My guest for Episode #316 of the My Favorite Mistake podcast is Davina Frederick, founder of Wealthy Woman Lawyer, host of the Wealthy Woman Lawyer Podcast, and a business coach who has helped women law firm owners scale their practices to seven figures and beyond.

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In our conversation, Davina shares why going to law school—an unconventional move at age 38—turned out to be her favorite mistake. Despite building a successful litigation practice, she realized that the traditional lawyer lifestyle wasn’t aligned with her long-term goals or well-being.

"I realized I didn’t want to spend the rest of my life sitting behind a desk or in a courtroom."

After stepping away from her first firm, Davina leveraged both her marketing background and the painful lessons of burnout to build a second, more sustainable law practice. That experience—and the power of hiring business coaches—ultimately led her to launch her own coaching firm. Today, Davina specializes in helping women lawyers grow their firms with clarity, confidence, and systems that reduce overwhelm and create balance.

We also dive into what it means to create a systems-driven law firm—and how that principle applies across professional services. From breaking the “grading papers” bottleneck to resisting perfectionism, Davina offers practical strategies for founders who are ready to scale without losing themselves in the process. Her journey is a powerful example of learning from mistakes, listening to your inner voice, and having the courage to change course.

• What’s your favorite mistake?
• Why do you see going to law school as a mistake?
• What was your career before law school?
• What inspired you to make law your second career?
• How did you come to the decision to leave your first law firm?
• What happened between your first and second law firms?
• Why did you choose to launch a virtual firm in 2011?
• How did others react to your decision to work virtually?
• What did you do differently the second time to avoid repeating mistakes?
• What does it mean to have a systems-driven law firm?
• How do you help lawyers stop being the bottleneck in their business?
• Can you share examples of systems you recommend, especially for marketing?
• How do you coach lawyers through the fear of hiring after a bad experience?
• What mindset shifts help women lawyers move past perfectionism and indecision?
• What led you to focus exclusively on coaching women law firm owners?

My guest for Episode #316 of the My Favorite Mistake podcast is Jim Schleckser, founder and CEO of The CEO Project.

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Jim is a seasoned business leader, bestselling author, and trusted advisor to CEOs around the world. With experience spanning 42 countries and multiple industries, Jim has spent decades helping leaders grow their companies and think more strategically. He’s also the author of Great CEOs Are Lazy and Professional Drinking, and he’s a certified sommelier—something we get to at the end of the episode!

In our conversation, Jim shares a formative early-career mistake—being too optimistic as a leader. His enthusiasm led to overpromising revenue, under-delivering on results, and ultimately damaging his credibility to the point where he had to leave the organization. Jim reflects on how he’s since learned to balance positivity with realism, buffer commitments, and truly listen to skeptics on his team. His story is a powerful reminder that leadership isn’t just about vision—it’s also about judgment, humility, and learning from painful experiences.

We also dive into what it means to be an effective CEO, including why Jim says great CEOs are lazy. He shares how high-performing executives focus their time on removing bottlenecks, not micromanaging, and why a trusted CEO peer group can be a game-changing support system. Plus, for fellow wine lovers, we cap off the episode with a fun bonus: wine mistakes, how to order like a pro, and Jim’s best tip for getting the most out of a wine list.

• What’s your favorite mistake, and what did you learn from it?
• Can you share specific examples of how your optimism led to overcommitment or missed expectations?
• How did that mistake affect your credibility and position in the company?
• How have you learned to balance optimism with realism in leadership?
• What’s your approach to setting stretch goals versus achievable targets?
• How can unrealistic goals create dysfunction or unethical behavior in organizations?
• What’s the best way to avoid data manipulation and maintain integrity in performance reporting?
• What is The CEO Project, and how does a CEO peer group provide value to its members?
• You say “great CEOs are lazy”—what does that really mean, and how does it work in practice?
• How can CEOs identify the biggest constraint or bottleneck in their business?
• Why do some CEOs struggle to admit mistakes, and how does that affect their leadership credibility?
• How do peer groups foster psychological safety for leaders?
• What inspired you to become a certified sommelier?
• What are some common mistakes people make when ordering wine?
• What’s your best tip for confidently ordering wine at a restaurant?
• If someone only drinks Napa Cabernets, what’s a good way to branch out?
• Have you observed gender bias in how sommeliers treat guests at the table?

My guest for Episode #315 of the My Favorite Mistake podcast is Kat Halushka, a business and visibility strategist for coaches, consultants, and speakers. She’s the founder of Profitable Impact Academy, where she helps entrepreneurs grow their audience, automate marketing, and land clients through speaking and streamlined funnels.

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Kat’s favorite mistake? She followed the classic advice to “go to networking events and have coffee meetings” to get clients—so she did, hundreds of times. But after exhausting herself with back-to-back coffee chats every Friday, she realized the ROI just wasn’t there.

Kat had a breakthrough when she nervously gave a short talk at a networking event—and walked away with two new clients that day. That lightbulb moment launched her on a mission to get in front of the room instead of meeting people one-on-one. Over time, she built her credibility by hosting her own events, attracting hundreds of attendees and growing a thriving business community. This shift helped her discover that strategic speaking, not endless small talk, was the true key to visibility and client conversion.

Today, Kat teaches entrepreneurs to stop chasing every opportunity and instead focus on clarity, messaging, and scalable systems. She shares powerful lessons on why most new speakers fail to connect—and how you can avoid those pitfalls by making offers that speak to your audience’s present-day pain points. Whether you’re brand-new to business or looking to scale with less hustle, Kat’s insights on visibility, messaging, and mistake-making will help light the way forward.

• What’s your favorite mistake?
• How did those endless coffee meetings affect you and your business?
• What changed after that first speaking engagement?
• How did you start landing more speaking opportunities after that breakthrough?
• What was the origin story behind Profitable Impact Academy?
• What are some of the most common mistakes entrepreneurs make when trying to grow through speaking?
• How can business owners get clearer on what their audience really needs?
• Why is it a mistake to create too many offers or talks?
• How do you help clients identify and refine the one talk that drives results?
• What are the differences between speaking as a business vs. speaking to grow a business?
• When offered a speaking fee, how do you decide whether to accept or negotiate for something else?
• Can you explain what you mean by making an “offer from the stage”?
• How do you structure a win-win-win when working with event organizers?
• What’s one way speakers can make a compelling call-to-action without sounding salesy?
• Can you give an example of a “gift” that actually gets audience engagement?
• What’s your final advice for new entrepreneurs or aspiring speakers?