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Night Owl Tax & Resolution

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Parker, SD
Night Owl Tax & Resolution

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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. Through 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

10/28/2026

Your tax plan is only as reliable as your bookkeeping.

Year-end tax planning often begins with questions such as:

How much will I owe?

Should I make another estimated payment?

Would a retirement contribution help?

Should I purchase equipment before year-end?

But before those questions can be answered, the financial information behind the tax projection must be complete and accurate.

If income is missing, expenses are duplicated, accounts are unreconciled, or personal transactions are mixed with business activity, the projected tax result may be misleading.

Before relying on your books for year-end planning, review:

✓ Bank and credit-card reconciliations
✓ Outstanding customer invoices
✓ Unpaid vendor bills
✓ Loan and credit-card balances
✓ Equipment purchases and disposals
✓ Payroll and payroll-tax accounts
✓ Owner draws, contributions, and distributions
✓ Transactions sitting in uncategorized or clearing accounts
✓ Business expenses paid personally by the owner
✓ Personal expenses paid from business accounts

Also review the balance sheet—not just the profit-and-loss statement. Old receivables, negative asset balances, unreconciled loans, and unusual owner accounts may reveal problems that do not appear clearly on the income statement.

Tax planning based on incomplete books can lead to an unnecessary purchase, an incorrect estimated payment, or an unpleasant surprise during tax season.

The goal is not perfect bookkeeping for its own sake. The goal is financial information you can trust when making decisions.

Accurate books are the foundation of effective year-end tax planning.

Are your books ready for year-end tax planning?

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

10/27/2026

🦉 WHICH IRS RESOLUTION OPTION IS RIGHT FOR ME?

You owe the IRS. You know you need to address the debt. But how do you know which resolution option is right for your situation?

The answer depends on more than just how much you owe.

The IRS offers several ways to address unpaid federal taxes, but not every option is appropriate for every taxpayer.

Here are four possibilities worth understanding:

✔ INSTALLMENT AGREEMENT (PAYMENT PLAN)

If you can afford monthly payments but cannot pay your full balance immediately, an IRS installment agreement may allow you to pay your debt over time.

✔ CURRENTLY NOT COLLECTIBLE (CNC) STATUS

If paying your tax debt would prevent you from meeting necessary living expenses, the IRS may temporarily suspend enforced collection activity.

Your debt is not forgiven, and interest and applicable penalties generally continue.

✔ OFFER IN COMPROMISE (OIC)

Some taxpayers may qualify to settle their tax debt for less than the full amount owed.

The IRS evaluates factors such as income, allowable expenses, assets, and overall ability to pay. Approval is not guaranteed.

✔ PENALTY RELIEF

In certain circumstances, taxpayers may qualify for relief from IRS penalties.

Penalty relief does not automatically eliminate the underlying tax debt, but it may reduce the total amount owed.

💡 GOOD TO KNOW:

These options are not always mutually exclusive. For example, a taxpayer may qualify for penalty relief while also establishing an installment agreement.

⚠️ COMMON MISTAKE:

Choosing a resolution option based only on the monthly payment or the possibility of settling for less.

Before deciding, it's important to understand your tax balance, financial circumstances, filing compliance, and the requirements of each option.

THE BOTTOM LINE:

There is no single IRS resolution option that works for everyone.

The right approach starts with understanding what you owe, what you can afford, and which options you may qualify for.

📘 Explore IRS Payment & Resolution Options at IRSHelpHub.com.

Understand the process. Protect your rights.

Presented by Night Owl Tax & Resolution

Educational information only. Eligibility and resolution outcomes depend on individual circumstances.

10/26/2026

Being good at the work doesn’t automatically make you good at running the business.

Many businesses begin because someone is excellent at a trade, profession, or service.

A talented mechanic opens a repair shop.

A skilled contractor starts a construction company.

A great cook opens a restaurant.

An experienced bookkeeper begins serving clients independently.

But performing the work and running the business require two different sets of skills.

Being excellent at what you do does not automatically teach you how to:

✓ Set prices that cover every cost and produce a profit
✓ Manage cash when customers pay slowly
✓ Understand financial statements
✓ Plan for taxes
✓ Hire, train, and lead employees
✓ Create systems others can follow
✓ Handle difficult customers and unpaid invoices
✓ Decide when—or whether—to grow

This is one reason a business can stay busy while the owner remains financially stressed and overwhelmed.

The quality of the work may not be the problem. The business may simply need stronger pricing, financial management, systems, or leadership.

That does not mean the owner has failed. Most first-generation business owners were taught their trade—not how to build a company around it.

Business ownership is a separate skill, and it can be learned.

The first step is recognizing where the business depends on guesswork, memory, or constant intervention from the owner. The next step is developing the knowledge and systems needed to make better decisions.

You do not have to know everything before starting a business. But you must remain willing to learn what the business needs from you now.

Your expertise may have started the business, but business skills will help it survive and grow.

What part of running your business have you had to learn the hard way?

10/24/2026

🦉 HOW DOES THE IRS DECIDE WHAT I CAN AFFORD TO PAY?

You owe the IRS, but how does the IRS determine what you can realistically afford to pay?

It's not always as simple as looking at your paycheck or bank account balance.

When evaluating certain tax debt resolution options, the IRS may conduct a financial analysis to determine your ability to pay.

Here are four important factors the IRS considers:

✔ INCOME — Your wages, self-employment income, retirement income, and other sources of income.

✔ LIVING EXPENSES — Necessary expenses such as housing, utilities, food, transportation, and healthcare. The IRS uses financial standards to determine allowable amounts for many expenses.

✔ ASSETS — Bank accounts, vehicles, real estate, and other property that may have available equity.

✔ ABILITY TO PAY — The IRS evaluates your financial circumstances to determine what you may be able to pay toward your tax debt.

💡 GOOD TO KNOW:

The IRS doesn't necessarily allow every expense you actually pay.

For certain financial evaluations, the IRS uses National and Local Standards to determine reasonable living expenses. Some expenses are evaluated based on actual costs and applicable rules.

⚠️ COMMON MISTAKE:

Assuming that because you have very little money left at the end of the month, the IRS will automatically agree that you cannot afford payments.

The IRS may calculate your available income differently based on its allowable expense guidelines.

THE BOTTOM LINE:

Understanding how the IRS evaluates your finances can help you determine which tax resolution options may be appropriate for your situation.

Whether you're considering an installment agreement, Currently Not Collectible status, or an Offer in Compromise, your financial circumstances can play an important role.

📘 Continue learning about IRS Payment & Resolution Options at IRSHelpHub.com.

Understand the process. Protect your rights.

Educational information only. IRS financial analysis requirements vary depending on the resolution option and individual circumstances.

10/21/2026

Do a tax projection before year-end—not during tax season.

Many business owners wait until their tax return is prepared to find out how much they owe.

But tax preparation happens after the year has ended. At that point, most of the decisions that could have affected the outcome have already been made.

A year-end tax projection uses your current information to estimate your potential tax liability before December 31.

The process may include:

✓ Reviewing year-to-date business profit
✓ Estimating income and expenses for the remaining months
✓ Including wages, investments, rentals, or other household income
✓ Calculating self-employment or payroll-related taxes
✓ Reviewing estimated payments and withholding already paid
✓ Considering available deductions and tax credits
✓ Estimating both federal and state obligations

A projection may reveal that you are on track for a larger tax bill than expected—or that you have been setting aside more than necessary.

While time remains, you may be able to:

✓ Adjust your remaining estimated tax payments
✓ Increase withholding from a paycheck
✓ Make an eligible retirement contribution
✓ Complete necessary equipment purchases
✓ Pay legitimate business expenses that are already planned
✓ Correct bookkeeping or payroll issues before year-end
✓ Set aside additional cash for the expected balance

The goal is not to spend money simply to create deductions. Spending $10,000 to save a portion of that amount in taxes still leaves the business with less cash.

The goal is to make informed decisions based on what the business is actually earning.

Your bookkeeping must also be current and accurate. A projection built from incomplete income, missing expenses, or unreconciled accounts can produce a misleading result.

You may not be able to predict the final tax bill down to the dollar, but you can enter tax season with a reasonable estimate and a plan.

Tax preparation reports what already happened. Tax planning helps shape what happens next.

Do you know what your projected tax bill looks like?

10/19/2026

Gross profit tells you whether the work itself is working.

A business may generate impressive sales while keeping too little from each job to cover overhead, pay the owner, and produce a healthy profit.

That is why revenue alone does not tell the entire story.

Gross profit is generally calculated as:

Revenue − Direct costs = Gross profit

Direct costs are the expenses specifically required to deliver the product or service. Depending on the business, they may include:

✓ Materials and parts
✓ Inventory sold
✓ Direct labor
✓ Subcontractors
✓ Freight or delivery costs
✓ Other costs directly connected to the work

For example, suppose a business charges $10,000 for a project. If materials, direct labor, and subcontractors cost $7,500, the gross profit is $2,500.

That $2,500 must still help cover expenses such as rent, office payroll, insurance, software, marketing, professional fees, and owner compensation.

If too little remains, the problem may be:

✓ Prices that do not reflect the true cost of the work
✓ Labor hours exceeding the estimate
✓ Material costs that have increased
✓ Too many discounts or unbilled extras
✓ A service that generates revenue but not enough profit

Review gross profit by service, product, customer, project, or division whenever possible. An overall company total can hide work that consistently underperforms.

Also make sure direct costs are categorized correctly. If job-related expenses are recorded as general overhead, the gross-profit report may appear healthier than it truly is.

Revenue shows how much you sold. Gross profit shows whether the work is financially worth doing.

Do you know which work produces your strongest gross profit?

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

10/16/2026

Your business needs boundaries, too.

Many business owners want to be helpful, responsive, and easy to work with. But without clear boundaries, good customer service can slowly become unlimited access, unpaid work, and constant exceptions.

It may begin with one customer who contacts you after hours.

One project that expands beyond the original agreement.

One invoice that remains unpaid while additional work continues.

One discount granted because you feel uncomfortable defending your price.

One day off interrupted because every decision still depends on you.

An occasional exception may be reasonable. But when exceptions become the normal way of doing business, they can affect your time, cash flow, profitability, and ability to serve other customers.

Healthy business boundaries may include:

✓ Clearly defined office and response hours
✓ Written project scopes and change-order procedures
✓ Deposits before work begins
✓ Consistent payment terms and collection practices
✓ Additional charges for work outside the agreement
✓ Limits on discounts, rush requests, and repeated exceptions
✓ Responsibilities that employees can handle without the owner

Boundaries do not make you difficult or uncaring. They establish what customers, employees, and vendors can reasonably expect from the relationship.

They also help prevent resentment. When expectations are clear from the beginning, you are less likely to feel taken advantage of—and the other person is less likely to be surprised when you enforce a policy.

You can be flexible without allowing every request to disrupt your business.

Clear boundaries protect your time, your profit, and your ability to serve customers well.

Where does your business need a stronger boundary?

Protect your income. Build your legacy.

10/14/2026

Retirement contributions can be a business tax-planning tool.

Business owners often focus on purchasing equipment or accelerating expenses when they want to reduce taxable income. But a retirement plan may allow you to direct money toward your future while also creating potential tax benefits.

Depending on the business and the plan selected, options may include:

✓ SEP IRA
✓ SIMPLE IRA
✓ Solo 401(k)
✓ Traditional 401(k)
✓ Profit-sharing plan
✓ Defined benefit or cash-balance plan

Each option has different contribution limits, deadlines, administrative responsibilities, employee eligibility rules, and employer contribution requirements.

The right choice depends on factors such as:

✓ Your business structure
✓ Whether you have employees
✓ Your age and retirement goals
✓ The amount you want to contribute
✓ Your compensation or self-employment income
✓ The consistency of the business’s cash flow

Traditional pretax contributions may reduce current taxable income, while Roth contributions generally do not provide an immediate deduction. For an S corporation owner, contribution calculations are generally based on W-2 compensation—not shareholder distributions.

Timing also matters. Some plans must be established or employee elections made before year-end, even when certain contributions can be deposited later. Waiting until the tax return is prepared may limit the options still available.

Retirement contributions should not leave the business unable to meet payroll, taxes, debt payments, or other obligations. A deduction is helpful, but the plan must also fit the business’s cash position.

The goal is not simply to reduce this year’s tax bill. It is to coordinate taxes, cash flow, employee benefits, and long-term financial security.

Is retirement planning part of your business tax strategy?

Protect your income. Build your legacy.

10/12/2026

Revenue is not the same as cash flow.

A business can generate strong sales—and even show a profit—while struggling to pay its bills.

Why? Because revenue, profit, and cash flow measure different things:

✓ Revenue is the income the business earns from sales.
✓ Profit is what remains after the related expenses are subtracted.
✓ Cash flow reflects when money actually enters and leaves the bank account.

Suppose your business completes $20,000 of work and sends the customer an invoice. That revenue may appear in your financial reports immediately, but the cash will not be available until the customer pays.

Meanwhile, the business may need to cover:

✓ Payroll and payroll taxes
✓ Materials or inventory
✓ Rent and utilities
✓ Insurance
✓ Vendor bills
✓ Loan and equipment payments

If the customer takes 30, 60, or 90 days to pay, the business must fund those expenses from cash already on hand.

Cash can also become tied up when:

✓ Too much inventory is purchased
✓ Customers pay slowly
✓ Deposits are not required before work begins
✓ Debt payments consume a large portion of monthly cash
✓ The owner withdraws more than the business can support
✓ Expenses must be paid before the related revenue is collected

This is why looking only at revenue—or even net profit—does not provide a complete picture of financial health.

Review your accounts receivable, upcoming bills, payroll obligations, debt payments, and expected deposits. A short-term cash-flow forecast can help identify a shortage while there is still time to respond.

Revenue tells you what the business is earning. Cash flow tells you whether it can continue operating.

Do you know whether your business has enough cash for the next 30 days?

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/

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