Other Services

Additional Support Services for Our Tax Resolution Clients

At Thinking Outside the Box Law, our primary mission is to help individuals and businesses resolve serious tax and debt challenges. Along the way, we know other financial and legal issues often come up—and we’re here to help our clients navigate those as part of their larger recovery.

While we don’t offer general tax preparation, planning, or business consulting to the public, we do provide targeted support services to our tax resolution and bankruptcy clients when it makes sense for their situation.

Below you’ll find several of the additional services we may assist with as part of a comprehensive plan to help our clients get back on stable ground and move forward with confidence.

If you have questions about these services or want to know whether they apply to your situation, feel free to contact us. We’re here to help you find the right path forward.

Tax Preparation

Stop missing out on potential deductions that could be saving you big money!

Tax Planning

Real strategies and solutions to help you minimize your IRS liability.

Payroll Services

Scrimping on payroll services will red-flag your business with the IRS.

Starting a Business

Know the simple steps for starting your business right.

Tax Liens and Bankruptcy: Can Federal Taxes Be Discharged in Bankruptcy If a Tax Lien Survives?

Many people are surprised to learn that bankruptcy can sometimes wipe out federal income taxes — but not always. One of the most common points of confusion involves tax liens and dischargeability. Clients often ask: “If the IRS tax lien survives bankruptcy anyway, why...

What Happens After DuPage Taxpayers Appeal IRS Decisions?

Key TakeawaysThe IRS has launched an IRS Post-Appeals Mediation (PAM) pilot program for certain unresolved Appeals cases. PAM allows a facilitated negotiation with a neutral mediator and a new Appeals team. Not every case qualifies, but the program shows...

FAQ: IRS Debt & Bankruptcy in the 7th Circuit

Can federal income taxes be discharged in bankruptcy in the 7th Circuit? Yes, but only if strict timing rules are met. In the 7th Circuit (including Illinois), federal income taxes may be discharged in bankruptcy only if all of the following are true: The tax return...

Student Loans & Bankruptcy FAQs: Can Student Loans be Discharged in Bankruptcy?

Q1. Can student loans be discharged in bankruptcy? While student loans are still harder to discharge than credit cards or medical bills, there is now a new, nationwide process that is working for many borrowers with federal student loans. Q2. What’s the new process...

Illinois Bankruptcy Exemptions: Is Bankruptcy More Accessible For DuPage Taxpayers?

Changes in Illinois law have increased the Illinois bankruptcy exemptions for 2026. Why is this good News? It is good news because the higher bankruptcy exemptions will allow more people can file bankruptcy without the fear of having to sell their home or vehicles. ...

Bankruptcy Misconceptions

There are a lot of common bankruptcy misconceptions out there. Fears caused by these bankruptcy myths discourage consumers from filing for bankruptcy and getting relief from taxes, credit cards, and student loans. Myth #1: Taxes cannot be discharged in...

Streamlined Installment Agreement: A Tax Debt Repayment Option for DuPage Owers

Key Takeaways The Streamlined Installment Agreement (SIA) is an ideal option for paying back taxes to the IRS… IF you owe $50,000 or less. Most people get immediate approval... no financial disclosures required. You have 72 months to pay off your...

IRS Audit Representation: When Your DuPage Tax Pro Shines

Key TakeawaysThe way you communicate with the IRS can shape the entire outcome of your audit. Filing a Power of Attorney form allows your tax professional to legally handle all communication for you. Speaking directly with the IRS can unintentionally...

What Documents Are Needed for an IRS Audit: Thinking Outside The Box Law, Inc.’s Insights

Key TakeawaysThe IRS requires three separate forms of proof for nearly every deductible business expense: purchase, payment, and purpose. Missing even one element can lead to a denied deduction and possibly trigger a 20% Accuracy-Related Penalty. Certain...

How Should DuPage Taxpayers Start Preparing For An Audit?

Quick Takeaways: How Should I Start Preparing For An Audit?Only send copies of the documents the IRS specifically asks for — nothing more. Start with the notice. The audit letter itself tells you the scope, type of audit, and deadlines. Anticipate triggers...

How You’re Missing Critical Tax Relief

Here’s the hard truth: when you’re behind on taxes or buried in debt, the IRS is not going to help you find ways to reduce what you owe. In fact, they’re counting on your confusion and fear to keep you paying more than you should.

The good news? Even if you’re years behind, we can help you uncover legal, powerful ways to reduce or resolve your tax debt. From reconstructing missing records and filing back tax returns to negotiating settlements and discharging eligible taxes through bankruptcy, we know how to protect your rights—and your wallet.

Don’t leave money on the table or let fear keep you stuck. Take back control with our proven tax resolution strategies.

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