Tax Season Hit Him Like a Freight Train

Welcome to this week's edition of The Weekly Trail Report, where we share,

1 Story, where real stories of architects and engineers meet tailored financial strategies,

1 Actionable Tip, to provide actionable insights and guide you towards financial success,

1 Financial Term, to demystify key concepts and empower your decisions.

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1. Story: Terry’s Tax Planning Wake-Up Call

When Terry, an architect and business owner, sat down with me, he had one thing on his mind—taxes. Every year, it seemed like tax season hit him like a freight train, and this year was no different.

“I don’t know why, but I’m always caught off guard,” Terry admitted, visibly frustrated. “I’ve had to file an extension every year, and every time I think I’m done, another tax deadline sneaks up on me.”

Terry’s situation is all too common.?

Like many business owners, he was focused on the day-to-day operations of his firm, and tax planning had become an afterthought. As a result, he found himself in a constant cycle of rushing to meet deadlines, filing for extensions, and being hit with unexpected tax bills.

“Let’s break the cycle,” I suggested. “The problem isn’t just the deadlines—it’s the lack of proactive tax planning. When taxes are left to the last minute, they feel like an emergency every time.”

We started by mapping out a clear tax plan for Terry:

1. We pinpointed the upcoming deadlines:

a) 3rd quarter estimated payments were due on September 16th for his S-Corp

b) His extended tax return was due on October 15th

2. We set up quarterly reviews to track his income and adjust for estimated taxes in advance.?

Terry didn’t just need to remember deadlines—he needed a system that helped him plan ahead. By integrating tax planning into his broader financial strategy, Terry was no longer scrambling.

He knew what was coming and could handle his taxes with ease.

By the time the October deadline rolled around, Terry was ready. “For once, I’m not stressing over taxes,” he said, relieved. “I finally feel like I’m in control.”

Tax planning isn’t just about minimizing your tax burden—it’s about eliminating surprises.?

By making tax planning a proactive part of your financial strategy, you can avoid the last-minute panic and stay ahead of the game.

2. Actionable Tip: Separate Your Tax Savings

One of the easiest ways to stay ahead of tax season is to set aside money regularly—without even thinking about it. Open a dedicated savings account specifically for taxes and automatically transfer a portion of your income into that account each month.

By doing this, you’ll always have the funds ready when tax time rolls around. No more scrambling to cover unexpected tax bills or filing for extensions because you weren’t prepared. Separating your tax savings ensures you’re setting yourself up for success and eliminates the stress of last-minute payments.

Proactive tax planning is about more than just minimizing your tax burden—it’s about being prepared and in control.

3. Financial Term: Quarterly Estimated Tax Payments

Quarterly Estimated Tax Payments are required for individuals, freelancers, and business owners who don’t have taxes automatically withheld from their income. These payments are made throughout the year—typically on a quarterly basis—to cover income tax, self-employment tax, and other applicable taxes.

For businesses like S-Corps or sole proprietors, the IRS expects taxes to be paid as you earn income. If you wait until the end of the year to pay your taxes in full, you may face penalties and interest. To avoid this, it’s important to calculate and submit quarterly estimated payments by the following deadlines each year:

• April 15th
• June 15th
• September 15th
• January 15th of the following year

Properly calculating these payments requires estimating your income, deductions, and tax credits for the year. By keeping up with your quarterly payments, you can avoid large tax bills and stay in control of your cash flow.

Happy Trails,

Ryan

Disclaimer: We employ fictional characters to illustrate financial concepts faced by individuals in the architecture and engineering industry. Any resemblance to real persons, living or dead, is coincidental. While the stories are inspired by our experiences, the specific details, circumstances, and outcomes mentioned are entirely fictional and created for educational purposes only. Real client information is strictly confidential and never disclosed without explicit consent. Our aim is to provide relatable examples for educational purposes, respecting the privacy and confidentiality of our clients. This information is presented for educational purposes only and is not to be considered financial, tax, legal, or investment advice.