How to Prepare for Next Year’s Taxes Without the Stress

The Mission Driven Business Podcast

Tax season doesn’t have to be a scramble, but for most business owners, it is. In this episode, Brian Thompson offers a simple, practical system for taking the stress and surprise out of taxes by shifting from a once-a-year reaction to a year-round strategy. If last episode left you wondering whether you missed something, this one is your action plan.

 

Start With a Mindset Shift

Before getting into tactics, Brian makes an important reframe: taxes are not a once-a-year event. They are a year-round strategy. This matters especially for mission-driven business owners who are growing quickly, navigating variable income, and making values-based decisions with their money. The goal is to build a system that supports your business all year long, not just get through the filing season.

 

A Simple Four-Step System to Prepare for Next Year’s Taxes

Once the mindset shift is in place, Brian walks through four focused areas that make the biggest difference in tax planning.

Know your numbers

If you don’t know your revenue, expenses, or profit, everything else becomes a guess. Get your bookkeeping in order and review your numbers monthly, not just at tax time. Monthly profit and loss statements, balance sheets, and reconciliation reports give you the clarity to estimate taxes accurately, spot opportunities earlier, and make better decisions overall.

Build a tax habit

For self-employed business owners, making estimated tax payments is non-negotiable, and yet it’s one of the biggest sources of stress. Brian’s recommendation is to set aside a percentage of income every single month rather than scrambling quarterly to find the money. Start with 15% of gross revenue and adjust up or down based on your profit margin. The key is consistency, ideally in a separate account that’s ready when you need it.

Plan around the big levers

A few tax strategies tend to move the needle most for small business owners. Brian highlights SALT deductions, which may now offer new planning opportunities with recent changes and could make itemizing worthwhile if you’re paying state and local taxes, mortgage interest, or making charitable contributions. Retirement contributions through a solo 401k or SEP IRA are among the biggest benefits available to solo entrepreneurs, reducing taxable income while building wealth at the same time. Health insurance and HSA contributions deserve attention too. The HSA stands out as one of Brian’s favorite savings vehicles, offering a triple tax benefit: a deduction on contributions, tax-free growth, and tax-free withdrawals for medical expenses.

Schedule a mid-year tax check-in

Schedule a check-in around June or July and ask three questions:

  • How is my income tracking?
  • Am I on pace with my tax payments?
  • Are there opportunities I should act on now?

Waiting until February, March, or April means there’s very little you can do about the numbers at that point. One mid-year meeting can prevent surprises, penalties, and missed opportunities.

 

Your Action Step

Pick one of these four areas to improve on this month, just one. Maybe it’s cleaning up your books, opening a dedicated tax savings account, or putting a mid-year check-in on the calendar. Small, consistent improvements are what actually reduce stress over time and build a financial system that supports your business, your growth, and your life. If you found this episode helpful, share it with another business owner who’s tired of feeling surprised at tax time.

 

Resources + Links

 

About Brian and the Mission Driven Business Podcast

Brian Thompson, JD/CFP®, is a tax attorney and Certified Financial Planner® who specializes in providing comprehensive financial planning to LGBTQ+ entrepreneurs who run mission-driven businesses. The Mission Driven Business podcast was born out of his passion for helping social entrepreneurs create businesses with purpose and profit.

On the podcast, Brian talks with diverse entrepreneurs and the people who support them. Listeners hear stories of experiences, strength, and hope and get practical advice to help them build businesses that might just change the world, too.