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#83 - Investing in Retirement - Part 4: Putting the Pieces Together for a Successful Retirement
In this final installment of the four-part series on the Seven Essential Strategies for Successful Investing in Retirement, Eric Blake explores tax-smart portfolio management, how to anticipate and navigate risks in retirement, and when to consider partnering with a financial advisor during the retirement income phase.
Introduction
Eric Blake: On today's show, we are wrapping up our series on these seven essential strategies for successful investing in retirement, and we are closing with two strategies that can make or break your retirement plan. How to manage your retirement portfolio tax burden, and whether working with an advisor during the retirement income phase of life is the right decision for you.
Welcome to another episode of the Simply Retirement Podcast, where we want to empower and educate women to live your retirement on your terms. I'm your host, Eric Blake, practicing retirement planner with over 25 years of experience, founder of Blake Wealth Management, and I would not be the man I am today without the women in my life.
Over the past three episodes, we have covered some very key strategies. Number one, we talked about the importance of having a plan. It starts with your values and includes your goals. You have to have point A, and you have to have point B before we ever figure out how we are going to get from one to the other.
Then we talked about understanding the true objective of a retirement portfolio, which should be growth of income. We also talked about how to reframe risk in retirement, and then in our last episode, we discussed the important role of stocks to maintain purchasing power over what could be a 30-plus-year retirement, and the value of dividend growth investing — these two being the key building blocks of your retirement portfolio.
Today, we will bring it all together with our final two strategies, and as always, joining me is Wendy McConnell. Wendy, how are you?
Wendy McConnell: I'm good. Thanks for having me.
Eric Blake: Absolutely. So I have a question for you before we get to these last two strategies. Are there any of the strategies we've discussed so far that you felt really resonated with you, or that made you say, “Hey, I just did not realize how important that actually is in my retirement years?”
Wendy McConnell: Yeah. There are two things. As you just mentioned, the value of the dividend growth — I thought that was very eye-opening because I really do not ever hear people talk about that. But also the success of the market over time, even after a huge downturn. It is just way more successful than I thought.
Listener Reflections
Eric Blake: Well, and I think that is the challenge.
Wendy McConnell: Then let's keep it going.
Eric Blake: Well, and that is the challenge, because none of that is the good stuff on the news, right? That does not get clicks. Historically, “just stick with it and you will be fine” does not get clicks. It does not get eyeballs looking at your stuff.
Wendy McConnell: Right. Well, I have heard the growth — you know, a normal growth is 7% and 12% and all that — but it sounded a lot higher when we were talking about it.
Eric Blake: It is not necessarily that the returns are higher. It is just that when you hear on the news, all you hear about are the big swings: the downturns, the market. What is funny, I think, is that the Dow — you hear on the news that the Dow Jones has dropped 200 points. But what is funny to me is they stress it the same way today as they did 30 years ago. And 200 points today is not anywhere near as impactful as 200 points 30 years ago.
Wendy McConnell: Right.
Eric Blake: But they make it sound like it is just as critical. “You better watch this. You better pay attention. Something bad might happen.”
Wendy McConnell: Fear sells.
Eric Blake: Exactly. And I think that is really the thing I wanted to set expectations around in this series. When you are talking about retirement investing, people have fears. They worry, “I am in my retirement years — I do not want to go back to work. I do not want to have to go back to work.” If they choose to, maybe they will, but they do not want to have to.
So as we start putting together what I consider these seven essential strategies to successful investing, it is: how do we deal with those fears? Because they are going to come. That is the one thing I want people to understand — it is not if we see a down market, it is when. But how prepared are we in advance, rather than getting into the middle of that down market and panicking because we do not know what our strategy is?
That is really the biggest thing: having your strategy well in advance of these difficult periods, not trying to figure out what to do and making emotional reactions or emotional decisions. Because emotional decisions when it comes to money are almost always the wrong decision.
Risk & Purchasing Power
Wendy McConnell: Yeah. So it is about our purchasing power.
Eric Blake: Mm-hmm.
Wendy McConnell: And, you know, I do not want to lose my money. I want my money.
Eric Blake: Right. Well, and again, back to reframing risk — people so many times think that in retirement, “I have to be safe, I have to be conservative.” And all you are doing is trading one type of risk for another: loss of purchasing power. Maybe you are getting rid of market risk because your money is not going to go down. But that does not mean you are not going to run out of money if prices increase faster than your returns. Inflation — you are still going to run out of money.
Wendy McConnell: Yeah. And that was a good eye-opening example, you know, lesson as well. So yeah, I mean, you are just a smarty.
Eric Blake: I appreciate that. I am going to put that on my business card.
Wendy McConnell: “A smarty.”
Eric Blake: That is right. That has got to be a selling point, right?
Wendy McConnell: I would think.
Minimizing Lifetime Tax Liability
Eric Blake: Alright, so you definitely want us to transition to these next two strategies — our final two strategies. Because, you know, the one thing we have to be aware of is that in retirement, there is more to consider than just the investments, just the portfolio. And one of the most important, and often the most surprising, is managing your tax burden.
A big part of it is that you do not have the same tools in retirement that you had while you were working. You do not have a 401(k) you can contribute to in order to reduce your taxable income. You do not have pre-tax health insurance premiums that reduce your taxable income. You do not have child tax credits anymore. You do not get that benefit. If you have children, you no longer have that. And for the most part, most of your children are probably grown if you are retired.
Wendy McConnell: You would hope.
Eric Blake: We think so. Not for everybody. Actually, we know there are, you know, some of the celebrities — who knows.
Wendy McConnell: Oh yeah. Janet Jackson — pop ’em out at 50.
Eric Blake: That is right. But for most of us normal people, when you get to retirement, your children are probably grown. So there are no child tax credits. There are none of those other ways you could reduce your taxable income once you get to those retirement years.
And the other part is that taxes in retirement are filled with a lot of these hidden surprises that people just do not know about.
Tax Surprises in Retirement
Eric Blake: For example, there is IRMAA — “Aunt Irma” — and Uncle Sam. IRMAA is the Income-Related Monthly Adjustment Amount, which is basically an extra Medicare premium that sneaks up on people because their income is higher than they thought it would be. A lot of times it is triggered because of required distributions — people not planning in advance for required distributions that push their income higher than they expected it to be — or other sources of income.
One of the things I see a lot is when people decide to downsize or maybe they sell a piece of real estate. They have capital gains, they sell that property, and that income pushes them above some of these IRMAA thresholds — not thinking that is going to be the case.
So you have to be aware of these when you are making big decisions on selling an asset, whether it is investments or real estate. You want to make sure you understand what the implications are going to be.
And then when we talk about RMDs — how confusing has that been over the last handful of years? They have gone from 70½ to 72. Now they are somewhere between 73 and 75. Who knows? Somebody might know. But you have to make sure you understand, based on your year of birth:When do my required distributions actually start?And also: When will Congress just leave it alone? Just pick an age and leave it there.
Wendy McConnell: Yeah. I mean, you have to keep up with all of this stuff. You know, it is always changing.
Eric Blake: Exactly. And then we get to Social Security taxation — not actually knowing what income gets included and how much of your Social Security is going to get taxed. So you have those types of issues as well.
And then they throw on top this One Big Beautiful Bill Act this year, which adds a whole new set of provisions that retirees need to be aware of, like the new age-65-plus deduction. The other part is some of these provisions eventually expire. So how do you use them to your advantage while they are still available?
It is not just about knowing what the taxes are — it is trying to keep up with tax laws that are constantly shifting under your feet.
Key Tax Strategies
Eric Blake: So here are some key strategies that we use with our clients. I want to share a few of these:
1. Managing Asset Location
Most people think only about what they own — stocks, bonds, etc. But where you hold them matters too.
Bonds typically generate more taxable income, so they may belong in IRAs or other tax-deferred accounts.
Stocks may be better positioned in taxable accounts where gains are only triggered when sold and dividends may be more tax-efficient.
2. Managing IRA Withdrawals and Timing
Questions you must consider:
When should I start taking IRA withdrawals?
How will those withdrawals affect my Social Security?
How do RMDs change the equation?
Which accounts should I draw from first?
3. Low-Cost, Low-Turnover Funds
Using ETFs or funds with low turnover can reduce the “tax drag” in taxable accounts.
4. Strategic Roth Conversions
If you are in a lower tax bracket now — particularly early in retirement — it may make sense to convert pre-tax dollars to Roth IRAs so that future income is tax-free.
5. Tax-Loss Harvesting
If an investment in a taxable account is worth less today than when you bought it, you may be able to sell it, harvest the loss, and reduce your taxable income for the year.
Additional Podcast Resources
Eric Blake: If you want to go deeper into any of these topics, I have recorded full episodes on them:
Episode 65: Deep dive into the new tax law and how it could impact retirees
Episode 48: How to actually pay taxes in retirement
Episode 54: How Social Security gets taxed
Episode 75: Year-end tax planning checklist
Big Picture: Tax Planning Is Ongoing
Eric Blake: The bottom line is that managing your taxes in retirement is not a set-it-and-forget-it activity. It is definitely a moving target. One thing I say to clients regularly is this:
“The biggest advantage we have over Uncle Sam is that Uncle Sam only looks at one year at a time, but we can look several years down the road.”
We can make educated decisions now that reduce your lifetime tax liability.
Wendy McConnell: Yeah. I like that.
Eric Blake: Make sense?
Wendy McConnell: Yeah.
Should You Work With an Advisor?
Eric Blake: Awesome.
Wendy McConnell: It is a lot though.
Eric Blake: It is. It is. So that leads us perfectly into our next — our final — strategy, number seven.
Wendy McConnell: Okay.
Eric Blake: And that is: Should you work with an advisor during this important phase of life? Again, there are a lot of people who candidly may rightly believe they can manage their own financial affairs in retirement.
But the big question is:
Do you want to commit the time and energy necessary to design these strategies?
Do you want to understand tax laws and tax implications yourself?
Do you want to stay on top of changes in order to ensure a successful retirement?
Or would you prefer to partner with an advisor who can walk with you every step of the way?
That is everybody's choice to make. But tax planning, in particular, can be the ultimate differentiator when deciding whether to work with an advisor, because the tax implications can be so significant.
Think about it: You spend two-thirds of your life saving and accumulating wealth so you can retire happily and comfortably… and then you spend the final third of your life living on what you have accumulated. For many people, there is no plan B, unless you either want to or are able to go back to work. And depending on your health, that may not even be an option.
Wendy McConnell: Right.
Eric Blake: That is the thing. Getting this phase wrong is not just a mistake — it could jeopardize your entire retirement.
When Should Someone Seek Help?
Wendy McConnell: Well, let me ask you a question. Somebody who, say through their forties or early fifties, has been stocking away money in the 401(k) and contributing for years and years… When is the point where you say, “Alright, I need to start really paying attention to this stuff”? What is the age when someone should think, I probably should get somebody to help me with this?
Eric Blake: To me — and again, using our practice as an example — most of our clients come to us somewhere in that two- to five-year window before retirement, or maybe recently retired, because they’re in the midst of making some of these decisions.
When you think about Social Security, I tell people in their forties:
“Just plan on taking Social Security at your full retirement age.”
But once you get into that two- to five-year window, now we have to be much more diligent. If it is a couple:
When will one spouse start?
When will the other?
Do we delay one benefit and start the other earlier?
Once you get close to retirement — two to five years away — these decisions become very important.
And then you look at: How are my assets structured? If everything you have is in pre-tax accounts, like a 401(k), then everything you withdraw will be taxable. And we just talked about how big that impact can be — RMDs, taxation of Social Security, and more.
You want to nail down:
Your retirement income strategy
Your tax strategy
Your Social Security approach
Your withdrawal priority (which accounts to draw from first)
And that does not even get into:
“What if I retire at 60 or 62 before Medicare? How will I handle healthcare for several years?”
That two- to five-year window is the time to get clarity so that once you retire, you're focused on what you want to do, not on worrying about taxes and markets.
Planning Earlier Than Two to Five Years
Wendy McConnell: It just seems late to me. As someone in their mid-fifties, I am like, I do not want to wait until two to five years before I retire. I want to take care of this stuff now — get it off my mind.
Eric Blake: Well, I would not say that means you do not start planning earlier.
Wendy McConnell: Okay.
Eric Blake: It just means that the retirement income strategy — the exact sequence, timing, and structure — becomes most relevant once you are in that window.
Here’s the thing: when you work with a financial advisor, there are many great ones out there, and you want someone who specializes in you and your problems.
If you are 45, you may have kids at home, or kids approaching college. Your decisions are different than a 65-year-old who is planning withdrawals and Social Security.
So yes — you want to be saving, preparing, and planning in your forties and fifties. But I suggest focusing on:
Having the right habits
Saving consistently
Hitting your annual savings targets
If a 35-year-old advisor tells a 35-year-old client they need $5 million to retire, that can be extremely overwhelming. It is much better to focus on the annual habit:
“Did I save what I committed to save this year?”
Wendy McConnell: True. Yes.
Eric Blake: Exactly. If you hit your annual savings goals and increase them over time, you are building the right foundation. Then once you get within that two- to five-year window, you refine the details.
Saving and the Psychology of Big Numbers
Eric Blake: There used to be a commercial — I cannot remember if it was Schwab or someone else — with the tagline, “What’s your number?” People walking around carrying these huge dollar amounts. But if you are 35 and your “number” is $3 million, that can feel unattainable.
Wendy McConnell: But are those numbers necessary, though? Three million dollars?
Eric Blake: It depends on your circumstances — lifestyle, resources, goals. But again, that two- to five-year window is where we determine what your true number is.
Then the question becomes:How do I turn that number into income?How do I convert a portfolio into the lifestyle you want?
That is why our practice focuses on the retirement income phase, not the accumulation phase.
Wendy McConnell: I just worry people hear “two, three, five million dollars” and get scared, thinking they’ll never be able to do it.
Eric Blake: Absolutely. And that is why I encourage people in their accumulation years to focus on their habits:
“What is my savings goal this year? Did I hit it?”
Wendy McConnell: Okay.
Eric Blake: If I am saving $25,000 in 2025, can I increase it 3% in 2026? Those habits compound over decades.
Starting Where You Are
Wendy McConnell: I mean, I wish I could go back to 35 and start over.
Eric Blake: I can see that. And many people feel that way. But you have to start where you are. That is the best any of us can do.
Wendy McConnell: Yeah. We were all told as young adults — “Put money away. Don’t cash in the pension. Save your money.” And I did not listen.
Eric Blake: Because the urgency grows the closer you get. Absolutely.
What to Look for When Hiring an Advisor
Eric Blake: So I wanted to talk about — as you are thinking about working with an advisor — we have talked about someone who understands tax implications and the distribution phase of life. When you are transitioning into retirement, I want to share a few questions that can be helpful if you are considering hiring an advisor.
These apply whether you are preparing for retirement or are in your early 30s, 40s, or 50s.
1. Are you a fiduciary?
The reason I include this is because it has become a real buzzword in our industry. Advisors throw this term around like a selling point. What is funny is that everyone tells you to ask the question — “Are you a fiduciary?” — but they rarely tell you what it means.
A fiduciary is:
Legally and ethically obligated to put your best interest first
Required to put the client’s interest ahead of their own
Expected to minimize conflicts of interest and be transparent
Why does this even need to be said? It should be assumed. But because the term gets misused, you need to understand what you are actually asking.
Wendy McConnell: Right. And the fact that a lot of fees are a percentage of what you have or earn — it really is in your best interest to make sure I am getting what is in my best interest.
Eric Blake: Exactly. And that ties into conflicts of interest. For example, under an assets-under-management model, if you call your advisor and say, “I need to pay off this debt,” or “I need a large expense covered,” that could technically reduce the advisor’s compensation if money is withdrawn.
Now — every advisor has conflicts of interest. It does not matter what type of fee structure they use: AUM, flat fee, hourly. If an advisor says they have no conflicts, you should run the other direction.
You just need to understand:
What are the conflicts?
Do they impact you?
Does the advisor communicate them clearly?
Do you trust the advisor anyway?
And one thing I always encourage: Ask for references. Ask to speak to two or three people in a similar situation. If an advisor hesitates beyond simply giving those clients a heads-up, that is a red flag.
Wendy McConnell: Okay. Good to know.
2. What services do you provide?
Eric Blake: Not all advisors do the same thing.
Some:
Only manage investments
Do not do planning
Do not analyze taxes or Social Security
Do not help with Medicare decisions
Do not support estate planning conversations
Others — like us — do comprehensive planning that includes:
Retirement income
Tax strategy
Social Security
Medicare
Estate planning
Ongoing planning and support throughout the year
Know:
What services the advisor actually provides
Whether those services align with your needs
Whether they have experience with people like you and your situation
If you are 35, an advisor who only does retirement income planning is not a good fit.If you are 65, an advisor who only focuses on accumulation is not a good fit.
3. What does a typical year of service look like?
Eric Blake: This one is important because some advisors are great at sales, get you to sign the dotted line… and then what happens?
You want to know:
How often will we meet?
What happens between meetings?
What will those meetings focus on?
What is the advisor proactively watching for throughout the year?
For example, here is how we do it: We meet with every client at least twice a year.
Spring meeting (May/June):
After tax season
Review the tax return
Identify tax planning opportunities for the current year
Fall meeting (October/November):
Evaluate income for the year
Make decisions before year-end deadlines
Ensure RMDs are handled
Execute Roth conversions if appropriate
Update the retirement income plan
And in between, we are always available for unexpected life events, questions, or major decisions.
Wendy McConnell: Sounds good. So I do not have to wait until May or June or October or November to say, “I have a purchase coming up.”
Eric Blake: Exactly. Clients feel comfortable knowing:
When we will reach out to schedule formal meetings
When to call us right away
When something can be added to the agenda for the next meeting
For example, we recently had a client whose husband passed away last year. He was the one who always handled the car leases and buying decisions. She emailed me:
“I am still paying this auto lease. I am thinking about getting a new car. What do you think I should do?”
I replied with some considerations and then asked:
“Do you want to set up a time to talk?” or
“Are you comfortable adding this to our next meeting agenda?”
There is always something going on, and the question is simply: Does this need attention now, or can it wait until our next strategy meeting?
The Emotional Value of an Advisor
Eric Blake: Beyond the technical side, a professional advisor brings something equally important:
A calm, steady voice when emotions run high.
Market volatility, big decisions, fear around running out of money — these things can cause people to react emotionally. And emotional decisions are rarely the right ones.
Another value:If you are the primary financial decision-maker in your household, one of the greatest benefits of having an advisor is knowing your spouse will have a professional to rely on if something happens to you.
A Real Story: When Someone Is Not Included
Eric Blake: I want to share something I am extremely passionate about. This came up last week, and it has been weighing on me. I posted about it on LinkedIn.
A prospective client called me. She is getting divorced. They have been married for over 20 years. And this is what she said — word for word:
“My husband has had a financial advisor since we have been married. I have never talked to him.”
To me, that is completely unacceptable. “Unacceptable” is probably too nice. I would call it malpractice.
She was never included. She was never allowed to be part of the finances. And now she does not know what they have.
Wendy McConnell: Oh, that is really bad.
Eric Blake: She told me, “I saw your story — raised by a single mom. That is going to be me.” They have an 18-year-old son. She said she reached out because she did not know where to turn.
She is worried her husband may be trying to hide assets. Is he? Or does it just feel that way because she does not know where anything is? Hard to tell.
Wendy McConnell: Well, and how would you even know? If you do not know what you have, he could easily do that.
Eric Blake: Exactly. And unfortunately, this is a recurring story — not always intentional, but common. The husband handled everything. She was a stay-at-home mom. Now she’s concerned about Social Security, income, housing — everything.
We gave her resources. I referred her to a forensic accountant so she could get clarity and ask smart questions. We pointed her toward what to tell her attorney.
But here is the bigger point:
If your advisor is not making space for you, you do not have an advisor. He does.
If you are not being included:
Not asked questions
Not invited into meetings
Not kept informed
…then it may be time to find a new advisor who respects you, your goals, your future.
You deserve a seat at the table. You deserve to understand what you have. You deserve a voice in your own retirement.
Recap of the Seven Essential Strategies
Eric Blake: Alright, so a little bit more — we will wrap this episode up. Just a quick recap of our seven strategies.
1. Have a Plan
The investment portfolio is not the plan. The portfolio is what helps get you from point A to point B, but the plan itself is knowing:
Where you are
Where you want to go
What your goals and values are
2. Understand the True Objective of Your Retirement Portfolio
It should be growth of income, not simply accumulation or account balance.
3. Reframe Risk
Think about risk in terms of years of income, not percentage fluctuations. Ask: How many years of income do I have set aside to weather downturns?
4. Understand the Role of Stocks
Stocks provide:
Long-term growth
Rising income
Protection against inflation
Ups and downs are normal — but historically, stocks help maintain purchasing power over decades.
5. Value of Dividend Growth
Dividend growth is a powerful tool because historically it:
Provides steady income
Has grown faster than inflation in many periods
Helps stabilize income during retirement
6. Manage Taxes
The less you pay in taxes, the more you keep and the more you can spend. Tax planning is one of the most impactful retirement strategies.
7. Consider Working With an Advisor
An advisor can help you:
Tie all these pieces together
Avoid emotional decisions
Evaluate tax strategies
Navigate Social Security, Medicare, and income planning
Maintain confidence during volatility
Support your spouse or family if something happens to you
These seven strategies are timeless, but what makes them powerful is how you apply them to your own life.
Next Steps for Listeners
Eric Blake: So lastly, here are some key steps to put these strategies into action:
1. Seek Professional Guidance
If you are unsure whether you need an advisor, there are excellent organizations like Savvy Ladies and Purse Strings. We will share links to those episodes.
2. Develop a Plan
Write down:
Your goals
Your income needs
Your spending
How your savings will support your retirement lifestyle
3. Implement the Strategy
You have to put it into action:
Set up your accounts
Automate your savings
Organize your investments
Organize your taxes
4. Review and Adjust
Check in regularly:
With your advisor, or
With yourself if you are managing it on your own
Life changes — your plan must adapt.
5. Start Small
You do not need a perfect plan to begin. Take simple steps like:
Reviewing your spending
Setting aside a few months of cash
Reviewing your Social Security statement
These small steps add up.
Simply Retirement Roadmap Invitation
Eric Blake: Last thing — if you are looking for guidance, we would love the opportunity to chat.
We have talked about these seven strategies. This is what we do on a regular basis. If you would like a second opinion or are making a retirement decision in the next year or two, visit:
GetMySimplyRetirementRoadmap.com
There, you can schedule your complimentary tax and retirement analysis.
Our retirement process works like this:
Simply Retirement Roadmap Meeting: We take you through our three-step process.
Your Personalized Action Plan: We outline what we believe you should do to get from point A to point B.
Take-Your-Time Step: You review your Roadmap and decide if we are the right fit.
Ongoing Personalized Planning: If you hire us, we do the heavy lifting so you can enjoy retirement.
Hopefully, this gives you a clear picture of what an advisor relationship could look like.
Eric Blake: That is it for today’s episode and for our series on the seven essential strategies for successful investing in retirement. As a reminder, for all the links and resources mentioned today, visit TheSimplyRetirementPodcast.com.
Please do not forget to like, follow, and share our show. Until next time, please remember:
Retirement is not the end of the road. It is the start of a new journey.
Content here is for illustrative purposes and general information only. It is not legal, tax, or individualized financial advice; nor is it a recommendation to buy, sell, or hold any specific security, or engage in any specific trading strategy.
All investing involves risk including loss of principal. Results will vary. Past performance is no indication of future results or success. Market conditions change continuously.
Information here is provided, in part, by third-party sources. These sources are generally deemed to be reliable; however, neither Blake Wealth Management nor RFG Advisory guarantee the accuracy of third-party sources. The views expressed here are those of Blake Wealth Management. They do not necessarily represent those of RFG Advisory, their employees, or their clients.
This commentary should not be regarded as a description of advisory services provided by Blake Wealth Management or RFG Advisory, or performance returns of any client. The views reflected in the commentary are subject to change at any time without notice.