Tax Season

The Off-Season Work That Makes Tax Season Manageable

Earmark Team · March 23, 2026 ·

Imagine it’s mid-March, and an accounting professional just left for spring break with her family. The business tax deadline is days away, and she’s at the beach.

Meanwhile, at firms across the country, accountants are settling in for another late night, sustained by the promise of a half-day Friday sometime in June (if they’re lucky). Blackout dates stretch from January through April, and the unspoken rule is that personal lives get shelved until after the deadline.

These two realities coexist within the same profession during the same tax season. The difference isn’t luck or lighter client loads; it’s deliberate design.

Rachel and Marcus Dillon, owners of Dillon Business Advisors, have spent 15 years building a firm where tax season looks remarkably different from the industry norm. Their team of about 30 remote professionals works 36-hour weeks year-round, maintaining “Flex Fridays” even during peak filing season. Team members take spring break. And by mid-January, they’ve already filed dozens of returns because the real work happened months earlier.

During a recent episode of the Who’s Really the BOSS? podcast, the Dillons responded to a LinkedIn discussion that had been making the rounds. Their friend David Cristello asked, “How do you keep your team motivated during tax season?” When another friend jokingly suggested pizza parties—a tongue-in-cheek reference to the go-to perk at many firms—it sparked a deeper conversation.

The Foundation: Improvement Season Sets Up Success

When Marcus responded to that LinkedIn post about keeping teams motivated during tax season, his answer surprised some readers: “The hard work starts outside of tax season.”

It’s not a deflection. It’s the foundation that makes everything else at DBA possible. The firm operates on what they call “improvement season,” the period right after each tax deadline when the team identifies what went right and what went wrong and implements fixes before the next cycle.

The results speak for themselves. By mid-January 2025, DBA had already filed dozens of returns because the books were already closed. When you send financials to clients by the 15th of every month throughout the year, there’s nothing to catch up on in January.

This year-round engagement creates a ripple effect on tax season workload. The firm conducts tax projections in Q4, so clients already know roughly where they stand before the new year begins. When a business owner learns in October that they might owe $80,000 with their return, and the final number comes in at $50,000, that’s actually good news rather than a crisis. The cash flow conversation happened months ago, not in a panicked April phone call.

“We just try to minimize surprise as much as possible,” Marcus says.

But even with these systems in place, the Dillons are quick to point out they’re still learning. After acquiring two firms in 2025, they’re dealing with a higher volume of annual-only tax clients than they’ve had in years. This influx has highlighted some stark contrasts.

Take 1099 preparation. For monthly clients, the groundwork happens throughout the year. Client service managers review vendor payments quarterly and request W-9s as soon as they spot gaps. By January, there are usually only a handful of forms to chase down.

Annual-only clients are a different story. “We have no idea what’s been going on all year long,” Rachel explains. “We have no idea how many 1099s they’re going to need, if they’ve asked for W-9s or not, if they can get a hold of the people, if we can get a hold of the annual client.”

The experience has Marcus questioning whether they should even offer 1099 services to annual-only clients. “If you’re not engaging us for monthly recurring accounting services, you can do your own 1099s is kind of how I’m feeling at this point,” he says. Though he adds with a laugh that since team members probably listen to the podcast, they might hold him accountable for that change next year.

Team Structure That Creates Real Flexibility

Having year-round client touchpoints only works if you have the right people consistently delivering those services. At DBA, that happens through their “Team of Three” model, a structure Marcus calls “one of our biggest wins by far.”

For monthly clients, the model assigns three distinct roles to every client relationship. The Client Service Manager handles all communication and administrative tasks. The Client Controller focuses on preparation and review. The Client CFO provides complex review, planning conversations, and quality control.

This separation might sound simple, but the impact runs deep. When administrative tasks get pulled out and assigned to someone whose specific job is coordination, preparers and reviewers suddenly have hours back in their week.

“Breaking out the administrative parts and giving those to a professional who can handle them and communicate with clients gives a lot of time back to preparers and reviewers,” Rachel explains.

The same structure now applies to annual-only tax clients, a recent adaptation as they handle more of these relationships. The Tax Administrator manages all client communication, including sending organizers, accepting documents, generating engagement letters, and handling the back-end filing process. The Tax Controller handles preparation, often reviewing simpler returns. And their Director of Tax and Financial Planning provides oversight, education, and handles complex returns.

This structure creates essential coverage. When someone takes time off, two other team members understand each client relationship. Work doesn’t pile up while someone’s away.

The coverage philosophy shapes how DBA handles time-off requests. Before approaching leadership, team members coordinate with their Team of Three to ensure coverage. “You have to let your team of three know the dates and make sure it doesn’t put somebody else in a weird spot,” Marcus explains.

This approach makes possible what would seem impossible at traditional firms: client controllers taking spring break in March, right when business tax deadlines hit.

Rachel addresses the human reality behind these decisions. “When someone takes more than a day or two of PTO, it’s rare that they’re going alone somewhere. Most of the time, they’re traveling with their family, extended family, or friends for a special occasion.”

The Dillons understand this firsthand. They started taking spring break specifically because it was the only time their daughters’ swim practice and school schedules aligned. Expecting employees to forfeit those windows because of arbitrary blackout dates ignores how life actually works.

Marcus doesn’t mince words. “If you have blackout dates and you tell people they can’t live life during four months out of the year, they’re not going to leave your accounting firm for another accounting firm. They’re going to leave your accounting firm for another profession or another industry altogether.”

The team also maximizes efficiency through technology. Every deliverable, from financials to tax returns and projections, includes video commentary recorded through Vimeo. Clients watch explanations on their own schedule, rather than booking meetings just to review numbers. Zoom phones enable text messaging that looks direct but feeds into practice management systems, meeting clients where they communicate while maintaining boundaries.

Marcus notes that team members are often most productive right before vacation. “You are most efficient and effective right before you go out of town,” he observes. The team plans accordingly, with people getting ahead on work before time off rather than dumping it on colleagues.

Building a Culture Beyond Temporary Perks

The LinkedIn discussion that sparked this podcast episode revealed something telling about the profession. When asked how to keep teams motivated during tax season, someone jokingly suggested pizza parties, and everyone got the joke because nearly everyone has worked somewhere that tried to make up for brutal hours with free food.

“For us, as a remote team, that would cost a lot of money to send everybody pizza,” Marcus notes about their 30-person team. But cost isn’t the real issue. “Being in different roles over my career, knowing my voice is being heard means way more to me than a slice of pizza.”

At DBA, that philosophy takes concrete form. The firm maintains a shared spreadsheet where any team member can nominate a client for exit at any time. Leadership might see completed work and paid invoices, but they don’t witness the difficult phone calls or patterns of disrespect that make certain clients exhausting to serve.

This isn’t just lip service. In what they’re calling their “year of refinement” for 2026, DBA has shortened its tolerance for poor-fit clients. “In the past, we would give people a couple of different opportunities to tell us no,” Marcus says. “Where we’re at today as a business, it’s just one time to tell us no before we exit that client relationship.”

The same philosophy of actually listening to the team’s needs shaped their benefits evolution. Half-day Fridays started as a summer perk to give back time worked during tax season. Then it expanded to most of the year. Now it runs year-round, including during tax season. A full-time employee at DBA works 36 hours, not 40.

“We didn’t want to take it away from people,” Marcus says simply. “A lot of clients aren’t around on Friday afternoons either.”

PTO evolved similarly. In 2025, the firm extended paid time off to part-time team members, in proportion to their hours. But tracking PTO across multiple systems created an administrative burden that defeated the purpose. “Ultimately, you want people to use their PTO and have time off, not necessarily be worried about tracking their PTO,” Marcus explains.

Effective January 1, 2026, DBA moved to unlimited PTO with guardrails around approval and booking limits. The policy includes part-time team members.

Marcus addresses the common criticism head-on. “I know it’s been discussed that people take less time off with unlimited PTO. That is not our intention at all.”

For individual tax clients who might otherwise only appear at filing time, DBA offers its Tax Advisory Plan (TAP). This monthly recurring service includes tax preparation plus two annual projections, one mid-year and one year-end, each with a consultation. Clients get introduced to their dedicated team, so when questions come up, someone familiar with their situation responds without hours of research.

“We have solved for that with our tax advisory plan,” Rachel says. The service transforms annual relationships into year-round engagement, turning filing-time scrambles into predictable workflows.

“Allowing your team more freedom to go home at a normal time, every day and all year long, is going to go a lot further than a one-time meal or party,” Rachel says, capturing what actually matters to team members.

Taking Control of Your Firm’s Tax Season

The Dillons freely admit they’re not perfect. They’re dealing with integration challenges from two recent acquisitions. They’re still figuring out whether to offer certain services to annual-only clients. Marcus is currently working from a poorly insulated sunroom in an Airbnb because their Fort Worth house renovation isn’t finished. But their approach offers a blueprint built on three principles that any firm can adapt.

Start improvement season immediately after tax season

The work that makes January through April manageable happens in the months after the previous deadline. When clients know their tax position from Q4 projections and books stay current monthly, there’s nothing to scramble over in March.

Structure teams for coverage, not just efficiency

The Team of Three model distributes work and creates redundancy. When someone leaves for spring break, two others understand every client relationship. Breaking out administrative from technical work maximizes everyone’s strengths.

Listen to what teams actually want

Sustainable practices beat temporary perks every time. Team members want their concerns heard and acted on. They want to attend their kids’ events, travel when their families can travel, and not have their lives dictated by arbitrary deadlines.

“We’re not up against the CPA firm down the street anymore. It’s a different ballgame,” Marcus says, putting the stakes in perspective. Talented professionals have options beyond public accounting, and firms that don’t adapt will lose team members to other industries.

Listen to the full conversation on the Who’s Really the BOSS? podcast for additional insights about managing life transitions during busy season, specific tools for client communication, and how the Dillons are applying these principles during their own busy season. As Rachel notes at the end, “All of these things eliminate the need for staying at the office until midnight doing actual work because all you’ve done all day is put out fires.”

Tax season doesn’t have to control your firm. But escaping that cycle requires doing the hard work when everyone else is taking a breather. The firms having calm tax seasons aren’t lucky; they’re prepared.

Listen to the complete episode to hear how DBA is navigating tax season, managing team growth from recent acquisitions, and keeping their Flex Friday promise even in the thick of filing season.

Rachel and Marcus Dillon, CPA, own a Texas-based, remote client accounting and advisory services firm, Dillon Business Advisors, with a team of 15 professionals. Their latest organization, Collective by DBA, supports and guides accounting firm owners and leaders with firm resources, education, and operational strategy through community, groups, and one-on-one advisory.

From Data Entry Nightmare to Automated Workflow in One Demo Session

Earmark Team · February 2, 2026 ·

You’re ten days away from the 1099 and W-2 deadline, and you’re still wrestling with QuickBooks, fielding a flood of W-9 request emails, and dreading the inevitable data entry marathon. Sound familiar?

You’re not the only one. As David Leary admitted during a recent Earmark Expo webinar, “I’ve been procrastinating on issuing 1099s. It’s just not a great experience.” He described the dual frustration that many accountants know all too well. “It’s annoying work on both sides. I need to do my 1099s, but then, as a business that receives them, I get a slew of emails from other companies asking for a W-9.”

In the webinar, David and co-host Blake Oliver took TaxBandits for a test drive with Nikita Sullivent, the company’s Support Specialist, to explore how this IRS-authorized e-file platform handles over 70 tax forms. The live demo included the authentic technical hiccups we all face with real-world software and shared practical solutions for the compliance challenges that hit every January.

Getting your data in: from hours to minutes

Manual data entry for hundreds of 1099s is a bottleneck that keeps you from serving more clients. TaxBandits tackles this with multiple import options that meet you where your data lives.

The platform offers three main paths for getting data in. You can:

Enter forms manually one at a time (perfect for that forgotten contractor),
Use bulk upload templates for larger volumes, or
Connect directly with accounting software (current integrations include QuickBooks Online, Xero, Sage Intacct, and Zoho, with Karbon integration coming soon).

The bulk upload process stands out for its simplicity. As Nikita demonstrated, “You’re reviewing the columns at the top and inputting the data beneath them. Once we have all of that data input, we’ll just download it as a CSV and drag and drop it in.”

David particularly appreciated one detail. “I like how on your templates, in the header of each column, you give the instructions for the values you accept in that field.” No more guessing whether to use “CA” or “California,” or whether TINs need dashes.

The workflow breaks down like this:

Download the Excel template with clear column headers
Fill in your data following the built-in instructions for each field
Drag and drop the file into TaxBandits
Review the automatic error check that flags issues like missing digits in EINs or duplicate records
Fix any problems by either editing in the app or exporting just the error records for correction

For QuickBooks users wondering about the process, David confirmed you can export your vendor list, filter for 1099 vendors, and use the “upload your own file” feature. The first time requires mapping your fields to TaxBandits’ fields, but that mapping saves for future uploads.

One webinar attendee asked whether they needed to re-enter last year’s payees. “Absolutely not,” Nikita answered. “Everything stays in your account and rolls over year after year.” When you import this year’s data and the system finds a duplicate, you can either delete it or update the existing record with any changes.

The platform also distinguishes between importing only recipient data and importing both payer and recipient data. If you maintain TaxBandits throughout the year, importing just recipients during filing season works best since you’ve already set up your payers. But if you’re adding everything at once, the combined import saves steps.

With data flowing smoothly into the system, the next challenge is ensuring that data won’t bounce back from the IRS.

TIN verification: the new compliance reality

Getting data into the system efficiently matters only if it passes IRS validation. The agency’s transition from the FIRE system to IRIS (Information Returns Intake System) brings stricter requirements that every accountant needs to understand.

“The IRIS system is going to be far stricter on TIN matching than the FIRE system was,” Nikita warns. “Which means if the SSN, the EIN, the TIN, and the recipient name don’t identically match the IRS database, it’s going to kick the form back to you as accepted with errors, and you have to file a correction.”

The keyword is “identically.” A contractor who goes by “Mike” but whose Social Security card reads “Michael” could trigger a rejection. Even punctuation differences in business names can cause problems.

TaxBandits builds TIN verification into multiple touchpoints:

When collecting W-9s throughout the year
When adding recipients to your address book
During the 1099 workflow as a final check

The smart approach starts early. “When you get a W-9, when you get a new employee or contractor, you go ahead and do the TIN matching on that prior to the filing season,” Nikita advised. This prevents last-minute surprises when deadlines loom.

Verification typically returns within two to four hours during normal periods. But during peak season “it can be up to 24 hours,” Nikita warned. If you’re verifying TINs within the 1099 workflow itself, the system waits for results before transmitting, which is potentially problematic if you’re filing on January 31st.

For those worried about the cost of corrections, TaxBandits offers some protection. Their “TaxBandits Commitment” covers correction filings at no additional charge. But even free corrections cost you time and stress.

The platform also streamlines W-9 collection. Instead of chasing paperwork, you can send electronic W-9 requests. Recipients complete them online, and the data flows directly into your TaxBandits account, ready for immediate TIN verification if desired.

Once your forms are prepared and verified, you still need to get them into recipients’ hands compliantly.

Distribution flexibility that actually works

The old choice between hours at the post office or forcing everyone into electronic delivery is over. Modern distribution needs flexibility, and TaxBandits delivers exactly that.

“Everything is very customizable to your needs,” Nikita explained when asked about mixing delivery methods. “You can choose some postal mail, some online access, and some want both.”

The three distribution paths each serve different needs:

USPS postal mailing handled entirely by TaxBandits
Electronic recipient portal requiring just an email address
Both options for recipients who want backup

The electronic portal solves a critical compliance issue. The IRS requires formal consent for electronic delivery, so you can’t just email a PDF. TaxBandits automates this. Recipients receive a secure link, enter a PIN for verification, and provide documented consent.

If someone ignores that email, the system tracks everything. You can see who consented, who declined, and who never responded and then handle postal delivery for the holdouts.

For returning recipients, the portal builds value over time. “If you file for that same recipient next year, they’ll use the same link, and they’ll access all of the documents from the same portal,” Nikita noted. Recipients get their own organized tax document archive without any extra work from you.

State filing adds another compliance layer, but TaxBandits simplifies this, too. The platform tells you exactly what each state requires:

States requiring direct filing (you handle separately)
Combined Federal/State Filing participants (automatic forwarding)
States requiring no 1099 filing

Throughout the process, you get real-time status updates so you can see which forms were transmitted to, received by, and accepted by the agency. For postal mail, statuses are submitted to USPS and en route to the recipient. When a client claims they never received their form, you have documentation. After transmission, watermarks disappear from your copies, and you can reprint professional versions anytime.

For firms with multiple preparers, the platform offers even more control through team management features.

Scaling with teams and support

Larger firms need more than just bulk upload; they need workflow management. TaxBandits’ team management features let you maintain control while delegating the actual work.

The system offers three permission levels:

No roles: Any team member can prepare, approve, and transmit
Two roles: Preparers create forms, approvers review and transmit
Three roles: Preparers create, approvers review, transmitters handle payment and filing

You can also create location-based groups. Nikita shared an example. “Say you have a group in Indiana and a group in Tennessee. Anytime you add a new payer and assign them to the Tennessee group, then all of the team members included in the Tennessee group have access to that payer.”

Support is critical when things get complex. During busy season, TaxBandits extends hours to 8 a.m. to 8 p.m. Eastern. They offer phone, email, and chat support, plus an AI assistant that pulls from both their knowledge base and IRS guidelines.

The platform’s YouTube channel provides step-by-step videos for specific workflows. For Sage Intacct users who asked about integration, Nikita recommended checking their channel for detailed walkthroughs showing the complete process from Sage to TaxBandits.

Pricing works on a credits system with bulk discounts. Buy more credits upfront, pay less per form—and credits never expire. As Nikita confirmed when asked about rollover, “Your credits will never expire. So if you want to purchase for the next five years now and get the best price we can give you, go for it.”

Making next year easier starts now

The strategies demonstrated in this webinar show a fundamentally different approach to information returns. TaxBandits treats compliance as a year-round process rather than a January panic.

The IRS’s push toward e-filing mandates and stricter validation isn’t slowing down. The IRIS system is just the beginning of modernization efforts that will continue tightening requirements. But the webinar demonstrated real workflows you can adopt immediately, from template imports to electronic W-9 collection to role-based team permissions.

Ready to transform your 1099 and W-2 workflow? Watch the full Earmark Expo webinar to see TaxBandits in action, including the complete demo of bulk uploads, error checking, and team management features. The platform offers over 70 tax forms beyond just 1099s and W-2s, making it a comprehensive solution for year-round compliance needs.

The Fun CPA Shares How to Work No More Than 40 Hours In Tax Season

Earmark Team · March 3, 2025 ·

For many accountants, working just 40 hours a week during tax season sounds like a fantasy.Tax pros often work 60+ hours for months straight, wearing those long hours as a “badge of honor” in a profession that glorifies the grind.

Yuri Kapilovich, known as “The Fun CPA,” has rejected that model entirely. He’s built a practice where he works just 40 hours during tax season and just 10-15 hours per week the rest of the year. His firm generates roughly $225,000–$250,000 annually, giving him time for family, fitness, and hosting memorable networking events.

Earn CPE for this episode: You can earn Continuing Professional Education credit by listening to the podcast and then taking a brief quiz in the Earmark app.

Escaping the Public Accounting Treadmill

After 12 years and seven different firms, Yuri kept encountering the same frustrating culture: pressure to bill more hours, looking busy for appearance’s sake, and efficiency being punished.

“I would look at these partners who are in the office more than I am. I’m leaving and they’re still there,” he recalls. “They have a boss, just like I have a boss. If I can make $800,000 and work 10 to 2, I would have stayed. But you can’t.”

Yuri decided to break free by purchasing a small block of clients from a friend. That deal unexpectedly fell apart, but he decided to move forward anyway. He contracted part-time with two CPA firms, working two or three days a week while gradually building his client base. This bridge approach kept his income steady and let him say “no” to prospective clients who weren’t a good fit.

The Economics of Premium Pricing

The foundation of Yuri’s business model is simple but powerful: charge more, serve fewer clients, and provide exceptional value. He started with a minimum fee of $800 and now won’t take on any tax-only client for less than $2,000.

Yuri emphasizes that working fewer hours doesn’t mean delivering less value. It’s about charging enough to serve clients well without drowning in low-fee work. He explains the difference between accepting hundreds of returns at $300–$500 each—earning decent revenue but shouldering an avalanche of busywork—and serving fewer clients at a much higher minimum fee.

Here’s how the math works when comparing traditional high-volume practices to his approach:

Traditional Model:

300 clients at $500 per return = $150,000 revenue
At least 1 hour per client (realistically more with admin, communication, etc.)
300 hours over just 8 weeks (Feb 15 – Apr 15) = 37.5 hours weekly at a minimum
Reality: Information arrives late, questions pile up, schedule compresses
Result: 60+ hour weeks, constant administrative chaos

Yuri’s Model:

100 clients at $2,000+ per return = $200,000+ revenue
Higher-value clients with more complex needs
Work spread more evenly, better boundaries
Result: 40-hour weeks max, even during tax season

That doesn’t simply triple his revenue per client—it dramatically changes his day-to-day life. He feels in control of his workload, and his clients benefit from more personalized attention.

The most surprising discovery? Yuri says, “As the price went up and as you’re dealing with somebody who’s seeing your value, you know what goes down? The number of questions, the number of bothers.”

Service Packages That Create Value for Both Sides

Beyond standalone tax returns, Yuri offers:

Quarterly Package: Starting at $1,500 per quarter ($6,000 annually)

Tax preparation for business and personal returns
Proactive tax strategy discussions
Quarterly planning meetings (approximately one hour each). Having this regular touchpoint helps avoid unpleasant surprises in April.

Monthly Package: The “full service” option

Everything in the quarterly package
Bookkeeping (outsourced locally in Brooklyn)
He still maintains a quarterly meeting schedule rather than monthly. This structure keeps everyone on track but prevents excessive demands on his time.

Life by Design: What Freedom Looks Like

In large firms, partners can earn very high incomes—sometimes $800,000 or more a year. But from Yuri’s perspective, those partners often trade away family time, mental health, and control of their schedules to hit those numbers. Many are still at their desks long after younger staff have gone home.

Yuri has optimized his practice to support his priorities:

family time with his two young children (ages 2 and 6),
fitness, and
enjoying life.

His summer schedule is particularly enviable. “My friends make fun of me, and it’s partially true—I don’t really work. Especially in the summertime, it’s like 2 to 3 hours a day at most. And we can do it from anywhere.”

He’s accessible to clients (they can text him directly), but because he’s selective about who he works with, this accessibility doesn’t become overwhelming. He even occasionally takes client calls while at the gym.

Yuri also hosts creative networking events to bring business owners together. When asked what he gets from these events, he answers simply: “I have no goal. I literally am here to put these people together so they can interact and do business together.”

Breaking Free: Advice for Building Your Practice

If you’re considering a similar path, Yuri offers these tips:

Start with Contract Work
“My advice to anybody looking to go out on their own—try to find a contracting gig. Those 2 to 3 days will keep the lights on while you build your firm the way you want to with the other 2 or 3 days.”

Start with Higher Fees Than You Think

“If you’ve already built a firm with a lot of volume but want to get to the value aspect, it is extremely difficult to just all of a sudden say, ‘By the way, I know I was charging you $500, it’s $1,000 now.’ Not only will you lose the client, but you’ll lose reputation and street cred.”

Be Ruthlessly Selective About Clients
“Here’s how the conversation typically goes with a prospect looking for cheaper returns: ‘Hey, are you taking on clients like me?’ And I’ll say, ‘Are you a business owner?’ And they’ll say, ‘No, I have a W-2 only.’ I’m like, ‘I’m happy to work with you W-2 only. My minimum fee is $2,000.’ Then I stop talking.”

Create a Memorable Brand

Whether intentional or not, having something that makes you stand out helps attract the right clients and sets expectations about your approach to accounting.

Building the “Fun CPA” Brand

Establishing a personal brand was a key part of Yuri’s strategy. His Instagram handle and hashtag—#thefunCPA—emerged almost by accident. But it quickly set him apart in an industry that often feels stiff. He showed up at events with “Fun CPA” banners, printed T-shirts, and a big smile, which made people do a double take.

Yuri also hosts networking events that don’t feel anything like typical “mixers.” He might invite business owners on a boat outing or to a local hangar party where private jets are on display. His main purpose is to connect people and let them create business opportunities together. If they want to talk taxes or accounting, they’ll ask.

Rethinking Success in Accounting

The accounting profession often measures success by top-line revenue and billable hours—metrics Yuri calls “trash” and “imaginary.”

“I think as a profession we need to refocus. And especially if we want to fix this pipeline problem, the way we do that is by focusing on the people—your number one asset,” he says. “When you neglect that and just grind them for billable hours that mean absolutely nothing, it is of no surprise to me that people are leaving.”

Yuri’s model shows that building a profitable, sustainable practice that prioritizes accountant and client well-being is possible. By serving the right clients at the right price, you can transform accounting from a seasonal grind into a genuinely rewarding career—one with time for birthday celebrations, family dinners, and maybe even the occasional boat day.

Want more details? Listen to the full Earmark Podcast episode with Yuri Kapilovich, and don’t forget you can earn CPE credit by downloading the Earmark app and taking a quick quiz after you listen.

Building Sustainable Accountability: How to Maintain Momentum Year-Round

Earmark Team · February 24, 2025 ·

Every January, millions of people set out to transform their habits, only to find themselves struggling by mid-month. In fact, the second Friday of January is known as “Quitters Day,” when many throw in the towel on their New Year’s resolutions. For accounting professionals, the challenges compound: a 2024 Forbes study reports that 50% of resolution-makers quit by March—precisely when tax season intensity is at its peak.

In a recent episode of the Who’s Really the BOSS? podcast, Rachel and Marcus Dillon of Dillon Business Advisors (DBA) acknowledge these hurdles but also share practical ways to overcome them. As accounting firm owners, they see firsthand how easy it is for accounting professionals to abandon both personal and professional goals amid looming deadlines and long work hours. Yet the Dillons have developed reliable strategies—grounded in accountability and careful planning—that can keep momentum strong year-round.

The Unique Pressure on CPA Firm Owners

While most people struggle to sustain enthusiasm after the holidays, accounting firm owners have a double challenge. January’s fresh start quickly collides with ramping up for busy season, and by the end of March, many people’s goals have fallen by the wayside. After April 15th, it’s tempting to celebrate the season’s end or simply recover, making it even harder to pick up abandoned routines.

“I just do not like January at all,” admits Marcus. “A lot of us grew up in accounting—we dread January and starting the year new.” When you start with a clean P&L and the celebration of last year’s successes ends, accountants often feel they’re starting from scratch. Layer on the time crunch of tax deadlines, and it’s easy to see why many resolutions vanish by March.

Rachel adds, “You think ‘I just need to get through the next few weeks or this deadline,’ and really, you just let everything from January and February go.” Instead of waiting for post-deadline recovery to refocus, the Dillons recommend building accountability systems that prevent goals from slipping in the first place.

Goals for 2025: Firm Growth and Beyond

The Dillons prefer the concept of measurable goals over open-ended resolutions. DBA heads into 2025 with clear objectives:

Organic growth. DBA plans to add 15 new monthly recurring clients in 2025. With a price point for each client at $2,000 or more per month, this goal translates to adding $30,000 in new monthly recurring revenue by year’s end. To manage quality control, DBA limits each “pod” to two new client onboardings per month.
Potential firm acquisition. Beyond organic growth, the Dillons are open to non-organic expansion through the right acquisition. This approach provides additional career advancement opportunities for existing team members.
Technology & process improvements. Newly hired Director of Technology, Angel Sabino, will evaluate DBA’s IT systems and relationships to ensure they can support future growth. The team plans to expand its use of Keeper for client workflows and more automation in their onboarding process. They also plan to eliminate software they’re not fully testing or utilizing to free up room in the budget and focus on enhancing core platforms.
Team development. Client Service Managers meet monthly to share best practices, while Controllers hold their own dedicated development sessions. This ensures training and collaboration throughout the year. New and existing SMEs (Payroll, Tax, QBO) serve as go-to resources for the rest of the team. DBA plans to hire additional staff, including a Controller and a new Client Service Manager Assistant through TOA Global.

“Even though goals like these can feel daunting, we break them down,” Marcus explains. “We track them month by month, adding them to our weekly meeting agendas and quarterly reviews. That way, no one person is carrying the full burden, and we can re-evaluate often.”

Personal Accountability: Small Steps, Big Payoffs

Both Rachel and Marcus rely on personal accountability to stay on track.

Fifteen years ago, Rachel began a morning weightlifting habit and hasn’t stopped. In 2024, she hit 302 workouts—exceeding her personal target of 300—by tracking each session in a free app. Visibility of her progress, especially late in the year, motivated her to stick with the plan.

“I track everything so I can see how far I’ve come,” Rachel explains. “When we traveled to New York, I still got up early because I knew I had a goal I wanted to meet.”

Marcus uses a structured approach spanning faith, marriage, health, and more. “I assign a measurable goal or metric to each category—did I do it or not?” he says. That clarity helps him refocus on days he would rather skip workouts or other commitments.

“Sometimes I literally break a workout into percentage points. If I’m halfway done, that’s 50%, and I tell myself I’m not going to quit at 50%. Same when I’m at 75%. It keeps me motivated.”

Accountability Strategies to Withstand Tax Season

How do you maintain progress toward goals when you’re knee-deep in client work? The Dillons recommend three main strategies:

Break it down. Make goals specific and measurable, then divide them into weekly or daily steps. Whether it’s limiting client onboarding each month or aiming for 20-minute workouts, smaller tasks are more achievable.

Keep it visible. DBA incorporates goals into weekly meeting agendas, ensuring they’re never “out of sight, out of mind.” Similarly, Rachel’s app and Marcus’s weekly check-ins with his accountability partner keep them aware of their personal targets.

Stay flexible. Life happens—especially during busy season. The Dillons suggest building in reassessment milestones (e.g., a mid-year retreat in May or June) to pivot if goals no longer make sense. Instead of abandoning them, adjust and realign.

Looking Ahead: The Collective by DBA Event

For accountants seeking deeper connections and guidance, the Dillons’ peer community, Collective by DBA, is hosting an in-person event on May 5th–6th in The Woodlands, Texas (with a third-day session on May 7th for forum members and one-on-one advisory clients).

Registration opens on January 28th, and only 50 seats are available. The retreat provides an opportunity to fine-tune your firm’s processes, swap insights with other leaders, and solidify your goals for the rest of the year.

“If it’s anything like our event last May, it’ll fill up fast,” Marcus says. “We’re building an agenda that dives into topics like firm growth, technology, and team structure—all the areas we’re working on ourselves.”

Maintaining Momentum Beyond January

While most resolutions taper off by March, the Dillons prove that real progress can happen any time of year—with the right structure. By breaking down targets, checking in frequently, and involving others, firm owners can continue working toward their goals well past busy season. Whether you’re building better habits in your personal life, scaling your firm, or both, the key is accountability—layered at the individual, team, and organizational levels.

Ready to learn more? Tune in to the Who’s Really the BOSS? podcast for the Dillons’ full conversation on goals and accountability, and consider joining them in May at Collective by DBA’s in-person event. Even in the throes of tax season, sustainable, measurable goals are possible when you have a plan—and a team—to keep you on track.

Balancing Efficiency and Quality: How One CPA Firm Transformed Their Tax Season

Earmark Team · July 23, 2024 ·

For many CPA firms, tax season means long hours, stressed employees, and a frantic rush to meet deadlines. But Marcus and Rachel Dillon, owners of a family-run CPA firm and hosts of the Who’s Really the BOSS? podcast, have found a way to break that cycle.

In 2024, the Dillons filed 165 tax returns before April 15th while maintaining a strict no-overtime policy and growing their recurring revenue by 10%. How did they do it? By leveraging innovative tools, adapting their team structure, and fostering a culture of continuous improvement.

The Dillons’ journey wasn’t without challenges. Heading into the 2024 tax season, they faced significant changes:

• Their full-time tax director had left to start his own firm

• They had downsized by three full-time employees

• They had exited about 35 family-client relationships

To address these challenges, the Dillons made several strategic moves:

1. Implementing Innovative Tools

The firm rolled out Canopy software, replacing its existing practice management system. This improved internal project tracking and time management. More importantly, it enhanced client communication through automated tax status updates.

“What we did build out and tested during tax season was tax status updates being sent to the clients through Canopy,” Marcus explained. “It’s essentially the Domino’s Pizza tracker.” This system provided clients real-time updates about their tax returns without requiring additional staff time—a perfect example of technology improving efficiency and quality.

2. Adapting Team Structure

Rather than hiring a new full-time tax director, the Dillons hired a “tax director of counsel” on a flexible, as-needed basis. This arrangement allowed the firm to maintain high-quality tax services without the overhead of a full-time position.

They also hired a Director of Operations, Amy, who took on many administrative tasks previously handled by the tax director. This freed up other team members to focus on client work.

3. Fostering Continuous Improvement

When the Dillons identified knowledge gaps in their team, particularly for those without strong tax backgrounds, they implemented weekly training sessions. Marcus personally reviewed tax returns with team members, using actual client work as teaching material. This hands-on approach allowed team members to learn in real-time and improve their skills.

The Results

The Dillons’ strategic changes paid off. Here are some key metrics from their 2024 tax season:

• 165 tax returns filed before April 15th (down from 224 in 2023, but with fewer staff)

• No overtime or weekend work required

• Maintained half-day Fridays throughout tax season

• 10% increase in recurring Client Accounting Services (CAS) revenue

• Overall revenue on track to reach $3 million for the year

Perhaps most impressively, they achieved these results while maintaining a 36-hour work week for most employees. This focus on work-life balance starkly contrasts the grueling schedules often associated with tax season.

Lessons Learned

The Dillons’ experience offers valuable insights for other CPA firms:

Embrace technology: The right tools can dramatically improve both internal efficiency and client communication.
Be flexible with staffing: Consider alternative arrangements like fractional or on-call experts to fill skill gaps.
Invest in continuous learning: Regular training sessions can quickly address knowledge gaps and improve team capabilities.
Prioritize work-life balance: It’s possible to maintain high standards without sacrificing employee wellbeing.

As the accounting industry evolves, firms that can balance efficiency and quality will have a significant competitive advantage. The Dillons’ story shows that with the right strategies, it’s possible to thrive during tax season while still maintaining a healthy work environment. For more tips and tricks, listen to the full episode of Who’s Really the BOSS?

Rachel and Marcus Dillon, CPA, own a Texas-based, remote client accounting and advisory services firm, Dillon Business Advisors, with a team of 15 professionals. Their latest organization, DBA | FIRM, supports and guides accounting firm owners and leaders with free resources, education, and operational strategy.