You've spent decades saving for retirement, but are you about to make the same mistakes thousands of retirees only spot when it's too late? In this episode, I walk through the five biggest regrets I see in my work as a retirement planner, and exactly what you can do right now to avoid them.

Tune into this episode to find out:

(01:14) Regret #1 – Claiming Social Security too early costs you

(01:44) Early claiming locks in a permanent 30% benefit cut

(02:49) How claiming early closes your Roth conversion window

(04:12) Regret #2 – Playing it too safe with your investments

(06:43) Using the bucket system to balance safety and growth

(08:37) Regret #3 – Not spending enough early on

(11:06) Regret #4 – Putting off tax planning until it's too late

(12:14) How RMDs, Social Security taxes, and IRMAA blindside you

(13:46) Regret #5 – Juggling too many accounts and strategies

(14:30) Why simplicity leads to clarity and lasting retirement confidence

👉 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.

You're saving for retirement, but are you saving too much into the wrong accounts? Most retirees don't realize this common issue until it's too late.

In this episode, I explain why having all of your retirement savings in pre-tax accounts is major risk and how you can begin to fix things.

👉 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.

01:00 Early Retirement Access Trap

02:31 Risk One: Future Taxes

04:03 Risk Two: RMD Time Bomb

06:50 Risk Three: Income Control

09:37 Risk Four: Psychological Barriers

11:51 Risk Five: Lack of Flexibility

12:51 Tax Diversification

16:28 How To Fix The Problem

19:12 Conclusion

Have you ever wondered if chasing “more” could actually make retirement harder instead of better? In this episode of Retirement Answers, Jacob is sharing how “more is not better, better is better” applies to retirement...

More money can create fear, over-optimizing can steal joy, more stuff adds complexity and decision fatigue, and more time without purpose can lead to dissatisfaction. Tune in to rethink what “enough” means for you and focus on using your money, lifestyle, and time in a better way that supports a meaningful retirement.

👉 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 Welcome
00:56 More Is Not Better
01:37 Defining Enough
02:27 Money Can Add Fear
05:43 Stop Over Optimizing
08:40 More Stuff Adds Complexity
10:34 Time Needs Purpose
12:43 Final Takeaways

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.