The Tax Conversation Most People Are Not Having
There are two classes of tax filers in the United States. One files a return and pays the bill.
The other spends the year building a plan designed to keepmore of what they earn, reinvest it intentionally, and use the tax code as atool rather than deadline. Both are legal. The difference between the two isaccess to the right team and the discipline to act well before the year closes.
The people who consistently come out ahead do somethingdifferent. They are intentional about tax planning and treat tax planning as ayear-round habit. They have conversations in January about what the year aheadcould look like. They check in quarterly, mid-year, and during the fall to makesure nothing is left undone before December 31. And they work with a team thatis thinking about their tax picture even when they are not.
A Tax Return Is Not a Strategy
Filing a tax return is a look backward. It captures whathappened. Tax planning is a look forward, and for business owners, highearners, and investors in Central Oregon, the window of opportunity is almostalways wider than people realize.
The question worth asking yourself is this: When was thelast time someone sat down with you early in the year to talk about what thisyear could look like, and then again in the fall to make sure you werepositioned well before year-end? If the answer is never, or not recently, thereis likely money being directed to Uncle Sam or the state of Oregon that couldhave stayed in your plan.
Where the Opportunities Live
The tax code is layered with planning opportunities that gountouched when no one is actively looking for them. Here are several worthknowing about, regardless of whether you are a salaried professional, abusiness owner, or someone managing investments and retirement accounts.
High earners and retirement contributions. Ifyou earn a strong W-2 income, your standard 401(k) contribution is a startingpoint, not the finish line. After-tax 401(k) contributions and the megabackdoor Roth strategy can allow significantly more money to move intotax-advantaged accounts each year, money that could grow without being taxedagain. The tax benefit is not this year, it is many decades from now with taxfree growth.
Roth conversions and market timing. When equitymarkets pull back, a meaningful planning opportunity often appears discomfort.Converting pre-tax retirement funds into a Roth account during a down market ora lower-income year means converting at lower values, paying tax on less, andallowing the recovery to happen inside a tax-free account. This requires aproactive conversation, not a reactive one.
Real estate and cost segregation. In high-incomeyears, acquiring investment property paired with a cost segregation study cangenerate substantial depreciation deductions that may offset ordinary income.This strategy does not announce itself. It requires a financial planner and a CPA working together toward the same goal.
Property and business sales. Whether you areselling a business, investment property, a primary residence, or a portfolio ofstocks, each carries its own tax treatment and timing considerations.Understanding your basis, your holding period, and your options, includinginstallment sales,1031 exchanges, or opportunity zone investments, canmeaningfully change the outcome. Waiting until after the sale to ask questionsis almost always too late.
Tax-loss harvesting throughout the year. Portfoliosfluctuate. When individual positions are down, there may be an opportunity torealize a loss that offsets gains elsewhere without meaningfully changing youroverall investment strategy. Done consistently and intentionally, this is oneof the quieter ways a well-managed portfolio works harder for you across thefull calendar year.
The Cost of No Plan
Each year, money that could have been redirected toward yourgoals, your family, or your business ends up with the federal government or states. Not because the tax code required it, but because noone was watching it and being intentional ahead of time.
A plan does not have to be complicated. It starts with twoor three proactive conversations a year, a CFP® and a tax planner working inthe same direction, and a willingness to act before the deadline rather thanafter.
We Are Here When You Are Ready
True Wealth Group and M Squared Tax are separate firms, both growing,both accepting new clients, and both focused on helping businessowners and families build proactive financial and tax strategies at everystage. If this conversation is overdue, we would be glad to have it with you.