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 keep more of what they earn, reinvest it intentionally, and use the tax code as a tool rather than a deadline. Both are legal. The difference between the two is access to the right team and the discipline to act well before the year closes.
The people who consistently come out ahead do something different. They are intentional about tax planning and treat tax planning as a year-round habit. They have conversations in January about what the year ahead could look like. They check in quarterly, mid-year, and during the fall to make sure nothing is left undone before December 31. And they work with a team that is 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 what happened. Tax planning is a look forward, and for business owners, high earners, and investors in Central Oregon, the window of opportunity is almost always wider than people realize.
The question worth asking yourself is this: When was the last time someone sat down with you early in the year to talk about what this year could look like, and then again in the fall to make sure you were positioned well before year-end? If the answer is never, or not recently, there is likely money being directed to Uncle Sam or the state of Oregon that could have stayed in your plan.
Where the Opportunities Live
The tax code is layered with planning opportunities that go untouched when no one is actively looking for them. Here are several worth knowing about, regardless of whether you are a salaried professional, a business owner, or someone managing investments and retirement accounts.
High earners and retirement contributions. If you earn a strong W-2 income, your standard 401(k) contribution is a starting point, not the finish line. After-tax 401(k) contributions and the mega backdoor Roth strategy can allow significantly more money to move into tax-advantaged accounts each year, money that could grow without being taxed again. The tax benefit is not this year, it is many decades from now with tax free growth.
Roth conversions and market timing. When equity markets pull back, a meaningful planning opportunity often appears alongside the discomfort. Converting pre-tax retirement funds into a Roth account during a down market or a lower-income year means converting at lower values, paying tax on less, and allowing the recovery to happen inside a tax-free account. This requires a proactive conversation, not a reactive one.
Real estate and cost segregation. In high-income years, acquiring investment property paired with a cost segregation study can generate 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 are selling a business, investment property, a primary residence, or a portfolio of stocks, each carries its own tax treatment and timing considerations. Understanding your basis, your holding period, and your options, including installment sales, 1031 exchanges, or opportunity zone investments, can meaningfully change the outcome. Waiting until after the sale to ask questions is almost always too late.
Tax-loss harvesting throughout the year. Portfolios fluctuate. When individual positions are down, there may be an opportunity to realize a loss that offsets gains elsewhere without meaningfully changing your overall investment strategy. Done consistently and intentionally, this is one of the quieter ways a well-managed portfolio works harder for you across the full calendar year.
The Cost of No Plan
Each year, money that could have been redirected toward your goals, your family, or your business ends up with the federal government or the state of Oregon instead. Not because the tax code required it, but because no one was watching it and being intentional ahead of time.
A plan does not have to be complicated. It starts with two or three proactive conversations a year, a CFP and a tax planner working in the same direction, and a willingness to act before the deadline rather than after.
We Are Here When You Are Ready
True Wealth Group and M Squared Tax are separate firms based in Bend. Both are growing, accepting new clients, and helping Central Oregon business owners and families build proactive financial and tax strategies at every stage. If this conversation is overdue, we’d be glad to have it with you.
Ian Laimbeer is a CFP with True Wealth Group and Moses Man is a CPA with M Squared Tax, both are based in Bend.
Advisory Services offered through Skyliner Wealth, LLC dba True Wealth Group, a registered investment advisor.
