In this special Office Hours session, hosted by Nancy Gates, Senior Manager of Services at Boldin, we take a deep dive into an essential retirement planning topic: estimating and paying taxes in retirement. Nancy guides you through the complexities of retirement income taxes — from understanding how each income source is taxed, to developing a smart tax payment strategy that keeps you compliant and stress-free.
This session is focused on education and empowerment, helping you take control of your financial future with confidence. Whether you’re newly retired or planning ahead, this video will equip you with the knowledge you need to avoid tax penalties and make informed decisions about your retirement income.
Key Topics Discussed in this Office Hours Session
✅ Overview of the retirement paycheck and income sources
✅ Tax implications of various retirement income streams
✅ How FICA, federal, state, and capital gains taxes apply in retirement
✅ Safe harbor rules and the IRS $1,000 rule
✅ Tax withholding strategies
✅ How to use estimated quarterly tax payments
✅ Practical tips for developing your retirement tax payment strategy
Timestamps
00:00 Introduction & Housekeeping
00:20 What is the Retirement Paycheck?
01:25 Common sources of taxable income in retirement
02:30 Overview of U.S. tax categories: FICA, federal, state, capital gains
03:45 Tax treatment of various income sources
05:50 Social Security tax rules
07:30 Investment income and savings drawdown taxation
10:00 Safe Harbor Rule & $1,000 Rule explained
12:00 How to avoid tax penalties in retirement
13:25 Four methods to pay taxes in retirement
15:35 Tax withholding strategies from pensions and annuities
17:45 Using IRA distributions for tax payments
19:10 Making quarterly estimated tax payments
21:00 Next steps and planning tips
About Boldin and the Award Winning Boldin Retirement Planner
The Boldin Planner is powerful software that puts you in control. It’s almost like having a financial expert at your fingertips. Research shows that people with a written financial plan do 2.7 times better financially. They’re also 54% more likely to live comfortably in retirement. That’s not luck, that’s taking control of your money. The Boldin Planner has been named the Best Financial Planning Software of 2025 and the company was selected as a Top Innovator in UpLink’s Prospering in Longevity Challenge and named to the FinTech 100 by CBInsights.
The tool is ideal for planning because it covers a comprehensive set of information relevant to retirement and lets you customize everything – including your own life expectancy.