What are the opening hours?

Monday 8am - 6pm Tuesday 8am - 6pm Wednesday 8am - 6pm Thursday 8am - 6pm Friday 8am - 6pm Saturday 9am - 4pm

Night Owl Tax & Resolution

Home
United States
Parker, SD
Night Owl Tax & Resolution

Night Owl Tax helps business owners and entrepreneurs navigate taxes with confidence. We help you protect what you've built and help build your legacy.

From business advisory services, tax strategies and proactive planning to IRS resolution. Empowering individuals and businesses to overcome tax challenges and regain financial stability. With more than 14 years in the accounting and tax industry, our mission at Night Owl Tax Resolution is to provide expert guidance and compassionate support throughout every step of the tax resolution process. Thro

ugh personalized strategies, transparent communication, and relentless advocacy, we strive to alleviate the burden of tax debt, negotiate favorable resolutions with taxing authorities, and pave the way for a brighter financial future for our clients. With integrity, professionalism, and a commitment to excellence, we are dedicated to being a trusted partner on the journey to resolution, offering clarity, relief, and peace of mind to those facing tax-related obstacles." As an enrolled agent, Jackie Benson is an Enrolled Agent and tax resolution expert. She has helped countless clients overcome the burden of back tax liability. Night Owl Tax Resolution is dedicated to providing peace of mind from the first contact because it’s always about our clients. Hours of Availability:

Monday - Friday 8:00 am - 6:00 pm CT

Saturday 9:00 am - 4:00 pm CT

Sunday - by appointment only

09/04/2026

The business cannot grow if you refuse to delegate.

Most owners begin by doing nearly everything themselves. They answer the phone, serve the customers, send the invoices, solve the problems, and make every decision.

That may be necessary in the beginning—but it eventually becomes a limitation.

When every task and decision must pass through the owner:
✓ Work slows down while everyone waits
✓ Employees stop taking initiative
✓ Important decisions are delayed
✓ The owner has no time to plan or improve the business
✓ Growth creates more stress instead of more capacity

Delegation does not mean handing off a task with no instructions and hoping for the best. It requires creating a system that allows someone else to succeed.

Start by identifying work that:
✓ Is repetitive or routine
✓ Does not require your specialized knowledge
✓ Can be explained and documented
✓ Someone else could perform with the right training
✓ Consumes time you should spend on higher-value decisions

Then clearly communicate the expected result, deadline, available resources, decision-making authority, and when you want an update.

The hardest part may be accepting that someone else will not complete the task exactly as you would. Different does not automatically mean wrong. If the result meets the standard, the process does not always have to mirror yours.

You should still review financial information, monitor important controls, and remain accountable for the business. Delegation does not eliminate oversight—it changes your role from doing every task to making sure the right work gets done.

A business that depends on the owner for everything has not created freedom. It has created another job—one that cannot operate when the owner steps away.

Delegation is not giving up control. It is building a business that can function without depending on you for everything.

Are you leading your business—or carrying every part of it?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

09/02/2026

Mileage requires more than a year-end estimate.

Many business owners use their personal vehicles for client meetings, supply runs, trips between work locations, and other legitimate business purposes.

But when tax time arrives, they try to reconstruct an entire year of driving from memory.

“I probably drove about 15,000 business miles” is not the same as maintaining a mileage record.

A useful mileage log should include:
✓ The date of each trip
✓ The destination
✓ The number of miles driven
✓ The specific business purpose
✓ The vehicle used

It is also helpful to record the vehicle’s odometer reading at the beginning and end of the year so your total annual mileage can be supported and divided among business, commuting, and personal use.

Be specific about the business purpose. “Business trip” or “errands” may not explain enough. A description such as “met with Smith Company to review project proposal” or “purchased supplies for client order” creates a much clearer connection to the business.

Remember that your normal commute between home and your regular place of business is generally personal mileage—not deductible business travel. Different rules may apply when your home qualifies as your principal place of business or when you travel between business locations.

You can track mileage with an app, a spreadsheet, a calendar-based system, or a written log. The best method is the one you will use consistently.

Record the trip when it happens—or as close to that time as possible. Waiting until tax season makes it easier to forget trips, confuse their purpose, or rely on an estimate that may not hold up under review.

The deduction is based on supported business miles—not what you think you probably drove.

Could you support every business mile claimed on your tax return?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

08/31/2026

A simple way to get paid faster: make your payment process clear and consistent.

Many businesses do excellent work—and then become surprisingly informal when it is time to collect the money.

The invoice is sent several days later. The due date is unclear. No reminder goes out. Weeks pass before anyone follows up because asking for payment feels uncomfortable.

By then, the customer may have forgotten the invoice, misplaced it, or assumed there was no urgency.

Getting paid faster begins before the work starts.

A stronger process includes:
✓ Discussing the price and payment terms in advance
✓ Putting those terms in writing
✓ Requesting a deposit when appropriate
✓ Sending the invoice immediately after completing the work
✓ Providing convenient electronic payment options
✓ Sending reminders before and after the due date
✓ Following up promptly when payment is late

Your invoice should clearly show the amount due, the due date, available payment methods, and whom to contact with questions.

Then follow the same process with every customer. Consistency removes confusion and makes payment expectations feel like a normal part of doing business—not a personal request for money.

You do not need to apologize for collecting what your business has earned. Your customers agreed to the service, the price, and the payment terms.

The longer an invoice sits unpaid, the more pressure it places on your cash flow. A clear process helps protect the money needed for payroll, taxes, supplies, and other operating expenses.

A consistent invoicing process makes it easier for customers to pay—and harder for invoices to be forgotten.

Is your invoicing process helping you get paid—or slowing you down?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

08/28/2026

Avoiding your numbers doesn’t change them.

When business finances feel overwhelming, it is tempting to stop looking.

You avoid opening the report. You check the bank balance but not the outstanding bills. You postpone calculating what is owed for taxes. You tell yourself you will review everything when business slows down—or when there is more money in the account.

But ignoring the numbers does not stop them from affecting your business.

The unpaid tax balance can continue to grow.

The unprofitable service keeps consuming resources.

The overdue receivables keep straining cash flow.

The expenses keep increasing.

And the decisions become more difficult the longer they are delayed.

Looking at your numbers does not mean you must solve every problem today. It simply gives you a place to begin.

Start with a few basic questions:
✓ How much cash is actually available?
✓ What bills and taxes are coming due?
✓ How much do customers owe the business?
✓ Which services or products are generating profit?
✓ Where is money leaving the business unnecessarily?

The first review may be uncomfortable—but uncertainty is usually more frightening than the facts. Once you understand what is happening, you can make a plan, prioritize the problems, and begin taking back control.

Your numbers are not a judgment of you as a business owner. They are information—and information helps you make better decisions.

The numbers may be uncomfortable, but understanding them gives you the power to change them.

What number have you been avoiding in your business?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

08/26/2026

Meals are not automatically 100% deductible.

Buying lunch with a client—or paying with a business credit card—does not automatically make the entire cost deductible.

Most qualifying business meals are limited to a 50% deduction. To qualify, the expense generally must have a legitimate business purpose, cannot be lavish or extravagant under the circumstances, and the business owner or an employee must be present.

Good documentation should show:

✓ The date and location
✓ The amount spent
✓ Who attended
✓ Their business relationship
✓ The business purpose or topic discussed

For example, writing “lunch with Sarah” on a receipt may not tell the full story. “Lunch with Sarah Jones, prospective client, to discuss bookkeeping services” provides a much clearer business connection.

Be especially careful when meals are connected to entertainment. Entertainment expenses are generally nondeductible, and food or beverages may need to be purchased separately or separately stated on the invoice to qualify for the meal deduction.

Some meals fall under exceptions and may receive different tax treatment, but those exceptions should not be assumed.

The safest approach is to document the expense when it occurs—before you forget who attended or what was discussed.

Calling it a “business lunch” is not enough. The purpose and documentation matter.

Could your meal deductions stand up to closer review?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

08/24/2026

Your largest customer may be your biggest financial risk.

Landing a major customer can transform a small business. Their account may provide steady work, reliable revenue, and the confidence to hire employees or purchase equipment.

But when too much of the business depends on one customer, that success can quietly become a vulnerability.

What would happen if that customer:

✓ Reduced the amount of work they send you?
✓ Began taking longer to pay?
✓ Changed vendors or brought the work in-house?
✓ Experienced financial problems of its own?
✓ Asked for lower prices because it knew you depended on the account?

The risk is not that the customer is doing anything wrong. The risk is that one decision outside your control could immediately affect your payroll, cash flow, and ability to cover expenses.

Start by reviewing your revenue by customer for the past 12 months. Calculate what percentage came from your largest customer—and then ask what the business would look like without it.

You do not need to walk away from a valuable relationship. You need to reduce the consequences if that relationship changes.

That may mean:

✓ Building relationships with additional customers
✓ Avoiding fixed expenses based on one account alone
✓ Maintaining an adequate cash reserve
✓ Creating services that appeal to a broader market
✓ Monitoring customer concentration regularly

Your largest customer should be an important part of your business—not the only thing holding it together.

How much of your business depends on one customer?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

08/21/2026

You cannot build a healthy business by constantly rescuing it with personal money.

Most business owners invest personal funds at some point. Startup costs, expansion, equipment purchases, or a temporary emergency may justify putting additional money into the business.

But there is a difference between funding a plan and repeatedly covering a pattern.

When the business cannot make payroll, pay its taxes, cover routine expenses, or compensate the owner without another personal deposit, the
money may be masking a deeper problem:
✓ Prices that do not cover the true cost of the work
✓ Customers who take too long to pay
✓ Expenses that have grown faster than revenue
✓ Services that generate sales but little profit
✓ Debt payments the business cannot comfortably support
✓ Owner withdrawals the cash flow cannot sustain
✓ A business model that needs to change

Each personal contribution may solve today’s emergency, but it also makes it easier to postpone the questions that could protect the business tomorrow.

If you regularly move personal money into the business, track every contribution properly and ask:
• How much have I contributed during the past 12 months?
• What specific expenses required the money?
• Is the shortfall temporary, seasonal, or recurring?
• What must change so the business can support itself?
• Is there a date when I will stop contributing and reassess?

Supporting your business is not a failure. But personal savings should not become an unlimited line of credit for a business that continues operating without addressing the cause of its cash shortages.

A temporary investment may support growth.

Constant rescue money is a warning sign.
Is your personal money funding a plan—or covering a pattern?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

08/19/2026

Estimated tax payments should reflect what your business is earning now—not what it earned a year ago.
Many business owners calculate their estimated payments once and continue paying the same amount every quarter. That may work while income remains steady, but it can create an unexpected tax bill when the business grows.

Suppose your business earned $50,000 in profit last year, but this year’s profit is on track to reach $90,000. Continuing to make payments based only on last year’s numbers may leave you underprepared for the tax created by this year’s income.

Your estimated tax calculation may need to be revisited when:
✓ Revenue increases or decreases significantly
✓ Profit margins change
✓ You add or lose a major customer
✓ Business expenses rise or fall
✓ You begin earning income from another source
✓ Your household income or withholding changes
✓ Your business structure changes

Prior-year tax can sometimes be used to calculate a safe-harbor payment that helps avoid an underpayment penalty. But avoiding a penalty and paying enough to cover your actual tax bill are not necessarily the same thing. If this year’s income is substantially higher, you could satisfy a safe-harbor rule and still owe a significant balance when you file.

Review your year-to-date profit, project where the business is heading, and adjust both your estimated payments and tax reserve when necessary.

For businesses with seasonal or uneven income, the calculation may require additional planning because the business does not earn its profit evenly throughout the year.

Estimated taxes should keep pace with your business—not remain on autopilot.

When was the last time you recalculated your estimated tax payments?

The IRS generally requires taxpayers to pay tax throughout the year and provides current-year and prior-year thresholds that may help avoid an estimated-tax penalty.

Night Owl Tax & Resolution
Protect your income. Build your legacy.

08/17/2026

Your business account has a healthy balance, so you hire someone, purchase equipment, pay
down debt, or take a larger owner draw.

Then the estimated tax deadline arrives—and suddenly, the money isn’t there.

The problem wasn’t necessarily that the business failed to earn enough. The problem may be that tax money was treated like operating cash.

Your bank balance can be misleading because some of that money may already be needed for:
✓ Federal estimated taxes
✓ State income taxes
✓ Self-employment taxes
✓ Payroll tax deposits
✓ Sales tax collected from customers

Leaving tax money in the operating account makes it easy to see those funds as available—even when they have already been assigned a job.

A stronger system is to:
1. Open a separate savings account for taxes.
2. Transfer money into it consistently as revenue comes in.
3. Review year-to-date profit throughout the year.
4. Adjust the amount you set aside when income or expenses change.
5. Make estimated payments on time instead of waiting until tax season.

The percentage you need to reserve will depend on your profit, business structure, other household income, state taxes, credits, and individual tax situation. That is why choosing a random percentage and never revisiting it can still lead to a shortfall.

And remember: transferring money into a tax savings account does not reduce taxable income. It simply prevents money intended for taxes from being spent elsewhere.

Tax money may sit in your account, but it has already been assigned a job.

If your estimated tax payment were due today, would the money be ready?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

08/14/2026

Growth can make a weak business weaker.

More customers, higher sales, and a larger team may look like signs of success. But growth does not automatically solve the problems already hiding inside a business.

It often magnifies them.

If your pricing is too low, growth creates more unprofitable work.

If your cash flow is already tight, larger sales may require more payroll, supplies, inventory, or equipment before the customer pays.

If your processes are inconsistent, adding customers creates more mistakes and confusion.

If every decision still depends on the owner, growth increases the pressure on the one person who is already stretched too thin.

Before pursuing the next level of revenue, ask whether the business has the foundation to support it:
✓ Is your pricing producing enough profit?
✓ Can your cash flow support increased expenses?
✓ Are your processes documented and repeatable?
✓ Does your team understand its responsibilities?
✓ Can the business operate without every decision coming through you?

Growth should make a healthy business stronger—not push an unstable business closer to its breaking point.

Sometimes the smartest growth strategy is to pause long enough to strengthen the systems, finances, and leadership behind the business.
Is your business prepared to handle the growth you are working toward?

Night Owl Tax & Resolution
Protect your income. Build your legacy.

Address

45730 SD Highway 44
Parker, SD
57053

Opening Hours

Monday	8am - 6pm
Tuesday	8am - 6pm
Wednesday	8am - 6pm
Thursday	8am - 6pm
Friday	8am - 6pm
Saturday	9am - 4pm

Telephone

(605)7995388

Website

http://nightowltaxpro.com/

Alerts

Be the first to know and let us send you an email when Night Owl Tax & Resolution posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Night Owl Tax & Resolution: