Jay Kirkwood

Clear Skies Retirement

Business EN ↓ 92 episodes

Welcome to "Clear Skies Retirement," the podcast dedicated to guiding you through the unpredictable journey of retirement planning. Whether you're approaching retirement or already adjusting to its reality, "Clear Skies Retirement" helps you manage your finances to ensure a stable, secure, and fulfilling future. From investment strategies and savings tips to tax planning and estate management, we cover all aspects of financial stability in your golden years. Join us every week as we tackle the toughest challenges facing retirees and answer your burning questions about retirement. No matter the...

Author

Jay Kirkwood

Episodes

5 Golden Rules of Retirement Planning | Dividend Stocks Are on the Rise | Confidence About Retirement Is Up for a Strange Reason 04.11.2025 25:17

On this episode: Kiplinger’s list of things you need to get right before you retire. Why are people jumping into dividend paying stocks in record numbers? People feel better about retirement than they did a few years ago. What has changed? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Se...

Retirement Help for the DIYer | Inflation Is Different in Retirement | Figuring Out Your REAL Retirement Savings Number 25.10.2025 24:09

On this episode: You spend hours on your portfolio. What are you missing? The rising cost of retirement. The financial headlines tell us we need over a million to retire. What’s the real truth? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, including their "Ge...

The Rules Are Changing on Your 401(k) Next Year | How Can You Be a “Smart Rabbit” in Retirement? 21.10.2025 26:39

On this episode: Starting in 2026, there are new rules if you are using the 401(k) "catch up" provision. Making you a "smart rabbit" when it comes to your money in the stock market. 50% of people have no idea the steps to take to plan for retirement. Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team...

Retirement Advice You’ve Heard—And Why It Might Be Wrong 14.10.2025 26:37

This episode takes a hard look at popular retirement rules—from the 4% withdrawal strategy to the myth that you need a million dollars to retire. Jay Kirkwood breaks down why these one-size-fits-all formulas often fall short and how real planning requires a deeper understanding of your lifestyle, risks, and goals. Subscribe or follow so you never miss an episode! Check out our YouTube page f...

Is it Time for a Year-End Retirement Meeting Already? | Warren Buffett and Tony Robbins Agree on This Regarding Your Investing | A Retirement Lesson from Nate Bargatze 07.10.2025 23:05

On this episode of Clear Skies Retirement: Talking about taxes for this year, next year, and all the years to come.  Warren Buffett and Tony Robbins have a retirement warning for you. Nate Bargatze, New Math, and your Retirement. Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financ...

Are You Missing the Obvious in Your Retirement Planning? | Watch Your 401(k) Target Date Fund for Changes 20.09.2025 24:48

On this episode: You may have saved a nice number in your retirement accounts, but there might be something missing. President Trump is paving the way for new offerings in your 401(k). Should you consider them? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, includin...

Retirement Rules Are Changing—Are You Still Playing by the Old Ones? 06.09.2025 26:35

What does Warren Buffett’s $315 billion cash stash mean for your retirement strategy? In this episode, Jay Kirkwood explores the psychology of cash, the risks of over-concentration in portfolios, and why old financial rules like the 4% withdrawal rate may no longer apply. He discusses Roth conversions, RMDs, and how emotional comfort plays a role in financial planning. Subscribe or follow so...

New Data on How Much a Retired Couple Spends Each Month | A Retirement Lesson From George Carlin | Beware the New Offerings in Your 401(k) 30.08.2025 26:12

On this episode: How much do you need in retirement? Compare against the new average monthly spend numbers. Finding a place for all your financial “stuff.” President Trump is making the way for Private Equity offerings in 401(k)s. What is Private Equity and do you want it? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! Cl...

7 Assumptions About Retirement That Might Be Wrong 16.08.2025 27:38

If you believe these 7 things about retirement, you may be in trouble. Plus: Dealing with the volatility of the stock market and the downside of dividend paying stocks. Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! Click Here to schedule an appointment with Jay and the team at Secure Financial Management. To learn more about Secure...

Four Retirement Issues to Focus On Other Than the Stock Market | What to Do If You Went to Cash in April and Now the Market Is Roaring Again | Financial Concepts That Have Stood the Test of Time 14.08.2025 26:40

On this episode: There is more to worry about in retirement than the stock market. You tried to time the market, and failed, now what? Financial products and concepts are constantly changing. What has remained solid for over 30 years? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financ...

Overcoming Your Worries About Money and Retirement | There’s No Reason to Overpay Taxes | Retirement Planning for the Self-Employed | We Need a Bigger Boat 12.08.2025 25:19

On this episode: No matter the size of your account, we all worry about money. Death and Taxes: Is there something you can do about the second one? Like the Jaws movie, when do we need a bigger boat in retirement planning? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Manageme...

What Do You Need to Know About the Big Beautiful Bill? | Are You Confident About Retirement? You May Be Looking at the Wrong Number | When Is the Right Time to Hire a Financial Advisor? 29.07.2025 26:29

On this episode: How the BBB changes taxes, social security, and filing. Many advisors say that people are focused on the wrong number. Common reasons people finally seek out a financial advisor.   Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, including their...

How is This Stock Market Like Rocky? | How Much of a Cash Cushion Should You Have in Retirement? | Where You Live Is a Factor on How Long Your Money Will Last 15.07.2025 22:38

On this episode: Will this stock market get knocked out or come up off the mat? How much money do we need that is easily assessable and out of the stock market? The cost of living in your state may determine if you run out of money. Where does your state rank? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and...

The Magic Number You Need for Retirement Has Dropped! | Don’t Fall for Uncle Sam’s Plan for Your IRA | Do You Have a “Newark” Retirement Portfolio? 08.07.2025 24:03

On this episode: For the first time in memory, the number you need for retirement has dropped! Why? Should you wait until 73 to access your IRA? Maybe not. The Newark Airport is plagued with poor communication, outdated equipment, and no future plan. Is your advisor the same way? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To lear...

How Wall Street Uses “Fuzzy Math” | Does Everything in Your Financial Life Have a Purpose? | The #1 Retirement Fear Has Caused a New Retirement Problem 01.07.2025 26:22

On this episode: Actual math and "Wall Street" math are two different things. What in your retirement plan is outdated or unnecessary? The fear of running out of money is causing people not to spend and enjoy they retirement. Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Manag...

Keeping Your Financial Cool Through All the Tariffs | People Who Have Pension-Like Income Spend WAY More in Retirement | An Example of Why You Should Consider an IRA-to-Roth Conversion 21.06.2025 23:51

On this episode: Politics are bouncing the market. How do you adjust? A steady retirement paycheck seems to be the secret of spending confidently. A “don’t let this happen to you” tax story. Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, including...

How Many “Buckets” of Money Do You Need in Retirement? | What to Look Out for When Doing an IRA-to-Roth Conversion | Is the Fear of Running Out of Money Overblown? 17.06.2025 23:40

On this episode: Portioning your money with purpose: taxes, risk, long term, and short term. Watch out for this IRA conversion misstep. Is running out of money really that common? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, including their "Get Me To Retirement"...

Is Now a Time to Up Your Cash Reserves? | How Fees Can Eat Away at Your Retirement Accounts | 70% of People in a Survey Say THIS Gives Them Confidence in Retirement 03.06.2025 27:14

On this episode: Some big names in business are selling stock for cash. Is there something to learn here? There are likely financial fees in your 401(k) and IRAs. What is the long-term impact? Some people say they don’t worry about running out of money. What is their secret? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To lea...

When Should You Dial Back Risk Before Retirement? | Are You Pushing Off Retirement Longer Than You Should? | Are You Maximizing Your 401(k)? | DOGE and Your Retirement Portfolio: Where is the waste? 27.05.2025 52:25

On this episode: 1 year, 5 years, 10 years? When is the right time to start talking about dialing back your market risk as you approach retirement? Are Boomers so worried about running out of money that they are neglecting estate planning? How your 401(k) comes up short. How getting financial advice from your family, friends or even Tik Tok can hurt your retirement. Subscribe or follow so you neve...

Will Tariffs Continue to Affect Our Markets? How Do You Position Your Money? | What Has Better Odds: Vegas or the Stock Market? | How Long Before Retirement Should You Be Locking in Income? 20.05.2025 26:12

On this episode: If the current market volatility has you worried, what are your options? Replacing your paycheck in retirement. When do you start? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, including their "Get Me To Retirement" 5-Step Process, go to www.retire...

Have We Found the Bottom in this Market Craziness? | What is the MVP of Your Retirement Plan? | Death By 1000 Financial Cuts 13.05.2025 26:08

On this episode: Is this current market the beginning of something bigger? The Roth IRA may be your biggest retirement asset. How money is leaking out of your budget. Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, including their "Get Me To Retirement" 5-Step Proces...

Do You Have an Exit Strategy for a Market Downturn? | Over Half of Retirees Don't Have This | Applying DOGE to Your Retirement Plan 06.05.2025 25:41

On this episode: With all the current volatility, is it time to think outside the stock market? Why it's important to have an income plan in retirement. How much waste do you have in your retirement plan? The author of the 4% Rule says you should INCREASE your market risk in retirement. Why is this not realistic? Subscribe or follow so you never miss an episode! Check out our YouTube page for more...

Is a Recession Coming? | Determining How Much Money You Want in the Stock Market | Now Might Be a Great Time for an IRA-to-Roth Conversion 29.04.2025 27:15

On this episode: The chance of a recession is growing. How do you protect your retirement money? How “buying the dip” can apply to tax planning. Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, including their "Get Me To Retirement" 5-Step Process, go to w...

Retirement Strategies in Uncertain Times: What Should You Do? 15.04.2025 24:06

Feeling overwhelmed by market fluctuations? Jay Kirkwood tells you why it's crucial to structure your assets to ensure a reliable income stream, even when the market is unpredictable. Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To learn more about Jay and the team at Secure Financial Management, including their "Get Me To Retireme...

Are Federal Layoffs Changing Retirement Plans? | Are Boomers Moving Away from Passing Down an Inheritance? | Are You Pushing Off Retirement Longer Than You Should? 08.04.2025 19:56

On this episode: With DOGE cutting nearly 300,000 Federal jobs, many federal employees are facing early retirement or job loss.  Are Boomers so worried about running out of money that they are neglecting estate planning? If the math says you can retire, why are you still working? Subscribe or follow so you never miss an episode! Check out our YouTube page for more retirement tips from Jay! To...