Let’s face it — Tax Day isn’t anyone’s favorite holiday. But it doesn’t have to be the same story next year.
The best tax planning is proactive, not reactive. And the most efficient strategies don’t just reduce your tax bill — they help build long-term wealth.
Even when you’ve done “everything right,” there’s often money left on the table simply because most people don’t know all their options. This article is your reference point for the rest of 2025 — a list of powerful tactics that can lead to real savings and better financial outcomes.
Do you want the tax break now or in retirement?
General Rule of thumb:
If you earn too much to contribute directly to a Roth IRA (2025 income phaseout begins at $246K for married couples), this workaround still allows you to get money into a Roth:
Note: Be aware of the pro-rata and IRA aggregation rules before moving forward.
Tax-smart investing isn’t just what you buy — it’s where you hold it.
If your workplace 401(k) plan supports after-tax contributions and in-plan Roth conversions, you could save significantly more to Roth than the standard limits allow.
This is an advanced strategy, but powerful for high earners who want more tax-free retirement growth.
If you’re having a year with unusually low income (job transition, sabbatical, retirement gap year), consider converting part of your traditional IRA or 401(k) to Roth.
If you’re covered by a high-deductible health plan, a Health Savings Account (HSA) is one of the most powerful — and underutilized — tax tools available:
Pro tip: Pay out-of-pocket for current medical costs and let your HSA grow untouched. Keep receipts. You can reimburse yourself years later — tax-free.
What if you don’t need the funds for health related expenses?
That’s where the real power shows up:
In short: an HSA can double as a stealth retirement account — especially valuable if you stay healthy and let it grow.
If you own investments that are down in value, use them to offset gains or income.
Example:
Just be sure to avoid the wash sale rule if you plan to re-enter that position.
College savings can also reduce your tax bill — depending on where you live.
Bonus: Under Secure Act 2.0, $35,000 of unused funds may be rolled into a Roth IRA for the beneficiary (subject to income requirements & annual limits).
Source: https://www.investopedia.com/articles/investing/112015/review-vanguard-529-college-savings-plan.asp
Generosity and tax planning can go hand-in-hand:
Ideal in high-income years or when selling a large asset.
If you receive equity from your employer — RSUs, ISOs, NSOs, or ESPPs — proper planning can save you thousands in taxes and reduce risk.
Next year’s tax bill is being written today, tomorrow and every day moving forward— not next March. Now is the time to start proactively planning ahead.
Whether you’re a business owner, high earner, executive, or athlete, these strategies can help you reduce what you owe while increasing what you own.
If your current team is more reactive than proactive — or if you’d like a fresh set of eyes on your plan — let’s talk.
Investopedia.com https://www.investopedia.com/articles/investing/112015/review-vanguard-529-college-savings-plan.asp
Nerdwallet.com –https://www.nerdwallet.com/article/taxes/tips-save-taxes
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