Tax Planning Services
Expert tax planning strategies that save Chicago businesses money
Most people think about taxes once a year – usually in a panic right before the deadline. But smart tax planning happens throughout the year, with strategic decisions that save you thousands and eliminate those stressful April surprises.
When you only think about taxes during filing season, you’re missing opportunities to reduce your tax bill. The decisions you make today about retirement contributions, business expenses, entity structure, and income timing can save you tens of thousands over your lifetime.
Business tax planning
Business owners face tax decisions every quarter that can save or cost thousands of dollars.
We help you navigate entity structure choices, expense timing, and quarterly tax strategies that reduce what you owe. Our year-round approach means we review your financials regularly to identify planning opportunities before year-end, not after.
As tax planning advisors, we can help you plan for all aspects of your business growth-span:
- Entity structure optimization based on your revenue and growth plans
- Quarterly tax strategies that improve cash flow
- Proactive compliance review to avoid IRS issues
- Multi-state tax planning for businesses operating across state lines
- Succession and exit planning that minimizes tax impact
- Corporate tax strategy for complex structures
Rob Pasquesi and his team are absolutely incredible at creating a seamless experience for business owners looking to file their taxes. For the past two years, Rob has walked me through every step of the process and has ensured that deadlines were met. Helpful planners and reminders throughout the year are a nice touch to keep your company in line. Thanks for everything Rob!
– Christopher J.
Tax planning for individuals and high-earners
High-earners and professionals need year-round strategies to keep more of what they make.
If you earn over $165,000, standard deductions and simple tax prep won’t cut it. You need specialized strategies for retirement contributions, investment income, and deduction optimization. We work with high-net-worth individuals, business owners, and families to build tax plans that align with your financial goals.
Our individual tax planning services include:
- Income tax planning and estimated payment strategies
- Retirement contribution optimization
- Investment and capital gains planning
- Life event tax planning (marriage, divorce, home purchase)
- Quarterly tax planning reviews and adjustments
- Charitable giving strategies
Retirement Tax Planning
Retirement tax planning isn’t just about contributing to your 401(k). This is one of the most overlooked opportunities for building long-term wealth.
Key retirement tax planning strategies we help you plan:
Traditional vs. Roth IRA conversion analysis
Required minimum distribution (RMD) planning
Social Security tax optimization
Healthcare and Medicare tax considerations
Estate planning tax implications
Tax-efficient retirement income strategies
The decisions you make today about retirement contributions, withdrawals, and account types can save or cost you tens of thousands of dollars over your lifetime. Schedule a free call with a tax planning advisor and start saving today.
I’ve been working with Rob for our business accounting since 2018, and he’s been a game-changer. As someone who dreads dealing with anything financial, I truly appreciate his proactive approach. Rob always ensures we’re on the right track and handling things properly, making the whole process so much easier.
– Matt W.
Rob is awesome! He has been my accountant for the past several years, and is always quick to respond and help. Accounting and tax prep is typically very stressful to me, but he puts me at ease and makes sure everything is done easily and properly. I am a small business owner of 13 years and would definitely recommend their services!
– Jen Z.
Get ahead of tax season.
Strategic tax planning throughout the year means lower tax bills, better cash flow management, and no stressful surprises at filing time.
Ask a CPA
Free tax planning resources
The IRS generally recommends keeping copies of tax returns and supporting documents at least three years. However, some tax documents should be kept for up to seven years, especially if you need to file an amended return or claimed losses from worthless securities or bad debt deductions. Employment tax records require four years of retention after the tax due date or payment date, whichever is later. Keep copies of previously filed returns to help prepare current-year returns and calculate amendments. Store all tax records securely, whether physical or digital, and dispose of them properly when retention periods end—shred paper documents and permanently delete digital files to prevent identity theft.
Yes, you can deduct 401(k) company contributions made after year-end but before filing your tax return. For example, if your company’s year-end is December 31, 2025 and you report on a cash basis, any 401(k) company contributions made in 2024 before filing your current year tax return can be deducted on the 2024 business tax return. This applies to employer contributions only. Employee deferrals must still be made by December 31 of the tax year to qualify for that year’s deduction.
Many of our clients came to us after their CPA retired. We understand you need more than just a new tax preparer—you need someone who takes time to understand your financial history and provides the same proactive service you relied on before. We review your past returns, learn your situation, and build a long-term relationship based on trust and expertise. We’re here for the long term, providing stable tax planning and advisory services you can count on year after year.
From the blog: Tax planning
7 Essential Elements of Smarter Tax Planning
Smart tax planning could be the difference between just getting by and truly thriving financially. Our free download, 7 Essential Elements of Smarter Tax Planning, helps you to develop a proactive tax strategy that works.
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