The Smart Investor’s Guide to Last-Minute Tax Prep

My friend Mark is one of the sharpest investors I know. He’s the guy who always seems to be a step ahead—whether it’s spotting a market trend before everyone else or restructuring his portfolio just in time to avoid a tax hit. But even Mark, with all his planning, found himself staring at a pile of tax documents a little too close to the deadline this year.

“Man, I thought I had everything squared away,” he told me over coffee last week. “But then I started going through my accounts, and it hit me—this is way more complicated than last year.”

Mark’s job was straightforward regarding taxes—his W-2 covered his salary and bonuses. But his investments? That was a different beast. Between capital gains, dividend reinvestments, and a handful of private equity deals, he had multiple 1099s to comb through. And that wasn’t even counting his real estate partnership or the international investments that needed extra reporting.

First, he did double-check that every piece of income was accounted for. The last thing he wanted was an unexpected IRS notice six months down the road because he forgot to report a sale. “I went back through my brokerage accounts just to be sure,” he said. “I’m not leaving anything to chance.”

But the real kicker was his offshore investments. Mark’s been expanding globally, and with the IRS and SEC tightening the rules on foreign-held assets, he needed to make sure he was fully compliant. “I don’t mess around with FATCA and FBAR rules,” he told me. “The penalties are brutal.” He spent a solid hour reviewing the requirements to ensure he wasn’t missing anything.

Then came the deductions. Mark’s a big believer in strategic giving—he donates generously, not just because it’s the right thing to do, but because it also helps his tax position. “I had some big donations this year,” he said, “but I wanted to ensure I was maximizing them. My advisor suggested a donor-advised fund, and I’m seriously considering it for next year.”

And, of course, there was retirement planning. Mark had maxed out his 401(k), but his self-directed IRA was a little trickier. “Alternative investments are great, but the tax rules can get messy,” he admitted. Between that and the SEC tightening regulations on certain assets, he knew he had to be extra careful.

At one point, he realized he might have a problem with a recent stock sale. “I think I might’ve triggered a wash sale,” he said, shaking his head. “I sold at a loss, then repurchased too soon. I’m gonna have my CPA look at it.” A wash sale could mean losing out on a deduction or, worse, an IRS headache later. That was a smart call—something small could mean losing out on a deduction or, worse, an IRS headache later.

Mark debated whether to file independently or bring in a professional as the deadline loomed. “I can handle the basics,” he said, “but with this many moving parts, I’d rather have someone double-check my work.” He booked a call with his CPA, who flagged a few areas that needed tweaking, particularly in his real estate holdings and investment losses. The relief he felt after this consultation was palpable. He knew that his tax situation was in good hands, and the reassurance that he was maximizing his deductions and minimizing his tax liability was a weight off his shoulders.

Finally, after running all the numbers and ensuring he was covered, he sat down to file. “No way I’m mailing this thing in,” he laughed. “E-filing is faster, and I don’t need the stress of wondering if the IRS lost my paperwork.” He submitted his return, took a deep breath, and leaned back in his chair, feeling the convenience and efficiency of modern tax preparation methods. E-filing not only saves time but also provides a sense of security, knowing that your return has been received and processed.

“Glad that’s over,” he told me. “Now I can return to what I like doing—growing my portfolio instead of just reporting on it.”

Takeaway for Investors

One thing to learn from Mark’s experience is that taxes aren’t just an obligation—they’re an opportunity. Savvy investors know that every decision, from asset allocation to charitable giving, has a tax impact. The key is to stay ahead of the game, keep records organized, and work with professionals who can spot opportunities and risks you might not see on your own. This sense of control and preparedness can save you money and headaches.

So, before you hit submit on your return, take a page from Mark’s playbook—review, strategize, and make sure your money is working for you, not against you. Remember, staying organized and seeking professional help are not just options, they are necessities in the complex world of tax preparation.

Disclosure

The character of Mark referenced in this material is entirely fictional and is utilized solely for illustrative purposes. Any resemblance to actual persons, living or dead, is purely coincidental. The purpose of including Mark in this context is to provide hypothetical scenarios that may help elucidate various tax scenarios.

This article is for informational purposes only and does not constitute financial, tax, or investment advice. The information contained herein is based on publicly available data and personal anecdotes and should not be considered as individualized recommendations.

This material is not intended to serve as personalized tax, legal and/or investment advice since the availability and effectiveness of any strategy is dependent upon your individual facts and circumstances. Duncan Williams Asset Management  is not a legal or accounting firm. Please consult with your legal or tax professional regarding your specific tax situation when determining if any of the mentioned strategies are right for you.

Readers should consult with a qualified tax professional, financial advisor, or legal counsel before making any investment or tax-related decisions. Tax laws and regulations are subject to change, and compliance requirements may vary based on individual circumstances. The author and publisher make no representations or warranties as to the accuracy, completeness, or applicability of any information provided.

Furthermore, any references to specific investment strategies, securities, or financial products do not constitute an endorsement or recommendation by the author or publisher. Past performance is not indicative of future results. Investments involve risks, including the potential loss of principal.

The views expressed in this article are solely those of the author and do not necessarily reflect the opinions or positions of any financial institution, regulatory agency, or government entity.

Sources

·  RS Free File Program – https://www.irs.gov/filing/free-file-do-your-federal-taxes-for-free

·  IRS Interactive Tax Tools – https://www.irs.gov/help/ita

·  IRS Official Website – https://www.irs.gov/

·  SEC Investor Assistance – https://www.sec.gov/oiea

·  FATCA (Foreign Account Tax Compliance Act) Information – https://www.irs.gov/businesses/corporations/foreign-account-tax-compliance-act-fatca

·  FBAR (Report of Foreign Bank and Financial Accounts) Guidance – https://www.fincen.gov/report-foreign-bank-and-financial-accounts

·  SEC Homepage – https://www.sec.gov/

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