Paying Taxes is a Good Thing? Consider All Your Strategies This Tax Day

Consider it the “holiday” no one wants. Tax Day is almost upon us once again, and nearly everyone around the country is scrambling to uncover those last-minute loopholes that might save them at least little on how much they owe.

The question of whether paying taxes is beneficial is nuanced and depends on one’s perspective. Taxes are undeniably essential to a well-functioning society, supporting critical infrastructure and services such as law enforcement, transportation networks, educational institutions, and public safety. They also enable access to healthcare, social programs, and recreational spaces that enhance our quality of life.

While these contributions are widely understood as necessary, they’re not always embraced with enthusiasm.

That said, Tax Day - approaching very soon on April 15, 2025 - rarely feels like a cause for celebration. It’s natural for individuals to seek ways to retain more of their hard-earned income, driving the annual search for strategic deductions and planning opportunities. This tension underscores the need for a balanced approach: fulfilling civic obligations while optimizing personal financial outcomes.

Let's look more closely at two scenarios you might be facing this tax season and how you can achieve that balance when April 15 arrives.

Scenario 1: Realize those gains

Consider a situation we’ve encountered with a client: This individual made a $50,000 private investment that, following a company’s public offering and subsequent acquisition, grew to more than $1 million. Given the all-cash nature of the deal, they’re required to realize the gains, facing a 20% capital gains tax due to their high-income bracket.

We had previously established a donor-advised fund for this client, which could absorb some appreciated assets to offset the tax burden. However, with that fund already well-funded, alternative strategies were limited. In this case, accepting the tax liability may align with their broader objectives, such as generational wealth planning. It’s a fortunate challenge, and sometimes the most prudent decision is to pay the tax and focus on long-term growth.

Scenario 2: Pre-tax vs. post-tax

Another common dilemma we address involves retirement planning, particularly the choice between pre-tax and Roth contributions to 401(k) plans. For younger professionals in lower tax brackets, we often advocate for Roth contributions, allowing them to pay taxes now and enjoy tax-free withdrawals later. Conversely, for those in their peak earning years, pre-tax contributions can reduce current tax exposure. A frequent oversight, however, is an overreliance on pre-tax vehicles. While this minimizes taxes today, it can limit flexibility in retirement. By diversifying across Roth, pre-tax, and after-tax accounts, clients gain the ability to manage income strategically post-retirement—potentially reducing tax liabilities related to Medicare premiums or Social Security. This approach, tailored to individual circumstances, enhances control over future obligations.

Help for the Tangles Tax Maze

In essence, taxes are a vital component of societal stability, yet the goal remains to strike an equilibrium—meeting responsibilities without overextending. Many default to tax avoidance out of habit, when a proactive and nuanced strategy might yield better results. Whether it’s navigating investment gains or optimizing retirement contributions, the focus is on aligning short-term actions with long-term financial security.

If you’re ready to explore the ideal strategy for you – to find that balance of paying your fair share while also protecting your wealth – give us a call. Together, we can make Tax Day a holiday we can actually celebrate!