Fiscal Foxhole

Tax Withholding: The Nerdery Miniseries Begins


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Episode Summary

Welcome to the Foxhole! Hosts Omen Quelvog and Rob Moore kick off a three-part miniseries on tax nerdery, starting with the surprisingly complex world of tax withholdings. Whether you’re a military veteran, retiree, or just someone who wants to keep more of your paycheck, this episode is packed with practical advice, fun tax facts, and actionable steps to help you avoid giving the IRS an interest-free loan.

Key Topics Covered

  • Why Withholdings Matter: How underpaying or overpaying taxes throughout the year can impact your finances—and why a big refund isn’t always a win.
  • Safe Harbor Rules: What they are, why they matter, and how to use last year’s tax return to avoid penalties.
  • W-2 vs. Self-Employed: Strategies for managing withholdings across multiple jobs, pensions, and self-employment income.
  • Fun Tax Facts: From England’s window tax to Missouri’s bachelor tax, plus ABBA’s glittery costumes and the “vanishing children” of 1987.
  • How to Check Your Withholdings: Step-by-step breakdown of the basic tax formula, plus recommended online calculators (IRS and Dinky Town).
  • Action Steps: When and how to adjust your W-4, and what to do if your life changes (marriage, divorce, new dependents, moving states, bonuses).

Featured Resources & Links

  • IRS Withholding Estimator (note: may not be updated for the latest tax law)
  • Dinky Town Tax Calculator
  • Email your questions: [email protected]
  • Book a free consultation with Rob
  • Book a free consultation with Omen

Practical Takeaways

  1. Lifelong savers often struggle to spend in retirement. Identify what matters most and spend intentionally with a plan.
  2. Your tax refund or bill isn’t a grade. Aim to break even—no big refund, no big liability.
  3. Tax planning is a year-round habit. Review withholdings and estimated payments after major life changes.

If you found this episode helpful, please share it with a friend—especially fellow military veterans and retirees who could benefit from smarter tax planning. Rate and comment wherever you listen to podcasts. Your feedback helps us reach more listeners and keeps the educational mission alive!

Disclaimer

Rob Moore and Omen Quelvog are registered investment advisor representatives. This podcast is for educational and entertainment purposes only. Nothing you hear should be taken as specific investment, legal, or tax advice. Please consult a qualified professional for guidance tailored to your situation.

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Fiscal FoxholeBy Rob Moore and Omen Quelvog