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Archives for November 2025

The Real Cost of Being Everyone’s Favorite Boss

Blake Oliver · November 4, 2025 ·

Madeline Reeves thought she’d hit rock bottom when she found herself face-down in a parking lot. She was wrong. That was before her million-dollar agency lost half its revenue in 30 days while she scrambled to save a monthly payroll costing anywhere from $88,000 to $102,000.

Meanwhile, Lynnette Oss Connell had engineered what she calls “a life of overfunctioning”—using technology and systems to layer on more and more responsibility instead of freeing up her time. When Oss Connell told her assistant she planned to add overnight Thursday shifts to handle overflow work, she expected pushback. Instead, her assistant asked how she could support the plan. That’s when Oss Connell realized, “Nobody’s coming to rescue me.”

In this episode of the Earmark Podcast, recorded at the Advisory Amplified Tour in Seattle, host Blake Oliver sits down with these two leaders who rebuilt their careers after burnout. Reeves, founder of Fearless Foundry and host of the Finding Fearless podcast, and Oss Connell, a CPA turned burnout prevention coach and founder of Burnout Bestie, share raw stories about what happens when professional success comes at the cost of personal destruction.

The Accounting Burnout Trap

The accounting profession doesn’t just attract service-oriented people. It rewards behaviors that lead to burnout. During one marketing event Reeves attended, personality testing matched attendees with unique drinks based on their personality types. The result? Out of 100 accountants, 97 received the same drink.

“This profession attracts a certain type of person,” Reeves observed. “For most accountants, their primary love language is acts of service. You live to serve. And that’s why I love accounting professionals.”

But that service mentality became destructive during the pandemic. Reeves led two firm communities during that period—one for female firm founders and another for advisory firms. For two years, she held space for leaders to “just cry privately together on Zoom because they were holding it together for their families and their staff.”

These professionals delayed their own compensation to maintain cash flow. They were filing PPP loans, figuring out EIDL requirements, and watching clients’ businesses collapse, all while absorbing the emotional and financial aftershocks.

“We went back to conferences and nobody was talking about what happened,” Reeves noted. “Doing that work for your clients was incredible, but it has a real impact on people.”

When Rock Bottom Has a Basement

Both Reeves and Oss Connell discovered that what feels like rock bottom often isn’t. “We all think we know what the burnout bottom feels like,” Reeves explained. “And then you’re like, oh wait, it can go even deeper.”

For Oss Connell, 15 years of building and rebuilding her CAS practice meant multiple burnout cycles. She had all the right support systems: a nanny, her mother as backup for her children, workflow software, and backup systems for clients.

“I had all the things you’re supposed to have,” she reflected. “But I didn’t put solutions in place that freed me up. I put solutions in place so that I could just layer more on.”

Her rainbow-blocked calendar, once a source of pride, actually represented something darker. “I was where the buck stopped and started, both at work and at home,” she explained. Even though work sometimes felt like a respite from personal stress, she wasn’t setting any real boundaries.

Reeves’s journey from that parking lot to losing half her revenue revealed similar patterns. As a service-oriented leader who loved building teams and culture, she initially got energy from mentoring her growing team. But soon she was coaching 12 employees while simultaneously mentoring all their clients, with two young children at home, a new marriage, and a recent move during the pandemic.

When four major clients, each worth over $100,000, canceled within 30 days through no fault of her team’s work, she scrambled to save everyone. She closed a $100,000 funding round in 30 days to save payroll. “That money was gone within a couple of months,” she admitted. “I was in the red for anyone who’s doing that math.”

The Three Warning Signs You Can’t Ignore

According to Oss Connell, burnout shows up in three distinct ways that serve as critical warnings.

First is emotional exhaustion. This can manifest in various ways, as seen with accountants, teachers, and healthcare workers during the pandemic.

Second is cynicism. It’s “that feeling of being jaded, the feeling that something you love doing, you now no longer find joy in. That is a big red flag,” Oss Connell says.

Third is a lack of accomplishment. You feel like “you’re on a hamster wheel, and no matter what you’re doing, you’re not getting ahead,” Oss Connell explains.

“Burnout isn’t the end of something,” she emphasizes. “It’s an indicator that you need to adjust something to be your most successful self.”

But recognizing these symptoms intellectually is different from acknowledging them emotionally. Both Reeves and Oss Connell waited for someone else to give them permission to stop.

“I was very conditioned, as I think most women are, to be a people pleaser,” Reeves admitted. She lived off the feedback of being told she did a good job, taking on clients from very large accounting firms despite values misalignment, because they represented good money and validation.

Oss Connell’s breaking point came when nobody challenged her plan to work overnight. “I desperately wanted somebody to intervene and say, ‘Hey, you’re doing too much.’ And nobody did.”

Rebuilding on Your Own Terms

Recovery required dismantling old structures and rebuilding with new boundaries. For Reeves, the first step was radical. “I stopped trying to be so likable.”

She audited every client in the firm’s history, dividing them into two categories: “love them or hate them.” Using this data, she analyzed patterns across services, timelines, and engagement types. This informed a complete overhaul of their service offerings.

“We redid our brand strategy, which clarified our ideal client. And that quickly kicked some people off the menu,” she explained. They productized all services, implemented annual repricing, and built documented processes so no single person was “the glue.”

“If I went on vacation for a week or two, people need to know how to onboard clients,” Reeves said. “If I’m the only person who can tell you how to do those things, that’s not very scalable.”

The firm now operates by a simple mantra: “Life is too short to work with people and projects you hate, so don’t do it.”

For Oss Connell, the solution involved honest conversations with her husband about their different visions for their co-owned firm. He wanted to grow and scale; she wanted to keep it lifestyle-oriented and small. They ultimately decided to sell the firm so neither had to compromise their vision.

These changes weren’t overnight. “It took us well over a year or two,” Reeves said, “but we stacked them one on top of the other and they unlocked.”

Community as Life Support

Strategic changes created the framework, but emotional support proved equally critical. Reeves and Oss Connell emphasize that isolation accelerates burnout.

“We need to have smaller spaces where we can talk candidly about what we’re going through,” Reeves said. This means being vulnerable—not in a performative way, but simply admitting “this is a part that I’m still working on” or “this part I haven’t figured out yet.”

The challenge is that many professional communities create pressure to present a polished image. “We’re all like A-plus students around here,” Reeves observed. “That pressure to show up and just show your shiny, polished ‘I have it figured out’ self is really high.”

But community requires effort to find. “Nobody’s going to come and be like, join our community, you really need this,” Reeves emphasized. “A lot of people who are like, ‘Well, I’m all alone.’ And I’m like, but are you seeking it?”

For Oss Connell, losing her entire support system during divorce while building her firm was devastating. “When I was struggling with my personal life and my firm, I had no support system, and I did not go out and search for it. That is probably the number one problem when I look back.”

Being in a community helps clarify identity. “I can see other people have these skills, and then I begin to see who I am better because I see who you are,” Oss Connell explained.

This extends to leadership transparency. Reeves now openly expresses stress to her team, clarifying, “This is not about you, this is just me getting it out of my body.” She’s learned to show anger or disappointment directly rather than always being the “nice boss.”

Oliver confirmed this approach works. “I talk to my employees when I feel stressed out, and it’s okay. You don’t have to be the perfect boss who has it all figured out. They really appreciate it when I’m honest.”

Breaking the Cycle for Good

The path forward requires accepting that sustainable success doesn’t require self-destruction. As Oss Connell frames it, burnout is an indication that you need to change something,” and that adjustment is ongoing. “As life moves on, your firm evolves. Society evolves. Your clients evolve. You’re going to need to continually recalibrate.”

The accounting profession faces a choice: continue celebrating martyrdom or recognize that sustainable success requires energized, not exhausted, practitioners. The pandemic showed us the incredible resilience of accounting professionals and the devastating personal cost of that resilience.

“When we set good examples of reducing stress for the organization, we equip our employees to be more sustainable as well,” Oss Connell noted. It’s about creating firms where everyone can thrive.

Listen to this episode to hear the full stories from Reeves and Oss Connell. Whether you’re experiencing warning signs or rebuilding from your own rock bottom, the conversation provides validation that you’re not alone and strategies for creating a practice that doesn’t require your destruction to achieve success.

When Auditors Become Robots: The Hidden Cost of Mechanical Box-Checking

Earmark Team · November 3, 2025 ·

For four to five straight years, an audit team meticulously completed their control testing checklists, dutifully checking every box and signing off on every procedure. Their work papers looked pristine. Their compliance documentation was flawless. And all the while, an employee was systematically committing fraud right under their noses.

When questioned about the controls they’d supposedly tested year after year, these auditors couldn’t explain how a single one actually worked. They had fallen into what CPA Sam Mansour calls “the checklist trap”—a dangerous mindset where the very tools designed to ensure audit quality become the biggest threats to it.

This eye-opening example comes from a recent Audit Smarter podcast episode where host Sam Mansour digs into the mechanical box-checking that passes for diligent auditing in too many firms today. While audit checklists are useful tools for quality control, they become dangerous crutches when auditors stop thinking beyond the boxes they’re checking.

When Good Tools Become Dangerous Crutches

Checklists start life as helpful guides. They’re designed by experienced professionals who’ve seen common audit problems and want to prevent them. They’re meant to be guardrails, keeping auditors on track while still allowing room for professional judgment and client-specific thinking. But somewhere along the way, these helpful tools can become dangerous.

The transformation happens gradually. As Mansour explains, “If the checklists say to go look at an area, you go look at that area. If they’re silent on a specific area, then you just don’t even consider going in there. So basically, instead of it being a helpful guide, it becomes a literal crutch.”

What starts as a helpful framework eventually limits an auditor’s perspective to what’s written on forms. 

The checklist mentality is particularly dangerous because it feels so professional. Auditors complete every step, sign off on every procedure, and produce work papers that look thorough. The documentation appears complete and compliant. But underneath the surface, there’s no critical thinking.

Consider the real-world example from the podcast: auditors who marked controls as “tested” year after year, checking all the right boxes and completing all the required procedures. Their checklists were perfect. Their sign-offs were current. But when questioned about how these controls actually worked, they couldn’t provide a single coherent explanation.

“There were severe control issues at the client which allowed for fraud to occur,” Mansour explains. “And it just wasn’t discovered by the audit team. The person committed fraud for four or five years. And I think the auditors just kept coming in and checking that box.”

The consequences were predictable and severe. The fraud continued undetected, not because the checklists were inadequate, but because no one was thinking beyond them.

This creates blind spots where fraud and errors can flourish. As Mansour notes, “Checklists are designed kind of as a textbook solution. The checklists don’t necessarily catch everything..”

The Hidden Forces That Kill Critical Thinking

The checklist trap isn’t the result of lazy auditors or character flaws; it’s the predictable outcome of systemic problems that even dedicated professionals can’t overcome through willpower alone. When we look beneath the surface of mechanical box-checking, we discover forces that make thoughtful auditing nearly impossible.

The most damaging culprit is budget pressure created by systematic underbidding. As Mansour explains: “Some firms tend to price engagements very low. And so let’s say, for example, your budget is $5,000 for an engagement, when really it should be $15,000.”

The math is brutal. If your firm targets $150 per hour but you’re forced to complete work in one-third the appropriate time, you’re effectively working for $50 per hour while still being held to $150-per-hour quality standards. This creates an impossible situation where taking time to truly understand complex checklists is financially unsustainable.

The cultural reinforcement runs deep. In many firms, the message from leadership focuses on completion rather than understanding: “Make sure you fill out these checklists, make sure they’re done correctly, make sure every box is checked.” This message, coupled with crushing deadlines and impossible budgets, transforms checklists from investigative tools into speed tests.

“A lot of times, unfortunately, in public accounting, that kind of curiosity, that dialog is seen as a waste of time because it takes up billable hours,” Mansour observes. The system rewards speed over understanding and punishes the curiosity that leads to quality work.

The training gap makes things worse, particularly for new auditors who find themselves drowning in technical terms they never learned in school. Mansour recalls his own experience: “I actually remember sitting there, looking at my computer, looking at my screen, and thinking, oh my gosh, I had no freaking clue what I’m doing.”

When new auditors are handed complex checklists filled with unfamiliar concepts but given no time to learn, mechanical completion becomes their only survival strategy. The system even punishes the behaviors it claims to want. Mansour describes being criticized early in his career: “The criticism that I used to get is look at this person next to you, how quick they are.”

While his colleague was flying through checklists, Mansour was taking time to understand the work and feeling “so far behind” and “so dumb” as a result. The irony? Years later, Mansour had surpassed his speedy colleague in seniority, proving that thoroughness ultimately beats speed. But how many talented auditors give up or develop bad habits before they can prove this point?

This creates a cycle where underbidding forces rushed work, rushed work requires increased checklist dependency, and checklist dependency reduces the quality that justifies higher fees. Breaking free requires systematic change.

Breaking Free: The Strategic Approach to Better Auditing

The path out of the checklist trap isn’t about abandoning structure or telling auditors to simply “think more.” It requires systematic changes that address the root causes we’ve identified. Forward-thinking firms are implementing coordinated solutions that transform their economic models, training approaches, and cultural expectations.

The foundation starts with honest pricing. Firms must have the courage to move their fees to industry-standard levels, even if it means difficult conversations with clients. As Mansour explains, when firms properly price their engagements and explain the increases, the client, a lot of times, will stay. Because if they ask around, they’ll find those fees are industry standard, and what they were getting with you was really an unreasonable deal.

Adequate pricing creates the breathing room necessary for thoughtful analysis rather than mechanical box-checking. With realistic budgets in place, firms can modernize their training by focusing on the “why” behind procedures rather than just the “what.”

Effective training requires creating psychological safety for new auditors to admit knowledge gaps. Mansour offers this advice to entry-level staff: “Look, if you don’t know it, you’re better asking the questions now. Because if I hear you asking in 12 months or 24 months those questions you should have asked in the first two, three, four months, I’m going to be very concerned.”

The shift requires moving beyond speed-focused metrics to value-based evaluation. Instead of comparing new auditors to experienced colleagues on time alone, managers should emphasize quality development first. As Mansour learned through experience, “You’re better off going slow and then picking up the speed later. Whereas if you start out with the speed to impress people, it’s difficult, I found, to pick up the quality.”

Practical implementation involves several concrete tools. Firms should customize audit programs for each engagement rather than using generic templates. Modern audit software can generate tailored checklists based on client-specific risk assessments. Adding professional judgment prompts throughout checklists helps auditors think beyond simple completion.

Mansour suggests incorporating “memory joggers,” brief explanations of how conclusions were reached. For example, when testing missing check numbers in a sequence, document not just what was done, but why. “We decided to test missing check numbers because we noticed irregularities in the sequence that could indicate control weaknesses or potential fraud.”

Successful firms also restructure their wrap-up meetings to discuss what was done and why it mattered. “We could say that we audited a specific area. But why did we choose to audit that area, especially if it’s not something we typically do?” Mansour asks.

The red flags that indicate continued checklist dependency are easy to spot. Work papers that remain essentially identical year over year signal mechanical copying rather than thoughtful analysis. Missing documentation of key discussions suggests auditors are focused on completion rather than understanding. Outdated information, like wrong contact names scattered throughout documents, reveals the copy-paste mentality that characterizes checklist traps.

Teams that successfully break free demonstrate clear evolution in their work. Their audit programs adapt as clients change and grow. They identify new risks and modify procedures accordingly. Most importantly, they can articulate the reasoning behind their decisions.

As Mansour’s technical reviewer wisely noted: “When the peer reviewers come in, they have a checklist, and their checklist is checking in on your checklist.” Understanding that audits exist within layers of professional oversight reinforces why thoughtful checklist use serves everyone’s interests better.

The Choice Between Clerks and Professionals

When auditors become mechanical box-checkers rather than analytical investigators, the tools that promise consistency and quality destroy the very thinking that makes work professional in the first place.  Clients deserve better.

This isn’t about individual auditors lacking motivation or intelligence. It’s about good professionals working within systems that punish the curiosity and analytical rigor their profession demands. When firms underbid engagements, create crushing time pressures, and reward speed over understanding, they train their staff to stop thinking.

On the other hand, firms that properly price their services, invest in real training, and create cultures that reward analytical thinking avoid the checklist trap and position themselves as the strategic partners their clients need.

The goal is to use checklists as launching points for professional judgment rather than substitutes for it. The firms that learn to balance structure with thinking will build stronger relationships, deliver higher value, and attract the talent that drives long-term success.

The complete roadmap for avoiding checklist dependency is available in the full Audit Smarter podcast episode, where Mansour provides detailed implementation strategies, specific examples of cultural transformation, and the exact frameworks successful firms use to turn checklist-dependent teams into strategic thinking powerhouses.

Because in the end, the choice is simple: Continue training clerks who check boxes, or develop professionals who think, analyze, and protect the interests they’re hired to serve.

Why This Firm Owner Woke Up Unable to Move After Planning Her Path to $3 Million

Earmark Team · November 3, 2025 ·

Picture being six months pregnant, climbing a ladder—not stairs, a ladder—in slingback heels to reach your desk in a famous New York fashion stylist’s loft. For most people, this would be a wake-up call about workplace safety. For Justine Lackey, it became the spark that pioneered virtual bookkeeping in the early 1990s, using FedEx, zip drives, and messengers to revolutionize an entire industry before online banking even existed.

In this episode of She Counts, hosts Nancy McClelland and Questian Telka welcome Lackey, a true trailblazer who built and sold a successful bookkeeping firm while challenging every assumption about what business success should look like. As McClelland shares in her introduction, Lackey is “a devoted mother to three and mentor and coach in her incubator program for bookkeepers and accountants growing their firms.”

When Your Body Knows What Your Mind Won’t Admit

“I’m an accidental entrepreneur,” Lackey explains early in the conversation. She landed in bookkeeping through a roommate’s invitation and never planned to build what she calls “the H&R Block of bookkeeping firms.” Without a college degree (she didn’t finish until 2009, well after she established her firm, Good Cents Management) or corporate experience, she lacked the traditional frameworks most firm owners bring to their businesses.

This lack of traditional structure had consequences. “Everybody says, ‘I wanna be successful,’ but that’s ambiguous,” Lackey says. “You have to get into the details of it. I wanna make $250,000 a year, or $500,000 a year. I wanna work 20 hours. I wanna have a team of five.” Without this clarity, she found herself swept along by what she identifies as cultural pressure to constantly expand.

The breaking point came during an Entrepreneurial Operating System (EOS) planning session with her team. Together, they mapped out a roadmap to $3 million in revenue. The math was clear: seven to nine bookkeeping teams with redundancy meant 14 to 18 bookkeepers. Add client service managers and a true integrator or COO, and they’d need approximately 28 employees.

“The energy in the room was like, yeah, woo!” Lackey recalls. “Like when you’re at conference world and you’re walking on hot coals.” Everyone left excited, including Lackey—until the next morning.

“I woke up and I literally could not move my right shoulder,” she shares. The pain was so severe her massage therapist couldn’t even work through the tension. “What is this weight on your shoulders?” the therapist asked. As Lackey recounted the previous day’s planning, the connection became clear. This wasn’t an injury; it was her body rejecting a path that violated her values.

The Hard Conversation Nobody Wants to Have

Recognizing she didn’t want to build a 28-person company meant facing her excited team with a complete reversal. “That’s ethical leadership in action,” Lackey explains. “That’s hard conversations.”

Lackey returned to her team with honesty, “It was really exciting and I believe this can be done. But at the end of the day, this is my life. I don’t wanna do that.”

“It’s terrifying to put your tail between your legs,” she admits. But as Telka points out, “Admitting that you have taken a wrong turn builds a lot of respect.”

This moment revealed a deeper truth about integrity. “We often talk about integrity in relation to other people,” Lackey notes, “but we don’t talk about integrity in relation to ourselves. When we’re out of alignment with integrity, that causes inner conflict and stress.”

Why Growing Sideways Beats Growing Up

The conversation then turns to a concept that challenges everything the industry teaches about success: lateral growth versus vertical growth.

“Whenever people on LinkedIn talk about having a successful firm, they always talk about revenue,” McClelland observes. “They almost never, ever, ever talk about profit or net income margins.”

Telka adds her favorite quote, “Revenue is vanity, profit is sanity.”

Lackey explains the difference. “Vertical growth is the most common type of growth people discuss—raising your revenue number and client acquisition. Those are really sexy numbers.” But lateral growth—the systems, processes, technology, and team development—”requires patience. It is very detailed, hard work.”

The challenge is that small firms can’t do both simultaneously. “There are very few people, particularly in smaller firms, who can do this all at once,” Lackey emphasizes. “So you need to make a choice.”

Her choice involved intentional constraints that seemed counterintuitive. She worked exclusively with QuickBooks Online, turning away Xero users even when they begged. She refused wholesale clients with inventory because she “hated counting bits and bobs and COGS.” These weren’t limitations; they were strategic decisions to build deep expertise.

Even technology decisions followed this principle. When Good Cents invested months implementing a new practice management system that the team hated, they made a shocking choice: abandon it entirely and return to Google Sheets. “Sometimes lo-fi is hi-fi,” Lackey explains. “Technology platforms are like people, and not all people are your people.”

The Blindfold Moment That Changed Everything

Perhaps the most powerful part of the conversation comes when Lackey shares how she discovered her business was actually a sellable asset. “When you live in a scarcity-based poverty mentality,” she explains, “it is hard for you to see a different reality for yourself.”

During one particularly frustrating period, she vented to a designer friend, “I’m so frustrated. I just wanna quit.”

“But you could just sell it,” the designer replied casually.

“Sell what?” Lackey asked, genuinely confused.

“It’s like I was blindfolded and somebody snatched the blindfold off,” she recalls. The designer pointed out the obvious: recurring revenue, strong operations, great clients. “You’re a great business. You could sell it.”

This revelation sent Lackey on a research journey. She devoured “Built to Sell” by John Warrillow in a single day and discovered firms were selling for about one times annual revenue. Her firm was worth more than her 960-square-foot cottage.

“I couldn’t even see what was possible for myself,” she admits.

When she eventually sold Good Cents in 2023, 28 potential buyers courted her. The relationships she’d built—including one client who’d been with her 22 years and had hosted her baby shower— created incredible value. “Relationships are assets,” Lackey emphasizes, “even if we can’t line item them on a balance sheet.”

The Secret Every Firm Owner Needs to Hear

Near the end of the conversation, Lackey shares what she calls “a secret that nobody talks about.” Every firm owner wants help.

This insight applies whether you run your own firm or work in someone else’s. “When you can come into a conversation and say, ‘I really like working here and I really like the work I’m doing, but these are the recurring problems and this is the solution I propose’—that takes courage,” she explains.

McClelland adds her own experience, “My best mentor ever taught me that important lesson. She said, ‘Come to me with solutions, not problems.’”

Your Next Step Toward Intentional Growth

Lackey now channels these lessons through her Modern Firm Challenge, a free five-day program running one hour per day. “My personal mission statement is that I help the world by helping people,” she shares. The challenge focuses on the biggest pain points: onboarding, monthly close, pricing, and increasingly, technology and AI.

“You’re not gonna fix all the things,” she tells participants. “You’re gonna look at the lessons and say, this is what I’m gonna focus on right now.”

McClelland predicts some firm owners might initially resist. “You’re telling me I need to slow down to speed up? I don’t have five days to take off to do this.”

But Lackey’s response is practical: “The classes are only an hour a day. We run them from one to two.” Plus, they record everything for those who can’t attend live.

The results speak for themselves. As Lackey notes, “I’m not here to tell you you can build a million dollar firm overnight. I’m here to tell you you can do whatever you wanna do, but it’s going to take time.”

Permission to Choose Your Own Path

The conversation closes with McClelland sharing a powerful quote from author Laurie Perez: “I reserve the right to evolve. What I think and feel today is subject to revision tomorrow.”

This perfectly captures what Lackey has given listeners: permission to have clarity about what they want and to change their minds when their goals no longer serve them.

Ready to build the business you actually want? Sign up to get on the VIP list for Lackey’s next Modern Firm Challenge at justinelackey.com/register. You can also find her on LinkedIn or join her free Facebook group, The Incubator, with about 4,000 members building community together.

As this episode of She Counts proves, building with intention rather than endless expansion might just be the key to creating the valuable, sustainable business you’ve always dreamed of, even if you didn’t know it was possible.

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