just become more intentional about pulling back the curtain and more clearly explaining how we do what we do and why we do it this way, especially for people trying to evaluate what thoughtful, coordinated and truly comprehensive retirement planning should look like, not just a collection of good ideas. At its core, the total retirement system is a four-step framework designed specifically for people over age 50 who are retired or nearing retirement and want more than a collection of disconnected recommendations.

It’s built for those who want lower lifetime taxes, maximum sustainable income they can actually enjoy, investments aligned with retirement, not accumulation, and clarity around legacy planning, health care decisions, and retirement spending. What makes this system different comes down to two things.

1. First, it’s fully customized for every client and not a cookie-cutter solution.
2. And second, no major decision is ever made in isolation. Tax planning affects income. Income decisions influence investment strategy.

Investment choices shape legacy outcomes. Every piece is designed to support the others because retirement planning is not a one-time event or a simple math problem. It’s a decades-long transition full of moving parts that all have to work together. And the people who feel most confident in retirement aren’t guessing or reacting as issues come up. They’re following a clear, coordinated process, one that adapts as life changes and keeps the entire plan working together.

Now, before we walk through the four-step framework, I think it helps to take a step back and ask a more fundamental question. What problems does a good retirement plan actually need to solve? Over the years, we found that nearly every retirement challenge traces back to the same seven questions. In fact, these are the exact questions that ultimately form the backbone of the total retirement system, and each one influences the others.

1.) Number one, what proactive steps can I take to avoid overpaying the IRS? You see, in retirement, taxes aren’t just something that happened to you. With the right planning, they’re actually one of the few variables you have control over.

2.) Number two, how do I turn my savings into a steady, sustainable paycheck? Retirement forces this shift from accumulation to distribution, and figuring out how to live off your savings without running out of money is often one of the biggest challenges people face.

3.) Number three, how should my investments evolve now that I’m living off them instead of building them? Many portfolios are built for accumulation and then left largely unchanged in retirement, but the transition into and early years of retirement are the most sensitive phase of your financial life, and without adjusting how your investments are positioned, market volatility can have an outsized impact on income, confidence and long-term outcomes.

4.) Number four, in what order should I draw from my accounts to minimize taxes? Withdrawal sequencing, i.e. deciding which account types to tap and which investments to liquidate every time you take a withdrawal, can have a dramatic impact on your lifetime tax bill and long-term returns.

5.) Number five, how can I ensure my estate plan and legacy align with my intentions? Legacy planning isn’t just about what happens when you’re gone, it’s about using your resources intentionally in a way that reflects your values while you’re still here.

6.) Number six, what’s my plan for health insurance before Medicare? For anyone retiring before age 65, this is often the final obstacle standing between them and financial independence.

7.) And number seven, after decades of saving, how do I actually get comfortable spending? As I’ve discussed many times here on the show, after years of discipline and delayed gratification, many retirees struggle to shift from saving their money to actually enjoying it.

The key thing to recognize throughout all seven questions is that these aren’t separate problems to address one at a time. They’re interconnected pieces of a much larger puzzle. And that’s exactly why our process doesn’t treat them as isolated issues. It connects them into one coordinated process through four steps done in a very specific order.

The Total Retirement System (4-Step Process)

With that understanding, let’s now walk through each of the four steps that power the total retirement system.

Step number one is tax planning. Now, most people want to start the process by analyzing investments or discussing income strategies. That’s completely understandable, but to us, doing so without a tax strategy is like building a house without a detailed blueprint. Every decision that follows becomes guesswork, and mistakes, especially in retirement, can be costly. We start with a comprehensive, long-term tax analysis because taxes touch nearly every decision you’ll make in retirement.

Your account withdrawals, Social Security benefits, Medicare premiums, required minimum distributions, each one has meaningful tax implications. When taxes are done right, everything else improves. Income becomes more efficient, investments align with your unique tax picture, and your legacy plan adopts the right strategies to reduce estate taxes and maximize what you leave behind. Simply put, starting with taxes allows you to move from hoping you’re making tax smart decisions to knowing you are.

Step number two is retirement income. Once taxes are addressed, the next question is obvious. How do I turn my savings into a paycheck I won’t outlive? And this is where I see many plans fall short. Too often, retirees are given a generic withdrawal rate that assumes perfect markets and emotionless decisions, but real life doesn’t work that way. That’s why we build a retirement paycheck that adapts. We start by mapping guaranteed income sources like Social Security, pensions, or rental income. Then we design a portfolio withdrawal strategy using our retirement guardrails framework.

Now, despite the name, guardrails aren’t about restriction, they’re about protection. This framework is designed to safely maximize spending, especially during the early active years of retirement, while still protecting against running out of money later. By removing guesswork and replacing it with structure, this approach is proven to reduce anxiety around retirement spending and give clients the confidence to actually enjoy what they worked so hard to save.

Step number three is legacy planning. Once income is secure, we then turn our focus to legacy, making sure your wealth reflects your values. That might mean leaving an inheritance, supporting charities, or simply spending intentionally during your lifetime. We integrate these goals and values into every part of the system, addressing estate taxes, long-term care, trusts, beneficiary designations, and charitable giving strategies. Legacy planning isn’t just about what happens when you’re gone, it’s about using your resources purposefully while you’re here.

Finally, step number four, investments. With taxes, income, and legacy defined, we now build the investment portfolio specifically to match your retirement needs and goals. Your working years rewarded high risk and growth, but retirement rewards balance, flexibility, and resilience. For that reason, we designed diversified, tax-efficient portfolios and pair them with a thoughtful cash management strategy to help stabilize income, manage volatility, and weather those unexpected storms. This structure helps reduce sequence of returns risk and provides the confidence to stay invested when markets get shaky. No speculation, no market timing, just disciplined, evidence-based investing, fully aligned with your total retirement system.

Each of these steps informs the next, nothing ever happens in a vacuum, and that coordination when implemented properly is the difference between hoping your plan works and knowing it does.

Working Together

So how does someone actually get started with the total retirement system and evaluate our firm to see if we are a good fit to work together? Well, the very first step is to simply schedule a free 45-minute retirement strategy session.

This isn’t a sales pitch or a generic overview of our services, it’s a genuine conversation designed for us to understand your situation, for you to get to know us, and for both sides to thoughtfully determine whether our approach and expertise are potentially the right fit for your needs.

More specifically, during this meeting, we focus on three things.

• Number one, understanding what matters most to you, your goals, your concerns, and the decisions you’re currently wrestling with.
• Number two, walking you through in more detail how the total retirement system works and how it would benefit and be implemented for your unique situation.
• And number three, answering all of your big questions and determining if there’s a mutual fit to work together. We are not a high-volume firm, and we are very intentional about only working with people we truly have the expertise to help.

This conversation is as much about us determining if we can truly help you, as it is about you evaluating us. We don’t pressure you to move forward. We don’t rush decisions, and we don’t try to be everything to everyone. If we mutually determine there is a fit, we’ll explain exactly what the next steps look like.

If it’s not a fit for any reason, we’ll offer to make a personal introduction to someone who is and ensure that you leave the meeting with actionable insights regardless. With that said, part of making sure this is a good experience for everyone is being upfront and clear about our expertise and who we’re truly best positioned to help.

Just like you wouldn’t hire a neurosurgeon if you needed heart surgery, we believe you should approach evaluating and hiring financial professionals the same exact way. Not every firm or advisor is right for every situation.

At our firm, we specialize in comprehensive retirement and tax planning for people over age 50 who are retired or nearing retirement. We do our best work and have the greatest impact with families who have accumulated a nest egg between $2 million and $10 million and value a full-service, coordinated planning approach so they can spend more time enjoying the things that matter most to them in retirement. If that sounds like you and you’re interested in exploring whether we might be a good fit, we’d be honored to have a conversation.

You can schedule a retirement strategy session through the link in the episode description right there in your podcast app or by visiting definedfinancial.com and clicking Get Started.

And as always, if we don’t appear to have the right expertise to help but you need and want professional help, just shoot me a note at podcast at youstaywealthy dot com and I’d be happy to try and help you find the right person.

Bottom Line

Before we part ways, I want to emphasize and reiterate that retirement should not be about crossing your fingers and just hoping everything works out. It should be about having a fully customized, coordinated plan that evolves with you, protects what you’ve built, and gives you the confidence to live the life you’ve imagined on your terms.

Whether you work with us, another advisor, or navigate retirement on your own, my hope is that today’s episode gave you a clearer picture of what a truly comprehensive retirement planning process looks like.

The seven questions we covered are not theoretical. When they’re answered thoughtfully and in coordination with one another, they can be the difference between a retirement filled with uncertainty and one that’s filled with clarity and confidence. Happy New Year, thank you as always for tuning in, and to view the show notes and transcript for this episode, just head over to youstaywealthy.com/264.

Disclaimer

This podcast is for informational and entertainment purposes only, and should not be relied upon as a basis for investment decisions. This podcast is not engaged in rendering legal, financial, or other professional services.