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Burnout

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.

Stop Talking About Culture and Start Fixing These Three Problems

Blake Oliver · September 13, 2025 ·

“There’s nothing worse we can do for our people and our organizations than doing it the way we’ve always done it,” says Erin Daiber, CPA and founder of Well Balanced Accountants. In this episode of the Earmark Podcast, Daiber joins host Blake Oliver to tackle one of accounting’s biggest challenges: how to actually change firm culture instead of just talking about it.

From Big Four Burnout to Culture Coach

Daiber’s story starts with an ironic twist. When she entered business school, she told her parents she’d do “anything but accounting.” Yet a professor convinced her she was good at it, and at 19 or 20 years old, she took that advice to heart. “Being at that moldable stage, I thought, well, okay, I guess that’s what I need to do,” she recalls.

While she doesn’t regret her path, Daiber discovered a fundamental mismatch between her personality and the detailed work required at the staff and senior levels. “I’m not naturally detail oriented,” she admits. “I would get review notes back from my manager and the partners, and I just had nothing left to give. I really couldn’t care less about some of those details, as important as they may have been.”

What kept her going was the people. “I loved interacting with my colleagues on a day-to-day basis,” she explains. But when the managers she connected with left the firm, things unraveled. By the time she reached senior level—about three and a half years in—burnout had taken hold. “I was driving to work, looking at other people doing their jobs and thinking, gosh, that looks nice. Even the guys that were mowing the lawn on the side of the highway, I’m like, at least they get to be outdoors and breathing fresh air every day.”

After leaving for industry work that didn’t solve her problems, Daiber enrolled in a coach training program for self-discovery. Eventually, she found her way back to serving the accounting profession, but with a different mission: helping firms navigate the challenges that drove her away.

The Gap Between What We Say and What We Do

When discussing firm culture, Daiber cuts straight to the heart of the problem. “There’s often the one that we say we have, and then there’s the one that we actually have,” she states. Culture isn’t about the values on your website, it’s about “the values we live by, the behaviors that show up and are accepted and tolerated and encouraged inside of a firm.”

She shares an exercise from her firm retreats: projecting the firm’s stated values on a slide without commentary. “Oftentimes they don’t recognize them because they are not living those values every single day,” she observes. These values become “almost a mythical thing out there that we’re working towards, but not very intentionally.”

To expose this disconnect, Daiber challenges firms with a thought experiment: “If I was observing your organization from the outside in and could hear and see what’s going on, what would I say your values are? Is it profit first? Is it billable hour is king?”

Oliver agrees, sharing his preference for honesty over hypocrisy. “I would almost prefer it if the firms that are not people-first were just open about it,” he says, comparing it to Wall Street investment banks that make no pretense about prioritizing profits. “At least that’s honest.”

What Keeps Firms Stuck in Old Patterns

The conversation reveals three main forces preventing real culture change in accounting firms.

First is the scarcity mindset that infects decision-making. Oliver openly shares his struggle with saying yes to too many speaking engagements, even though he knows it prevents him from focusing on long-term goals and family time. “I say yes to these things, even though I shouldn’t, I know I shouldn’t, but then I do it anyway,” he admits.

Daiber sees the same pattern with client acceptance. She walks firm owners through their fears. “Usually within five or six steps we can get a firm owner to, well, we’ll be bankrupt. We won’t exist anymore.” The reality? “They’re so far away from that, that’s not really going to happen.”

Second is the resistance to change itself. “When I hear of firms that say, ‘we’re just doing it the way we’ve always done it,’ that is like Kryptonite,” Daiber emphasizes. “Nothing in the world is the same as it was even five years ago. How can you justify not changing how you’ve done things and how you’re serving your clients?”

Third is simple busyness. “As soon as we step back into our day-to-day, there is an almost insurmountable inertia that keeps you in that sway of busyness,” Daiber explains. Without creating what she calls “white space” in the day, there’s no capacity to implement changes.

The conversation also touches on structural problems like billable hours (“every hour is not created equal”) and micromanagement that develops when leaders lack diverse management tools. As Daiber notes about micromanaging leaders, “They actually don’t have to take responsibility for it, because you’re going to check in with them all the time.”

Making Change Actually Happen

Moving from theory to practice requires specific actions and uncomfortable decisions. Here’s what Daiber recommends:

Start by saying no

This includes “cleaning up your own mess” by transitioning out clients who don’t align with your values. “Finish out your term of working with that client, but let them know we’re not going to continue,” Daiber advises. Firms need what she calls a “red velvet rope policy” that only accepts clients who “treat our people with respect, value our services, and are willing to pay.”

Create structural changes that force new behaviors

One firm Daiber mentions implemented mental health days with a twist. “If you said, I’m taking a mental health day and anyone was caught making a request of that person on that day, they were the ones in trouble.” Oliver suggests an even more radical experiment: turning off firm email during certain weekend hours.

Build real accountability

“The firms that are really successful with this are willing to call each other out in a respectful way,” Daiber states. This means partners holding each other to commitments. “Hey, that was one of the things we said we were going to not do. Let’s fix that going forward.”

Show genuine appreciation

This goes beyond generic praise. “Catching people doing a good job is so simple. It’s free,” Daiber notes. But it also means “checking in on someone, not just about their progress on a task. How are they feeling? Do they feel like they’ve grown?”

Exit interviews reveal what happens without genuine appreciation. People say, “I don’t feel like I’m a valuable or valued member of the team. No one’s training me. No one’s taking me under their wing,” Daiber shares. “I’m going to go somewhere where I feel like somebody cares about my development.”

Most importantly, leaders must model the values they claim. “Encourage them to take time off and unplug during their time off, don’t email them on the weekend,” Daiber emphasizes. “All of those things that we wish people would do for us, we need to do for them.”

The Choice Every Firm Must Make

As the conversation wraps up, both Oliver and Daiber acknowledge that changing firm culture isn’t mysterious; it’s just uncomfortable. It requires letting go of profitable but problematic clients, breaking long-held habits, and having difficult conversations with colleagues.

“We have to start creating a culture of ownership and responsibility,” Daiber explains. But this can’t happen while clinging to old metrics and methods. Each leader must take personal responsibility for “working through their own blocks and concerns or scarcity or fears around letting go of this old way of doing things.”

The accounting profession faces a clear choice: continue losing talented people to outdated practices and fear-based management, or do the hard work of aligning daily operations with stated values. As Daiber’s own journey shows, when good accountants leave the profession entirely, everyone loses.

Listen to the full episode to hear more about Daiber’s framework for culture transformation, including additional exercises for exposing true firm values and strategies for breaking the micromanagement cycle. Whether you’re a partner watching good people leave, a manager caught between competing demands, or staff wondering if change is possible, the conversation offers a practical roadmap for moving from culture as concept to culture as daily experience.

When Your Time-Blocking Superpower Becomes Your Kryptonite

Earmark Team · August 19, 2025 ·

“I’m proud of my time-blocking superpower,” Nancy McClelland admitted during a recent episode of She Counts. Co-host Questian Telka nodded in recognition. They both lived by elaborate color-coded calendars that managed every minute of their days.

But their guest, burnout coach and CPA Lynnette Oss Connell, was about to challenge everything they thought they knew about professional efficiency. What followed was one of the most honest conversations about burnout you’ll hear in the accounting profession.

Nancy and Questian were upfront about why they brought in an expert. “This is something where we both feel completely lost,” McClelland explained. “We don’t have advice for others because we’re both struggling with burnout ourselves, at times sort of teetering on the edge.”

Lynnette, known as “the Burnout Bestie,” built and sold her own successful CAS practice before becoming a coach for accountants struggling with chronic stress. Her story reveals why our greatest professional strengths often become our biggest vulnerabilities (and what we can do about it).

The Efficiency Trap: Engineering Your Own Over-functioning

Lynnette’s story starts exactly where many of us find ourselves. She had what looked like the perfect setup: a thriving firm, organized systems, and the ability to juggle multiple roles with precision.

“I had engineered a life of my own over-functioning,” she explains. Her elaborate time-blocked calendar enabled her to serve as a firm owner, CFO of several companies, and soccer team manager for her kids. When other parents marveled at her ability to manage it all, she’d think, “I just time block—it’s a superpower, right?”

But here’s the problem she discovered: despite all her backup plans and support systems, everything still required her to function as the central hub. “I thought I had done all the right things,” she recalls. “My mom is my backup with the kids, I have a neighbor who’s a backup, and I have employees with tasks. But at the end of the day, all of those systems relied on me to keep them going.”

The most deceptive part? By traditional metrics, Lynnette had achieved work-life balance. She worked only 3.5 hours per day running her successful firm. But those remaining hours weren’t filled with rest. They were packed with equally demanding caregiving responsibilities.

“I’m working the rest of the time, too,” she explains. “Your family work is work, too.”

This led to her biggest realization: she had trained herself to override her feelings “like a light switch.” Whenever she felt resistance or exhaustion, she would do what she calls an “analytical assessment” by asking herself, ”Does this feeling serve my goals?” If not, she would simply shut it off and continue with her perfectly planned schedule.

Energy Auditing: The Game-Changer You Haven’t Tried

This is where Lynnette introduced the concept of energy-blocking.

While we’ve mastered scheduling when we do things, we’ve completely ignored whether those things give us life or drain it. The energy audit reveals what’s really happening within each role we play.

“Within your role, are you balanced?” Lynnette asks. “There needs to beintentionality around what gives you life. Am I pouring out and receiving in?”

This isn’t about achieving a perfect 50-50 balance in every task. It’s about recognizing that some aspects of our work energize us while others deplete us, and being deliberate about maintaining that balance over time.

The efficiency trap is particularly seductive for women in accounting because our profession rewards exactness and the ability to manage complex systems. But what we’re actually doing is creating increasingly sophisticated ways to make ourselves indispensable and irreplaceable when everything falls apart.

Community vs. Connection: The Support System You Truly Need

Lynnette’s next revelation cuts deeper. “I have community,” she explains. I have friends, I have work friends, and I have family who cares about me deeply. But what I didn’t have was conversations around what happens when life gets lifey.”

The problem isn’t a lack of people in our lives. It’s that we prioritize efficiency over intimacy in relationships. We collect connections like productivity tools: broadly and systematically, but without the deep investment required for them to support us when our systems fail.

This lesson became crystal clear during Lynnette’s son’s medical emergency. After spending all night in the hospital, she found herself at 8 a.m. in the parking lot, calling a client to explain why she couldn’t make their regular appointment.

When her client—a father himself—learned what was happening, his response stunned her: “Get off the phone right now. I don’t want to hear from you for a week. Why did you even call me?”

He wasn’t upset at her absence. He was upset that she even thought she needed to work while her child was in the hospital.

“I was living in this tunnel where I was holding myself to these impossibly high standards,” Lynnette reflects. By failing to give people credit for basic human decency, she created a world where no one was allowed to show up for her.

The solution requires what Lynnette calls “controlled vulnerability”—sharing appropriately about where you’re struggling and observing how people respond. This creates a sense of “who your community really is, who you can go to, and who has the capacity for it.”

Why Women Burn Out Differently: The Biology Behind the Breakdown

When Nancy mentioned that many of her high-performing female friends have been diagnosed with anxiety, depression, and panic disorders, Lynnette’s response was both validating and alarming: “The research shows that those are all symptoms of burnout.”

The biological differences in how women and men respond to stress explain why traditional burnout advice often fails us. While men typically experience “fight-or-flight” responses dominated by testosterone and cortisol, women’s stress responses are dominated by oxytocin, creating “tend-and-befriend” behaviors.

“Women feel threatened, and so we nurture,” Lynnette explains, referencing research from “Burnout: The Secret to Unlocking the Stress Cycle” by sisters Emily Nagoski, PhD, and Amelia Nagoski, DMA. When accounting deadlines loom or client crises emerge, instead of getting forceful as male colleagues might, we internalize the pressure and respond by taking on more responsibility.

“Women don’t tend to get forceful or demonstrative in our stress until several more notches down the burnout journey,” Lynnette notes. “We instead internalize.”

By the time anyone recognizes we’re in trouble, we’ve already done significant damage to our nervous systems. The three warning signs to watch for are:

  1. Emotional exhaustion. Bone-deep depletion from constantly nurturing others while your own needs go unmet.
  2. Depersonalization. Suddenly resenting work you once loved because you’re running on fumes.
  3. Lack of accomplishment. Feeling like no matter how efficiently you work, you’re always behind.

“I could be hugely efficient for hours on end and leave the day and be like, darn it, I feel like I didn’t get ahead,” Lynnette recalls.

Building Prevention and Recovery Plans That Actually Work

The solution isn’t just better time management; it’s creating systems that work with women’s biology, not against it.

“I want everyone to respond to the stressors in their life, instead of reacting to the stressors in their life,” Lynnette explains. When you’re reacting, you’re putting out fires with a heightened stress response. When you’re responding, you’re coming from a grounded state, approaching challenges as a capable person with options.

Prevention strategies include:

  • Energy audits to balance life-giving and life-draining activities
  • Deep community relationships that provide practical support
  • Regular exercise that metabolizes stress hormones and adrenaline
  • Quiet practices that help you reconnect with what actually serves you

But equally important is having a recovery plan. “You don’t just take a break and go back to ground zero,” Lynnette warns. “You need to heal from burnout, because it’s a whole body experience.”

Recovery means knowing exactly who to call for different types of support, having scripts prepared for difficult conversations, and allowing yourself to scale back without shame.

The most profound insight is reframing resilience. Instead of viewing recovery as returning to who you were before, Lynnette challenges us to see it as “traveling through change in a way that honors who you’re becoming.”

The Bottom Line: Sustainable Success Starts with Honest Assessment

If you recognize yourself in this conversation—the proud efficiency expert, the person everyone counts on, the one who’s engineered elaborate systems of over-functioning—you’re not alone.

The question isn’t whether you’ll eventually hit the wall. It’s whether you’ll recognize the warning signs soon enough to choose your own path forward.

Start with an energy audit of your current roles. Which activities energize you? Which drain you? Begin shifting that balance deliberately. Practice giving people credit for their capacity to show up for you. Build movement into your routine as essential medicine for your nervous system.

Most importantly, challenge the metrics by which you measure success. The goal isn’t to eliminate efficiency—it’s to become efficiently sustainable and build systems that preserve the system builder.

Listen to the full episode to hear more of Lynnette’s story, including the difficult decision to sell her firm and her husband’s role in recognizing their diverging paths. You’ll also get practical scripts for difficult conversations and deeper insights into building the kind of community that can actually support you through crisis.

What does burnout look like to you? Share your experiences in the comments on the She Counts LinkedIn page. Your story might be exactly what another woman in accounting needs to hear.

Find Lynnette Oss Connell at burnoutbestie.com and follow her on LinkedIn and Instagram for practical burnout prevention tips.

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