Join hosts Chris Picciurro, CPA, and John Tripolsky as they explore an often-overlooked topic: the tax implications of changing jobs or transitioning into retirement. With career changes on the rise in recent years—whether due to new opportunities, layoffs, or retirement—understanding the tax side of employment transitions is crucial.

Chris and John walk listeners through everything from retirement plan rollovers and benefit changes to withholding adjustments and self-employment considerations. They also tackle what you need to know about flexible spending accounts, health savings accounts, vested stock options, and group insurance benefits when leaving an employer. Wrapping up, the conversation shifts toward self-employment and retirement, covering key planning points like self-employment taxes, Social Security timing, and Medicare enrollment.

What You'll Learn:
• How to manage 401(k) rollovers and avoid penalties
• Why updating W-4 withholdings is crucial after a job change
• What to do about group life insurance and other employer benefits
• Key tax considerations for transitioning into self-employment
• Planning strategies for retirement income, Social Security, and relocation taxes

Key Insights:
Leaving a job involves more than just changes in pay; it requires proactive tax planning. Whether you’re switching employers or entering retirement, knowing these key steps can prevent costly surprises and help you navigate this major transition with confidence.

Notable Quotes:
• “I didn’t realize all of the considerations when you change jobs...that is a podcast episode.” – Chris Picciurro
• “Make sure your withholdings from your W-2 wages are proper.” – Chris Picciurro
• “Even if you have great life insurance through your employer, have coverage outside of your employment.” – Chris Picciurro
• “There are definitely some benefits for rolling it out of that former employer’s plan.” – Chris Picciurro
• “When you leave a job, there’s a lot more things to consider than just pay.” – Chris Picciurro

Resources:
• Teaching Tax Flow Website
• Defeating Taxes Facebook Group
• Teaching Tax Flow Hub
• Teaching Tax Flow YouTube Channel

Episode Sponsor:
Integrated Investment Group (IIG)
Wondering if you qualify as an accredited investor? Visit teachingtaxflow.com/iig to learn more.

(00:02) - Tax Considerations When Changing Jobs or Retiring
(05:36) - Managing Retirement Plans and Benefits When Changing Jobs
(13:52) - Building a Non-Salesy Resource Hub for Tax Advice
(15:09) - Tax Implications of Job Relocation and Stock Options
(19:00) - Navigating Self-Employment Tax and Retirement Planning
(24:19) - Alaskan Fishermen Deductions and Missed Opportunities
(25:51) - Navigating Retirement Transitions and Financial Considerations
(28:05) - Navigating Job Changes and Tax Implications

Ep. 147 | Taxes to Consider When Changing Jobs or Retiring

Teaching Tax Flow: The Podcast