Many professionals find that retiring isn’t just about having enough money—it’s about feeling ready to leave behind the structure, identity, and comfort of a career. 

In this Root Financial podcast episode, James and Ari explore the emotional hurdles of retiring from a high-paying, high-stress job, even when financially prepared. They highlight the value of aligning retirement with your future self’s goals and priorities, not just your current fears. 

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here  

Timestamps:
0:00 - A comment from the Collective
3:03 - A first-day-of-school analogy
4:25 - What would my future self do?
6:47 - Helpful feedback
8:32 - Make sure you're ready financially
10:20 - A life you don't retire from
13:18 - The opportunity cost
16:39 - More words of wisdom
18:44 - Making the decision is the scary part

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Many retirees focus on achieving a high Monte Carlo “probability of success” in retirement—but is chasing a 99% success rate always the best move? In this episode, James highlights a real-life story of a man forced to delay retirement after a divorce dropped his probability of success from 99% to 70%. James explores why this single number shouldn't drive such massive decisions. He explains how context—like income sources, spending flexibility, and home equity—matters more than a static success rate. You’ll learn why 100% isn’t always ideal, and how to build a retirement plan that supports a meaningful life, not just a perfect score.

Questions answered?
1. Should I delay retirement if my Monte Carlo probability of success drops?

2. Is a 100% probability of success the best goal for my retirement plan?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - An encounter at the gym
2:37 - What is Monte Carlo analysis?
4:18 - Consider severity of failure
6:19 - Consider other assets, like property
7:35 - Is a 100% probability score really success?
10:55 - Monitor and course correct
14:13 - Margin
15:07 - No universal number
16:13 - Assumptions about spending
18:27 - Retirement spending smile
20:57 - Context matters

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Relying too much on Social Security? You’re not alone—over 40% of retirees count on it for at least half their income. But that safety net has some major gaps. In this video, I break down four key reasons why Social Security isn’t enough—and what you can do to secure a more stable retirement. 

Questions answered:
1. Why is it a mistake to rely too heavily on Social Security for retirement income?

2. What are some strategies to supplement Social Security income in retirement?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - One-off expenses
1:34 - Inflation & CPIW
4:21 - Tax on provisional income
7:33 - Peace of mind
8:33 - Maximize your benefit
9:22 - Supplement SS
10:24 - Leverage your home

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How do you keep things fun when markets—or life—get tough? We're breaking down why “fun” isn’t just about ping pong tables and perks—it’s about being prepared, building trust, and maintaining strong relationships before challenges arise.

James shares a personal story from the early Covid days, highlighting how mindset and self-care helped him show up for clients.

The takeaway? A great advisor isn’t just there for the good times—they’re prepared to guide you through the tough ones, too.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here  

Timestamps:
0:00 - About Root Collective
0:56 - Making a serious topic fun
2:07 - A lesson from Covid
5:06 - "Fun" is being prepared
8:04 - Emotional downtimes require a team
11:27 - On building trust
13:33 - Wrap-up

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If you're over 60, it's time to stop certain habits that may be holding you back from fully enjoying your retirement. In this video, I’ll share key lessons learned from working with retirees, including how small shifts can lead to a more meaningful and financially secure future.

From when to stop saving, how to spend wisely, prioritizing health, and letting go of worries that no longer serve you, these insights will help you make the most of your retirement years.

📌 Watch now to discover how to live with more freedom, joy, and financial confidence!

Questions answered:
1. How can I make the most of my retirement years financially and emotionally?

2. What habits should I stop after 60 to live a healthier, happier, and more fulfilling life?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - 1 - Saving
2:24 - 2 - Spending when it's not fun
3:38 - 3 - Trading time for money
4:52 - 4 - Putting off experiences
6:27 - 5 - Neglecting your health
8:15 - 6 - Caring what others think
9:17 - 7 - Watching dome-and-gloom news
11:16 - 8 - Neglecting your financial plan
13:00 - 9 - Making decisions as if you'll live forever

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Roth IRAs are a great way to build tax-free retirement income—but the withdrawal rules can be tricky. In this video, I’ll break down the five-year rules, how contributions, conversions, and growth are treated, and smart strategies to avoid unnecessary taxes.

Understanding these rules can help you make the most of your Roth IRA and keep more of your money tax-free. Let’s dive in!

Questions answered?
1. When can you withdraw money from a Roth IRA without paying taxes or penalties?

2. How do the two different five-year rules for Roth IRAs affect withdrawals?

Questions answered?
1. When can you withdraw money from a Roth IRA without paying taxes or penalties?

2. How do the two different five-year rules for Roth IRAs affect withdrawals?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - The 5-year rule
1:09 - Contributions
3:39 - Conversions
5:36 - Growth
6:51 - An example
8:55 - Conversions before 59.5 years
10:23 - Summary

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Root Collective member Gary asks how to fund a $40K home remodel before retiring—should he use a taxable brokerage account, tax-deferred 401(k), Roth IRA, or cash?

Ari and I break down how to handle big one-off expenses into a three-part framework:

• Portfolio Sustainability – Can your investments handle both recurring and one-time expenses?
• Investment Allocation – Ensure your assets are positioned to avoid selling at a loss.
• Tax Optimization – Withdraw strategically to minimize lifetime taxes.

The key? Plan ahead, align financial decisions with long-term goals, and make the most of your retirement funds.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here  

Timestamps:
0:00 - Gary R's question
2:52 - Can your retirement support it?
4:43 - How should investments be allocated?
6:28 - Have a tax strategy
8:54 - A caution; a reminder about sleep
12:03 - Intentionally set aside
14:23 - Mental hang-ups and biases
16:37 - The Collective Community

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Are You Spending Your Money on What Truly Matters?

A few weeks ago, I challenged you to do the most important thing you can with your money this year—not Roth conversions, not optimizing Social Security, but something far more impactful: aligning your spending with what truly brings you joy. I asked you to write down one thing you've always wanted to do or buy but haven't, set a date to make it happen, and identify where the funds would come from.

In today’s episode, I’m sharing some of the incredible responses I received—stories of travel, family experiences, and meaningful purchases that turned dreams into reality. These stories serve as a reminder: financial planning isn’t just about growing wealth; it’s about using it to create a life you love.

If you haven’t already, take that step. Don’t wait for "someday." Let’s make sure we’re spending in a way that truly reflects what we value most.

Questions answered:
1. Why is it important to align your spending with what you truly value?

2. How can you take action to ensure your money is being spent in a way that brings you joy?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Reviewing the challenge
1:42 - Ice fishing and family trips
2:46 - Urgency
4:19 - Diving the Red Sea, family cruise
5:35 - Pets and optimizing travel plans
7:28 - Uncertainty and urgency
8:53 - Values, purpose, and happiness

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One of the biggest ironies in retirement is that the people who save and invest the most often struggle the most with actually spending their money in retirement. In this video, I’ll walk you through a simple framework to make spending easier—without guilt or second-guessing.

I’ll share a compelling client story, a personal experience, and actionable steps you can take to shift your mindset and enjoy the retirement you’ve worked so hard for. If you’ve ever hesitated to spend on things you value, even when you can afford to, this is for you.

We’ll cover:

• Why our money habits from the past shape how we spend (or don’t spend) today
• A five-step process to help you feel comfortable spending in retirement
• A practical tip that makes it easier to say “yes” to the things that truly matter

🎯 Don't let a scarcity mindset hold you back—start living your best retirement!

Questions answered:
1. Why do some retirees struggle to spend money, even when they have more than enough saved?

2. How can retirees overcome a lifetime of saving habits and confidently spend on things they truly value?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - A pertinent story
3:24 - A personal story
5:10 - Steps 1& 2—acknowledge and evaluate
7:05 - Steps 4 & 5—Identify values and make it easy
9:44 - Healthy tension
12:30 - Step 5—Withdrawal and set aside
14:49 - Wrap-up

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

You’ve worked hard, built wealth, and reached financial security… so why is it still so hard to spend? In this episode, we dive into the unexpected challenge of shifting from a saver’s mindset to actually enjoying your money.

From a millionaire couple hesitating over a $5 bag of M&Ms to a husband upset about a bottle of Fiji water—this is more common than you think! Behavioral finance reveals why past money habits stick with us, even when we don’t need them anymore.

We’ll break down how to retrain your mindset, align spending with what truly matters, and ensure your wealth enhances your life instead of holding you back. Plus, a practical strategy to help you finally enjoy your money guilt-free!

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here  

Timestamps:
0:00 - A scarcity mindset story
2:36 - Comment that sparked conversation
4:12 - Identifying the problem
7:00 - A personal story from James
10:00 - Practical takeaways
12:18 - Make small, aligned shifts
16:14 - An example from Ben
18:04 - Death is coming
19:55 - The wrap-up

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Retirement isn’t just about the numbers—it’s about time, health, and the life you want to live. Too many people delay retirement, chasing "one more bonus" or "one more year" without considering the bigger picture.

In this video, we’ll walk through five key questions that can help you decide. If you answered yes to any of these, retirement might be closer than you think! Watch now to gain clarity on your next steps.

Questions answered?
1. How do you know if it's the right time to retire?

2. What are the risks of delaying retirement for financial reasons?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Is time passing you by?
2:30 - Is your health suffering?
3:40 - Want more time for relationships?
4:50 - What is your life and health span
6:25 - Are you financially ready?
7:59 - Wrap-up

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!