Dennis O'Keefe

Your Successful Retirement

Business EN ↓ 150 episodes

Discover the secrets to a successful retirement with Dennis O’Keefe, a seasoned CERTIFIED FINANCIAL PLANNER™ with over 30 years of expertise. Whether you’ve been retired for years, are on the verge of retirement, or are wondering how to plan for your “some-day” retirement – this podcast is your go-to guide. Gain exclusive strategies tailored to optimizing your retirement benefits, hear real-life stories from retirees, and absorb invaluable wisdom from our guest leaders.

Author

Dennis O'Keefe

Category

Business

Latest episode

Jul 9, 2026

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Episodes

The Hidden Strategy to Maximize Your Retirement Wealth 19.05.2023

On this episode of Your Telecom Retirement, I unveil a little-known approach to maximizing your retirement wealth using Roth IRAs and Roth 401(k)s. Based on my 30 years of experience in retirement planning specific to telecom employees, I'll guide you through managing distributions effectively for a tax-free retirement. Join me as I share my insights on the five-year rule, navigating tax brackets,...

The Importance of Spring Cleaning Your Finances 12.05.2023

The longer your career, the wider your trail of various retirement and financial accounts littered behind you. This and other financial clutter makes focused saving and investment difficult, and can lead to costly misunderstandings of our positions and can slow your overall retirement savings. In this episode, we dig into the importance of “spring cleaning” your finances, what it means, how to do...

How to Prepare for a Recession 05.05.2023

Whenever there’s talk of a recession, people wonder what they should be doing. But how do you prepare for a future nobody can predict? In this episode, we discuss the false belief that we know what’s going to happen, what this means for retirement planning, and how to ensure you don’t fall for the trap of “timing” your way to a huge nest egg. EPISODE LINKS You can download a free digital copy of D...

Retirement in 1993 versus today—the new reality 28.04.2023

Retiring today is 180 degrees from what it was in 1993, and there are huge implications for anyone who wants to enjoy a comfortable retirement. In this episode, we’ll examine how the shift from pensions and employer-paid healthcare has changed the game, and who you must depend on to ensure your money lasts as long as you need. EPISODE LINKS You can download a free digital copy of Dennis' book “Ret...

What Nana’s Mac & Cheese Says About Your Retirement Prep 21.04.2023

I love my Nana, but let’s just say her culinary adventures were trips to avoid. For her signature Mac & Cheese dish, she got a lot of things right — but missed some crucial details that would have transformed the results. In this episode, we look at a retirement planning error I’ve noticed in several people I’ve been talking to, and why getting this wrong isn’t something that can easily be recover...

I Bonds — Are they really worth the hype? 14.04.2023

I Bonds are the current popular kid at the party. It seems like every financial news outlet and publication is pushing them. So are they REALLY a good deal? In this episode, I demystify I Bonds, including the benefits and limitations of these financial instruments — so you can judge for yourself whether they’re worth a place in your portfolio. EPISODE LINKS You can download a free digital copy of...

An Insider’s Look at Big Banks, Small Banks, and Credit Unions 07.04.2023

Banks are the foundation of the financial system (and the recent turmoil reminds us how important banks are to all of us). Join me and our special guest and banking insider, Samantha, for a peek behind the curtain at banking institutions small, large, and local, and how to know which option fits your financial needs and temperament. EPISODE LINKS You can download a free digital copy of Dennis' boo...

Why George Costanza Might Be An Investment Genius 31.03.2023

George Constanza was many things, but an investment genius wasn’t one of them. In this episode, we discuss the myth of market momentum, the common mistake investors make when chasing returns, and why Costanza’s goofball antics have a lesson about staying focused in the face of a fluctuating market. EPISODE LINKS You can download a free digital copy of Dennis' book “Retirement Built Right – The Ess...

The Secret to a Content Retirement (Among Other Adventures) 24.03.2023

Nothing like some CEOs on a tropical island complaining about their pay to steer the way toward a content retirement. In this episode, we discuss the importance of avoiding the comparison game, and how you can appreciate where you are and where you’re going without settling for less than you deserve. EPISODE LINKS You can download a free digital copy of Dennis' book “Retirement Built Right – The E...

Why College is Unaffordable 17.03.2023

When my college started capping the concrete stairs in granite at The Quad, we knew something was up. In fact, with tuition rising 10% a year at the time, the students protested. This was 36 years ago, and it’s only gotten more expensive to send kids to college. In this episode, we explore what happened to get us here, and what to consider when thinking about how to send your kids into the world....

When a “Fix” Breaks More Than it Helps 10.03.2023

Markets often move based on government reports — good or bad. The problem is distinguishing between noise and signal. Too often the seasonal adjustments made with the intent of allowing investors to compare apples to apples completely miss the mark. In this episode, I’ll share some common sense ways to think deeper about the financial news, and help you make decisions based on reality — not on a f...

What a Free, Discontinued Pen Teaches About Your Retirement 03.03.2023

25 years ago when I grabbed a stack of free pens at a conference, little did I know the heartache I’d feel when the last pen was finally used up. And when I had an opportunity to buy these discontinued pens on Ebay for $0.75 a pop twelve months ago (and refused), imagine my shock when today they’re going for $16 each! In this episode, we talk about pricing discrepancies that most people ignore at...

How Your Plan Can Be Ahead of 87% of New Retirees 24.02.2023

When the richest, most powerful, and beloved pillars of your community hire the best legal help to handle their estate planning — and they get sub-par results — what chance do we regular people have? My honest answer: a lot. In this episode, I share a surprising story about how even the most successful people can (falsely) think they have their estate plan squared away, and the three documents tha...

The Truth About Retirement Expectations Versus Reality According to Retirees 17.02.2023

After helping hundreds of people make the transition from the workforce into retirement, I can tell you that retirement is the single most stressful event of your life. In this episode, we break down a survey that illustrates the chasm between pre-retirement expectations and the reality of stepping away from the workforce. EPISODE LINKS You can download a free digital copy of Dennis' book “Retirem...

Two Similar Couples — Two Very Different Outcomes 10.02.2023

When the retirement accounts of two couples who make similar incomes, are the same age, and have similar circumstances end up in very different places, it makes you wonder what happened to cause the difference. In this episode, we dig into a surprising “intangible” that grew one couple’s account by 8X their peers. EPISODE LINKS You can download a free digital copy of Dennis' book “Retirement Built...

A Personal Message From the Future 03.02.2023

In my 30 years as a financial planner, not one person reached retirement age and wished they had done less to prepare — which is why a prospect telling me, “I’m not retiring yet!” was a sad surprise. In this episode, I reveal the three most common reasons people avoid financial planning, and what you can do to ensure your future self looks back to today with gratitude. EPISODE LINKS You can downlo...

What a Golf Course Hazmat Crew Can Teach About Your Finances 27.01.2023

About 25 years ago I went golfing with a buddy and his dad at his favorite golf course. Things were rough at the start, but when guys in hazmat suits appeared in a water hazard, I knew this wouldn’t be a normal afternoon of golf. In this episode, we discuss how the “new normal” is dangerous to your portfolio, and a lesson that will keep your financial plan pointed at true north regardless of what’...

3 Portfolio Lessons From a Tragic Night in 1892 20.01.2023

In the winter of 1892, a freak accident and a perfect storm of events combined to decimate the heart of Fall River, MA. In this episode, we look at three lessons this tragedy can teach us that will help prevent your portfolio from suffering the same fate. EPISODE LINKS You can download a free digital copy of Dennis' book “Retirement Built Right – The Essential Guide for Telephone Employees!” here:...

How to Be Smarter Than the Cable News Talking Heads 13.01.2023

Why are the talking heads on TV and online so often wrong? And why does the market tend to zig when it should zag? In this episode, I share the two economic reports that can give you the real state of the economy — and what to look for that reveals where the economy is going while most of the market is focused on the wrong thing. EPISODE LINKS You can download a free digital copy of Dennis' book “...

The Real Cost of “DIY Anything” 06.01.2023

Four years ago I was motivated to become fit, and did everything I knew how to boost my health. I made progress, but it wasn’t until I met Dave that I made significant strides. In this episode, I share why even motivated DIYers can benefit from professional help (plus the true cost of DIY in any situation). EPISODE LINKS You can download a free digital copy of Dennis' book “Retirement Built Right...

Should I Collect Social Security Early? 29.12.2022

This is one of the most common questions I hear from people nearing retirement age: when should I begin taking social security? And the truth is . . . it depends. In this episode, I’ll share why the common wisdom about taking social security may have it wrong, and what you need to consider when choosing when to start taking social security. EPISODE LINKS You can download a free digital copy of Den...

Real Stories of a Spendthrift Retirement 22.12.2022

Retirement is as much about enjoyment as it is about spending management. But what happens when a retiree swings the spending pendulum too far and outlives their nest egg? In this episode, we look at the life and times of a big spender and how we can learn from his good timey ways. EPISODE LINKS You can download a free digital copy of Dennis' book “Retirement Built Right – The Essential Guide for...

Uncovering the Jones’s Secret 16.12.2022

It’s tough to stay out of the comparison game, especially when your peers seem to be doing so much better than you. What’s their secret? What are you doing wrong? In this episode, I pull back the curtain and reveal what’s really going on with so many of the people you secretly admire. EPISODE LINKS You can download a free digital copy of Dennis' book “Retirement Built Right – The Essential Guide f...

My Controversial Take on AARP 09.12.2022

When I was growing up, you couldn’t turn on the TV without seeing a dozen AARP ads. By the time my parents reached age fifty, they refused to join—they didn’t see themselves as old, which is the image AARP members had. In this episode, I give you my take on AARP, and some surprising truths that may cause you to reconsider your position. EPISODE LINKS You can download a free digital copy of Dennis'...

5 Keys to Protect Your Future From Layoffs 02.12.2022

In my 30+ year career, you’d be surprised how many people I’ve worked with who thought their job was safe, only to be stunned by a pink slip. With telecoms (and everyone else) looking at cost-cutting in the face of a potential recession, it’s wise to give yourself options in case your job gets the ax. In this episode, I share five ways to protect yourself that you won’t hear in the media. EPISODE...

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