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The September 15 Tax Deadline Is Coming: What Business Owners Need to Know

September 15 is coming up quickly, and for many business owners it is an important tax deadline that can be easy to forget about once the spring tax season is behind us.

If you own an S corporation or are part of a partnership and filed an extension earlier this year, September 15 is generally the deadline for getting that business return filed. For calendar-year S corporations, that means Form 1120-S, and for partnerships, it means Form 1065.

When an extension is filed in the spring, September can feel like it is a long way off. Then summer gets busy, the months go by, and suddenly the extended deadline is right around the corner. If your return still needs to be completed, now is the time to make sure your bookkeeping is caught up and your tax preparer has everything needed to finish the return.

This is especially important for S corporations and partnerships because the business return may also affect the owners’ personal tax returns. These businesses generally issue a Schedule K-1 to each shareholder or partner. That information is then used when preparing the individual’s tax return. When the business return is delayed, it can hold up the personal return as well.

September 15 is also the third estimated tax payment deadline for 2026. This is something many small business owners, independent contractors and self-employed individuals need to pay attention to because taxes aren’t always automatically withheld from the income they receive.

Now is also a good time to look at how your business has actually performed this year. The income you expected at the beginning of 2026 may be very different from where you are today. Maybe business has been better than expected, you picked up a few large clients, or you added another source of income. On the other hand, business may have slowed down or you may have had some significant expenses that weren’t anticipated earlier in the year.

Those changes can affect how much you should be paying in estimated taxes. Rather than automatically assuming the amount you calculated months ago is still appropriate, it can be worth taking another look at the numbers.

Another thing I see people misunderstand is what a tax extension actually does. An extension gives you additional time to file your return, but it generally does not give you additional time to pay taxes that were already due. If you filed an extension and haven’t looked at your tax situation since then, you may want to find out where things stand before the September deadline arrives.

If you owe more than you expected, don’t ignore the return because you are worried about paying the balance. Filing the required return and dealing with what is owed is generally a much better approach than allowing the problem to grow. Depending on the circumstances, there may also be options available when someone cannot pay a tax balance in full.

Even if September 15 isn’t a filing deadline for your particular business, September is a good time to take a look at your taxes. We are far enough into the year to have a pretty good idea of how the business is performing, but there are still several months left before the end of the year.

That gives us time to look at income and expenses, estimated payments, payroll, retirement contributions, upcoming purchases and other financial decisions before December 31. There may be things we can address now that we won’t be able to change once the year is over.

This is one of the reasons I encourage business owners not to think about taxes only during tax season. By the time we are preparing a return next year, we are looking backward at decisions that have already been made. When we review things before the end of the year, we have an opportunity to plan ahead.

If you have a September 15 deadline, don’t wait until the last few days to start pulling everything together. Make sure your bookkeeping is current, check whether your tax preparer is waiting for anything from you, and take care of any unanswered questions now.

And if you’re not sure whether the September 15 deadline applies to you, that’s something we can help you determine.

At TaxPointe, we work with individuals and business owners throughout the year to help them stay on top of their tax obligations and avoid unnecessary surprises. If you have an extended return that still needs to be filed, need help with your estimated taxes, or simply want to review where you stand heading into the last few months of 2026, contact TaxPointe and we’ll be happy to help.

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Independent Contractor or Employee? Why the Difference Matters at Tax Time

If you own a business, there’s a good chance you’ve hired someone as an independent contractor at some point. It’s common, it’s convenient, and for the right situation it makes perfect sense. But one mistake we see business owners make is assuming that simply paying someone as a contractor automatically makes them one.

Unfortunately, that’s not how the IRS looks at it.

Whether someone is an employee or an independent contractor depends largely on the actual working relationship. The IRS looks at things like how much control you have over the person’s work, how they are paid, who provides the tools and equipment, whether they have an opportunity for profit or loss, and the overall nature of their relationship with your business.

For example, let’s say you hire someone to redesign your office. They have their own business, bring their own tools, determine how the work gets done, give you a price for the project and work for several other customers. That sounds much more like a traditional independent contractor.

Now imagine you have someone who works for you every Monday through Friday, you determine their hours, provide the equipment they use, train them on how you want the work performed and oversee their day-to-day responsibilities. Calling that person a contractor and giving them a 1099 doesn’t necessarily make them an independent contractor.

That distinction matters because the tax treatment is very different.

When you have an employee, you generally have payroll responsibilities. Federal income taxes are withheld from their pay, along with their portion of Social Security and Medicare taxes. As the employer, you also have your portion of payroll taxes to pay and additional reporting requirements.

With a legitimate independent contractor, you generally don’t withhold those taxes from their payments. The contractor is self-employed and is responsible for reporting the income and paying the applicable income and self-employment taxes themselves. Depending on how much you pay them and the circumstances, you may also be required to issue a Form 1099-NEC.

Where business owners can run into trouble is when someone has been treated as a contractor but should have been classified as an employee.

If that happens, the business could potentially become responsible for employment taxes that should have been withheld or paid. Depending on the situation, there can also be penalties and interest. What seemed like a simpler arrangement at the beginning can turn into a much more expensive problem later.

Another important thing to remember is that there isn’t one magic test that determines whether someone is an employee. Having a contract that says “independent contractor” isn’t enough by itself. Neither is paying someone without withholding taxes or issuing them a 1099.

The actual facts matter.

This can become especially confusing as a business grows. Maybe you originally hired someone for an occasional project, but over time they started working for you every week. Their responsibilities increased, you began setting their schedule, and eventually they became an important part of the daily operation of your business.

At that point, the relationship may look very different than it did when you originally hired them.

That’s why it’s worth reviewing these arrangements periodically instead of waiting until tax season or until you receive a notice questioning the classification.

If you’re hiring your first contractor, adding employees, or you’ve had the same contractors working with your business for years, this is one of those areas where asking the question ahead of time can save you a major headache later.

And if you’re unsure whether someone working for your business should be classified as an employee or independent contractor, TaxPointe can help you look at the situation and understand the tax implications before it becomes a bigger problem.

Sometimes a small tax question today can prevent a very expensive tax problem tomorrow.

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Can You Hire Your Children and Deduct Their Pay From Your Business?

One tax strategy I find many small business owners are surprised to learn about is hiring their children to work in the family business.

And yes, this can be completely legitimate.

If your child is doing real work for your business and you pay them a reasonable wage for that work, their wages can generally be treated as a business expense just like wages paid to another employee. Depending on how your business is structured and the age of your child, there may also be some additional payroll tax advantages.

The important part is that this needs to be a real employment arrangement.

Maybe your teenager helps answer phones, organizes files, cleans the office, packages orders, takes photos for social media, helps with administrative work, or handles other age-appropriate tasks. Those are all examples of work a business might otherwise have to pay someone else to perform.

What you can’t do is simply decide to give your child money and call it payroll because you want a deduction.

Their compensation should be reasonable for the work they’re performing, and I recommend treating them like any other employee. Keep records of the hours they work, document their responsibilities, run their compensation through your payroll system when appropriate, and actually pay the wages to them.

This is also one of those areas where your business structure makes a big difference.

Under current IRS rules, if you’re operating as a sole proprietorship or a partnership where every partner is a parent of the child, wages paid to a child under age 18 generally aren’t subject to Social Security and Medicare taxes. Wages paid to a child under age 21 are also generally exempt from federal unemployment tax.

Those rules change when the business is operated as a corporation. If your business is an S corporation or C corporation, for example, wages paid to your child are generally subject to the normal payroll taxes regardless of their age.

That distinction is important, and it’s why I don’t recommend hearing about this strategy from another business owner and automatically assuming the same rules apply to you.

There can also be a benefit on the child’s side of the equation. Instead of the business owner taking additional taxable business income and then giving money to their child personally, the child is earning their own income. Depending on how much they earn and their individual tax situation, some or potentially all of those wages may fall within their available standard deduction.

And there’s another opportunity I like parents to think about: earned income can potentially allow the child to contribute to a Roth IRA.

Imagine your teenager legitimately earns money working in your business and begins putting some of those earnings into a Roth IRA. You’re not only teaching them how a business operates and helping them develop a work ethic, you’re giving them an opportunity to begin saving for retirement decades earlier than most people do.

That’s where I think this strategy becomes especially interesting. It isn’t simply about finding another deduction. When it’s structured correctly, you’re moving money out of the business for legitimate services, giving your child real work experience, and potentially helping them begin building their own financial future.

But documentation matters.

If you’re going to hire your children, don’t treat their employment casually just because they’re family. Give them legitimate responsibilities. Track the work they perform. Pay a reasonable wage. Keep payroll and employment records. And make sure you’re following the rules that apply to your particular business structure.

I’ve seen plenty of tax strategies that sound great in a 30-second video or social media post but leave out the details that actually determine whether they work. Hiring your children can be a very useful strategy for the right family business, but it needs to be done correctly.

If you own a business and have children who could legitimately work in it, let’s talk about it. We can look at your business structure, your child’s age, the type of work they could perform, and whether adding them to the business makes sense for your family.

Sometimes good tax planning isn’t about finding a complicated strategy. It’s simply about recognizing opportunities that are already sitting right in front of you.

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Self Employed Retirement Plans

If you’ve been self-employed for any length of time, you’ve probably had the same thought at least once: “What am I doing for retirement?” It’s easy to put it off. When you’re running your own business, cash flow, taxes, payroll, and growth always feel more urgent than something 20 or 30 years down the road. I’ve seen it countless times over the past two decades. Smart, hardworking business owners making great money, but with very little set aside for the future.

The good news is that self-employed retirement plans are not only flexible, they can be extremely powerful if you use them correctly. In many cases, they’re actually better than what traditional employees get through a typical 401(k). The challenge is understanding your options and choosing the one that fits how your business operates.

Let’s start with the mindset shift. When you work for yourself, no one is setting up your retirement for you. There’s no HR department enrolling you automatically, no employer match coming in the background. You are both the employee and the employer. That means you get more control, but also more responsibility. Once you accept that, the rest starts to fall into place.

One of the simplest and most common plans I recommend is a SEP IRA. This is usually where I start with clients who are either just getting serious about retirement or want something easy to manage. A SEP IRA allows you to contribute as the employer, which in this case is you. The contribution limits are generous compared to traditional IRAs, and the setup is straightforward. There’s no complicated annual filing requirement, and most custodians make it easy to open and fund.

The real advantage of a SEP IRA is flexibility. If you have a great year, you can contribute a larger amount. If cash flow is tight, you can scale it back or skip a contribution altogether. That kind of flexibility matters when your income isn’t perfectly predictable. I’ve had clients who use SEP IRAs almost like a year-end tax planning tool. Once we see where their numbers land, we can decide how much to contribute to reduce taxable income.

That said, SEP IRAs are not always the best fit, especially as your income grows or if you want to maximize contributions more aggressively. That’s where a Solo 401(k) comes into play. This is one of the most powerful retirement tools available to self-employed individuals, and it’s often underutilized simply because people don’t realize how much they can put away.

With a Solo 401(k), you wear two hats. As the employee, you can defer a portion of your income. As the employer, you can also make a profit-sharing contribution. When you combine those two, the total contribution limit can be significantly higher than what you can do with a SEP IRA, especially at certain income levels.

Another benefit of a Solo 401(k) is the option for Roth contributions on the employee side. This gives you some tax diversification. Instead of everything being pre-tax, you can build a portion of your retirement savings that grows tax-free. Over the long term, that can make a meaningful difference depending on how tax rates change and what your retirement income looks like.

There is a little more administration involved with a Solo 401(k), particularly once the balance reaches certain thresholds, but in my experience, the extra effort is worth it for many business owners. If you’re consistently generating strong income, this is often the plan that gives you the most leverage.

Then there’s the SIMPLE IRA, which tends to fall somewhere in between. I don’t recommend it as often for solo operators, but it can make sense if you have a small team and want a retirement plan that’s easy to implement without the complexity of a full 401(k) plan. The contribution limits are lower than a Solo 401(k), but it still provides a structured way to save and offer benefits to employees.

Now let’s talk about something that doesn’t get enough attention. Timing and consistency matter more than perfection. I’ve worked with business owners who spent years trying to decide on the “best” plan and ended up doing nothing. Meanwhile, others picked a solid option and contributed consistently, even if it wasn’t optimized from day one. Guess who ends up in a better position over time.

You don’t need to get everything perfect right away. You need to start. Once you have a plan in place, you can adjust as your business evolves. Your income will change, your goals will shift, and tax laws will move. That’s normal. Retirement planning for a self-employed person is not a one-time decision. It’s something you revisit regularly.

Another piece that often gets overlooked is how retirement contributions tie into your overall tax strategy. This is where experience really matters. Contributions to plans like SEP IRAs and Solo 401(k)s can significantly reduce your taxable income. That can help you manage your tax bracket, reduce self-employment tax exposure in certain cases, and create more predictable outcomes when we’re planning at year-end.

I’ve had plenty of conversations where a client thought they were going to owe a large tax bill, and we were able to soften that impact by making a strategic retirement contribution. On the flip side, I’ve also seen people miss that opportunity because they waited too long or didn’t have a plan in place.

One thing I always stress is cash flow. Retirement contributions are powerful, but they shouldn’t put your business in a tight spot. You still need working capital. You still need reserves. The goal is to strike a balance between building for the future and keeping your current operation healthy. That balance looks different for everyone.

If your income is more volatile, you might lean toward a SEP IRA for flexibility. If your income is stable and strong, a Solo 401(k) might allow you to push more into retirement each year. If you’re growing a team, you might look at options that include employee benefits. There’s no one-size-fits-all answer, and anyone telling you there is probably hasn’t spent enough time in the real world with business owners.

Let’s also address the elephant in the room. A lot of self-employed individuals assume they’ll just sell their business and use that as their retirement plan. That can work, but it’s risky to rely on it entirely. Markets change, industries shift, and not every business sells for what the owner expects. I’ve seen people build great companies and still struggle to convert that into a clean exit.

Think of your retirement plan as a separate pillar. Your business can absolutely be part of your long-term strategy, but it shouldn’t be the only piece. Having dedicated retirement savings gives you options. It gives you flexibility if you decide to slow down, pivot, or step away sooner than expected.

Another practical point is keeping things organized. If you set up a retirement plan, make sure contributions are tracked properly, deadlines are met, and everything is reported correctly on your tax return. This sounds basic, but mistakes here can create headaches. I’ve seen missed deductions, incorrect filings, and contributions made outside the allowable window. Those are avoidable issues with the right guidance.

At the end of the day, self-employed retirement planning comes down to being intentional. You’ve already taken control of your income by working for yourself. This is just the next step in taking control of your future.

If you’re not sure where to start, start with a conversation. Look at your income, your business structure, your goals, and your timeline. From there, it becomes much clearer which plan makes sense and how much you should be putting away each year.

After more than 20 years in this field, I can tell you the people who take this seriously early on are almost always glad they did. And the ones who wait usually wish they hadn’t. The gap between those two outcomes isn’t luck. It’s just a matter of making a decision and sticking with it.

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When should you consider going from Schedule C to S Corp?

Most people don’t think about changing their tax structure until something starts to feel off. Usually it’s the tax bill. You finish a solid year, your business finally has momentum, and then you see how much is going out the door. That’s when Schedule C stops feeling simple and starts feeling expensive.

I’ve had this conversation hundreds of times with business owners. The question is always the same: when does it actually make sense to move from a Schedule C to an S Corporation? Not based on what someone said in a Facebook group, but based on real numbers.

Let’s walk through it the way it should be approached.

Schedule C is where you should start. It’s straightforward, easy to maintain, and gives you flexibility while you’re building. There’s nothing wrong with staying there in the early stages. In fact, trying to get fancy too early usually creates more problems than it solves.

But the downside is how the income is taxed. When you’re on Schedule C, every dollar of net profit is subject to self-employment tax. That’s 15.3 percent, before you even get into federal or state income taxes. At lower income levels, it’s manageable. As your income grows, that number starts to climb quickly.

There isn’t a single number where the switch suddenly becomes right, but there is a range where it starts to make sense to look at it seriously. In most cases, once a business is consistently netting somewhere in the neighborhood of sixty to seventy-five thousand dollars or more, it’s worth running the numbers. When you’re pushing into six figures, it becomes a much more important conversation.

What changes with an S Corporation is not your business itself, but how the income is treated. Instead of everything being hit with self-employment tax, you split your income into two parts. One portion is paid to you as a salary, which is subject to payroll taxes. The rest comes through as distributions, which are not subject to that same self-employment tax.

That difference is where the savings come from.

Now, this is the part people tend to oversimplify. An S Corporation is not a loophole, and it’s not free money. There are additional responsibilities that come with it. You’re running payroll, filing a separate business return, issuing yourself a W-2, and generally keeping cleaner books. There are also higher accounting costs to do it correctly.

So the real question is not “can I elect S Corp status?” It’s “do the tax savings outweigh the added cost and complexity?”

At lower profit levels, they usually don’t. You might save a little on taxes, but it gets eaten up by payroll costs, filings, and administrative work. That’s why a lot of business owners who switch too early end up frustrated. They took on more complexity without a meaningful benefit.

On the other hand, once profits reach a certain level and stay there consistently, the math changes. The savings start to become noticeable, and then significant. That’s when it becomes a tool instead of a burden.

Consistency matters here more than anything. If your income swings wildly from year to year, it’s harder to justify the move. If your business is stable, predictable, and no longer in that early “figuring it out” phase, that’s when an S Corporation starts to fit.

There’s also one rule that can’t be ignored, and it’s where a lot of people get into trouble. You have to pay yourself a reasonable salary. The IRS expects that if you’re actively working in the business, you’re paying yourself something that reflects the work you’re doing.

You can’t just take a minimal salary and call everything else a distribution to avoid taxes. That’s the kind of thing that raises flags. At the same time, if your salary is too high, you’re defeating the purpose of the structure. Finding that balance is where experience actually matters.

The way I explain it to clients is simple. Schedule C is a great place to start, but it’s not always the best place to stay once the business matures. Moving to an S Corporation isn’t about being clever with taxes. It’s about aligning your structure with the level your business has reached.

If your business is still in the early stages, still growing, or not consistently profitable, keep it simple. Focus on building. But if you’ve reached a point where the income is steady and the tax bill is starting to feel out of proportion, it’s time to take a closer look.

The right answer always comes down to your numbers. Not a rule of thumb, not something you heard online, but your actual situation.

And when you run those numbers correctly, the decision usually becomes pretty clear.

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