Tax Planning for Sustainable Recovery

If you’re facing IRS debt or bankruptcy, tax planning is part of how we protect your future.
tax planning

​​If you’re working to resolve tax debt, settle with the IRS, or navigate bankruptcy, how you handle your taxes moving forward matters just as much as resolving the current crisis. At Thinking Outside the Box Law, Inc., we provide strategic, situation-specific tax planning.

Why? Because once we’ve helped you address your tax issues, we want to help ensure you don’t end up back in the same place.

Our tax planning support is built around your real circumstances. Whether that means adjusting future tax filings after bankruptcy, managing estimated payments after a settlement, or making smarter withholding decisions to avoid future balances due, our goal is to help you stay protected and proactive.

We help our clients:

Make tax decisions aligned with their settlement or bankruptcy terms
Avoid new tax liabilities through strategic adjustments
Prepare for IRS payment plan obligations with smart forecasting
Stay compliant and avoid red flags on future returns

Build financial habits that keep tax problems from resurfacing

This isn’t one-size-fits-all advice—it’s practical, personalized guidance that fits your bigger financial plan. We help clients take the necessary steps to avoid falling back into debt, so they can move forward with confidence.

Already working with us on a tax issue? Schedule a call to talk with us about how smart tax planning can help you stay one step ahead.

Let Us Help:

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...

Ready to come in for an appointment?

Click here to schedule a time to meet with us. We will NOT make dealing with a tax professional as painful as it’s been in the past!