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Blog Your guide to financial planning and retirement
March 13, 2026 • 3 minutes
Retirement changes everything about how you pay taxes – and most people aren’t prepared for it. In this Office Hours session, Boldin Lead Educator Nancy Gates walks you through exactly what you need to know: where your retirement income comes from, how each source is taxed, and – critically – how to actually pay those taxes so you stay compliant and avoid IRS penalties.
✅ What your “retirement paycheck” actually looks like – and the income sources that replace your salary
✅ How Social Security, RMDs, pensions, Roth accounts, and investment income are each taxed differently
✅ The IRS “pay as you go” rule — and why ignoring it can trigger penalties even if you eventually pay what you owe
✅ The safe harbor provisions that protect you when retirement income fluctuates year to year
✅ 4 practical ways to handle tax payments in retirement: withholding from income sources, partial distributions, 100% withholding distributions, and quarterly estimated payments
✅ How the Boldin Planner projects your tax liability annually so you can plan ahead – not scramble at tax time
00:00 Welcome + what we’re covering
02:18 Your retirement paycheck – the income sources that replace your salary
04:03 How each income source is taxed (Social Security, RMDs, pensions, Roth, and more)
09:36 The IRS “pay as you go” rule and why it matters in retirement
10:33 The safe harbor provisions – how to stay protected even if your income fluctuates
11:37 4 ways to pay taxes in retirement: withholding, distributions, and quarterly estimated payments
17:02 Q&A – real questions from Boldin members
One of the most overlooked retirement planning challenges is that your employer stops withholding taxes for you the moment you stop working. Suddenly, managing tax payments is your responsibility – and the rules are different for every income source you’ll have.
The Boldin Planner can project your tax liability year by year through your entire retirement – giving you a foundation to build your tax payment strategy before you need it. This is general educational content. Nothing in this video should be considered specific financial, tax, investment, or legal advice.
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.
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