In this episode of Money and Taxes from BB to XYZ, Jason Speciner, CFP®, EA, and Regina Neenan, CFP®, ABFP®, discuss what to do when a mid-year income boost — like a raise, bonus, RSU vest, or ESPP benefit — creates new tax planning opportunities. They explain why more income can mean more taxes, but also more ways to strategically reduce taxable income and redirect cash flow. The conversation covers bonus withholding, pre-tax employer retirement plan contributions, HSAs, deferred compensation, RSUs, ESPPs, charitable giving, and donor-advised funds. Regina and Jason emphasize that the key is building a tax projection early enough in the year to understand what’s changing and make smart decisions before year-end.

Takeaways

• Start by looking for ways to reduce taxable income at the source, such as 401(k), HSA, IRA, or deferred compensation options.
• Consider selling RSU or ESPP shares when they vest so you can diversify, manage tax exposure, and redeploy the cash intentionally.
• After source-level planning, review tax-return strategies like charitable contributions, appreciated stock gifts, and donor-advised funds.

Have a tax question for the show?

Email [email protected], and Jason or Regina might answer it in a future episode! New episodes drop every other Thursday, and they’re always ad-free with no subscription required. Learn more about FPFoCo at fpfoco.com and connect with us on social media @fpfoco.

Disclosures

Jason Speciner and Regina Neenan are investment advisor representatives of FPFoCo, a registered investment advisor. The information in this podcast is for general educational and entertainment purposes only. It may not apply to your individual circumstances and should not be considered financial, investment, or tax advice.

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