Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)

Tax gain harvesting is one of the most underused but powerful strategies available to early retirees and those pursuing financial independence. In this episode, we explore how it works, who it's best suited for, and how it can help reduce long-term tax liability.Unlike tax loss harvesting, which involves selling investments at a loss to offset gains, tax gain harvesting is about intentionally realizing gains when you're in a low or zero percent tax bracket—allowing you to reset your cost basis without triggering federal tax in certain situations.This strategy is most effective in taxable brokerage accounts and is typically not applicable to retirement accounts like IRAs or 401(k)s. It tends to work best in years where your income is lower, such as early retirement or transition periods before drawing Social Security.Even with additional income from dividends or part-time work, many people can still benefit from this approach. However, it’s important to consider potential state tax implications as well.We’ll break down how tax gain harvesting fits into a broader retirement tax strategy, what makes someone a good candidate, and how to use it thoughtfully as part of your long-term financial plan.- 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 your CPA or attorney 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 Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

What does it really mean to change someone’s life through financial advice? While we’re not saving lives like doctors, the impact we have on our clients’ futures can be just as meaningful. Often, it’s not about the numbers—it’s about helping someone move forward when fear is holding them back.We’ve seen it firsthand. Like the dentist who had every detail in place to open her own practice but couldn’t take the final step. What helped wasn’t another spreadsheet—it was a mindset shift. Or the couple who had more than enough to retire but needed a gentle nudge to believe it was truly okay. These are the moments where great financial advice becomes personal and transformative.At Root, we believe a solid financial plan is about more than projections. It’s about building a life you’re excited to live. That’s why we focus not only on technical guidance, but on walking with our clients through the real-life decisions that matter most.-Viewing this video does not create an advisory relationship with Root Financial. We only provide advisory services to clients under a written agreement.Investment strategies discussed may not be suitable for everyone. All investments involve risk, and past performance is not indicative of future results.Any opinions expressed are as of the date of recording and are subject to change.Comments left on this video reflect the views and opinions of the individual commenters and do not necessarily represent the views of Root Financial Partners, LLC. Comments should not be considered a testimonial or endorsement of our services and have not been solicited or compensated. Root does not verify the accuracy of comments and is not responsible for their content.Create Your Custom Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

You don’t need $2 to $3 million to retire unless your lifestyle truly requires it. In this episode, we break down why your retirement number should be built around your personal spending needs, not a one-size-fits-all benchmark.With a well-diversified $1.5 million portfolio, many retirees can support $60,000 to $75,000 per year in spending, especially when using flexible withdrawal strategies that adjust with market conditions. We dive into how spending can adapt over time and how Social Security benefits can reduce the burden on your investments.We also explore a real-world retirement budget to show how far your money can go, including housing, healthcare, travel, and more. Plus, we discuss one of the most overlooked issues: retirees often underspend out of fear, even when their financial plan says they’re in the clear.Whether you’re years away or nearing the transition, this episode helps you shift from anxiety to clarity and reminds you that retirement isn’t just a number, it’s a 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 your CPA or attorney 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 Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Discover how to achieve early retirement without sacrificing the joys of life. The conversation highlights essential trade-offs, revealing which expenses to cut for financial freedom and which ones to keep for personal satisfaction. Learn about balancing luxury travel with budgeting, and the importance of investing in quality of life through thoughtful purchases like high-speed Wi-Fi and family experiences. Enhance your well-being while navigating your financial journey, all while aligning spending with your core values.

In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career.Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collective members who’ve taken the leap, insights on counteroffers, and a powerful reframe: every “yes” to more work is a “no” to your time, your family, your dreams.Hear more stories from the Root Community here:  https://www.skool.com/rootcollective/what-was-your-experience-when-you-told-your-employer-you-were-retiring - 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 endorsementsParticipation 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 Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

The 4% withdrawal rule does not apply to early retirees since it's based on a 30-year timeline, not the 40+ years needed for early retirement. Guyton's guardrails approach offers a better alternative, allowing for 5.2-5.6% withdrawal rates by adapting spending based on market performance.• Guardrails approach uses flexible withdrawal rates that increase when markets perform well and decrease during downturns• Traditional 4% rule based only on S&P 500 and intermediate US bonds, while diversification across asset classes can increase safe withdrawal rates• First years of retirement often have high expenses (healthcare, education, travel) when your portfolio is most vulnerable• Bowling analogy: retirement planning with guardrails is like bowling with bumpers to avoid gutter balls• Business analogy: like a business owner, spend more when times are good, cut back when they aren't• Creating a "war chest" of safe assets reduces pressure on your growth investments during market downturns• Stress test your retirement plan against worst-case scenarios: market crashes, reduced Social Security, high inflation, living to 100- 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 your CPA or attorney 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 Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Building a retirement income strategy involves more than selecting dividend-paying stocks. A focus on total return — which includes both growth and income — can offer a more comprehensive approach for long-term planning.• Relying solely on dividend-paying stocks may reduce portfolio diversification and growth potential• Total return (income + growth) can provide a broader view of long-term investment outcomes• Asset location strategies may improve tax efficiency depending on the type of account• Bond ladders with staggered maturities can help create more consistent income over time• Annuities can provide structured income, though they may have limitations such as fees or inflation sensitivity• The most effective strategy is one that aligns with your goals, risk tolerance, and understanding• Be cautious with complex products — understanding fees, liquidity restrictions, and structure is essentialAdvisory services are offered through Root Financial, an SEC-registered investment adviser. This content is intended for general informational purposes only and should not be construed as personalized investment, tax, or legal advice. Advisory relationships are established only through a signed agreement. Any examples discussed are hypothetical and for illustrative purposes. If client experiences are referenced, no compensation was provided and their experience may not be representative of others. Comments shared publicly are unsolicited and do not reflect the views or experience of all clients. They are not verified and should not be construed as testimonials or endorsements. Root Financial does not provide tax or legal advice. Tax planning topics are discussed in the context of comprehensive financial planning and should not be relied upon as a substitute for professional advice. All investments involve risk, including possible loss of principal. Past performance is not indicative of future results. Watching or listening to this content does not create an advisory relationship.Create Your Custom Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Retired with millions—but full of regret?In this episode of Root Talks, James and Ari share the real stories no one talks about: wealthy retirees who did everything “right” financially but still feel like they missed out. From sacrificing health and relationships for more savings, to realizing too late that they were planning for someone else’s version of success, these lessons are emotional, practical, and essential.What you’ll learn:Common regrets wealthy retirees confess after leaving workWhy financial freedom means nothing without health, time, or joyHow to avoid estate planning mistakes that burden your spouse or familyWhy intentional living matters more than chasing a numberSimple, high-impact ways to prepare for retirement nowIf you're building wealth, nearing retirement, or want to live more meaningfully today—this conversation is for youCreate Your Custom Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Even when the financial plan indicates you're on track, many people experience anxiety—especially between ages 50 and 65, before traditional retirement benefits begin. This episode explores ways to prepare for that critical transition with clarity and confidence.• One of the most impactful retirement risks is withdrawing too much from your portfolio in the early years• Many individuals are “qualified rich, cash limited” with the majority of assets in tax-advantaged retirement accounts• Building a taxable brokerage account can provide additional flexibility before age-based access to retirement funds• For some, temporarily adjusting retirement account contributions may help support short-term liquidity needs (consider your specific situation and consult a financial professional)• Planning ahead for early retirement expenses—such as travel, healthcare, or home projects—can reduce surprises• Avoiding large discretionary expenses early in retirement may help reduce stress on your portfolio• Focus on what you can control: spending, timing of retirement, asset allocation, and strategic withdrawalsAdvisory services are offered through Root Financial, an SEC-registered investment adviser. This content is intended for general informational purposes only and should not be construed as personalized investment, tax, or legal advice. Advisory relationships are established only through a signed agreement. Any examples discussed are hypothetical and for illustrative purposes. If client experiences are referenced, no compensation was provided and their experience may not be representative of others. Root Financial does not provide tax or legal advice. Tax planning topics are discussed in the context of comprehensive financial planning and should not be relied upon as a substitute for professional advice. All investments involve risk, including possible loss of principal. Past performance is not indicative of future results. Watching or listening to this content does not create an advisory relationship. The Early Retirement Academy is an educational resource offered by Root Financial. Participation may involve a fee. Use of the tool does not establish a client relationship or constitute personalized advice. Comments shared publicly are unsolicited and do not reflect the views or experience of all clients. They are not verified and should not be construed as testimonials or endorsements. Create Your Custom Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

In this episode, Ari explores six common oversights in early retirement planning that can create unnecessary stress and limit flexibility in the long run.• Not establishing a taxable brokerage account to access funds before traditional retirement age• Overlooking healthcare planning, including available subsidies, which may impact retirement timing• Missing opportunities for tax efficiency through strategies like Roth conversions or coordinated withdrawals• Underestimating the importance of physical health when planning for an active retirement lifestyle• Limiting retirement vision to essential expenses, rather than factoring in meaningful goals and experiences• Focusing only on finances without considering purpose, routine, or fulfillment during retirementSubmit your questions at earlyretirementpodcast.com for future episodes. Are you sabotaging your early retirement with what I call "head trash"? These are the unnecessary worries that keep you working years longer than you need to - like comparing your finances to neighbors without knowing their full picture.Advisory services are offered through Root Financial, an SEC-registered investment adviser. This content is intended for general informational purposes only and should not be construed as personalized investment, tax, or legal advice. Advisory relationships are established only through a signed agreement. Any examples discussed are hypothetical and for illustrative purposes. If client experiences are referenced, no compensation was provided and their experience may not be representative of others. Comments shared publicly are unsolicited and do not reflect the views or experience of all clients. They are not verified and should not be construed as testimonials or endorsements. Root Financial does not provide tax or legal advice. Tax planning topics are discussed in the context of comprehensive financial planning and should not be relied upon as a substitute for professional advice. All investments involve risk, including possible loss of principal. Past performance is not indicative of future results. Watching or listening to this content does not create an advisory relationship. To learn more about Root or to explore working together, please visit www.rootfinancialpartners.com.Create Your Custom Early Retirement Strategy HereGet access to the same software I use for my clients and join the Early Retirement Academy hereAri Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.