_ _ 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.
_ _ 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.It took me 10 years to learn this about retirement planning.James Conole, CFP®2026-09-25 | It took me 10 years to learn this about retirement planning.
Follow to get the most out of life with your money!Do not do this with your 401(K) when you retire... Follow to get the most out of life with your monJames Conole, CFP®2026-09-25 | Do not do this with your 401(K) when you retire...
Follow to get the most out of life with your money!Do Not Make This Social Security Mistake!James Conole, CFP®2026-09-24 | If you're married, this Social Security mistake can cut your spouse's check for life.
Follow to get the most out of life with your money!Retirement expert rates best income sources... Follow to get the most out of life with your money!James Conole, CFP®2026-09-24 | Retirement expert rates best income sources...
Follow to get the most out of life with your money!Ranking retirement tax strategies from worst to best.James Conole, CFP®2026-09-23 | Ranking retirement tax strategies from worst to best.
Follow to get the most out of life with your money!Which is better? Follow to get the most out of life with your money!James Conole, CFP®2026-09-23 | Which is better?
Follow to get the most out of life with your money!When To Collect Social SecurityJames Conole, CFP®2026-09-22 | Everyone says wait until 70 to collect Social Security.
There are four cases where filing at 62 leaves you with more.
Follow to get the most out of life with your money!Retiring before medicare? Follow to get the most out of life with your money!James Conole, CFP®2026-09-22 | Retiring before medicare?
Follow to get the most out of life with your money!Blind Ranking Retirement Accounts... Follow to get the most out of life with your money!James Conole, CFP®2026-09-21 | Blind Ranking Retirement Accounts
Follow to get the most out of life with your money!Ranking retirement purchases from worst to best.James Conole, CFP®2026-09-21 | Ranking retirement purchases from worst to best.Can you claim Social Security early and still keep working?James Conole, CFP®2026-09-20 | Can you claim Social Security early and still keep working?
Follow to get the most out of life with your money!The dark truth about hoarding your money... Follow to get the most out of life with your money!James Conole, CFP®2026-09-20 | Here's somethings I'd tell you as a CFP of 15 years...
Follow to get the most out of life with your money!Ranking retirement withdrawal strategies from worst to bestJames Conole, CFP®2026-09-19 | Ranking retirement withdrawal strategies from worst to best.
Follow to get the most out of life with your money!My Honest Advice To Anyone Retiring With $2 MillionJames Conole, CFP®2026-09-19 | Free retirement training for people within 10 years of retirement, watch “The Sequoia System Training” here: learn.rootfinancial.com/a8aca2
=======================
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
00:00 Retirement Reality Check 01:17 Why The Number Fails 02:58 Discipline To Judgment 04:22 Don’t Waste Go Go Years 06:57 Closing Tax Window 09:49 Don’t Leave It To Luck 12:55 The Retirement Spending Smile 15:57 Four Phases Of Retirement 19:34 Plan First Final Steps
_ _ 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.Make too much for Roth? Follow to get the most out of life with your money!James Conole, CFP®2026-09-19 | Make too much for Roth?
Follow to get the most out of life with your money!How Much To Spend $10K/Mo In Retirement?James Conole, CFP®2026-09-18 | The exact math to spend $10,000 a month in retirement.
Hint: It doesn't require a $3,000,000 portfolio. Here is the formula everyone ignores.
Follow to get the most out of life with your money!You dont have 30 years.... How much can you withdraw?James Conole, CFP®2026-09-18 | How much can you withdrawal in retirement?Ranking popular retirement accounts from worst to best.James Conole, CFP®2026-09-17 | Ranking popular retirement accounts from worst to best.
Most people know about the Roth IRA, but its contribution limits are tiny.
Follow to get the most out of life with your money!You dont have 30 years.... Follow to get the most out of life with your money!James Conole, CFP®2026-09-17 | You don't have 30 years....
Follow to get the most out of life with your money!How Much Can You Withdraw From Your Portfolio?James Conole, CFP®2026-09-16 | The 4% rule is officially outdated.
I interviewed the exact guy who created the 4% rule, and he admitted the data has changed.
Follow to get the most out of life with your money!The Dark Truth about Retiring... Follow to get the most out of life with your money!James Conole, CFP®2026-09-16 | After seeing hundreds of retirements, here is the brutal truth....
Follow to get the most out of life with your money!What is the absolute best state to retire in?James Conole, CFP®2026-09-15 | What is the absolute best state to retire in?
The "greatest" state isn't found on a tax chart. It is simply the one that gives you the best mix of family, healthcare, and happiness.
Follow to get the most out of life with your money!Are You Paying More Retirement Taxes Than You Need To?James Conole, CFP®2026-09-14 | Are you secretly volunteering thousands of dollars to the IRS?
If you are over 60 and taking random withdrawals from your retirement accounts, the answer is yes.
Follow to get the most out of life with your money!The Best Age to Take Social Security... Follow to get the most out of life with your money!James Conole, CFP®2026-09-14 | The Best Age to Take Social Security...
Follow to get the most out of life with your money!Better To Retire Debt-Free Or Bigger Nest EggJames Conole, CFP®2026-09-14 | Are you rushing to pay off everything before you stop working?
Don't let old-school advice ruin your golden years.
Follow to get the most out of life with your money!Whats The Best State To Retire In?James Conole, CFP®2026-09-13 | Which state actually wins once you stop looking only at taxes?
Add healthcare access, add weather, and the ranking you've got in your head reshuffles. Two of the answers you'll probably guess. The third is not a state anyone puts on this list, and there's a reason it keeps coming back in the research.
Follow to get the most out of life with your money!How to claim Social Security (Bad, Good, & Great).James Conole, CFP®2026-09-13 | How to claim Social Security (Bad, Good, & Great).
Where does your current retirement plan fall on this list?
Follow to get the most out of life with your money!How to know if youre ready to retire? Follow to get the most out of life with your money!James Conole, CFP®2026-09-13 | How to know if you're ready to retire?
Follow to get the most out of life with your money!Biggest Regrets I Hear From Retirees As A Financial PlannerJames Conole, CFP®2026-09-13 | Almost none of these are about running out of money.
The regrets that surface once someone is well into retirement are about the years, not the balance. Being too afraid to touch the portfolio. Waiting for a number that had already arrived. And the one that comes up more than any of the others has nothing to do with a portfolio at all.
Follow to get the most out of life with your money!Should you pay off your house before you retire?James Conole, CFP®2026-09-12 | Should you pay off your house before you retire?
Follow to get the most out of life with your money!Why working while collecting Social Security is a massive mistake!James Conole, CFP®2026-09-12 | Why working while collecting Social Security is a massive mistake.
Follow to get the most out of life with your money!If I Started With $1M, Heres My Exact Plan To Retire In 5 YearsJames Conole, CFP®2026-09-12 | Free retirement training for people within 10 years of retirement and $1M+ saved. Watch “The Sequoia System Training” here: 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
_ _
⏱Timestamps:⏱ 00:00 Last Five Years Matter 00:57 Why One Million Changes Everything 03:17 Step 1 Price Your Retirement 04:51 Step 2 Income Gap Math 08:17 Step 3 Target Allocation 11:00 Working Backwards to Today 12:06 Step 5 Recalibrate Options 14:30 Wrap Up and Next Steps _ _ 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.Can you retire if everything is in your 401k? Follow to get the most out of life with your money!James Conole, CFP®2026-09-12 | Can you retire if everything is in your 401k?
Follow to get the most out of life with your money!Sighns Youre Ready To Retire But Youre Emotionally StallingJames Conole, CFP®2026-09-12 | What does one more year actually change?
If you can't answer that, you're not being cautious, you're stalling.
Follow to get the most out of life with your money!What To Do With 401(k) In RetirementJames Conole, CFP®2026-09-11 | What's the first thing you're supposed to do with the 401k the day you retire?
There are two correct answers and they're opposites. Which one is yours comes down to a single threshold that has nothing to do with your balance, your employer, or what the market did last year. Get it backwards and you hand over money you never had to.
Follow to get the most out of life with your money!0% Tax on Social Security?? Follow to get the most out of life with your money!James Conole, CFP®2026-09-11 | 0% Tax on Social Security??
Follow to get the most out of life with your money!Ranking the 5 most popular retirement accounts!James Conole, CFP®2026-09-11 | Ranking the 5 most popular retirement accounts!
Most people default to a Traditional 401(k), not realizing every dollar is taxable when they need it most.
Follow to get the most out of life with your money!Did You Know This About Social Security?James Conole, CFP®2026-09-11 | The gap between the right filing strategy and the standard one can run into tens of thousands of dollars.
That's not a rounding error, that's a piece of the retirement itself. And it happens quietly, because a filing decision never comes with a receipt showing what the alternative would have paid. If all you've heard is file early or wait for the maximum, you're sitting inside that gap.
Follow to get the most out of life with your money!Which Account To Pull From First In Retirement?James Conole, CFP®2026-09-10 | Which account do you pull from first?
Wrong question to start on. The order gets built backwards, from the one you protect the longest, and once that's settled the rest of the sequence mostly falls into place. Most people never work it out that way, so the order ends up decided by convenience instead.
Follow to get the most out of life with your money!4 Signs You Can Retire!James Conole, CFP®2026-09-10 | 4 questions that prove you can retire tomorrow.
Most people spend decades building a bulletproof financial plan. They know their exact monthly budget. They have a 10-year income runway. They’ve even stress-tested for a recession.
Yet, they still refuse to hand in their two weeks' notice.
Follow to get the most out of life with your money!How much can you withdraw in retirement? Follow to get the most out of life with your money!James Conole, CFP®2026-09-10 | How much can you withdraw in retirement?
Follow to get the most out of life with your money!Make Too Much For Roth? Try This!James Conole, CFP®2026-09-10 | When someone told you that you earn too much for a Roth, did they tell you what to do instead?
Probably not, because that's usually where the conversation ends. The income limit is real and it applies to exactly one way of contributing. Two other ways exist, both above board, and one of them comes with a trap.
Follow to get the most out of life with your money!Is your state on the good list or the bad one?James Conole, CFP®2026-09-09 | Is your state on the good list or the bad one?
Most people have never checked, because state taxes feel like a fixed cost rather than a choice. They're a choice, and they're one of the few retirement levers you can still pull after you've stopped working.
Follow to get the most out of life with your money!4 massive retirement myths you probably believe right now!James Conole, CFP®2026-09-09 | 4 massive retirement myths you probably believe right now.
Stop treating old-school retirement rules as absolute facts. What works on a generic spreadsheet could drain your real-life savings.
Follow to get the most out of life with your money!How much money should you have by 60? Follow to get the most out of life with your money!James Conole, CFP®2026-09-09 | How much money should you have by 60?
Follow to get the most out of life with your money!Born Between 1958 And 1965? Dont Miss ThisJames Conole, CFP®2026-09-09 | Born between 1958 and 1965, you're in the window where a filing mistake gets expensive.
Not wrong, not illegal, just expensive in a way you don't feel until it's permanent. Three questions decide whether you're about to make one, and none of them are about which age gets you the biggest monthly check. That's the question everybody's stuck on.
Follow to get the most out of life with your money!58 And Behind On Savings, Can You Retire?James Conole, CFP®2026-09-08 | Saving harder is not the answer at 58!
Every piece of advice at this stage is some version of max it out and hope. But money you start late has less time to do the work, which means the biggest lever left is not the one everybody points at. It's the one most people at 58 don't realize they still control.
Follow to get the most out of life with your money!How To Spend Money In Retirement!James Conole, CFP®2026-09-08 | The safest thing you can do with your retirement money is also the most expensive.
You spent a whole working life learning how to save, and nobody handed you instructions for the other side of it. So you underspend, call it discipline, and never count what it costs.
Follow to get the most out of life with your money!If You Watch One Video on Index Funds, Make It ThisJames Conole, CFP®2026-09-08 | You probably don't think twice about buying an index fund today — click a button, own the market, pay almost nothing. But when the idea first launched, the entire investment industry fought it. Some people called it un-American.
In this episode, James sits down with David Booth, who helped launch the first index fund at Wells Fargo in the 1960s and went on to co-found Dimensional Fund Advisors, now managing over $1 trillion in assets. David shares what investing looked like before data and computers changed everything, why the index fund was so controversial when it debuted, and what he learned building Dimensional from a two-bedroom apartment into a global firm.
They also dig into why staying invested through downturns — the pandemic crash, Brexit, and more — has always paid off over the long run, and what David wants readers to take away from his new book, Stay Calm: Learn to Embrace Uncertainty in Investing and Life.
In this episode:
- The Wells Fargo origins of the first index fund - Why "un-American" was a real objection to indexing in the 1960s - How Dimensional's approach differs from a pure index strategy - What David learned from decades of market downturns - Why execution matters more than prediction
00:42 The World Before Index Funds 01:27 Investing in the “Dark Ages” 03:09 The Research That Changed Finance Forever 04:56 How the First Index Fund Was Born 06:48 Why Index Investing Was Once “Un-American” 08:50 The Vision Behind Dimensional Fund Advisors 11:18 From Indexing to Better Portfolio Execution 14:24 Building a $1 Trillion Firm Without Predictions 17:21 Why Staying Invested Matters Most 19:16 How Dimensional Handles Market Crashes 20:43 The Biggest Investing Mistake People Still Make 23:10 The Mindset Behind Long-Term Investing
_ _ 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.Should you wait until 70 to collect Social Security?James Conole, CFP®2026-09-08 | Should you wait until 70 to collect Social Security?
Follow to get the most out of life with your money!