Why High Earners Should Sometimes Pay MORE Taxes On Purpose!

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Would you ever pay more to the IRS… on purpose? Sometimes the smartest move in retirement planning is the one that feels most counterintuitive, like voluntarily paying more taxes now. In this episode, Matt breaks down why certain high earners should consider a Roth 401(k) conversion during a lower-income year if their plan allows it.  

Matt explains how the in-plan Roth conversion works, the potential tax impact, and the importance of planning ahead for payment. You’ll also hear why this strategy isn’t just about lowering your taxes, it’s about long-term tax control for you and your heirs. We’ll cover key pitfalls to avoid, from bumping into higher tax brackets to understanding the “five-year clock.” When you hit the right window, one strategic move may buy (you and the next generation) decades of tax-free growth. 

Key Topics We Discuss: 

💡 How paying more taxes now could save high earners later

📈 How Roth 401(k) conversions create tax-free growth

🗓️ The “hidden window” for high earners in lower tax years

⚠️ Key mistakes to avoid when converting

👨‍👩‍👧 Passing wealth to your heirs tax-efficiently

0:00 – Intro

0:58 – In-Plan Roth Conversion Strategy

2:21 – Why Should High Earners Do This?

4:48 – Who Should Consider This?

5:46 – Mistakes to Avoid

Resources for Why High Earners Should Sometimes Pay MORE Taxes- On Purpose!

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About Matthew Nelson

Matt has over 20 years of experience in the financial services industry. He is passionate about helping MedTech professionals maximize their benefits, reduce their taxes, and plan for financial freedom. As the Founder, Managing Partner, and Senior Financial Advisor at Perspective 6 Group, he leads a team of dedicated professionals. The team provides comprehensive and personalized financial planning and investment management services to our clients.

As a CERTIFIED FINANCIAL PLANNER™ (CFP®), Accredited Investment Fiduciary® (AIF®), and Equity Compensation Associate (ECA) Matt specializes in helping our clients navigate the complex and evolving landscape of equity compensation, financial independence, portfolio management, and income tax minimization. Further, he leverages his experience as a private equity investor at Focus Financial Network, Inc., to offer strategic insights and guidance on business succession, valuation, and exit planning. Matt’s mission is to empower our clients to achieve their financial and personal goals with confidence and clarity.