Your 401(k) is likely your largest retirement asset—so the decisions made about it can have a lasting impact. This episode explores the pros and cons of keeping a 401(k) versus rolling it over to an IRA.

Learn when it makes sense to stay in a 401(k), especially for those retiring between ages 55 and 59½, when a special IRS rule allows penalty-free withdrawals not available in IRAs. Keeping pre-tax funds in a 401(k) may also support more efficient backdoor Roth strategies.

Six key factors influence the decision: cost, control, investment options, account consolidation, ease of use, and coordination across accounts. The discussion also dives into advanced strategies—such as in-plan Roth conversions, the tax treatment of after-tax contributions, and Net Unrealized Appreciation (NUA) for company stock.

The right choice depends on individual retirement timelines, tax strategies, and long-term financial goals. This episode helps uncover what to consider before making a final decision.

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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 ⬇️

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Join the new Root Collective HERE!

If you’ve ever found yourself wondering whether you really need a financial advisor, this episode is for you. James and Ari unpack the deeper reasons people seek financial guidance—and why the decision often goes far beyond dollars and cents.

Much like seeing a doctor for preventative care, working with the right advisor is about protecting your future, reducing stress, and reclaiming your most precious resource: time. From saving 20+ hours a month of DIY management to gaining peace of mind, better sleep, and a trusted partner for life’s biggest financial decisions—this conversation explores the emotional and practical value of professional advice.

You’ll hear a powerful testimonial from a self-proclaimed DIY-er who discovered five unexpected benefits of hiring an advisor—and why, in hindsight, it was one of the best investments they’ve made.

Whether you’re confident in your current strategy or simply curious if you could be doing more with your time and money, this episode will help you ask the right questions about your financial life.

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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!

At 90 years old, will you remember that final bonus or the time you didn’t spend with the people you love? This powerful question reframes how we think about retirement timing beyond the numbers.

Yes, financial readiness matters. But delaying retirement for "just one more cycle" or "just one more raise" often leads to a dangerous pattern—constantly moving the goalpost while trading away your most vibrant, healthy years.

In this episode, we explore the critical difference between lifespan and healthspan. While many Americans live into their 80s or 90s, our healthiest years typically decline around age 66. Waiting too long to retire may leave you with more money, but fewer active years to travel, hike, or be present with grandchildren.

We also unpack the emotional side of retirement: the identity loss many face when stepping away from their career, and how this psychological barrier—paired with strained relationships from decades of overwork—can keep people stuck longer than they should be.

Retirement isn't just about having enough money. It's about having enough life left to enjoy it.

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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!

A seven-figure portfolio can feel like a green light for retirement—but the numbers don’t always tell the full story. In one case study, a couple with over $1 million saved faced a withdrawal rate close to 14% based on their desired lifestyle. That’s nearly three times higher than what’s typically considered sustainable.

This story is a reminder that retirement success isn’t just about hitting a number, it’s about how your money is structured to support your life.

A solid plan makes the difference between retiring with confidence and retiring with uncertainty.

Let’s help you build the kind of plan that lasts.

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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!

Retirement accounts like 401(k)s and IRAs often get all the attention, but there’s another tool that can play a powerful role in your long-term strategy: the humble brokerage account.

Unlike retirement accounts with age restrictions and penalties, brokerage accounts offer flexibility. You can access funds at any time, for any purpose without early withdrawal penalties. That kind of control can be incredibly valuable, especially if your goals include retiring early, helping family, or funding big life moments along the way.

Having a mix of account types—pre-tax, Roth, and brokerage—can give you more control over your income and taxes in retirement. It also helps you avoid a common challenge: having most of your wealth tied up in accounts that are difficult (or costly) to access when you need them most.

A thoughtful strategy includes more than just maxing out retirement accounts. It’s about building flexibility, tax efficiency, and confidence into every stage of your financial life.

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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!

After working with hundreds of people navigating retirement, we’ve seen a clear pattern: the biggest regrets aren’t about money. They’re about meaning.

Too often, people retire from something—but never toward something. They solve the financial side without planning for the life side. And that leads to some common regrets:

• No clear purpose after work: Retirement without direction quickly turns from freedom to restlessness.
• Neglecting health too long: Wellness is what fuels the retirement you’ve dreamed about—don’t wait to prioritize it.
• Losing social connection: The workplace offers more structure and belonging than many realize until it’s gone.
• Expecting retirement to feel like a vacation forever: It won’t. But with intention, it can become a reinvention.
• Being too afraid to spend: Your money is a tool to live—not something to hoard while life passes by.

Don’t wait to think about what really matters. The best retirements are built not just on financial security—but on vision, relationships, health, and joy.

Start designing a life you won’t regret.

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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!

The biggest question I hear from people planning for retirement is this: Am I going to run out of money before I run out of life? But here’s the thing, no matter how much you’ve saved, that fear doesn’t automatically go away. In this video, I walk through what the data actually says about your chances of running out of money, where the 4% rule comes from, and why many people end up being far too conservative with their spending.

I’ll also share a more flexible way to approach withdrawals so you can protect your future without missing out on the life you want to live right now. This isn’t about guessing or hoping for the best. It’s about building a plan that supports the kind of retirement you’re excited to wake up to.

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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!

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.

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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 Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

If your goal is to spend $10,000 a month in retirement, how much do you really need saved? The answer isn’t as simple—or as overwhelming—as it might seem.

In this episode, I break down the key factors that influence your retirement number beyond the common 4% rule. We’ll explore how Social Security can significantly reduce what you need to save, why account types like Roth vs. traditional IRAs make a major difference, and how your withdrawal strategy and retirement age can shift the numbers by hundreds of thousands of dollars. Using real planning software, I walk through examples that show how all these variables come together.

Whether you plan to spend $5K or $15K a month, these principles apply. It’s not about hitting a one-size-fits-all number—it’s about understanding what works for your unique plan. 

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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. We do not provide tax preparation or legal services. Always consult with your CPA or attorney regarding your specific situation.

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.

The Retirement Planning Academy is an educational program offered by Root Financial Partners, LLC. Access to the Academy is provided through a one-time payment and does not establish an advisory relationship. The content is for general informational and educational purposes only and does not include personalized financial, investment, tax, or legal advice. Participation in the Academy does not make you a client of Root Financial Partners, LLC. Please consult a qualified professional for advice specific to your situation.

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 Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!

Retirement planning isn’t about chasing numbers, it’s about building a life with intention.

The Sequoia System helps you get clear on what matters most, organize your finances around that vision, and create a plan that supports the freedom, peace of mind, and purpose you’re truly after.

We start with your life vision, translate that into a monthly income goal, and map out your cash flow using a mix of reliable income sources and portfolio withdrawals. Then we align your investments with those needs, optimize for taxes, and protect the plan through insurance and estate strategies, so everything works together to support the life you want to live.

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!