
Sign up to save your podcasts
Or


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: [email protected]
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.
By Jacob Duke, CFP®4.9
9898 ratings
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: [email protected]
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.

450 Listeners

809 Listeners

1,331 Listeners

457 Listeners

538 Listeners

754 Listeners

545 Listeners

696 Listeners

198 Listeners

577 Listeners

825 Listeners

204 Listeners

586 Listeners

1,069 Listeners

187 Listeners