Posted by Jeff Green on March 4, 2026
Categories: Blog, Financial Wellness, Tax Strategies
For nearly 30 years, I’ve had the privilege of serving families as a financial advisor. And over that time, one thing has become very clear: earning a strong income and having a good CPA doesn’t automatically mean your tax strategy is optimized.
The main issue I see is that many successful families treat tax season like a routine task to check off the list.
The return gets filed. The payment gets made. The refund (or bill) gets handled. And life moves on.
But year after year, I see smart, hardworking, financially successful people leaving opportunities on the table… not because they’re careless, but because no one is looking at the full picture.
Having a good CPA is important. Earning a strong income is important. But neither automatically means your tax strategy is optimized.
Here are five common tax mistakes I see even high-income families make – and how to work to avoid them.
Treating Taxes as a Once-a-Year Event
For many people, taxes only come up between February and April.
That’s understandable, but it’s also costly.
The most effective tax strategies happen long before your return is prepared. Waiting until filing season limits your options.
Things like timing income, managing capital gains, making retirement contributions, or exploring Roth conversions all require advance planning. Once the year is over, many of those opportunities are gone.
Strong tax planning isn’t reactive. It’s proactive.
Not Coordinating Their CPA and Financial Advisor
Too often, people’s CPAs and financial advisors are working in separate lanes.
The CPA focuses on preparing accurate returns. The advisor focuses on long-term strategy.
When those two professionals aren’t communicating effectively, gaps appear.
Opportunities get missed. Strategies aren’t aligned. Decisions are made in isolation.
The best outcomes happen when everyone is working from the same playbook. That’s why we regularly coordinate with our clients’ tax professionals: to help make sure the investment strategy, retirement planning, and tax planning are all working together.
Ignoring After-Tax Investment Returns
Many investors focus on one number: performance.
But what really matters is what you keep after taxes.
Two portfolios can earn the same return and produce very different results once taxes are factored in. Tax-efficient investing looks at:
- Where assets are held
- Which accounts generate taxable income
- How gains and losses are managed
- When assets are sold
This isn’t about avoiding taxes. It’s about managing them intelligently.
Over time, even small improvements in tax efficiency can make a meaningful difference.
Overlooking Charitable and Legacy Planning Opportunities
Many generous families give consistently, but not always strategically.
Writing checks to charities is admirable. But there are often more tax-efficient ways to give that can benefit both the organization and your family.
Tools like donor-advised funds, gifting appreciated securities, or creating structured giving plans can enhance your impact while reducing your tax burden.
Charitable planning can also be a powerful way to involve children and grandchildren in values-based financial conversations.
When giving is aligned with your broader plan, it becomes part of your legacy, not just a transaction.
Letting “Good Enough” Become the Standard
This may be the most common mistake of all.
“I’ve always done it this way.”
“It’s probably fine.”
“My CPA hasn’t mentioned anything.”
Life changes. Tax laws change. Your goals change. But many families never revisit their approach.
What worked five or ten years ago may no longer be ideal today. Staying proactive means regularly reviewing your strategy and asking, “Is this still the best approach for where we are now?”
Successful families don’t settle for “good enough.” They refine and improve over time.
Putting It All Together
Taxes are not an isolated event. They are only one piece of your overall financial picture.
When investment strategy, retirement planning, estate planning, and tax planning work together, you gain something far more valuable than savings alone: clarity and confidence.
If you’ve never taken a step back to look at how these pieces fit together, this is a great time to do it.
If you’d like a second set of eyes on how taxes fit into your overall plan, our team is always happy to have that conversation. Feel free to book a complimentary consultation by clicking here.
Our goal is simple: to help you make informed decisions that support the life you’re building, for today and for the future.
Please Note: Raymond James and its advisors do not offer tax advice. You should discuss any tax matters with the appropriate professional. This content was created with the assistance of artificial intelligence (AI). While efforts have been made to ensure the quality and reliability of the content, it is important to note that AI-generated content may not always reflect the most current developments or nuanced human perspectives.