Tax Planning in 2026–2027: Strategies for Professionals, Business Owners, and Retirees
- Greg Luken
- Jul 29
- 5 min read
Most people think about taxes in March or April.
That's understandable but it's also when many of the best opportunities have already passed.
At Luken Wealth Management, one of the most common questions we hear from families throughout Middle Tennessee is: "Is there anything I can still do to lower my taxes?"
Sometimes the answer is yes.
But more often, the biggest savings come from decisions made months before you ever meet with your CPA.
That's the difference between tax preparation and tax planning.
Tax Planning vs. Tax Preparation: What's the Difference?
These two terms are often used interchangeably, but they're very different.
Tax preparation looks backward.
It answers the question: "What happened last year, and how do we report it correctly?"
Your CPA plays an essential role here by preparing your tax return accurately and helping you stay compliant.
Tax planning looks forward.
It asks: "What decisions can we make today that may reduce your lifetime tax burden?"
That's where proactive planning can make a meaningful difference.
We're not tax preparers, and we don't replace your CPA. Instead, we work alongside your tax professional to help coordinate investment decisions, retirement income, charitable giving, Roth conversions, and other financial strategies before the calendar year ends.
For many high-income professionals and retirees, that coordination can be far more valuable than searching for one more deduction after the year is over.
Why Tax Planning Matters More as Your Wealth Grows
Many online tax tips are written for someone with a straightforward W-2 income and a simple return.
That's not who we typically serve.
Many of our clients are:
Business owners
Physicians and healthcare professionals
Corporate executives
Entrepreneurs
Retirees
Families with significant investment assets
As income and wealth grow, taxes become less about finding deductions and more about making smart decisions about timing.
Questions like these become much more important:
When should I take retirement distributions?
Does a Roth conversion make sense this year?
Should I sell appreciated investments now or spread the gains over several years?
How can charitable giving fit into my overall tax strategy?
Will this decision increase my Medicare premiums?
These are planning conversations not filing conversations.
Seven Tax Planning Strategies to Consider for 2026–2027
Every family is different, but these are some of the most valuable planning discussions we have with clients.
1. Build a Tax Projection Before Year-End
One of the simplest and most valuable planning exercises is creating a tax projection.
Instead of guessing what your taxes might look like, estimate:
Employment or business income
Social Security
Pension income
Retirement account withdrawals
Dividends and interest
Capital gains
Planned real estate sales
Business transactions
Large one-time income events
Having a roadmap allows you to make informed decisions before December 31 instead of reacting the following spring.
2. Watch Your Medicare IRMAA Thresholds
Many retirees are surprised to learn that Medicare premiums are tied to Modified Adjusted Gross Income (MAGI), not just taxable income.
A large Roth conversion, investment gain, or other income event may push you into a higher Medicare premium bracket.
Planning ahead can help you understand the tradeoffs before making those decisions.
3. Be Strategic About Roth Conversions
We're big believers that Roth conversions can be incredibly valuable but only when they're done thoughtfully.
A well-planned multi-year strategy often creates better long-term results than trying to convert everything at once.
4. Coordinate Investment Decisions With Taxes
Investment decisions shouldn't happen in a vacuum.
Selling appreciated stock, harvesting losses, rebalancing a portfolio, or diversifying concentrated positions can all have tax consequences.
Looking at investments and taxes together often creates better outcomes than making each decision independently.
5. Plan Charitable Giving Intentionally
If charitable giving is already part of your family's values, there may be opportunities to give more efficiently.
Depending on your circumstances, that could include:
Bunching charitable gifts
Coordinating giving with retirement distributions
Timing gifts during higher-income years
The goal isn't simply reducing taxes it's making generosity more impactful.
6. Avoid Surprises With Estimated Taxes
Many successful professionals don't have a tax problem.
They have a timing problem.
Bonuses, stock compensation, investment gains, or business income can create unexpected tax bills if withholding and estimated payments aren't adjusted throughout the year.
Planning ahead can help reduce those surprises.
7. Maximize Retirement Savings Opportunities
If you're still working, retirement contributions remain one of the simplest ways to improve long-term financial health while potentially reducing current taxes.
Contribution limits change periodically, so reviewing your retirement savings strategy annually is worthwhile especially if you're self-employed or own a business.
Tax Planning for Business Owners
Business owners often have opportunities that employees simply don't.
Depending on your situation, planning discussions may include:
Retirement plan design
Business income timing
Estimated tax planning
Entity structure
Qualified Business Income considerations
Succession planning
Preparing for the eventual sale of a business
These decisions rarely happen overnight.
The earlier planning begins, the more options you typically have.
Common Tax Planning Mistakes
Over the years, we've seen a few mistakes come up repeatedly.
Waiting Until Tax Season
By April, many opportunities are already gone.
Making Large Roth Conversions Without a Plan
Converting too much in a single year can affect taxes, Medicare premiums, and other planning considerations.
Ignoring Capital Gains
Selling appreciated investments without understanding the tax impact can create avoidable surprises.
Treating Investments and Taxes as Separate Conversations
Your investment strategy and tax strategy should work together not independently.
Not Coordinating Your Professional Team
Some of the best outcomes happen when your financial advisor and CPA work together throughout the year instead of only during tax season.
Frequently Asked Questions
Can a financial advisor help reduce my taxes?
Financial advisors generally don't prepare tax returns or provide tax advice in the same way a CPA does. However, they can work alongside your CPA to coordinate investment decisions, retirement withdrawals, Roth conversions, charitable giving, and other financial strategies that may improve long-term tax efficiency.
When should tax planning begin?
Ideally, tax planning should be an ongoing process throughout the year. Waiting until tax season often limits the strategies that are still available.
Who benefits most from tax planning?
Business owners, retirees, executives, physicians, and families with significant investment assets often have the greatest opportunities because they have more variables that can be planned proactively.
Is tax planning only for wealthy families?
Not at all. While planning becomes more complex as wealth grows, anyone making important financial decisions can benefit from understanding the tax implications before those decisions are finalized.
The Bottom Line
Taxes will always be part of your financial life.
The goal isn't to eliminate them.
The goal is to make thoughtful decisions that support the life you want to live while avoiding unnecessary surprises along the way.
At Luken Wealth Management, we believe tax planning works best when it's part of a comprehensive financial plan not a once-a-year conversation. By coordinating with your CPA and looking at your investments, retirement income, charitable giving, and long-term goals together, you can make decisions with greater confidence.
If you're a professional, business owner, or retiree in Brentwood, Franklin, or the greater Nashville area, now is an excellent time to review your tax strategy before another year passes. Many of the most meaningful planning opportunities happen well before tax season arrives. Contact us.
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