Clear Skies Retirement
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 turbulence in the markets or changes in regulations, with "Clear Skies Retirement," you’re never flying solo. Get ready to turn your retirement goals into your everyday reality. Subscribe now to step confidently into a future of clear skies! If our podcast has you thinking you might need a second opinion on your retirement plan, reach out to us here 👉 Schedule an Appointment
Episodes
You’ve climbed the retirement mountain and saved your millions, but is the IRS waiting at the peak to take a massive cut? In this episode of Clear Skies Retirement, Jay Kirkwood of Secure Financial Management explores the "two-sided coin" of income and tax management. Learn why high savings can lead to higher Medicare premi...
Your retirement spending isn't a straight line—it’s a smile. Join Jay Kirkwood from Secure Financial Management as he reveals why your expenses may peak at the start and end of retirement, creating a unique "spending smile" that requires strategic planning. We tackle the anxiety of outliving your money, the "whack-a-mole" complexity of Social Security timing, and the rising reality of "emergency retirements" triggered b...
On this episode:
- Should you push off your retirement due to the economy?
- There are over 4 million people retiring every year. Whenever there are a lot of people needing help sometimes bad actors will take advantage. What do you need to watch out for?
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 Mana...
On this episode:
- Vanguard is offering a Target Date Fund with an annuity option. What could go wrong?
- Turns out, retirees want more stability than the stock market provides.
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.reti...
On this episode:
- 75% of investors are pairing back their risk in the stock market. Are you?
- Paying off your house in retirement might make you feel good but is it the best financial move?
- A retirement lesson from AI and Hertz.
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 ...
On this episode:
- Are you pushing money into this market or pulling back?
- People with annuities spend more money in retirement.
- Will you use YOUR plan or Uncle Sam’s Plan for your 401(k)?
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-St...
On this episode:
- Will the "Warren Buffett" indicator be right in 2026?
- Does Uncle Sam have a headlock on your IRA?
- Why is the price of Gold going up so much in an up-market?
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.reti...
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 Secure Financial Managemen...
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 "Get Me to Retirement" 5-St...
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!
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 for more retirement tips from Jay!
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 Financial Management, includin...
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, including their "Get Me To Retir...
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 you never miss an episode!
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!
Click Here to schedule an ...
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 Financial Management, includin...
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 Financial Management, includin...
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 Management, including their "Get...
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 "Get Me To Retirem...
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!
Popular Podcasts
Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.
Listen to the latest news from the 2026 Winter Olympics.
Gregg Rosenthal and a rotating crew of elite NFL Media co-hosts, including Patrick Claybon, Colleen Wolfe, Steve Wyche, Nick Shook and Jourdan Rodrigue of The Athletic get you caught up daily on all the NFL news and analysis you need to be smarter and funnier than your friends.
The 2026 Winter Olympics in Milan Cortina are here and have everyone talking. iHeartPodcasts is buzzing with content in honor of the XXV Winter Olympics We’re bringing you episodes from a variety of iHeartPodcast shows to help you keep up with the action. Follow Milan Cortina Winter Olympics so you don’t miss any coverage of the 2026 Winter Olympics, and if you like what you hear, be sure to follow each Podcast in the feed for more great content from iHeartPodcasts.
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.