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Design Tax Strategies that Increase Control & Flexibility

When it comes to taxes, most people focus on what they owe today. But successful planning means looking ahead. Without realizing it, many high-income professionals and business owners overfund tax-deferred accounts—only to face massive tax burdens later.

At Woolman Financial Group, we help you diversify your tax exposure with clarity and purpose. Whether you’re in your peak earning years, approaching retirement, or already drawing income, our strategies help you:

  • Gain more control over your financial future

  • Reduce unnecessary tax exposure

  • Maximize flexibility for giving, investing, and spending

Because your wealth should empower your values—not be eroded by avoidable taxes.

The Tax Diversification Problem Most Don’t See Coming

The traditional retirement planning playbook emphasizes maxing out tax-deferred accounts like 401(k)s, IRAs, and similar vehicles. But that strategy comes with hidden risks:

  • Growing future tax liabilities

  • Limited access to capital when opportunities arise

  • Loss of tax efficiency at the moment you need it most

In short, the system trains you to defer, defer, defer. But deferral isn’t the same as strategy.

True diversification means spreading your tax exposure across different account types—so you have more control now and later.

Our Approach: Strategic, Personalized, and Collaborative

The Woolman Tax Diversification Process

1. Tax Exposure Mapping

We assess your current assets and identify their tax treatment: tax-deferred, tax-free, or taxable. This creates a visual understanding of where your money sits and how exposed it is.

2. Roth Conversion Planning

We evaluate if and when converting pre-tax assets into Roth accounts makes sense—and how to do it in the most efficient way possible.

3. Withdrawal Sequencing

We help structure income in retirement to minimize lifetime taxes by drawing from the right accounts at the right times.

4. Integrated CPA Collaboration

We work hand-in-hand with your tax advisor to ensure strategies are compliant, efficient, and aligned with your long-term goals.

This isn’t about chasing deductions. It’s about reclaiming control over your cash flow and opportunities.

20 minutes to assess your tax strategy and find opportunities for greater control.

Our Approach: Strategic, Personalized, and Collaborative

The Woolman Tax Diversification Process

1. Tax Exposure Mapping

We assess your current assets and identify their tax treatment: tax-deferred, tax-free, or taxable. This creates a visual understanding of where your money sits and how exposed it is.

2. Roth Conversion Planning

We evaluate if and when converting pre-tax assets into Roth accounts makes sense—and how to do it in the most efficient way possible.

3. Withdrawal Sequencing

We help structure income in retirement to minimize lifetime taxes by drawing from the right accounts at the right times

4. Integrated CPA Collaboration

We work hand-in-hand with your tax advisor to ensure strategies are compliant, efficient, and aligned with your long-term goals.

This isn’t about chasing deductions. It’s about reclaiming control over your cash flow and opportunities.

20 minutes to assess your tax strategy and find opportunities for greater control.

The Results You Can Expect

Our clients often tell us the real benefit isn’t just in what they save—but in how they feel. They feel more confident spending. More generous in giving. More equipped to face life’s transitions without hesitation.

With proper tax diversification, our clients often experience:

  • Greater financial flexibility in retirement and beyond

  • More freedom to invest, give, or respond to life’s surprises

  • Reduced tax burden over their lifetime

  • Increased after-tax wealth for future generations

  • Less reliance on rigid, government-driven plans

It’s not about beating the tax code. It’s about outsmarting it—with wisdom, not loopholes.

Because when your tax plan is designed with purpose, your entire financial life becomes more intentional.

What Makes Our Tax Strategy Different

Many advisors treat tax planning as an afterthought. We treat it as foundational.

We don’t default to "just max your 401(k) and hope for the best." Instead, we co-create custom strategies that blend technical insight with real-life application, based on your income, assets, giving plans, and long-term purpose.

We also coordinate directly with your CPA, so your whole financial team is on the same page and rowing in the same direction.

And because we know taxes impact more than spreadsheets—they impact confidence, generosity, and freedom—our process is built around values as much as it is numbers.

Don’t Let the Tax Tail Wag the Dog

Tax planning shouldn’t be about fear, procrastination, or blind faith in government-created plans.

It should be about intentional stewardship.

Let’s design a strategy that keeps more of your wealth working for your goals today—and secures more of it for the people and causes that matter most.

20 minutes to assess your tax liability and uncover opportunities for tax savings.

The information provided on this site is for educational purposes only and is not intended as investment, tax, or legal advice. Please consult your qualified professional before making any financial decisions.

Testimonials represent individual client experiences and do not guarantee similar outcomes. No compensation was provided for these testimonials.

Securities and investment advisory services offered through qualified registered representatives of MML Investors Services, LLC. Member SIPC. Supervisory Office: 900 East 96th Street, Suite 300, Indianapolis, IN 46240, (317) 469-9999. Woolman Financial Group is not a subsidiary or affiliate or MML Investors Services, LLC or its affiliated companies.

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