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 withdrawal rates, portfolio flexibility, and trade-offs between spending today and planning for tomorrow.

This isn’t just about getting by—it’s about using what you’ve saved to live intentionally. And just as important, it’s about avoiding the regret of leaving money (and meaningful experiences) unused.

If you're thinking about how to align your spending with your values in retirement, this conversation is for you.

Questions we explore:

1. How can I estimate a sustainable spending level in retirement?
2. How do I balance enjoying life now with preserving assets for the future?

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

Timestamps:
0:00 - Jeffrey and Cindy's plan
3:24 - Understand cash flows
5:45 - Projected portfolio withdrawals
7:22 - Probability of success
9:26 - Monitor your withdrawal rate
11:12 - Key takeaway
13:26 - Wrap-up

Create Your Custom Strategy ⬇️

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Many great savers hesitate to spend once they retire—unsure how to shift gears after years of discipline. In this episode, we talk through what it looks like to use money with intention, not just someday, but now.

Prompted by a thoughtful note from a Root Collective member, we share stories—personal and client-based—about the small upgrades that matter: better experiences, more time, stronger health, and generosity that deepens relationships.

We also walk through five areas where spending often brings clarity and connection: experiences, time, giving, health, and environment.


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

Advisory services are offered through Root Financial Partners, LLC, 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. 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 Strategy ⬇️

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Join the new Root Collective HERE!

Health Savings Accounts (HSAs) don’t get much attention—but they should. With triple tax advantages (tax-free contributions, growth, and qualified withdrawals), HSAs offer a level of flexibility that’s hard to beat.

I break down how to use an HSA not just for healthcare today, but as a long-term planning tool. That includes how to qualify, contribute, invest the funds, and take strategic withdrawals.

I also explain why it’s worth tracking medical expenses—even if you don’t reimburse yourself right away—to create future options for tax-free income.

What you'll learn:
1. How an HSA can help reduce your lifetime tax burden and fit into a broader retirement strategy
2. Ways to maximize the tax benefits beyond just paying current medical bills

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

Timestamps:
0:00 - How HSAs work
1:12 - Eligibility and contribution limits
3:19 - HSA details and nuances
4:36 - Timing flexibility
8:11 - Case study -- John
9:31 - Leveraging tax benefits
10:50 - Qualified medical expense
11:51 - Use HSA to the fullest extent
14:19 - HSAs in the grand scheme of things

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!