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Posted on May 28, 2024 by Dan Pascone
The High Earner’s Playbook to Donor-Advised Funds
TL;DR Answer Box Donor-Advised Funds (DAFs) let high earners “front-load” charitable deductions in a high-income year, then distribute grants to charities over time. You get an immediate tax deduction when you contribute, your donation can grow tax-free inside the DAF, and you keep advisory privileges on where/when grants go. DAFs are best when philanthropy is […]
Posted on May 20, 2024 by Dan Pascone
Tax Savvy Moonlighting: Tax Strategies for Side-Hustling High-Earners
TL;DR Answer Box Moonlighting income is usually treated as self-employment income, which means you may owe federal income tax + 15.3% self-employment tax (plus state tax where applicable). Since taxes aren’t withheld, you’ll often need to pay quarterly estimated taxes and track deductible business expenses to reduce what you owe. Last updated: February 12, 2026 […]
Posted on May 13, 2024 by Dan Pascone
Beyond Basics: HSAs as a Tool for Wealth and Health Management
TL;DR Answer Box Health Savings Accounts (HSAs) can offer a rare “triple tax advantage”: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. To contribute, you must be enrolled in a high-deductible health plan (HDHP). HSAs can be a powerful tool for high earners to reduce taxable income today and build a long-term […]
Posted on May 7, 2024 by Dan Pascone
Beyond Saving for College: 529 Plans as Strategic Legacy Planning Tools for High Earners
TL;DR Answer Box Superfunding a 529 plan lets you front-load five years of annual gift tax exclusions into a child’s 529 in one year, up to $90,000 per individual or $180,000 per couple in 2024, without triggering federal gift tax (if you properly elect the 5-year spread on Form 709). It can be a powerful […]
Posted on April 29, 2024 by Dan Pascone
Opportunity Zones 101: Opportunity or Overhype?
TL;DR Answer Box Qualified Opportunity Zones tax benefits can be real, but only if the underlying investment is strong and your timeline matches the rules. In 2026, the headline benefit is still the same: you may be able to defer eligible gains by investing in a Qualified Opportunity Fund (QOF) within 180 days, with deferral […]
Posted on April 23, 2024 by Dan Pascone
5 Smart High-Earner Moves to Maximize Your Tax Return
TL;DR Answer Box Tax strategies for W-2 employees are less about “finding write offs” and more about using the benefits already available through payroll, retirement plans, and taxable investing. In 2026, the biggest levers for many high earners are maximizing workplace retirement contributions, using Roth pathways when eligible, fully funding an HSA if you qualify, […]
Posted on April 16, 2024 by Dan Pascone
Breaking Down the Mega Backdoor Roth: A Tax-Saving Strategy for High Earners
TL;DR Answer Box Mega Backdoor Roth is a strategy that can let certain high earners move substantially more money into Roth each year by making after-tax (non-Roth) contributions to a 401(k) and then converting or rolling those dollars into Roth. It only works if your employer plan allows after-tax contributions and provides a Roth pathway […]
Posted on April 9, 2024 by Dan Pascone
All About the Backdoor Roth IRA
TL;DR Answer Box Backdoor Roth IRA is a two-step strategy that may allow high-income earners to fund a Roth IRA even when they are over the income limit for direct Roth contributions. The clean version is: contribute to a traditional IRA (often nondeductible), then convert to Roth, while tracking basis correctly on Form 8606 and […]
Posted on April 1, 2024 by Dan Pascone
3 Ways to Access Retirement Funds Early
TL;DR Answer Box If you want to access retirement funds early, you usually have three broad paths: build a Roth conversion ladder, use 72(t) substantially equal periodic payments (SEPP), or take a distribution and accept taxes plus the 10% early withdrawal penalty if no exception applies. The best fit depends on your timeline, tax brackets, […]
Posted on March 25, 2024 by Dan Pascone
Tax Deductions vs Tax Credits for High Earners: What You Need to Know
TL;DR Answer Box Tax credits vs tax deductions comes down to what they reduce. Credits reduce your tax bill directly, while deductions reduce taxable income and only save you a percentage based on your marginal tax rate. High earners often have fewer credits available due to phaseouts, but may still unlock meaningful credits with the […]