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The Real Cost of Being Everyone’s Favorite Boss

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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.

The Real Reason Your Female Colleagues Keep Disappearing from Leadership

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

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

The Pipeline Problem That Isn’t

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

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

Making the Invisible Visible

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

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

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

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

The Motherhood Penalty: Same Event, Opposite Outcomes

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

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

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

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

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

The Flexibility Trap: Benefits That Destroy Careers

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

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

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

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

Same situation. Completely different outcomes.

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

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

The Sponsorship Gap: Beyond Coffee and Advice

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

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

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

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

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

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

From Awareness to Action

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

The solutions are practical and achievable:

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

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

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

The Business Case for Breaking the Glass

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

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

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

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

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

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

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

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

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

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

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

When Leadership Lacks Heart: The Partnership from Hell

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

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

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

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

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

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

With a torn meniscus.

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

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

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

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

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

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

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

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

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

They forgave her. Now they text regularly.

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

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

Empathy as Your Secret Business Weapon

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Learning to Accept What You Give: The Hardest Lesson

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

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

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

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

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

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

Practical Tools for Building Your Empathy Muscle

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

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

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

Your Empathy Is Revolutionary

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

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

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

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

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