Some of the biggest retirement mistakes don’t show up until it’s too late to fix them. Today, I’m breaking down 8 costly mistakes I see over and over again and how to avoid them before they impact your income, taxes, and long-term freedom. A few small adjustments here can make a massive difference later.

👉 Work With Us: https://www.rivertreewealth.com/get-started

✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers

Email: jacob@rivertreewealth.com
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linkedin.com/in/jacobduke

Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast.

DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.

Not sure when to take Social Security? Well, in today's episode, I am sharing 5 reasons you shouldn't take your benefits early and the hidden risks of doing so.

👉 Work With Us: https://www.rivertreewealth.com/get-started

✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers

Email: jacob@rivertreewealth.com
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linkedin.com/in/jacobduke

Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast.

DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.

If you don't get things right during this important window of time, your retirement likely won't be what you hoped... This 10 year period of time will determine the trajectory of your entire retirement. Prepare correctly and you will enjoy a fulfilling life without worry. Little preparation and poor execution and you will be wishing you could get a do over... Only problem is, you get one shot at retiring right the first time.

👉 Work With Us: https://www.rivertreewealth.com/get-started

✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers

Email: jacob@rivertreewealth.com
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linkedin.com/in/jacobduke

Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast.

DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.

00:00 Intro

01:40 Last 5 Years of Work

11:44 First 5 Years of Retirement

14:16 Book a Call

Confused by the Roth IRA 5-year rule? Did you know there are two different 5-year rules? Well, it can get quite confusing, so this episode is meant to be your complete guide for everything around the Roth 5-year rules.

👉 Work With Us: https://www.rivertreewealth.com/get-started

✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers

Email: jacob@rivertreewealth.com
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linkedin.com/in/jacobduke

Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast.

DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.

Are you sure your retirement plan is optimized for the right things? In this episode, I discuss what the true mark of a successful retirement plan is and why most people's plans will fail, just not in the way they expected.

👉 See If You're a Fit: https://www.rivertreewealth.com/get-started

✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers

Email: jacob@rivertreewealth.com
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linkedin.com/in/jacobduke

Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast.

DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.

Is the brokerage account the secret to a fun and tax-efficient retirement? It might be a requirement, but it definitely helps. In fact, the brokerage account is my favorite account type and in this episode, I share 7 benefits that anyone can use to their advantage in retirement.

👉 See If You're a Fit: https://www.rivertreewealth.com/get-started

✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers

Email: jacob@rivertreewealth.com
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linkedin.com/in/jacobduke

Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast.

DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.

00:00 Welcome

00:47 How 401(k)s, Traditional IRAs, and Roth IRAs Are Taxed

03:06 What a Taxable Brokerage Account Is (and How It’s Taxed)

04:16 Flexibility

05:50 The “Bridge Account”

07:10 Tax-Gain Harvesting

11:39 Tax-Loss Harvesting

13:30 Asset Location

15:54 Liquidity

16:58 Estate Planning

19:04 How to Start Using a Brokerage Account in Your Plan

20:20 Wrap-Up

Are you still trying to decide when to take Social Security? Well, in this episode, I am deviating from my normal stance to share 4 reasons you might want to take your benefits ASAP rather than delay. And be sure to listen to the end, because I share why using a traditional break even analysis in your decision making process is not a good idea.

👉 Book a call with me: https://www.rivertreewealth.com/get-started

✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers

Email: jacob@rivertreewealth.com
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linkedin.com/in/jacobduke

Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast.

DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.

00:00 Introduction

01:31 Reason 1

03:07 Reason 2

04:19 Reason 3

06:10 Reason 4

07:51 The Flaws of Break Even Analysis

12:28 Conclusion

Are you anxious about an abrupt transition to retirement? In this episode of Retirement Answers, I share the concept of phased retirement, where you can gradually reduce work hours or stress levels instead of stopping work entirely. I explain the financial and emotional benefits, offering practical advice for a smoother, more comfortable path to retirement.

👉 Book a call with me: https://www.rivertreewealth.com/get-started

✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers

Email: jacob@rivertreewealth.com
Website: https://www.rivertreewealth.com
LinkedIn: https://www.linkedin.com/in/jacobduke

Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast.

DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only.

00:00 Introduction

00:48 The Anxiety of Full Retirement

01:25 Phased Retirement: A New Approach

02:37 Changes in Retirement Landscape

04:04 Practical Steps for Phased Retirement

05:17 Employer Negotiations and Alternatives

07:53 Consulting and Part-Time Work Options

11:45 Financial and Health Benefits

15:39 Finding Purpose in Retirement

17:19 Conclusion