Ready For Retirement

Hosted by James Conole, CFP®

Business Investing Education

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Episodes

382

Latest episode

Aug 2026

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EN-US

About the show

Ready For Retirement is the podcast dedicated to helping you learn the tips and strategies that will help you achieve your retirement goals. When it comes to retirement planning, it can quickly become overwhelming and easy to not take action. I designed this podcast because I want you to have the knowledge and confidence to create your secure retirement. My ultimate goal for all of my clients (and listeners) is to create peace of mind and that starts with having a strategy. I want you to spend more time thinking about what matters most to you in retirement. I post weekly episodes to keep you up-to-date on all the best tips and strategies to create a retirement that excites you. Everything from investing tips, tax planning, withdrawal strategies, insurance planning, Social Security, and that's just the start! Let's help you maximize your return on life. We use your money and the strategies I share in this podcast to do just that!

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60 recent

August 15, 202614 min

How Much Can You Spend With $2.5 Million In Retirement?

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://learn.rootfinancial.com/0ce92d ======================= This is the question I get more than any other after 15 years of doing this: how much can you actually spend in retirement without running out of money? John and Tina are 60, sitting on two and a half million dollars, and ready to retire. They want to travel. They want to finally renovate the house. They just don't know if their portfolio can actually support it. This video is the exact numbers we ran for them, and what we found changed how much they thought they could spend. We're going to cover: - the withdrawal rate in year one that looks dangerously high, until you see what happens to it seven years later - why their tax bill was basically zero for the first few years of retirement, and the mistake that would have cost them thousands if we hadn't caught it - the extra $40,000 a year we found room for without touching their core lifestyle at all - the one risk that could unravel their entire plan in the first seven years, and how we stress tested for it - how we restructured their portfolio so a market crash doesn't force them to sell at the worst possible time -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

August 8, 202623 min

19 Unsexy Habits That Lead to a Great Retirement

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://learn.rootfinancial.com/ad021b ======================= I've spent 15 years watching retirees blow up decades of saving with decisions that felt harmless in the moment. Not big mistakes. Small ones, repeated for years, that quietly cost people hundreds of thousands of dollars. The retirees who actually get it right aren't the smartest investors or the biggest savers. They just do the same boring things, over and over, starting years before anyone tells them to. This video is 19 of those habits, in the order that actually matters. We're going to cover: - the "tax torpedo" that turns a 12% withdrawal into a 22% one, and why almost nobody checks for it before pulling from their IRA - why I tell clients to start living on their retirement number a full year before they retire, and what usually happens when they try - the marathon analogy that explains why the biggest Roth conversion mistake isn't doing one, it's doing it all at once - the letter I tell every client to write for their spouse, and why not writing it is one of the cruelest things you can leave behind - the trip booking trick that costs you nothing and forces your family to actually follow through - the conversation with your adult children, or your parents, that most people avoid until it's too late -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

August 1, 202617 min

Every Retirement Withdrawal Strategy RANKED (Worst to Best)

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://youtu.be/7lpp3XXiDyQ ======================= You probably think the way you'll pull money out of retirement is a solid, sensible plan. There's a good chance you're wrong. Most people default to one withdrawal strategy without ever comparing it to the others. But this is the decision that determines how much stress you carry every time the market drops, and how much you actually get to spend over the next 20 to 30 years. I ranked the five most common withdrawal strategies, from my least favorite to my favorite, and one of them includes something Bill Bengen himself told me that changes the whole conversation. We're going to cover: - the strategy that lets you pull $57,000 a year from a million dollar portfolio, and the catch that makes it a bad idea for most people - why living off dividends alone quietly wrecks the one thing your portfolio is supposed to have - what I actually think about annuities after watching people get sold the wrong one over and over again - what the creator of the 4% rule told me directly that most retirees have never heard - the approach I rank number one, and why it can mean tens of thousands more per year without taking on more risk -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

July 25, 202618 min

The ONLY 5 Tax Strategies You Need In Retirement

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://youtu.be/7lpp3XXiDyQ ======================= Two people retire on the same day. Same savings, same investments, same effort over 30 years of working. A few years later, one of them has a lot more money than the other. It's not because of a better stock pick or a lucky year in the market. It comes down to five strategies almost nobody knows exist, and none of them require changing your life or taking on more risk. We're going to cover: - why a client giving $5,000 a year to charity was getting a zero dollar tax benefit for it, and the one move that changed that completely - the stock someone bought for $5,000 twenty years ago that's now worth $150,000, and why selling it outright would be a mistake - why only looking at this year's tax bill is quietly costing people tens of thousands over their lifetime - the client planning to leave 20 percent of his estate to charity, and the $600,000 decision that changed what everyone actually walks away with - what almost nobody thinks to check inside their own 401(k) before rolling it over - why 196 companies in the S&P 500 lost money in 2025 even though the index was up 18 percent, and how that becomes a tax strategy -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

July 18, 202614 min

Why Everything Changes After You Save $1.44 Million in Retirement

$1,440,000 sounds like the finish line. For a lot of people it's actually where a brand new problem starts, one nobody warns you about before you get there. I've sat across the table from hundreds of people getting ready to retire, and the same mistake keeps showing up right after they hit their number. It has nothing to do with how much they saved. This video is where that number actually comes from, and the one shift almost nobody makes once they cross it. We're going to cover: - how a $10,000 a month goal, a couple's real Social Security check, and one withdrawal rate turn into an exact $1.44 million target, and why your number could be zero or $3.8 million instead - the pension and rental income shortcut that skips the whole calculation entirely - the specific tax mistake that can quietly hand 20 to 30 percent of every withdrawal to the IRS - the two things I watch retirees do with their portfolio right after they cross their number, one of them wrecked people in 2007 - the "moat" I build around a portfolio before a single dollar goes toward growth again Learn the tips & strategies to get the most out of life with your money. -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

July 11, 202616 min

I'm A Retirement Advisor: Here's What I Tell Every Client At 62

I've sat with 100 retirees, and the biggest regret almost never has anything to do with a bad investment. It's something I call the momentum trap. At 62, every single signal tells you to keep going, and almost nobody sees it coming until it's too late to get those years back. This video is what I tell every client who walks in at 62, the trap, the blind spots, and how to actually manage what comes next. We're going to cover: - the momentum trap that convinces smart, disciplined people to keep working long after they don't need to - why delaying Social Security to 70 could quietly force a 7.5 percent withdrawal rate the moment you retire - the life insurance policy from your 30s you're probably still paying for and don't need anymore - what a long term care event does to your spouse after you're gone, even with a healthy portfolio - the tax planning window that opens the year you retire and closes faster than you think - why the clients I think about most aren't the ones who ran out of money Learn the tips & strategies to get the most out of life with your money. -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

July 4, 202614 min

Don’t Retire If This Is You - 5 Warning Signs

You can hit your number, be fully financially ready, hand in your notice, and still end up miserable. Or worse, running out of money. In 15 years as a retirement advisor, I've watched it happen again and again, and it almost always comes down to one of five warning signs. Most of them have nothing to do with how much you've saved. If even one of these is you, it's not a no. It's a not yet, and I'll show you exactly how to fix it. We're going to cover: - the story of a client we'll call Bob, who retired early to move across the country with his new wife, and kept calling us saying he needed more money - why two people can retire on the same day with the same average return and end up with completely opposite outcomes - the real reason depression and divorce rates are so high among retirees, and it's not about money at all - the conversation most married couples never actually have before one of them retires - what happens after the retirement honeymoon phase wears off, and why so many people feel lost when it does -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

June 27, 202613 min

Your Life When Retiring With $100K vs $1M vs $10M

You'd assume retiring with $10 million is a hundred times better than retiring with $100,000. It isn't. And the reason is stranger than you'd think. Because the size of your portfolio barely tells you what your life actually looks like. What changes from one level to the next isn't your lifestyle. It's the entire problem you're left trying to solve. This video runs the real numbers on all three, and the one thing every retiree has in common no matter which one they are. We're going to cover: - why going from $100,000 to $1 million does NOT ten times the income you live on - the $100 grocery slip that quietly drains a small portfolio 25% faster - the client I call Bob and Sally, and the conversation I still think about - the fear that makes millionaires spend less than they safely can, and why hitting a bigger number won't fix it - what suddenly becomes your only real problem once you cross $10 million - the handful of things the happiest retirees share, whether they have $100K or $10M -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

June 20, 202616 min

Sell These 10 Things BEFORE You Retire

There are 10 things sitting in your life right now that are quietly draining your retirement. Most people never notice them. This isn't the usual save more, buy more advice. After 15 years of helping people retire, the happiest ones I've seen didn't get there by adding. They got there by letting go of the right things at the right time. This video is all 10, ranked, with the biggest one saved for last. We're going to cover: - why the very first thing on this list is the one almost nobody expects, and why selling it could actually make you healthier - the 30/30 rule that tells you in seconds whether to keep something or get rid of it forever - what my father-in-law admitted about the hobby he loves, and why it changed how I think about retirement - the conversation my family keeps having with my grandma about the thing she's holding onto so tightly it's costing her freedom - the couple who retired on track, then made one decision out of love that quietly drained everything, and the daughter it was secretly hurting - the one item on this list that isn't clutter and isn't about money, but is the hardest to let go of -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!

June 13, 202614 min

If You Only Watch One Retirement Video, Make it This

Most retirement advice isn't wrong. It's incomplete. And following incomplete advice for 30 years is how people end up financially ready for retirement but completely unprepared to live it. I've seen it hundreds of times. Someone hits their number and feels nothing. So they keep working, keep deferring, keep waiting. By the time they stop, the years they actually wanted are already gone. This is the podcast I wish I could send to everyone in their 50s before those decisions get made. We're going to cover: - why David had $4 million at 61 and still couldn't give himself permission to retire - the three distinct phases inside every retirement, and why spreading your spending evenly across them is a mistake - what most Social Security calculators are missing that can quietly devastate your plan - a scenario where two retirees had identical portfolios and wildly different outcomes, without changing a single number - the risk I see ruin more retirements than running out of money ever does - five questions worth sitting with before you make any major retirement transition -- Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation. The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal. Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial. Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!