My name is Ray DeWitt, and after more than two decades working in financial services, I’ve noticed that, like many aspects of life, January has a way of bringing clarity. The pressure of year-end decisions fades, and people are finally able to step back and see their situation as it is.
For real estate owners, investors, and those managing complex assets, that clarity often reshapes how they think about taxes, timing, and structure.
Why Timing Feels Different at the Start of the Year
There is something unique about the beginning of a new year. The urgency of December is gone. The emotional pressure has eased. The numbers are no longer estimates. They are real and this is when many people first see their situation clearly.
Income is known. Transactions are settled. Tax exposure is no longer theoretical. That clarity creates space for better questions, thoughtful ones.
What actually worked last year?
What introduced unnecessary complexity?
What decisions were driven by timing rather than intention?
January is not loud but it is revealing.
Tax Awareness Is Not the Same as Tax Reduction
One of the most common misunderstandings I see is the idea that tax planning is about eliminating taxes. In reality, it is about understanding how decisions interact with the tax code over time.
Tax awareness means knowing where exposure exists, how timing affects outcomes, and which choices limit flexibility later. It also means recognizing when or where deferral, simplification, or coordination matters more.
For a lot of people like real estate owners and investors, this often shows up after a sale, or when a property no longer fits the lifestyle it once did. For business owners, it can surface after an exit, or when income shifts categories.
January is when these realizations tend to surface quietly.
Structure Matters More Than Strategy
Over time, I have learned that outcomes are often shaped less by individual strategies and more by the structures holding them together.
Structure determines how flexible an investor can be when circumstances change. It influences who controls decisions, how income flows, and how taxes are recognized. It also determines how easily assets can be coordinated with estate planning, charitable goals, or future transitions.
At the beginning of the year, people are often more open to evaluating structure because there is no immediate deadline forcing a decision.
That is when meaningful planning can actually happen.
A Practical Reality Check on Risk
No planning conversation is complete without acknowledging trade-offs.
Tax-aware strategies, including those involving real estate structures and alternative investments, often involve complexity. Many are illiquid. Some require long holding periods. Others limit operational control in exchange for professional management.
Tax outcomes depend on current law, which can change. Market conditions shift. Sponsors and managers play a critical role in execution.
These realities do not make planning ineffective. They make it necessary to approach decisions deliberately, with qualified professionals involved, and with a clear understanding of both benefits and limitations.
The most resilient plans I see are built through coordination, not isolation, where CPAs, attorneys, and advisors are aligned early rather than brought in after decisions are already made.
Why January Is a Missed Opportunity for Many
Ironically, the clarity that January offers is often underused. Once the year gets busy, decisions return to autopilot. Opportunities to adjust structure or timing quietly pass.
The value of early-year planning gives an unique perspective, without most of the noise and urgency of everyday life.
When people slow down just enough to ask better questions, the rest of the year tends to unfold with fewer surprises.
Closing Perspective
The calendar resets, but the real value comes from understanding what carried over, what no longer fits, and what deserves attention before momentum takes over again.
If you or someone you know would benefit from guidance on tax-aware investing considerations, 1031 DST Group offers educational resources and the opportunity to start a conversation. Learn more or request a free consultation at
https://www.1031dstgroup.com/free-consultation Or Download our free eBook: The 1031 DST Advantage: A Strategic Tax Deferral Guide for Financial Professionals. → Get the eBook.
Disclosure:
Portions of the written content in this article were assisted by artificial intelligence (AI) technology tools and reviewed by 1031 DST Group for quality and compliance. This material is provided for educational and informational purposes only and is not intended as investment advice or a recommendation to buy or sell any security. A 1031 exchange may not be suitable for all investors and may involve risks, including the potential for loss of principal. Always consult with a qualified tax advisor or financial professional. Some investments such as Alternative investments and DSTs involve significant risks and may be illiquid, speculative, and suitable only for accredited investors*.
*Accredited investors are defined under SEC Rule 506 of Regulation D. Generally, an investor is deemed accredited if their net worth is greater than $1,000,000 exclusive of their primary residence and/or their annual income exceeds $200,000 for the current and past two years. Click here to learn more.
Ray DeWitt is a Registered Representative of Realta Equities, Inc. and an Investment Advisory Representative of Realta Investment Advisors, Inc. Investment Advisory Services are offered through Realta Investment Advisors Inc., an SEC registered investment advisor. Securities are offered through Realta Equities, Inc., Member FINRA/SIPC. Neither Realta Equities, Inc. nor Realta Investment Advisors Inc. is affiliated with C-Suite Network Or 1031 DST Group. Realta Wealth is the trade name for the Realta Wealth Companies. The Realta Wealth Companies are Realta Equities, Inc., Realta Investment Advisors, Inc., and Realta Insurance Services, which consist of several affiliated insurance agencies.
