Do You Actually Have a Retirement Plan?
Written by Jessica Cannella, Co-Founder and President
Reviewed/Updated: October 2026
Having a financial advisor, CPA, estate attorney, investment portfolio, and Medicare strategy doesn’t necessarily mean you have a coordinated retirement plan. The bigger question is whether the decisions each of those areas creates are actually working together.
In this video, Jessica Cannella explains Oak Harvest’s Retirement Success Plan and what the financial planning process looks like from the initial discovery call through ongoing planning. She also shows why decisions involving Social Security, retirement income, investments, taxes, healthcare, and estate planning shouldn’t be made in isolation. A change in one area can create consequences somewhere else in your retirement plan.
Key Takeaways
- Having financial accounts and advisors isn’t the same as having a retirement plan. The different pieces need to work together toward the life you want in retirement.
- Your retirement plan should start with your life, not a financial product. Your spending, goals, family, concerns, and priorities help determine what your money actually needs to do.
- Five major areas need to be coordinated: income, investments, taxes, healthcare, and estate planning.
- One retirement decision can affect several others. For example, when you claim Social Security affects how much you need from investments, while the accounts you withdraw from can affect taxes and potentially Medicare costs.
- You should understand your own financial plan. That includes where your retirement income comes from, why you’re invested the way you are, what your tax strategy is trying to accomplish, and what happens when circumstances change.
- A retirement plan shouldn’t try to predict the next 20 or 30 years perfectly. It should provide a roadmap that can adjust as markets, tax laws, your family, and your priorities change.
- The process doesn’t end when the plan is created. If you work with Oak Harvest, the plan is implemented, monitored, and adjusted as life changes.
Who This Video Is For
This video may be especially useful if you’re approaching retirement or already retired and have accumulated investments, retirement accounts, insurance, estate documents, or other financial resources but aren’t sure whether everything is working together.
It may also be helpful if you already have a financial advisor or manage your investments yourself but still have unanswered questions such as: Can I retire? How much can I spend? Where should my retirement income come from? How could my tax decisions affect Medicare? What happens during a bad market? And what happens financially if something happens to me or my spouse?
Most importantly, this is for someone who wants to understand why they’re making financial decisions rather than simply being told what investments or accounts to own.
Transcript
You can have a financial advisor, a CPA, an estate attorney, and a great investment portfolio, and still not have an actual retirement plan. I know that sounds strange, but think about it. Your advisor might be managing your investments, your CPA is looking at your taxes, you’ve figured out Medicare, and you’ve got your estate documents. Everybody might be doing their job. But who’s making sure all those decisions actually work together?
Because the decision you make about Social Security affects how much you’ll need from your investments. Where you take that money from affects your taxes. Your income can affect what you’re actually paying for Medicare. And suddenly, what look like four separate financial decisions is really one decision creating a ripple effect across your retirement. That’s the problem our retirement success plan is designed to solve. So let me show you what we actually do.
The Discovery Call
Because it’s probably different from what you think when you hear the words financial planning. It often starts with a conversation. In fact, the first step is a discovery call, typically 15 to 20 minutes. And we’re really trying to figure out just two things. What’s going on in your life? And can we actually help you?
Maybe you’re three years from retirement and you’re thinking, I have no idea if I’m actually ready. Maybe you’re already retired and wondering if you’re taking too much risk. Or maybe you’ve done a great job saving, but now you’re realizing I’ve spent 35 years learning how to put money into these accounts and nobody ever told me how to take it back out. And that’s a completely different skill.
So before we are talking about investments or products or moving money anywhere, you want to understand you. What are you trying to accomplish? What’s keeping you up at night? What does a really good retirement look like for you?
And what would have to be true for you to feel confident that you’re going to be okay, that your spouse is going to be okay? And by the way, you’re interviewing us too. You should be. Do you like the way we think? Are you comfortable asking us questions? Can you see yourself calling us when something changes in your life?
Because if we’re going to help you navigate retirement for the next 20 or 30 years, the relationship is the most important thing. So if we both feel like it makes sense to keep talking,
Building a Plan Around Your Life
The next step is sitting down with one of our financial advisors. And yes, we are going to talk about your money, but we’re much more interested in what the money needs to do. When do you want to retire? What do you want retirement to look like? How much does that life actually cost?
Are you going to help your adult kids? Do you want to travel? Do you want to leave a significant amount behind? Are you terrified of running out of money? Or maybe you’ve saved plenty, but you’re still afraid to spend any of it?
The answers to those questions matter because we’re not trying to fit your life into one of our financial plans. We’re trying to build a plan around your life. One of the most valuable parts of the process is that we take what we’ve just heard, convey that we’ve understood what you are saying, and we compare it to what your money is actually doing today. And sometimes these two things don’t match.
Maybe you’re taking significantly more investment risk than your plan actually requires. Or maybe you’re sitting on a huge amount of cash because you’re scared of the market. Maybe you own seven different investments that look diversified, but when we dig into them, they’re doing essentially the same thing.
Maybe most of your retirement savings is sitting in tax-deferred accounts and nobody has really talked to you about what that could mean later. Or maybe you’re doing a lot of things really well. That’s important too. We’re not looking for problems just so we can tell you how we found something that’s wrong.
The 5 Areas of Retirement Planning
We’re trying to answer a much more useful question. Where are you today? Where are you trying to go? And does what you’re currently doing support that?
There are five major areas that we’re looking at when it comes to the retirement success process: income, investments, taxes, healthcare, estate planning. But I don’t want you to think about these as five separate boxes that we’re checking, because that’s not how your life works. Here’s a simple example. Let’s say you’re 62 and you’re ready to retire.
Great. When should you take Social Security? Well, what’s your spouse receiving? Are they still working? What other income do you have? How much do you need from your investment accounts?
And which accounts should that money come from? Because taking $50,000 from a brokerage account isn’t necessarily the same thing as taking $50,000 from an IRA. The taxes are different. And maybe we look at your tax situation and say, you know what? There might be an opportunity here to convert some of this money to Roth.
How Retirement Decisions Work Together
Okay, but now we’ve potentially changed your taxable income. Could that eventually affect what you pay for Medicare? Of course. And what happens if the market falls 20% while we’re doing all of this? Do we still have somewhere else to pull income from?
That’s the work. It’s not making five individual financial decisions. It’s understanding what happens to the rest of your plan every time you make one. After we’ve done the analysis, we sit down with you and we walk through it.
And I want this to be a conversation. Here’s how we think about income. Here’s how we’d approach your investment. Here are tax planning opportunities we think are worth exploring. Here’s what we need to prepare for healthcare. And here’s what we want coordinated on the estate side.
Understanding Your Financial Plan
And I want you asking questions, and we’ll be asking questions, because I don’t want you walking out and thinking, wow, that sounded really sophisticated. And I also have absolutely no idea what they just said. That’s not confidence.
You should understand your own financial plan. You should know where your retirement paycheck is coming from. You should understand why you’re invested the way that you are. You should know what we’re trying to accomplish with our tax strategy and what we’re going to do when something doesn’t go according to plan. Because something won’t go according to plan.
Planning for an Uncertain Future
And this is probably the biggest misconception about financial planning. People think we’re supposed to create this perfect plan today that predicts the next 20 years. We can’t. And neither can anybody else.
The market is going to change. Tax laws will change. Your family will change. Your priorities might change. You may sell a house. You may buy another one.
Maybe one of your kids needs help. Maybe you decide, you know what? We’re healthy, we’ve got the money. We’re taking the entire family to Europe. Great, call us.
Let’s figure out where the most efficient and effective place we should take that money from. Let’s look at the tax consequences. Let’s see what it does to the rest of the plan. And then make the decision with the full picture in front of us.
That’s why I don’t think of your retirement success plan as a set of railroad tracks, because it’s a roadmap. We may know where we’re trying to go, and we may have a path for starting to get there. But when life puts a roadblock in front of us, we can change the route without losing the destination. To me, that’s what having a financial advisor should actually feel like.
Questions Your Retirement Plan Should Answer
So what should you walk away knowing? Well, at the end of the process, I want you to be able to answer the questions that actually matter. Can we retire? How much can we spend? Where is our income going to come from?
What happens if the market has a terrible year? Because it will. Are we being intentional about our taxes? What are we doing about our healthcare? And what happens to everything if something happens to one of us?
And maybe the question people don’t ask enough is: are we actually using our money to live the life we worked so hard to create? Is it aligned with our values? Because you can have a $3 million portfolio and still not feel financially secure if you don’t understand how any of it works.
What It’s Like to Work With Oak Harvest
Let’s talk a little bit about our process. If you’re wondering about what actually happens when you come to see us, we think it’s pretty simple and painless. First, a discovery call. We get to know each other and figure out what it is that we can actually help with.
Then your first visit is in person or on Zoom with a financial advisor. We go deeper into your life, your money, and what you’re trying to accomplish. Next, the analysis overview. Our team does the homework for you. We look at what you have currently going on in your portfolio. Look under every stone.
And see what is working, where there might be gaps, what we can maximize, and where there may be opportunities, and then we build your customized retirement success plan. Income, investments, taxes, healthcare, estate planning, all coordinated around you. And if we decide to work together, that’s not the end of the process. It’s really the beginning.
We implement it, we monitor it, and when life changes, we adjust it. So when somebody asks me, what is oak harvest do. I could tell them we help with income planning, investments, social security, taxes, healthcare, and estate planning, because we do all of that too.
But I think the simplest answer is we help you to understand what your money needs to do, how all of the pieces work together, and what to do when life changes. Because retirement isn’t about having the biggest portfolio. It’s about knowing am I okay? Can I do the things I want to do? And do I have a plan that I can rely on and one that I actually understand.
Clarity, Confidence, and the Next Step
That’s what the retirement success plan is designed to do, to give you clarity, because clarity creates confidence and confidence creates freedom. So if you’re watching this thinking, we have an advisor or maybe you self-direct, we have investments, we have all this stuff, but I’m not sure anyone has really ever put it all together for us. That’s a great reason to have the conversation. And you can start with a 15 to 20 minute discovery call.
Where we’ll learn about you, you’ll learn a little bit about us, and together we’ll figure out whether it makes sense to take the next step. And even if you never work with us, here’s a question I’d like you to consider bringing up to your advisor. Can you show me how all of the decisions we’re making work together?
Because you shouldn’t just know what you own or what accounts you have. You should understand the wisdom behind your plan.
➡️ Since we mentioned the Will or Trust Guide, if you’re wondering which one may make sense for your family, we created a free guide that walks through the key differences and decisions to consider. Download your free copy: https://click2retire.com/4hWGaE2
If you’d like help seeing how all of these decisions come together in your retirement plan, you can schedule a complimentary visit with our team. We’ll learn more about your situation, what you’re trying to accomplish, and help you understand what the next steps could look like. https://click2retire.com/4z9YtLM
Frequently Asked Questions
What is a retirement plan?
In the video, Jessica describes a retirement plan as more than an investment portfolio or collection of financial products. A coordinated retirement plan considers how your income, investments, taxes, healthcare, and estate planning work together to support the life you want to live.
What are the five major areas of retirement planning?
Oak Harvest’s Retirement Success Process looks at five major areas: income, investments, taxes, healthcare, and estate planning. The important point is that these aren’t treated as five unrelated boxes to check. Decisions in one area can affect the others.
Why do retirement decisions need to be coordinated?
A decision about Social Security can change how much money you need to withdraw from investments. The account you withdraw that money from can change your taxes. Changes to taxable income can potentially affect what you pay for Medicare. Looking at the decisions together helps reveal consequences that may be missed when each area is considered separately.
What happens during an initial discovery call with Oak Harvest?
According to Jessica, the discovery call typically lasts 15 to 20 minutes. The purpose is to learn what’s happening in your life, what you’re trying to accomplish, and whether Oak Harvest may be able to help. It’s also an opportunity for you to learn about Oak Harvest and decide whether you’re comfortable continuing the conversation.
What happens after the discovery call?
If it makes sense to continue, the next step is a meeting with a financial advisor, either in person or over Zoom. The conversation goes deeper into your life, finances, goals, spending, concerns, and what you want your money to accomplish. Oak Harvest then analyzes your current situation and looks at what’s working, potential gaps, and possible opportunities before building a customized Retirement Success Plan.
How can Social Security affect the rest of a retirement plan?
When you claim Social Security can affect how much income you need from your investments. That raises another question: which accounts should provide the additional income? Different withdrawal sources can produce different tax consequences, which means the Social Security decision can create ripple effects elsewhere in the plan.
Why does it matter which retirement account I withdraw money from?
As Jessica explains in the video, taking $50,000 from a brokerage account isn’t necessarily the same as taking $50,000 from an IRA because the tax consequences can be different. That’s why withdrawal decisions should be considered alongside the broader income and tax strategy.
Should a retirement plan change over time?
Yes. The video specifically describes a retirement plan as a roadmap rather than railroad tracks. Markets can change, tax laws can change, family circumstances can change, and your priorities can change. The goal is to have a plan that can adjust when circumstances change without losing sight of where you’re trying to go.
How do I know whether my current financial plan is actually coordinated?
Jessica suggests asking your advisor a simple question: “Can you show me how all of the decisions we’re making work together?” You shouldn’t only know what accounts or investments you own. You should understand the reasoning behind the plan and how one financial decision affects the others.
What should I know when my retirement plan is complete?
Jessica says you should be able to answer questions such as: Can we retire? How much can we spend? Where will our income come from? What happens if the market has a terrible year? Are we being intentional about taxes? What are we doing about healthcare? What happens financially if something happens to one of us? And are we actually using our money to live the life we worked to create?
