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Whether you're nearing retirement or already enjoying your golden years, our blog is your trusted source for practical advice and thoughtful analysis to ensure you're well-prepared for the road ahead.

Thursday, November 12, 2026

Which Account Should You Draw From First in Retirement? If you needed to pay for a new roof this year, which account would you use? I’d start by looking at what else is going on in your tax return. A withdrawal of money you contributed...

Wednesday, November 11, 2026

What Could the National Debt Mean for Your Retirement Income? I once held up a conversation at the Columbus airport over four cents in change. The cashier was out of pennies, so I asked for a nickel. I got it, and Kristin still gives...

Tuesday, November 10, 2026

How Are Retirement Withdrawals Taxed? When we talk about retirement income, I like to ask where you’d go for the money if you needed a new roof. Would you pull it from your traditional IRA, your Roth IRA, or a brokerage account? The...

Monday, November 9, 2026

Could the National Debt Affect Your Retirement Taxes? I once asked for a manager at the Columbus airport over four cents. Kristin had asked me to break a hundred dollar bill so we’d have cash for tips. When the cashier handed me $75...

Saturday, November 7, 2026

What Should You Ask Before Buying an Annuity? On the show, I shared a review of two variable annuities owned by a woman who wanted help planning her retirement withdrawals. The fee layers we discussed added up to 3.65% annually. That...

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Friday, November 6, 2026

Should an Annuity Be Part of Your Retirement Plan? Kristin likes getting to the airport with plenty of time to spare. I sometimes wonder how long we really need to sit at the gate. But I know having that extra time makes the trip more...

Thursday, November 5, 2026

5 Questions to Ask Before Buying an Annuity “What am I actually paying for this?” That is a fair question about anything you own. It becomes especially important when the answer affects your retirement income for years. On our radio...

Wednesday, November 4, 2026

Are Annuities Good or Bad for Retirement? Kristin and I agree on plenty of things. How early we need to get to the airport is not always one of them. She wants time to spare. I look at how quickly we usually get through security and...

Saturday, October 31, 2026

Should You Stay With Your Firm When Your Advisor Leaves? When a financial advisor you trust leaves, it can feel personal. You have shared goals, asked difficult questions, and built a relationship over the years. Suddenly, you need to...

Friday, October 30, 2026

How Can You Prepare for Surprise Retirement Expenses? An unexpected bill can bring back a familiar feeling: How am I going to pay for this? I remember times when money was so tight that even lunch was a concern. Those experiences stay...

Thursday, October 29, 2026

What Should You Do When Your Financial Advisor Leaves? You can be happy for someone and frustrated by their decision at the same time. That came up on our show when our co-host Kristen shared that her financial advisor was leaving the...

Wednesday, October 28, 2026

How Do You Handle Unexpected Expenses in Retirement? A surprise repair bill has a way of making every other financial concern feel more urgent. I know that feeling. There was a time in my life when an invitation to lunch left me...

Saturday, October 24, 2026

3 Jobs Your Money Needs to Do in Retirement Your retirement account balance tells you how much you have today. I also want to know what that money needs to do tomorrow. At Legacy Retirement Group, we use a three bucket framework to...

Friday, October 23, 2026

Can Your Retirement Budget Handle a Car Payment? That new car smell wears off. The payment could stick around long after your last paycheck. Before buying a vehicle near retirement, I want to know how the full cost fits your future...

Thursday, October 22, 2026

How Can Your Retirement Income Keep Up With Inflation? You do not need an economic report to notice that the same grocery cart costs more than it used to. The harder question is what those rising costs could mean over 20 or 30 years of...

Wednesday, October 21, 2026

Should You Buy a Car Before Retirement? That new car smell eventually wears off. A payment can follow you into retirement for years. When someone asks me whether to buy a car before retiring, I want to look beyond the monthly payment....

Saturday, October 17, 2026

Will Retirement Really Cost You Less? Retirement can change your expenses without lowering them. I have been playing more golf lately, and Kristin reminds me that we pay for both the golf and a little extra help around the house while...

Friday, October 16, 2026

Do You Really Need $1 Million to Retire? You do not necessarily need $1 million to retire. The amount you need depends on what you spend, what income you can count on, and how much your savings must provide after taxes. Years ago,...

Thursday, October 15, 2026

Will You Really Spend Less and Pay Lower Taxes in Retirement? Retirement does not automatically mean lower spending or a lower tax bracket. Your expenses depend on how you live, and your taxes depend on your income and the accounts you...

Wednesday, October 14, 2026

Can You Retire With Less Than $1 Million? You may be able to retire with less than $1 million. What matters is how your savings fit with your income, spending, and future needs. I worked with two teachers who had saved about $890,000...

Saturday, October 10, 2026

How Can You Feel More Comfortable Spending Money in Retirement? Kristin and I recently enjoyed a date at Easton, complete with a meal, shopping, and a Corvette ride that ended in a downpour. The car was fine, and the time together was...

Friday, October 9, 2026

How Can Couples Plan for Retirement When They Disagree About Money? You can spend decades together and still think very differently about money. One spouse wants the reassurance of cash in the bank. The other wants investments with...

Wednesday, October 7, 2026

How Can You Feel More Comfortable Spending Money in Retirement? Kristin and I recently made time for a date at Easton. We ate at Bar Italia, did some shopping, and enjoyed a beautiful day with the top down in the Corvette. Then we...

Tuesday, October 6, 2026

How Can Couples Plan for Retirement When They Disagree About Money? You can share a home, raise a family, and spend decades together without seeing money the same way. One person checks the bank balance for reassurance. The other sees...

Sunday, October 4, 2026

What Risks Should Your Retirement Plan Prepare For? Ask someone about risk, and they might picture jumping out of an airplane. Kristen would tell you that is not for her. She did let me talk her into parasailing once, but I doubt there...

Saturday, October 3, 2026

Why Does Investment Risk Feel Different in Retirement? When I was a kid, my friends and I used to grab the big metal bumpers of passing cars and let them pull us along our icy neighborhood streets. We thought it was fun. Looking back,...

Friday, October 2, 2026

What Risks Should Your Retirement Plan Prepare For? Ask someone how they feel about risk, and they might picture jumping out of an airplane. Kristen would probably tell you that is not for her. She did let me talk her into parasailing...

Thursday, October 1, 2026

Why Does Investment Risk Feel Different in Retirement? When I was a kid, my friends and I had a winter activity that sounds terrible to me now. Our neighborhood streets rarely got plowed. Snow packed into ice, cars crept between rows...

Friday, September 18, 2026

How Often Should Retirees Check Their Investments? A recent U.S. News report caught my attention because it said nearly one in three Americans are not regularly checking their bank balances because of anxiety. I understand that feeling...

Thursday, September 17, 2026

What Is the Three Bucket Retirement Strategy? My mom used to say you should never put all your eggs in one basket. When I was younger, I remember thinking, why are we carrying around baskets of eggs in the first place? Eventually I...

Sunday, September 13, 2026

Saving for Retirement vs Living in Retirement: Why the Math Changes Why Does the Math Change When You Retire? For decades, most people have one basic retirement investing goal: Put money in. You contribute to your 401(k). You fund an...

Friday, September 11, 2026

Can I Really Afford to Retire? How to Know When You Are Financially Ready Can I Really Afford to Retire? One of the biggest questions I can answer for someone is also one of the shortest: "Greg, can I really afford to retire?" That is...

Sunday, September 6, 2026

The Happiest Retirees I Know Do These 5 Things What Makes Someone Happy in Retirement? I have had a front row seat to retirement for more than 33 years. I have watched people prepare for it, enter it, adjust to it, and hopefully enjoy...

Saturday, September 5, 2026

Should You Pay Off Your Mortgage Before You Retire? For years, retirees have heard a familiar piece of financial advice. Pay off your mortgage before you retire. I understand the appeal. There is something incredibly comforting about...

Saturday, September 5, 2026

Bored in Retirement? 5 Ways to Get Your Spark Back What Happens When Retirement Gets Boring? There is a phrase I have heard from retirees that always gets my attention: “I’m just bored.” Sometimes it goes even deeper. “Nobody needs me...

Friday, September 4, 2026

Retirement Is Not the Finish Line: How to Find Purpose After You Stop Working Retirement Is Not the Finish Line After helping families prepare for retirement for more than 33 years, I have learned something that might surprise you. You...

Thursday, September 3, 2026

Should You Get More Conservative With Investments in Retirement? I hear this question all the time from people approaching retirement. "Greg, now that I'm retiring, shouldn't I get really conservative with my investments?" Maybe. But...

Wednesday, September 2, 2026

4 Retirement Rules You May Want to Rethink A recent AAA study found something that probably will not surprise anyone who spends much time behind the wheel. Speeding has become pretty normal. Going 10 miles per hour over the speed limit...

Tuesday, September 1, 2026

Should You Retire at 65? Why the Right Retirement Age Is Personal A recent AAA study found that speeding has become pretty normal for American drivers. Going 10 miles per hour over the speed limit is widely considered acceptable, and...

Saturday, August 22, 2026

Do You Really Need a Written Retirement Plan? I recently saw some interesting findings from LIMRA's Retirement Income Readiness Report. According to the report, 88 percent of people approaching retirement have thought about how they...

Saturday, August 22, 2026

Can Your Retirement Plan Answer the What Ifs? One of the biggest advantages of having a written retirement plan is that you can actually see how the pieces of your financial life fit together. I can tell someone they are probably going...

Friday, August 21, 2026

Are You Prepared for the Unexpected in Retirement? When Kristin recently told the story of a stressful experience going through airport security with our son, something stood out to me. The people at the airport were prepared for what...

Friday, August 21, 2026

When younger people ask me what they should be doing for retirement, I often give them pretty simple advice. Get started. Pay yourself first. Contribute consistently. Take advantage of the retirement accounts available to you. Then...

Wednesday, August 19, 2026

Will Your Money Last? How to Build a Retirement Plan for the Unknown One of the biggest fears I hear from people approaching retirement isn't dying—it's running out of money while they're still alive. In fact, an Allianz survey found...

Tuesday, August 11, 2026

How Much Do I Need to Retire? Why Income Matters More Than a Magic Number As America celebrates its 250th anniversary, there’s a lot to appreciate about this country—the people, the opportunities, the innovation and the freedom to...

Tuesday, August 11, 2026

What Will You Leave Behind? Why Your Legacy Is About More Than Money When you hear the word legacy, what do you think about? For a lot of people, the first thing that comes to mind is money. Your retirement accounts. Your home....

Wednesday, August 5, 2026

What Retirement Planning Has in Common With Driving a Stick Shift Some Things Never Change. Others Need a Completely New Approach. There was a time when driving a stick shift wasn't unusual—it was the norm. In fact, according to...

Wednesday, August 5, 2026

What Will Your Family Remember About You? Have you ever driven past an estate sale and wondered about the person who lived there? In just a weekend, someone's lifetime of possessions is spread across a driveway. Furniture. Pictures....

Friday, May 23, 2025

Planning for retirement should be exciting—but for many Americans, it’s overwhelming. A recent survey found that 53% of people feel confused or paralyzed when it comes to making financial decisions. That’s not just a statistic—it’s a...

Tuesday, August 27, 2024

Now the only question is, “How much will short-term interest rates drop in September?” At his annual speech to global central bankers in Jackson Hole, Wyoming, Fed Chair Powell laid out a strategy to cut short-term interest rates, but...

Thursday, June 20, 2024

The Impact of Presidential Policies on Your 401(k): Trump vs. Biden In the most recent Winning Retirement Radio Podcast episode, Greg and Kristen Taylor discuss how the presidencies of Trump and Biden have affected Americans' 401(k)s...

Monday, May 20, 2024

As we continue through 2024, I wanted to share some data that many may find positive. Fidelity Investments just announced that 440,000 retirement savers reached an incredible milestone in 2023: $1 million in their 401(k).1 That's...

Thursday, May 16, 2024

The 2024 Employee Benefit Research Institute (EBRI) Retirement Confidence Survey was recently released, and it provides an illuminating look at the current state of retirement preparations and mindsets across the country. While the...

Sunday, April 28, 2024

Retirement opens up a whole new world of possibilities! Here are 10 bucket list ideas for things to do in retirement: Travel the World: Take that dream vacation you've always wanted. Explore different countries, immerse yourself in new...

Thursday, April 25, 2024

Transform your home into a haven of comfort and tranquility for your retirement years with these simple yet effective tips! From decluttering and organizing to creating cozy relaxation zones, discover how to make every corner of your...

Saturday, March 23, 2024

As we continue through 2024, I wanted to share some data that many may find positive. Fidelity Investments just announced that 440,000 retirement savers reached an incredible milestone in 2023: $1 million in their 401(k).1 That's...

Monday, June 19, 2023

Let’s hear it for the dads, the ones who help us grow, give us guidance, and look out for us in a million different ways. In celebration of Father’s Day, here are some of the ways you can honor the father-figures in your...

Monday, May 29, 2023

Memorial Day is a time for Americans to honor and remember those who lost their lives while serving in the armed forces. Veterans will think back on the men and women who served alongside them who gave the ultimate sacrifice for their...

Monday, May 15, 2023

A very special day is returning – Mother's Day. It is a day of gratitude, adoration, and relaxation for Mom, a time to treat her like the queen she is. Mother's Day gives you a chance to touch the hearts of all the mothers in...

Sunday, May 7, 2023

I wanted to take a moment to update you on the potential changes to Social Security benefits for 2024. As I'm sure you know, the Social Security Administration calculates annual cost-of-living adjustments (COLA) based on the Consumer...

Saturday, May 6, 2023

The Internal Revenue Service has released new limits for the coming year. After months of high inflation and financial uncertainty, some of these cost-of-living-based adjustments have reached near-record levels.Individual Retirement...

Friday, May 5, 2023

Financial markets can be challenging to understand. And when markets enter a “bad news is good news” cycle, it becomes even more challenging to follow along.Stock prices rallied at the end of April after the Commerce...

Thursday, November 12, 2020

It’s a startling statistic.45% of consumers with $100,000 or more investable assets expect to make changes to their investments due to the upcoming 2020 presidential election.1Second-guessing your investment strategy is natural,...

Wednesday, November 11, 2020

On October 13, 2020, the Social Security Administration (SSA) officially announced that Social Security recipients will receive a 1.3 percent cost-of-living adjustment (COLA) for 2021. This adjustment will begin with benefits payable...

Thursday, October 8, 2020

I met with a client a couple of weeks ago just to go over what she has and review her income situation. She worked a normal job all of her life making decent money but saved just about everything that she made. She is what we often...

Thursday, October 1, 2020

Rarely does a week ago by that we don’t have someone ask, “Which option should I take with my pension?” or “How can I get the most out of my 401(k)?” Recently, Kristin and I met with a retired woman who...

Thursday, September 24, 2020

A family that I met with seemed to be very concerned about their retirement future. As we discussed their financial situation, I discovered that they had done a wonderful job of preparing for retirement, saving more than $1 million....

Thursday, September 3, 2020

We’ve heard the stories about the architect whose house plans are never completed or the attorney with no estate plan. Those of us who manage our own businesses often get tied up in the day-to-day activities and miss the big...

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