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February 10th, 2026

When Does It Make Sense to Pay Retirement Account Penalties?

  1. When Does It Make Sense to Pay Retirement Account Penalties? Ross Anderson, CFP® and Daniel Messeca, CFP® 27:58

It’s the ultimate “break glass in case of emergency” move: tapping into your 401(k) or IRA before you hit age 59½. Usually, the advice is a resounding “don't do it,” thanks to that stinging 10% early withdrawal penalty plus ordinary income taxes.

But life rarely follows a linear spreadsheet. In this episode, we tackle the nuance of the “forbidden” withdrawal. We’re diving into the specific scenarios where paying the penalty might actually be the most logical—or least destructive—financial move available to you.

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Daniel Messeca Financial Planner

Daniel’s grandmother helped him buy his first shares of Coca Cola when he was just eight years old, igniting a lifelong interest in investing. A graduate with a degree in Finance from the University of Maryland’s Smith School of Business, Daniel chose a career in financial services to apply his passion for investing and strategic planning. Daniel possesses expertise in insurance planning, especially as it relates to life insurance and annuity contracts. Daniel’s background in the insurance industry makes him particularly adept at analyzing existing policies and evaluating new proposals.

In 2016, Daniel co-founded Crooked Crab Brewing Company, a craft brewery located in Odenton, MD. The experience of planning, financing and operating a company makes him an informed planner for business owners.

Daniel lives in Maryland with his wife, daughter and a rambunctious hound dog who shows no signs of aging. He plays guitar in his free time and will always take time to talk about music with whomever will listen.