Ready For Retirement

Hosted by James Conole, CFP®

Business Investing Education

Website RSS feed

Episodes

391

Latest episode

Oct 2026

Language

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!

Listen to episodes

60 recent

October 24, 202614 min

Retire NOW If You Answer "YES" to All 5 Questions

Ready to retire? See what it's like to work with us → https://learn.rootfinancial.com/9593a2 ======================= I've watched people with plenty of money retire and spend the first two years second-guessing everything. So before I tell any client they're ready, I ask them five questions. If you can honestly say yes to all five, you might be able to retire now. Not in a year. Not in five. Now. This video is those five questions, and the stories behind why each one matters. We're going to cover: - why the "magic number" you have in your head is probably the wrong place to start - the client who had exactly enough saved and still wasn't ready to retire - what happened to retirees who put everything in the S&P 500 on January 1st, 2000 - the healthcare belief that's keeping financially ready people stuck at work for years - the question I ask every married couple that almost nobody has an answer to -- 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!

October 17, 202614 min

Once You Understand This, You'll Stop Working Past 55

Ready to retire? See what it's like to work with us → https://learn.rootfinancial.com/7a0f48 ======================= Every time you add one more year to your retirement projection, the numbers get better. The math is right. But it only measures one part of your wealth. Your health, your time and your relationships don't show up anywhere on that screen. So most people keep chasing the one number that does, and they miss the point where the ideal time to retire already came and went. This video is how to find that point for you, and the shift you need to make once you've reached it. We're going to cover: - the scorecard that's quietly keeping you at work - why your next dollar is worth less than you think, and it has nothing to do with inflation - the question I'd ask Warren Buffett about his $100 billion - why the people most ready to retire are often the ones who never do - a client who always had a very responsible reason to work "one more year" - the 401(k) rule at 55 that most people have never heard 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!

October 10, 202617 min

How to Respond When Asked About Your Investment Philosophy

Ready to retire? See what it's like to work with us → https://learn.rootfinancial.com/15076a ======================= You saved well. You invested well. You built $2 million or more. But the habits that got you here aren't the ones that will carry you through retirement. After 15 years of building plans for retirees at this exact level, I've watched a few small shifts completely change how a retirement plays out. These are the eight things I tell every one of them. We're going to cover: - the spending assumption almost every retirement projection gets wrong - why the Social Security printouts I used to hand out at seminars drove me crazy - what one client asked me before retiring that showed me how much most people leave on the table - the $400,000 to $600,000 moment that tests every retiree's plan - the question every married couple needs to answer before either of them retires - why some people with the most optimized plans end up the most miserable -- 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!

October 3, 202612 min

Think Twice Before You Retire at 65

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://learn.rootfinancial.com/4f7f57 ======================= A couple came to me. Both 60. $2.5 million saved. Everything on paper said they were ready to stop working. They kept going anyway. One of them was doing it out of guilt. The other was doing it for a health insurance card. Neither reason had anything to do with the actual math, and once we ran it, the answer surprised both of them. This video is that math, the two questions it actually comes down to, and why getting this wrong costs you more than money. We're going to cover: - the real reason a couple with $2.5 million saved were still grinding away at 60 - why waiting could turn that $2.5 million into $4 million, and why that's exactly the trap - the two questions that actually decide if continuing to work is a mistake, not the ones everyone assumes - a client's story about the trips she and her husband never got to take, and why it still stays with me - why I still won't retire even once I don't need the paycheck anymore -- 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!

September 26, 202622 min

Don't Let Early Retirement Backfire (9 Things You NEED To Know)

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://learn.rootfinancial.com/a8aca2 ======================= The problem is, most retirement advice out there isn't built for people retiring early. Most people don't even realize how different it is. These are the 9 things you need to know before you retire early, broken into what's different, what gets riskier, and what actually works in your favor. We're going to cover: - the 401(k) rule that lets you pull money penalty-free at 55, and the one mistake that disqualifies most people from using it - why the exact same withdrawal rule everyone quotes can leave an early retiree completely out of luck - the spending gap that barely matters at 65 but can derail everything if you retire at 48 - the one thing almost nobody gets right about how aggressive your portfolio should actually be - the tax strategy window that's nearly impossible to use at 67, but wide open if you retire at 47 - why the real prize of early retirement was never actually the 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!

September 19, 202620 min

My Honest Advice To Anyone Retiring With $2 Million

If you've got $2 million or more saved, you probably think you already know how retirement goes. No more stress, finally enjoying life, doing whatever you want. That's not how it goes. Not because of the money. Because of what happens to your judgment, your spending, and your mental health once the paycheck actually stops, and almost nobody warns you about it in time. This is everything I tell my clients before they retire, including the story of a widow that still sits with me years later. We're going to cover: - the client whose husband died before they got to take the trip they'd planned their whole retirement around, and why I still think about it - why hitting $2 million, or any number, won't give you the feeling you think it's going to give you - the four phases every retiree goes through, and the one that quietly wrecks marriages and mental health if you get stuck in it - what happens to your tax bill the moment your spouse passes away, and why almost nobody plans for it in time - the shape your spending actually takes over a 20 or 30 year retirement, and why it's nothing like what you'd assume -- 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!

September 12, 202615 min

How I'd Retire in 5 Years Starting With $1M (2026)

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://learn.rootfinancial.com/c8e6cf ======================= If you have a million dollars saved and five years until retirement, this is the last stretch where you can actually change how it turns out. I've sat across from people in your exact position who assumed they were set, then had to cut back once they actually retired. This is the exact process I'd run if that was my situation right now, step by step. This video is that process, five steps, in order. We're going to cover: - the exact dollar amount where your portfolio starts doing more of the work than your paycheck does - a couple with a million dollars today, five years to retire, and a plan that only worked if the market cooperated - what changes about how this couple should be invested if they wait even a few years to collect Social Security - the monthly savings number we had to say out loud that made the original plan fall apart - the two decisions about their house and their zip code that rewrote the whole plan without adding a dollar of income -- 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!

September 5, 202616 min

10 Really Good Reasons to File for Social Security at Age 62

Two people, same age, same savings, same expenses. One files for Social Security at 62. The other waits until 70. Everyone knows the one who waits gets a bigger check. Almost nobody looks at what's happening to the other person's money while they wait. Here are 10 reasons the person who files at 62 might actually come out ahead, plus one thing that makes this decision far less permanent than you've been told. We're going to cover: - why the break-even calculator everyone gets handed (the one that says wait if you'll live past 81) is technically correct and still gets the real answer wrong - what a 40% market drop does to your withdrawal rate depending on which age you filed at, and why the gap is bigger than most people expect - the version of this decision I'd make differently if my own wife were 10 years older than me - the client who scrapped an "optimized" plan and told me exactly why she was right to - the Social Security benefit that disappears the longer you wait, and has nothing to do with your own check - the one move at 67 that can undo a decision you made at 62 -- 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 29, 202612 min

$3M vs $2M in Retirement: Here’s What Changes

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://learn.rootfinancial.com/6b74ff ======================= Andrew and Ellen are 62, sitting on 2 million dollars, and ready to walk away from work today. Then we ran one more scenario, and it changed the entire conversation. It's not really about how much you have. It's about what five more years of work actually buys you, and the number surprised even them. This video is that exact case study, numbers and all. We're going to cover: - why a 90 percent confidence retirement plan still wasn't the end of the conversation - the exact dollar amount that extra million dollars translates to every single month - the two hidden costs of retiring early that have nothing to do with your portfolio balance - why chasing the next million never actually satisfies, and where it stops - the three questions I'd ask anyone caught between more money and more time - a bonus strategy that only opens up once you actually retire -- 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 23, 202617 min

How To Invest Once You Retire

Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: https://learn.rootfinancial.com/9fc86c ======================= Your portfolio only had one job while you were working. The day you retire, it gets a second one, and almost nobody splits the money the right way between the two. I watched a client with three million dollars, all sitting in three stocks, get forced back to work after 2022. Those stocks have since fully recovered. It didn't matter. This is the exact framework I give every client before they retire, and the real math behind why "the market averages 12% a year" can still wreck a retirement. We're going to cover: the S&P 500's actual worst 12 month stretch over the last 50 years, and why that number should worry you more than the 12.1% average how a 7% withdrawal quietly turns into a 14% withdrawal without you changing a single thing why I told a client about to retire with three million dollars in three stocks to sell his winners, and why he couldn't bring himself to do it the way to slice your "safe money" into year one, year two, and year three buckets so each one is protected differently how to decide which part of your portfolio to actually spend from in a year like 2026, when tech is up 14% and small value stocks are up 22% -- 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!

Is this your show?

Claim this listing to keep it up to date, reach guests who want to pitch you, and manage bookings with Guestify.

Claim this listing

More Business podcasts

The Bottom Line

Alexander Spencer

BusinessInterviews guests