Ready For Retirement

Forget the myth that you need a million dollars to retire. What really matters is creating sustainable cash flow—not hitting a magic number.

Retirement success comes down to three things: your expenses, guaranteed income (like Social Security or pensions), and the gap your savings need to fill. For some, that gap is smaller than expected.

Real examples—like a couple living comfortably on $300K in investments—show it’s possible. Small...

Can a children’s poem change how you think about retirement? In this episode, we unpack the hidden wisdom in Shel Silverstein’s “Smart” and how it reflects a common retirement planning mistake: trading time and well-being for wealth you may no longer need.

We explore why it’s hard to step away from accumulation mode—even after reaching financial independence—and how this mindset can cost you more than it earns. The real risk isn’t r...

The hardest part of retirement isn’t always financial, it’s psychological. For many, stepping away from work isn’t a light switch, but a dimmer that adjusts over time. This episode of Root Talks unpacks what makes the retirement decision so complex, especially for high-achieving professionals whose identity is tied to their careers.

Through a real-life case study, the conversation explores how severance offers can become powerful “t...

Even with a strong financial plan in place, many professionals find themselves hesitating at the retirement decision—stuck in the cycle of “just one more year.” The numbers say it’s possible, yet the fear of leaving behind a paycheck, a title, or a sense of purpose keeps them working long past the point of “enough.”

This episode reframes retirement readiness through the lens of the five dimensions of wealth: financial, time, physica...

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 ...

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 2...

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...

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 ...

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 y...

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.
• Neglect...

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.

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 helpe...

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 ...

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...

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, ...

In this episode, we walk through a retirement planning scenario involving a couple in their early 60s with a $4 million investment portfolio. Their financial plan reveals something surprising: they may not need to wait until 65 to retire. Instead, thoughtful planning opens the door to retiring earlier—without compromising the lifestyle they value.

What we cover:
• A breakdown of how a $4 million portfolio can support early retir...

Deciding when to start your Social Security benefits might be the single most consequential financial decision of your retirement journey. Should you claim early at 62, wait until full retirement age at 67, or delay until 70 to maximize your monthly check? The answer isn't as straightforward as many think.

Your Social Security benefit is calculated using your 35 highest-earning years, adjusted for inflation. This form...

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.

Jeffrey and Cindy came to me with $3 million saved and one big question: How much can we actually spend in retirement? In this video, we walk through a retirement planning scenario—looking at spending goals, taxes, travel, healthcare, and how Social Security might factor in.

While the numbers vary, the framework we use applies whether you're working with $300,000 or $30 million. We explore how to think about sustainable withdra...