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Three Safe Harbor Elections Could Save Thousands on Your Next Big Repair Project

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When a rental property owner faces a $27,000 repair bill, can they deduct these costs immediately as repairs, or must they capitalize them as improvements and depreciate them over decades?

This exact situation confronted Jeremy Wells, CPA, EA, in his tax practice when a client’s simple plumbing leak turned into a complex restoration project. What started as a ceiling drip in a two-story rental property led to $4,000 in plumbing repairs, a $16,000 bathroom renovation, a $4,000 water heater replacement, and $3,000 in ceiling and floor repairs.

In this episode of Tax in Action, Wells walks through this real case to show how the IRS determines when expenditures qualify as immediately deductible repairs versus when they must capitalize them as improvements. The difference can mean thousands in tax savings if you understand the rules and make the right elections before filing your return.

The Framework That Changed Everything

For years, tax professionals struggled with the gap between two key code sections. Section 162 allows businesses to deduct ordinary and necessary expenses, including repairs. Section 263A requires businesses to capitalize amounts paid to improve tangible property. But the law didn’t clearly define when you’re repairing property versus when you’re improving it.

“If we want to know if a certain type of expense is ordinary or necessary, and if it’s therefore deductible by a business, we look to Section 162,” Wells explains. “We also have Section 263A,  which tells us we have to capitalize amounts paid to acquire, produce, or improve tangible property.”

Treasury Decision 9636 finally bridged this gap. Released in the early 2010s, this collection of regulations established a clear framework for making repair versus improvement decisions. The document includes about 60 pages of explanation in its preamble, showing how the Treasury Department arrived at these rules and addressed public comments.

The framework centers on a two-part test. First, you must determine the “unit of property”—the actual asset you’re repairing or improving. Second, you must assess whether your expenditures constitute improvements to that unit of property.

Understanding Units of Property

Determining the unit of property isn’t always straightforward. Wells uses a car engine replacement to illustrate the concept.

“Think about a vehicle. I have to replace the engine. Is the unit of property the engine? Is it the entire vehicle?” The answer depends on what appears on your balance sheet or depreciation schedule. Since you typically depreciate the entire vehicle rather than individual components, the whole vehicle is the unit of property.

For buildings, the analysis is more complex. The regulations distinguish between building structure and building systems. The structure includes the building itself: walls, doors, windows, floors, ceilings, and permanent coverings like tile or brick. The systems include HVAC, plumbing, electrical, elevators, fire protection, gas distribution, and security systems.

“We have to distinguish between what is happening with the structure of this building versus what’s happening with the specific systems,” Wells notes. This distinction matters because repairs to different units of property receive independent analysis under the improvement rules.

In Wells’ rental property case, this meant treating the ceiling and floor repairs (building structure) separately from the plumbing work (plumbing system). Each unit of property required its own improvement analysis.

The Three Types of Improvements

Once you identify the unit of property, you must determine if your expenditures constitute improvements. The regulations define improvements as expenditures that produce one of three results: betterments, restorations, or adaptations.

Betterments

Betterments include three scenarios. First, fixing conditions or defects that existed before you acquired the property or arose during its use. Using the car engine example, Wells explains, “There is something in that engine that’s not quite working right, and that’s causing a problem for the operation of that vehicle.” Replacing that faulty engine improves the vehicle.

Second, betterments include additions like enlargements, expansions, or capacity increases. Wells draws from Florida real estate: “A lot of people have paved patios right outside the back door. They’ll want to turn that into some usable space that doesn’t have the heat and the direct sunlight and the bugs. So they wall that in and create a sunroom.” This transformation adds value and functionality.

Third, betterments cover changes that increase productivity, efficiency, strength, quality, or output. Replacing an old engine with a high-performance version that delivers better speed and efficiency would qualify.

Restorations

Restorations focus on returning property to proper working condition after damage or deterioration. “Think of some piece of property that has either been damaged or it’s just worn out over time to the point where it’s become either nonfunctional or just unusable,” Wells explains.

This concept applies especially to properties affected by natural disasters. If a tornado rips off your roof or a tree damages a wall, restoring the property to its pre-damage condition qualifies as an improvement under tax law, even though you’re not making it better than before.

Adaptations

Adaptations involve converting property to entirely different uses. Wells points to pandemic-era commercial real estate: “There were attempts to convert some of that office space into apartments.” This conversion requires extensive investment to add kitchens, appropriate bathrooms, and residential layouts, adapting the property for a new use.

When Related Costs Get Bundled Together

The regulations include a rule that often catches taxpayers off guard. When multiple expenditures stem from the same project, taxpayers must capitalize together costs that directly benefit and result from improvements.

In Wells’ case, this meant the $3,000 in ceiling and floor repairs couldn’t be treated separately from the bathroom renovation and plumbing restoration, despite appearing on different invoices from different contractors.

“When these kinds of expenses are all based around the same event, those costs that directly benefit and result from the improvement have to be capitalized as all part of that improvement as well,” Wells explains. “We can’t differentiate between the expenditures that went into fixing the plumbing versus fixing the floor and the ceiling versus improving the bathroom. This is all one project.”

The water heater replacement stood apart only because it was an independent decision. “All of the work done on the bathroom and the ceiling and the floor would have still happened exactly the same way, regardless of whether or not the taxpayer actually replaced that water heater.”

Three Safe Harbors Can Help

The IRS provides three safe harbors that can transform required capitalizations into immediate deductions. But all three are elective—you must actively choose to use them and document that election on your tax return.

The De Minimis Safe Harbor

The de minimis safe harbor election allows taxpayers to expense invoices or items below certain dollar thresholds. For businesses with applicable financial statements (SEC filings, audited financials, or non-tax statements required by government agencies), the threshold is $5,000 per invoice or item.

Most small businesses and rental property owners don’t have applicable financial statements. For these taxpayers, the threshold started at just $500 when the regulations were finalized. That amount proved so restrictive that business owners and tax advisors immediately complained.

“Even ten years ago, the cost of normal business equipment like computers, tablets, and cell phones were easily over $500,” Wells recalls. The IRS eventually increased the threshold to $2,500 through Notice 2015-82, providing more meaningful relief for routine business purchases.

The Safe Harbor for Small Taxpayers

The safe harbor election for small taxpayers specifically targets rental property owners. To qualify, you must have average annual gross receipts of $10 million or less over three years and own eligible building property with an unadjusted basis of $1 million or less.

This safe harbor works building by building. You can expense all repairs, maintenance, and improvements on a qualifying building if total annual costs don’t exceed $10,000 or 2% of the building’s unadjusted basis, whichever is less.

The Routine Maintenance Safe Harbor

The routine maintenance safe harbor election applies to activities you reasonably expect to perform at least once every ten years to keep building structures or systems operating efficiently. However, it explicitly excludes betterments, adaptations, and restorations.

Water heater replacements are a classic example. “Water heaters seem to last like every 6 to 8, maybe ten years,” Wells observes. “Every ten years or so, you need to plan on replacing a water heater.” In his practice, Wells regularly applies this safe harbor to water heater replacements.

Applying the Rules to Real Situations

In Wells’ $27,000 rental property case, applying the improvement framework reveals how the rules work in practice:

  • The $4,000 plumbing repairs constitute restoration, replacing worn, corroded components to return the system to working order
  • The $16,000 bathroom renovation represents betterment, improving the appearance and quality of fixtures that weren’t actually broken
  • The $3,000 ceiling and floor repairs must be capitalized with the other improvements as incidental costs
  • The $4,000 water heater replacement stands apart as an independent decision eligible for the routine maintenance safe harbor

None of the individual expenditures qualified for the de minimis safe harbor since all exceeded $2,500. The total project costs far surpassed the small taxpayer safe harbor limits as well.

But the water heater replacement offered a strategic opportunity. As an independent maintenance decision that falls within the routine ten-year replacement cycle, the taxpayer could immediately deduct it under the routine maintenance safe harbor if they make the proper election.

Making Elections Before It’s Too Late

All safe harbor elections require specific statements attached to timely filed returns, including extensions. Miss the election deadline, and the opportunity disappears permanently for that tax year. Make the election, and it applies to all qualifying expenditures—there’s no cherry-picking individual items.

“You need to attach a statement to the return saying the taxpayer makes the election,” Wells emphasizes. Renew these statements annually for continued use, because there’s flexibility to use safe harbors in some years but not others.

The Bottom Line for Tax Professionals

Wells’ case study demonstrates how identical expenditures can receive dramatically different tax treatment based on understanding available options and making proactive elections. The $4,000 water heater could provide immediate relief through the routine maintenance safe harbor, while the taxpayer had to capitalize the remaining $23,000 and depreciate it over decades.

“When it comes to the decision of whether to repair versus improve, it’s important to look at these regulations, to read through them, to ask yourself, are we bettering this property?” Wells concludes.

The framework offers practical guidance that can save thousands in immediate tax relief or cost clients decades of unnecessary capitalization. But it only helps those who understand the rules, recognize when safe harbors apply, and make the required elections before filing deadlines pass.

For tax professionals, this is the difference between reactive compliance and proactive planning. Your clients need advisors who anticipate these situations and structure approaches to maximize immediate deductions within regulatory boundaries. Understanding these repair versus improvement rules before you need them could save thousands when that next unexpected repair bill arrives.

The Real Reason Your Female Colleagues Keep Disappearing from Leadership

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You’re watching your female colleagues disappear. One by one, the talented women who started their accounting careers alongside you vanish from the partnership track. When you look around the conference table at senior leadership meetings, you realize that although women make up half of all new hires, only 19% of firm partners are women.

In a recent episode of the She Counts podcast, “Still Under Glass,” hosts Questian Telka and Nancy McClelland tackle this leadership crisis head-on. But they’re not just naming the problem. They’re offering examples and solutions and calling on firm leaders to make fundamental cultural shifts.

The Pipeline Problem That Isn’t

Something dramatic happens between new CPAs entering the profession and reaching partnership, and it’s not a lack of talent.

Unfortunately, this problem isn’t unique to accounting. Across business sectors, women hold only 14% of executive roles. But accounting starts with gender parity, making the difference even more stark. “We know that we have 50% as women, and we know they’re talented,” Telka emphasizes. “The issue is that the profession is losing women mid-career, not because they aren’t capable, but because the system really isn’t designed for us to stay.”

Making the Invisible Visible

Telka shares that a male colleague recently told her he wants to help create positive change but doesn’t understand the issues or how to help. To eliminate that excuse, we need to spell out exactly what’s happening and what allies can do about it.

The biases start small but compound quickly. Studies show men interrupt women 2.5 times more often than women interrupt men. Women are routinely asked to take notes in meetings or organize office celebrations, rather than men. They receive vague feedback like, “you’re doing great, keep it up,” while men more often get specific, actionable guidance tied to promotions.

McClelland adds, “Women of color have a much harder time. There are many different kinds of privilege.” These biases get disguised with phrases like “she’s just not quite the right fit,” a convenient way to mask discrimination that’s hard to pinpoint.

However, recognizing bias is just the first step. Three critical barriers keep women under glass: the motherhood penalty, the flexibility trap, and the sponsorship gap.

The Motherhood Penalty: Same Event, Opposite Outcomes

The data is jaw-dropping. Mothers are considered 12% less committed to their jobs than non-mothers, while fathers are seen as 5% more committed than non-fathers. This perception gap translates directly into salary differences. Mothers receive starting salaries 7.9% lower than childless women and 8.6% lower than fathers.

“The exact same life event, becoming a parent, becomes either a career accelerator or a career killer depending solely on your gender,” the hosts note.

Telka shares a story about her ex-husband taking their son to a playground. When his brother asked how he felt about “babysitting” while the women went shopping, he immediately corrected him: “I’m not babysitting. This is my child.”

That single word—babysitting—captures everything. When fathers care for their children, they’re going above and beyond. When mothers do it, it’s just expected. Worse, it’s considered evidence that they’re not serious about their jobs.

This bias affects daily decisions that slowly strangle women’s careers. Women get passed over for major accounts based on assumptions about their availability. “They’re thinking: you’re a mom, you don’t want to have a larger account,” Telka explains. Instead of asking what support women need to keep advancing, firms quietly write them off.

The Flexibility Trap: Benefits That Destroy Careers

Many firms advertise flexible schedules and family-friendly policies. But there’s a massive gap between having these policies and creating a culture where women can use them without killing their career trajectory.

“Don’t say you’re going to give unlimited vacation or flexible schedules and then expect your employees not to use it,” Telka warns. “Real flexibility isn’t just a policy; it’s putting it in practice.”

McClelland shares an infuriating story that shows this trap in action. A lawyer friend, raising two children alone while her daughter faced serious health issues, negotiated a 25% pay cut for more flexibility. Despite maintaining her full workload and delivering the same results while working more from home, that pay cut became permanent. Future raises were calculated from her reduced salary, compounding the penalty year after year.

Meanwhile, another friend’s male boss responded completely differently to her caregiving needs. “You participate and contribute more than anybody here. I know you’ll get the work done. Take whatever time you need.”

Same situation. Completely different outcomes.

The flexibility trap extends to hiring practices. Most larger firms refuse to consider part-time senior-level roles, demanding 60-plus-hour workweeks as the baseline for showing commitment. “We could hire more women who are highly competent, highly skilled,” Telka argues. She left her position partly because there was no opportunity to work part-time while caring for her son.

The hosts challenge the entire premise of equating hours with value. “The bragging should be, ‘’I’m still hugely successful, and I’ve only had to work ten hours this week because I’m so efficient,’'” Telka suggests. Instead, the profession celebrates whoever logs the most hours, regardless of actual accomplishments.

The Sponsorship Gap: Beyond Coffee and Advice

While firms love their mentorship programs, women need sponsorship, and there’s a crucial difference. Mentors give advice. Sponsors give opportunities.

“Women need advocates who promote them even when they’re not in the room,” Telka explains. This means giving them the opportunity to work with big clients, putting them forward for promotions, and actively using influence on their behalf.

The “feedback gap” shows how this plays out. Telka noticed that men at her firm received specific, actionable feedback: complete these certifications, lead this type of project, and you’ll be ready for promotion. Women got vague encouragement that sounded supportive but functioned as a career ceiling.

McClelland’s experience breaking into professional speaking illustrates the power of sponsorship. She had no idea what to charge and accepted far less than market rates. When Telka learned what McClelland was charging, her response was direct: “You need to charge a lot more.” That single conversation of transparent peer mentorship immediately increased McClelland’s earning potential. But sponsorship is that next step: vouching for her quality of work to professional connections who were ready to pay market rates.

Because women need more than peer support. They need people—espectially men—in leadership roles actively using their privilege for change. This means interrupting when women themselves are interrupted, questioning why Jennifer’s client portfolio is smaller than John’s, and advocating for women who aren’t in the room.

“Don’t wait for women to ask for a promotion,” McClelland urges. Women are far less likely to self-advocate, since they have been socialized to be “nice and kind and warm” rather than assertive. “Intentionally promote women. Just because they’re not asking doesn’t mean they’re not qualified or don’t deserve it.”

From Awareness to Action

The good news? Change is already happening. Jason Ackerman’s firm has achieved 80% women employees with equal gender representation in leadership. Some firms tie partner bonuses to diversity outcomes. A male partner who took paternity leave shifted his entire firm’s culture simply by modeling the behavior.

The solutions are practical and achievable:

  • Track account assignments to ensure equity
  • Stop asking for prior salaries that perpetuate pay gaps
  • Provide bias interruption training for everyone
  • Create revenue-sharing models that reward value over hours
  • Hire skilled women seeking part-time or flexible roles
  • Make pay ranges transparent within organizations
  • Model the behavior you want to see

Companies like Luma Accounting have incorporated policies like these into their firm culture with such successful results that they started the Women+Workplaces community to connect talented women seeking flexible work with firms smart enough to recognize that 30 brilliant hours beat 60 mediocre ones.

“Culture is created based on what we celebrate and what we reinforce,” Telka notes. The profession rewards visibility and hours logged… but it should be rewarding impact, innovation, and results.

The Business Case for Breaking the Glass

When firms lose half their talent pipeline to preventable cultural barriers, they lose experienced professionals who could transform their practices. Women who navigate personal challenges often become more adaptable, empathetic leaders.

“My personal family struggles have made me a much more resilient individual and a more compassionate person and leader,” Telka shares. McClelland agrees, noting that her medical challenges made her more understanding and better able to support her team.

Telka shared a quote from Michelle Obama, “Strong men, men who are truly role models, don’t need to put down women to make themselves feel powerful. People who are truly strong lift others up. People who are truly powerful bring others together.”

The leadership gap in accounting won’t close on its own. But with awareness, commitment, and intentional action from everyone—not just women—the profession can finally move beyond keeping women under glass.

Whether you’re running a firm or just starting your career, you have the power to be part of this shift. Listen to the full episode for more insights, strategies, and an honest conversation about creating real change in accounting.

The hosts also invite you to join the conversation on the She Counts LinkedIn page by sharing your own stories of workplace bias and solutions that work. Recognizing the glass ceiling is just the first step. Breaking it requires all of us.

Why Accountants Are Both Thrilled and Terrified by QuickBooks’ Latest AI Push

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How much should we trust AI with our critical financial processes?

In a recent episode of The Unofficial QuickBooks Accountants Podcast, hosts Alicia Katz Pollock and Matthew “Spot” Fulton break down the August 2025 “In the Know” webinar from Intuit, where AI agents take center stage alongside major Enterprise Suite enhancements and ProAdvisor Academy improvements.

From payment collection to payroll processing, QuickBooks is pushing automation further than ever before. But as Fulton and Katz Pollock discuss, the technology that saves you hours today needs careful oversight to avoid compliance nightmares tomorrow.

ProAdvisor Academy Gets Smarter

Before diving into the AI updates, the hosts highlighted some welcome improvements to ProAdvisor Academy. You can now filter courses by length and CPE credit amount—perfect for those moments when you think, “I have an hour, what can I learn right now?”

Even better, the system finally saves your CPE certificates in the “My History” section. As Katz Pollock notes, “They used to email them to you and you had to save them, and that was it. So the fact that you can actually now track your CPE is pretty darn awesome.”

Intuit is also launching a new quarterly series called Solution Spotlight, where support experts will tackle complex challenges and deep-dive into underutilized tools. The first topic? Bank transactions and reconciliation—the community’s most requested subject.

Enterprise Suite: The Multi-Entity Game Changer

Fulton and Katz Pollock spent considerable time discussing Enterprise Suite’s powerful consolidation features, and for good reason. These updates address long-standing issues that have plagued multi-entity businesses for years.

The Shared Chart of Accounts feature uses AI to standardize accounting across all your entities. As Fulton explains it, “You choose which chart of accounts you want to be your primary one, and then you can use the AI to say, okay, we think these accounts are going to match up with those accounts. You still have the ability to review and say, yep, you got this right.”

The time savings are massive. Fulton speaks from experience, “As an accountant, the time and energy it takes to try to normalize a chart of accounts is extensive. There’s a lot of thought and knowledge and wisdom that goes into it.”

Multi-entity transactions are even more impressive. When you invoice another entity in your organization, the system automatically creates the corresponding bill in that entity, complete with a PDF attachment. Fulton recalls the old way: “You would pull up two browsers, you’d have both companies up, and you look at the intercompany exchanges between one company and the other, and you go line by line to make sure both sides are there.”

But Katz Pollock raises an important point about accessibility. She has clients with multiple small entities—”literally QuickBooks Ledger or Simple Start”—who desperately need these consolidation features but can’t justify Enterprise Suite’s price tag. Her suggestion? “I think they should make an Enterprise Lite version focused solely on multi-company functions.

The Payments Agent: Getting You Paid Faster (and Smarter)

The Payments agent analyzes customer behavior to optimize your collection strategy. When you create an invoice, it shows you how long they’ve been a customer, their payment history, open invoices, and average payment time.

But here’s where it gets interesting. The agent suggests payment methods based on what will get you paid fastest. It even calculates total time to receive funds, including your customer’s typical delay. When Katz Pollock saw “ACH 14 days” in the demo, she clarified, “It wasn’t that ACH takes 14 days to clear. It’s that the customer takes on average nine days to pay, and then you have the three to five days it takes to clear.”

Fulton cuts to why this matters, “As business owners, all too often we rely on small margins to where we are super sensitive to cash flow. If it’s going to take somebody longer to pay, we need to know that.”

The system can also parse invoices from text, images, or PDFs, though Katz Pollock admits it “doesn’t do the line items yet. But you know, it’s just the infancy of the technology.”

One limitation bothers Katz Pollock: Reminder settings apply to all customers universally. “I have placeholder invoices or agreements with customers where it’s okay that they’re not going to pay for another 90 days,” she explains. Her workaround? Adjust due dates to match actual payment expectations.

The Payroll Agent: Convenience Meets Controversy

The Payroll agent’s text-message time collection generated the most heated discussion. Employees receive texts asking for hours, overtime, and tips. They respond with simple messages, and the system compiles everything for manager approval.

Sounds great, right? Not so fast.

“If they’re not keeping a time card, you know they’re going to overestimate how much they actually worked,” Katz Pollock warns. Fulton agrees, “How many employees are always completely honest with their hours and their overtime and their tips?”

The system is heavily restricted during beta. It’s only for US customers who don’t use auto payroll or QuickBooks Time, have one pay schedule, and use basic pay types. Fulton sees wisdom here, “Let’s make sure this is working before we give it to all the crazies out there.”

Still, there are safeguards. The system flags anomalies, requires manager approval, creates audit logs, and needs employee consent for each payroll period. Fulton even sees potential for construction companies where daily time certification is required. “They’re having to certify by responding back to this the amount of time they worked.”

Katz Pollock’s verdict? “The technology is going to be great. It’s the humans that you can’t trust in this particular issue.”

Customer Leads: Your Email Becomes Your CRM

Currently in Gmail-only beta (Outlook coming soon), the Customer Leads agent scans your email for customer interactions and organizes them into a sales pipeline: inquiry, negotiation, finalization, contracted, or lost.

Fulton’s excited about consolidation. “I’ve been using 17 Hats, but the challenge I’ve always had is the integration piece. I can handle all this stuff up to the estimate and invoice somebody, but it’s always been external.”

Katz Pollock uses Method CRM currently and sees the appeal, “This will be really nice to be able to just keep it right inside QBO and not have to go to another app.”

The hosts admit they’re still learning this feature, and Katz Pollock has a future episode planned to dive deeper.

More Updates Worth Your Attention

A few other updates the hosts are looking forward to include:

Scheduled Compensation Changes

This might be the sleeper hit of the updates. You can now pre-program raises and bonuses with effective dates. As Fulton exclaims, “This is sunlight shining down onto us so we can take a vacation at the end of the year, too!”

Katz Pollock shares a perfect use case: “I had a client whose employee broke their field service iPad and was reimbursing them out of their payroll, $150 per month for six months.” With scheduling, that deduction would automatically end on the right date.

Sales Tax Automation Expands

QuickBooks now handles sales tax filing for Iowa, Minnesota, North Carolina, Rhode Island, Vermont, and West Virginia at $40 per filing. While the hosts debated the price, Fulton notes it’s actually market rate compared to services like Avalara.

Looking Ahead

The hosts emphasized community feedback throughout the episode. As Fulton puts it: “Are you using Enterprise yet? If you are, what features are you loving? If you aren’t, what features are most enticing?”

They’ve even started a LinkedIn group for the podcast where listeners can discuss episodes and share experiences.

Katz Pollock is launching her “Great QBO Refresh” training series in September, completely rebuilding her curriculum to address all the interface changes. 

Don’t miss Intuit Connect (October 27-29 in Las Vegas) or Reframe Conference (November in Florida), which Fulton calls “by far, hands down, the best conference I’ve been to in years.”

The Bottom Line

These AI agents aren’t replacing accounting professionals; they’re redefining the role. The firms that thrive will leverage AI for efficiency while maintaining the human judgment that ensures accuracy, compliance, and client trust.

As Katz Pollock wisely advises about the payroll agent’s rollout, “Intuit, go slow on this one. We want to actually see use cases before it becomes universal.”

The future of accounting isn’t human versus machine. It’s human with machine, each doing what they do best. Ready to dive deeper? Listen to the full episode above and join the conversation in the Unofficial QuickBooks Accountants Podcast LinkedIn group.

Alicia Katz Pollock’s Royalwise OWLS (On-Demand Web-based Learning Solutions) is the industry’s premier portal for top-notch QuickBooks Online training with CPE for accounting firms, bookkeepers, and small business owners. Visit Royalwise OWLS, where learning QBO is a HOOT!

Tax Law Rewards Professional Stagnation While Punishing Growth

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A Tennessee accountant diligently studies for and passes the CPA exam. His day-to-day work remains virtually identical: same clients, same responsibilities, same desk. Yet when tax season arrives, those CPA exam costs aren’t deductible. Why? Because becoming a CPA qualified him for a “new trade or business,” even though he had no intention of changing careers, and his actual work didn’t change at all.

This real case from Glenn v. Commissioner perfectly captures the absurd reality facing today’s professionals: the very credentials and education that make you more valuable in your current role often become non-deductible under tax law. Jeremy Wells dissects this paradox in his latest Tax in Action podcast episode, where he reveals how our tax system has created a knowledge economy trap that punishes professional advancement.

While tax law theoretically supports professional development through education deductions, it systematically penalizes advanced degrees, professional certifications, and career-expanding skills by classifying them as “personal investments” rather than business necessities. This leaves tax professionals and their clients caught in a regulatory maze where maintaining your current skill level is rewarded, while pursuing excellence faces potential penalties.

The Knowledge Economy Reality Check

“For quite a while now, most of the U.S. economy has been based on not the ability of people to produce things or do things with their hands, but rather the value of what they’re able to accomplish with their minds,” Wells explains.

The financial sector, insurance industry, and professional services all depend on knowledge work. Yet our tax system treats developing those valuable mental capabilities as personal indulgence rather than business necessity.

The existing education tax breaks demonstrate this disconnect clearly. The 529 plans that parents use to save for college offer no federal tax deduction for contributions, though some states do allow deductions. Student loan interest deductions under IRC Section 221 phase out based on income, effectively penalizing successful professionals. Education credits like the American Opportunity Credit and Lifetime Learning Credit focus on traditional college expenses, not the specialized training that drives value in today’s economy.

As Wells notes, these benefits can be rather limited. The problem isn’t that tax law ignores education entirely. It’s that the benefits don’t match the reality of professional development needs.

This brings us to the question Wells hears constantly from business owners: “Can I pay for my own education and use my business to do that?” The answer reveals just how complex this landscape has become.

Educational Assistance Programs: Promise and Pitfalls

The IRC Section 127 educational assistance programs initially appear to offer hope. These programs allow employers to provide up to $5,250 annually in tax-free educational benefits, and the definition of qualifying education is surprisingly broad.

Wells explains that under these programs, “education includes any form of instruction or training that improves or develops the capabilities of an individual.” Even better, “education is not limited to courses that are job-related or part of a degree program.” This could potentially cover everything from technical training to wellness courses that make employees “better people, more productive, happier.”

The program can cover tuition and fees, books, supplies, and equipment, and even student loan repayments. The definition of “employee” is also broad, including “self-employed individuals or what we might refer to as independent contractors.”

But here’s where the system reveals its bias against small business owners.

The fatal flaw lies in the anti-discrimination rules. Any business owner with more than a 5% stake in their company cannot claim more than 5% of the total benefits paid out by the program. As Wells explains, “If you are self-employed, and you want to use this program for yourself, and you have other employees, you, as a more than 5% owner of that business, cannot claim more than 5% of the benefits paid out by that program.”

The math is brutal. If you want to claim the full $5,250 benefit for your own education, your business would need to pay out at least $105,000 in total educational benefits to all participants. For most small businesses, this makes the program impractical.

The discrimination rules add another layer of complexity. Programs cannot favor highly compensated employees: those earning over $160,000 in 2025, those with 5% or greater ownership stakes, or those in the top 20% of employees ranked by compensation.

Wells notes that for many small business owners, this means they either “don’t do this program at all” or “just exclude themselves from the program.” And there’s another catch. Unlike cafeteria plans under IRC Section 125, you can’t offer employees a choice between the education benefit and additional cash compensation.

The program also has strict substantiation requirements. Employees must provide documented proof that expenses qualify, and they can’t double-dip by receiving reimbursement and then claiming education credits on their personal returns. Wells warns this is particularly important because “it’s entirely possible that that employee would then turn around and report those educational costs on their tax return and claim an education credit.”

When Business Owners Go Direct: The Section 162 Minefield

When educational assistance programs fail small business owners, they turn to direct business deductions under IRC Section 162. This is where things get really tricky.

Treasury Regulation 1.162-5 allows education deductions if the education “maintains or improves required skills” or “meets legal or employment requirements to maintain his or her present salary, status or job.” This generally includes professional continuing education and refresher courses.

The regulation also covers education to meet an employer’s minimum requirements “if the requirements are imposed for a bona fide business purpose.” Wells gives the example of requiring employees to take spreadsheet training because “we use a lot of spreadsheets in my business, and my employees need to be able to effectively use those spreadsheets.”

Even travel for education can be deductible if “the travel is directly related to the duties of the individual in employment” and “the major portion of that business needs to include activities directly maintaining or improving required skills.” However, taxpayers must allocate personal activities during the trip separately.

But here’s where the Tax Court draws its line in the sand.

The Tax Court’s War on Professional Growth

Treasury Regulation 1.162-5(b) establishes two types of education that are explicitly non-deductible, and the Tax Court has interpreted these restrictions aggressively.

First, taxpayers cannot deduct education that meets “necessary minimum educational requirements.”  Second, and far more damaging, education that “will lead to qualifying an individual for a new trade or business” is automatically disqualified.

The logic, Wells explains, is that these expenses are “essentially personal or perhaps capital expenditures” where “you’re investing in yourself.” The Tax Court views this as an “inseparable aggregate of personal and capital expenditures” rather than ordinary business expenses.

The cases reveal a pattern of hostility toward professional advancement that spans decades. In the Glenn case, the accountant couldn’t deduct CPA exam costs even though his work remained identical. The Tax Court ruled that becoming a CPA granted “certain rights, responsibilities, privileges that weren’t there before.”

The pattern repeats across professions. In Robinson v. Commissioner (1982), a licensed practical nurse completed an RN program while maintaining virtually identical duties. The Tax Court ruled against her because registered nurses have different capabilities than LPNs.

Even IRS employees get caught in this trap. In Weiler v. Commissioner (1970) and Taubman v. Commissioner (1973), IRS revenue agents couldn’t deduct law school costs despite arguing that legal training enhanced their current tax research abilities.

Law degrees face particularly harsh treatment. Wells notes that “law degrees generally qualify for a new trade or business” regardless of the taxpayer’s current profession or intentions.

The MBA Split Decision

The MBA cases show just how arbitrary these determinations can become. In 2016’s Gora v. Commissioner, the Tax Court allowed a financial controller’s executive MBA costs because his continued work in “management and finance” didn’t represent new qualifications.

Just one year later, in Kray v. Commissioner (2017), a computer design consultant’s identical executive MBA was ruled non-deductible because it qualified her for “new tasks” like “financial analysis, managing a business, managing and overseeing a staff.”

Wells warns that “an MBA may or may not qualify” as deductible, making this area particularly risky for taxpayers.

The Practical Reality for Tax Professionals

This creates impossible situations for tax professionals advising clients. The Tax Court’s standard isn’t whether you actually change careers or even want different opportunities. As Wells emphasizes, the keyword is “potentially”—education that could potentially qualify you for different work is probably non-deductible.

The system forces taxpayers to choose between pursuing valuable education that enhances their business capabilities but facing potential audit challenges, or limiting themselves to narrow, maintenance-level training that clearly fits within existing job requirements.

Wells notes that taxpayers must be “established in a trade or business” before education expenses become deductible, and the Tax Court has ruled that “a relatively short or temporary tenure in a job before starting the education doesn’t establish the taxpayer in the trade or business.”

Even holding a position doesn’t guarantee you’ve met minimum educational requirements. University teaching assistants, for example, haven’t met the minimum requirements for permanent faculty positions until they actually have their PhD.

Navigating the Knowledge Economy Trap

Our tax system rewards professional stagnation while punishing the learning that drives economic value. Tax professionals’ continuing education to maintain existing credentials? Fully deductible. Are the same professionals pursuing advanced degrees to better serve clients? Potentially non-deductible because it might qualify them for “new” responsibilities.

For tax professionals, this creates compliance challenges and ethical questions. Do we advise clients toward valuable education that faces potential tax challenges, or recommend they limit learning to “safe” options that maintain the status quo?

Wells warns that employers and self-employed individuals “really need to be careful when they’re trying to deduct those work-related education costs.” The Tax Court “can be pretty strict about education either meeting those minimum requirements for a profession or even more often than that, qualifying the recipient of that education for a new trade or business.”

Understanding these limitations is about recognizing how tax policy shapes professional development decisions across the entire economy. The knowledge economy demands continuous adaptation and skill development, but our tax code remains anchored to an industrial mindset that views capability expansion as personal indulgence rather than business necessity.

Listen to the full episode of the Tax in Action podcast for Wells’ complete analysis and detailed guidance to help clients make informed decisions about their professional development investments. Don’t let the knowledge economy trap catch you or your clients unprepared.

The Business Case for Leading with Heart in a Numbers-Driven World

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Dawn Brolin’s accounting firm partners told her she was fat. They criticized her for wearing the same clothes repeatedly. And when she tore her meniscus at the gym, they made her drive herself to the hospital with explicit instructions to be at work the next morning.

This wasn’t a scene from a workplace horror story. This was real life for a CPA who would later become one of accounting’s most passionate advocates for empathetic leadership. In a recent episode of the She Counts podcast, Brolin opened up to hosts Nancy McClelland and Questian Telka about the raw experiences she shares in her new book, “The Elevation of Empathy,” revealing how toxic leadership nearly broke her, and ultimately shaped her understanding of what authentic leadership looks like.

What makes Brolin’s story particularly powerful is that she doesn’t just talk about being a victim of empathy-free leadership. She also admits to her own failures and how she learned to recover from them. Her journey shows embracing empathy as a strategic advantage, rather than hiding emotional intelligence to appear “tough enough,” creates stronger teams and better business outcomes.

Before we dive deeper, if this topic triggers any emotions or struggles you’re facing, there is help available. The Crisis Text Line offers confidential professional mental health assistance: just text HOME to 741741.

When Leadership Lacks Heart: The Partnership from Hell

Brolin’s partnership nightmare wasn’t just about bad bosses. It was a masterclass in how the absence of empathy destroys people and businesses from the inside out.

At the time, Brolin was one of three partners in the firm. She brought in most of the clients, and was working to support her young family as the primary breadwinner. She was genuinely excited about building something meaningful. Then reality hit.

“There was zero empathy in that firm,” Brolin recalls. “None whatsoever.”

Because Brolin wasn’t yet a CPA, her partners—both women—relegated her to answering phones and fetching lunch, despite her being the primary rainmaker. The real cruelty went deeper than professional dismissal. They systematically attacked her personally, criticizing her weight and mocking her clothing choices.

The gym incident is an image of empathy-free leadership: when Brolin tore her meniscus during a step aerobics class they’d all attended together, she found herself writhing in pain on the gym floor. Her partners’ response? Figure it out yourself.

“I somehow dragged myself down to the office, and now I need to get to the hospital,” Brolin remembers. “And they were like, ‘All right, well, you’re gonna have to drive yourself to the hospital and make sure you’re at work tomorrow morning.'”

With a torn meniscus.

This wasn’t leadership, it was systematic dehumanization. The partners were creating a culture where employees watched this treatment and learned that success meant crushing others. “I watched how they treated the employees,” Brolin explains. “It wasn’t just me.”

But Brolin made a crucial decision in that toxic environment. Instead of absorbing these behaviors as normal, she used the experience as a reverse blueprint. “I was never going to do that as an employer,” she realized.

When the Empathy Champion Falls Short: Brolin’s Coaching Confession

Here’s what makes Brolin’s story so honest and powerful: she advocates for empathy and admits when she’s failed at it herself.

As a softball coach known as “The Designated Motivator,” Brolin poured her soul into her players. She made it her mission to be inclusive, to make every kid feel appreciated and loved. Then three players transferred to another school.

“My empathy went out the window,” Brolin admits. “I was devastated that they left. I poured my soul into them, and I was like, ‘You’re leaving me.’”

Instead of considering why these kids might have needed to transfer, Brolin took it personally. She withdrew her care and support from them completely. “That was so wrong,” she reflects.

But here’s the beautiful part: Brolin recognized her mistake and fixed it. About a year later, she went to each of the three kids and apologized.

“I want you to know something. This is an epic fail on my part, not yours,” she told them. She gave them permission not to forgive her, making it clear the apology was about them, not about making herself feel better.

They forgave her. Now they text regularly.

“My point in saying that is, for those people who have been unempathetic to an individual, you can fix that,” Brolin explains. “You can go to a person, and admit you messed up.”

In short, empathy isn’t about being perfect. It’s about recognizing your failures, owning them, and doing better.

Empathy as Your Secret Business Weapon

The accounting profession has operated under a fundamental misunderstanding: that empathy equals weakness. Brolin’s experiences prove exactly the opposite.

“Empathy doesn’t mean you’re soft,” Brolin emphasizes. “As a matter of fact, I think it’s a superpower.”

The American Psychological Association defines empathy as understanding a person from their frame of reference rather than your own. This breaks down into two skills: cognitive empathy (logically understanding someone’s perspective) and emotional empathy (actually feeling what they feel).

In business terms, this translates to measurable advantages that accounting firms can’t ignore. The research is overwhelming: empathetic leaders drive stronger team performance, higher retention rates, sharper decision-making, increased innovation, and improved mental health across their organizations.

“When leaders have empathy, people gravitate to that leader more than they do to a leader who doesn’t have empathy,” Brolin explains.

Consider Brad Smith, former CEO of Intuit, who Brolin cites as one of her favorite leaders. At industry conferences, Smith would stop mid-stride when he saw familiar faces, remembering personal details about employees’ families and asking about their daughters’ college plans.

“That is a leader who has empathy, who cares about other people by his actions more than his words,” Brolin notes. “They don’t superficially care about you because it’s going to give them an advantage. They care about you because of you.”

Being appointed to a leadership position doesn’t automatically make someone a leader. True leadership requires the ability to connect with and understand the people you’re leading. When your employees trust that you see them as whole humans rather than just billable resources, they bring their full creative potential to work.

The Burden Women Carry (And Why Men Need to Step Up Too)

Women in accounting firms often carry the invisible emotional labor of our workplaces. According to a 2023 Deloitte report, 51% of women say they’re expected to manage team wellbeing, compared to only 27% of men.

Telka knows this intimately. “I think about things like birthday gifts for colleagues or cards that have to be signed or someone’s ill and they need to be sent flowers,” she explains. “It often fell on me, probably because I was the most empathetic. The men were never the ones who were driving those situations.”

McClelland captures this perfectly with her favorite greeting card: “The front of the card says, ‘Happy birthday, from us.’ Inside: ‘But I think you know who went out and bought the card and wrote it and addressed it—and who just put the stamp on it.’”

But Brolin believes many men in the industry are more empathetic than we realize. “They’re just not being intentional about it,” she says. Take Randy Crabtree, who wrote the foreword to Brolin’s book, or Mike Paine, who told Telka, “I really want to help women in the field. Help me understand what the problem is and tell me what I can do, then I’m here for it.”

“And that’s empathy,” McClelland points out. “That is empathy right there.”

Learning to Accept What You Give: The Hardest Lesson

For Brolin, one of the biggest challenges has been learning to accept empathy, not just give it.

“People think because I keep going, I don’t hurt,” Brolin shares. “Let me be very clear. I hurt, and I keep going.”

Women leaders often become so focused on caring for others that they struggle to let others care for them. When Kellie Parks called after reading Brolin’s vulnerable Mother’s Day post, Brolin’s instinct was to deflect and hang up quickly.

Instead, she made a conscious choice to receive Parks’ empathy. “I let myself listen to what Kellie had to say and gave some space in my soul.”

McClelland offered Brolin a reframe that many women leaders need to hear: “Would you want me to hide my pain to protect you?” When Brolin said of course not, McClelland continued, “It’s an honor to have you turn to me when you need help. So if you ask for help, you’re showing us the same respect.”

As McClelland puts it, the goal is “unconditional love, but conditional involvement”—staying open to authentic connection while maintaining boundaries about what treatment you’ll accept.

Practical Tools for Building Your Empathy Muscle

Brolin offers specific practices for developing empathy as a leadership skill:

  • Practice mindfulness to build awareness. When you talk to someone, be truly present in that conversation. This is especially challenging at conferences with distractions everywhere, but it’s worth the effort.
  • Ask questions without making assumptions. Go into conversations with a blank slate rather than preconceived notions about what someone will say. As Telka notes, “Most of the time if I don’t make assumptions, things turn out much more positively.”
  • Pay attention to nonverbal cues. What are people not saying out-loud that you should consider asking about?
  • Ask for feedback. Be vulnerable enough to say, “This scenario happened with this client. What could we have done differently? Was it something I should have done that I didn’t do?”

Remember, as Brolin’s softball story shows, empathy can be learned and relearned. You can unlearn behaviors that hurt others. Most people aren’t out to hurt others. They’ve just learned harmful patterns that they can change.

Your Empathy Is Revolutionary

Brolin’s journey from victim of empathy-free leadership to champion of emotional intelligence demonstrates that our profession’s future depends on leaders who understand that strength and compassion are partners in creating sustainable success.

Empathetic leadership drives measurable results through higher retention, stronger teams, sharper decision-making, and improved mental health. In an industry grappling with talent shortages and burnout, leaders who can authentically connect with their teams while driving results are essential for survival.

Women in accounting must reject false choices. You don’t have to choose between empathy and strength, between caring and competence. Your emotional intelligence is your competitive advantage.

As Audre Lorde reminds us, “Caring for others doesn’t make you weak. It makes you dangerous to systems built on indifference.”

Ready to hear Brolin’s complete journey and discover more tools for empathetic leadership? Listen to the full She Counts episode to learn how to turn your emotional intelligence into your greatest professional asset. The future of accounting depends on leaders brave enough to lead with both their heads and their hearts, and you’re uniquely positioned to show the way.