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My guest for Episode #317 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. 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.
Questions and Topics:
- 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?
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- Full transcript
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Automated Transcript (May Contain Mistakes)
Mark Graban:
Hi, welcome to My Favorite Mistake. I'm your host, Mark Graban. Our guest today is Davina Frederick of Wealthy Woman Lawyer. For more than a decade, Davina has helped women law firm owners scale to a million dollars and beyond—while maintaining an enjoyable work-life balance. She also hosts a podcast called Wealthy Woman Lawyer.
Mark Graban:
It's the top podcast for women in law in the U.S., and she's the author of two books on marketing and management. There will be links to all of that in the show notes. So, Davina, welcome to the show. How are you?
Davina Frederick:
I'm doing well, Mark. Thanks so much for having me.
Mark Graban:
Yeah, it's great to have you here. For those who are just listening, you missed Davina pointing up to the books above her head. While we're at it, go ahead and tell everyone the titles of those two books, please.
Davina Frederick:
There are two books in the Wealthy Woman Lawyer guide series. I haven't gotten around to writing the third one yet, but the first one is The Wealthy Woman Lawyer’s Guide to Law Firm Marketing in the Virtual Age—there’s a long subtitle. And the other one is The Wealthy Woman Lawyer’s Guide to Building a Systems-Driven Law Firm Business. So marketing and systems are the two topics we cover in those books.
Mark Graban:
Great. I think we'll have a chance to talk about that later in the episode, and I’m sure there are ideas that apply to other professional services as well. So, as we always do here, Davina—first things first—the main question: of the different things you've done in your career, what's your favorite mistake?
Davina Frederick:
My favorite mistake, I think, would really surprise a lot of people—because going to law school is my favorite mistake. And I think a lot of people would be shocked that I would think that was a mistake. I’ve been a lawyer now for about 18 years, but I have not actively practiced. I'm still actively licensed, but I haven’t actively practiced in the last few years because I’ve been running a coaching business for lawyers—teaching them how to grow their law firm businesses like I did when I graduated from law school and started my own.
Davina Frederick:
And I felt that it was a mistake because some really hard years followed that decision. I was debt-free before I started law school, and obviously I invested money in going to law school—borrowed money to do that. I'm almost finished paying it off. That tells you how long it takes to pay off a loan. And it wasn’t nearly as much as a lot of my fellow students borrowed. I went to a private Catholic law school, so it was a little more costly, and I did have scholarships, which helped me.
But in the years that followed, I discovered the hard way that being a lawyer wasn't what I envisioned. And at that particular stage of my life—had I gone to law school when I was a lot younger, I think it would have been a really great decision. But because I was about 42 when I graduated and started my own firm, my life began to change. I began to go through changes myself as I aged. I didn’t see sitting all day behind a desk—or the stress of going to court, and I was a litigator—as something sustainable. It was too hard on me physically and emotionally.
I built my first law firm right out of law school, grew it very successfully, brought in a partner, hired lawyers and staff, set up systems, and we were making money. But I wound up walking away from it because I realized it wasn’t how I wanted to spend the rest of my life.
Eventually, I took about a year off and worked with my husband. We had a high-performance fitness training gym at the time. I’m a certified trainer, and we worked in that business for a year. And I kind of thought, “Okay, what am I going to do?” You know, I went to law school. So I started a second law firm and got really involved in hiring coaches.
I had several different coaches—some group, some private—that I hired to teach me a lot of things I was missing when I started my own business right out of law school. A lot of it was mindset, and also improving my ability to build better systems and stop trying to do everything myself. Even though I had people working for me, I was still stuck in the doing—way too much. I think that's a kind of curse for high-achieving people: we get very caught up in the doing because the doing is what got us there.
And then, when we’re trying to scale a business and grow it beyond ourselves, we don’t realize there's a next level that involves letting go of that. So I invested a lot in coaching. I opened my second law firm, and things were a lot different for me after that because I realized, okay, there was a lot I didn’t know about running a business.
And I thought I would know—because I had a career in marketing for 15 years before that. I thought, “This’ll be no problem. I’ll start my own business.” My husband was an entrepreneur, and he really inspired me. But I had to take a step back. That is what eventually led me to start my coaching business, because my experience with coaching was so powerful and transformative. I had a lot of other women lawyers asking me how I did it—how I was being successful. That led me down the coaching path, which I’ve now been doing for 12 years, coaching women law firm owners.
Davina Frederick:
I started out coaching all sorts of different professionals. I’ve worked with other professional service business owners, but eventually I made the decision to narrow my message and my niche—and focus just on women law firm owners.
Mark Graban:
Yeah. Well, thanks for sharing your story. I think there are things we can peel back from that. I'm glad that mistake of going to law school led to something you seem much happier with now.
Davina Frederick:
Yeah, well, not only that—I think one of the real benefits that came out of law school is that it made me a smarter person. It made me much better at learning how to analyze and problem solve—because that’s what they teach you in law school. They teach you how to think like a lawyer. You learn how to analyze problems and make an argument for either side.
That critical thinking skill has been very powerful in my life since then. So I look back and say, yes, it was a mistake in that, for many years, I wondered, “What did I do? Why did I make that investment? Now I’ve got to go down this path to make it work.” But reflecting on it now, many years later, there was a tremendous amount of benefit. I wouldn’t have the coaching business I have now if I hadn’t gone through that journey.
Other lawyers also relate to me more because I am a lawyer. I’ve had my own business, and I know what it takes to make it successful. And now, thankfully, I’ve had many wonderful success stories—women law firm owners who have grown really successful million-dollar, even multi-million dollar businesses—without grinding themselves into the ground in the process.
Mark Graban:
Yeah, I didn’t realize until you told the story that you didn’t go straight through. It sounds like the vast majority of law students go from undergrad straight into law school.
Davina Frederick:
Right. I did not do that. It was a second career for me.
Mark Graban:
What prompted that second career?
Davina Frederick:
Well, I went to undergrad to be a journalist. I graduated with a journalism degree and especially loved print journalism—newspapers. I worked during college at local papers. By the time I graduated, I had met and married my first husband. We lived in Orlando, and there was only one major paper in town: the Orlando Sentinel. I had been working at the Sanford Herald, and my supervisor was making about $13,000 a year. I thought, yeah, that’s probably not a great career path financially.
So I wound up going into marketing. Kind of by happenstance, I began applying for jobs that required writing skills, and marketing was one of those areas. That’s what got me started in professional services marketing. I worked for an engineering firm, then the largest law firm in town, and later an agency. I had this whole career, but it wasn’t something I deliberately chose—it was something I settled into and made work because we were staying in Orlando for my husband’s job.
Eventually, we divorced. Years later, I met and married my second husband, who was doing well financially. He said, “Go do whatever you want to do.” I didn’t have to worry about bills, and I really thought hard about it. I actually made a pro/con chart of several career ideas and talked to people I trusted. My cousin—who’s the only other attorney in our extended family—has a passion for the law. He told me, “You should go to law school. I think you’ll love it.” So I followed that advice.
Davina Frederick:
I weighed out my pros and cons—teacher was on the list too. But I only wanted to teach elementary students, and my husband joked, “You’ll get fired the first week for cursing at a kid.” And I was like, “Yeah, probably true.” So my personality was probably better suited to the courtroom—or so I thought.
So that’s what led me there. I’m super grateful for the people who supported me in that decision. My husband was a key person. He’s an entrepreneur and had a very successful business serving law firms—he’s a technology consultant, not a lawyer—but I really loved his lifestyle. The entrepreneur lifestyle inspired me.
From the start, my plan was to start my own law firm when I graduated. That’s kind of unusual, but I figured—I was in my 40s, I had already had a career, and I had an entrepreneurial spouse—I could figure it out. And I did, but I didn’t think through the challenge of being both a brand-new lawyer and a brand-new business owner at the same time. I knew how to get clients because of my marketing background—I’d been to a million rubber chicken dinners. I could network, no problem.
I also had great mentors. I was in Seminole County, a smaller, bedroom county outside of Orlando. It had a tight-knit legal community. My father-in-law, who had passed away before I married my husband, had been an attorney there for many years, so the Frederick name was well-known. I had a lot of support early on that helped me not give up.
Mark Graban:
Tell us more about what happened between the first firm and starting the second. Did you shut down the first firm? Did you sell it? What was the thought process?
Davina Frederick:
Yeah, that was a struggle. I didn’t technically shut it down. I had three law firms overall, but I kind of blend the first two together. I started the firm and had it for about a year. Then I brought in a partner—a good friend who had graduated law school the year before me. She was working elsewhere, and I asked her to join me. We built our business around real estate litigation.
I started my firm in late 2007. And if you remember, by 2008, the real estate crisis hit. I started hearing whispers about a foreclosure wave in Miami. Then I learned the chief judge in Orange County issued an administrative order requiring Miami foreclosure firms to hire local counsel.
I got wind of this the day the order came down. I called around, got a list of Miami firms needing local counsel, and cold-called them. I said, “I want to be your local counsel.” That’s how I kicked it off, and that’s how I made a lot of money quickly.
Mark Graban:
Wow. I made a mistake thinking 2008 would’ve been a bad time for a law firm. But in your case, it actually led to a boom.
Davina Frederick:
Right! All of us foreclosure lawyers joked back then, “When this crisis ends, we’ll be the ones filing for bankruptcy.” But we built a strong business. We diversified too—we did family law, estate planning, real estate law. I eventually sold my share to my partner. She had a different vision and was younger than I was. She continued running that firm and just closed it in December 2024. She turned it into a local counsel service that expanded throughout the Southeast. She built a great business.
When I started back, I focused on estate planning and business law. I launched a virtual firm in 2011—no office, just a home setup. That was almost unheard of then. I had naysayers. A fellow attorney wanted me to rent space in his building. I said, “No, I’m going to work virtually for now.” He said, “Clients won’t like that.” But really, he just wanted me to pay high rent.
Turned out, my clients loved it. Many were elderly, scattered across Florida—they didn’t want to drive to an office. We used email, phone, and mail. We didn’t have all the tools we have now, but we made it work. I grew it from there.
Eventually, when the coaching business grew, I had to choose. I couldn’t do both. They were both at a tipping point. I chose the coaching business.
Mark Graban:
Yeah. I appreciate that. It sounds like, with the second firm, you avoided some of the mistakes that made the first one unsatisfying—like staying out of the courtroom.
Davina Frederick:
Right, that was big. Also, the first time around, even though I had hired people, I was still too involved in reviewing everything before it went out. I didn’t trust the team enough, and that made me the bottleneck. That’s one of the things I teach my clients now—so many of us, especially high achievers, start as solos or small firms, then we hire people, but we still insist on reviewing everything. I call it “grading papers.”
You’re doing your own work, and then everyone else stacks things on your desk for you to review—because you don’t trust it’ll be done right. It’s a perfectionism thing. We fear that if something goes out under our name and it’s not perfect, it’ll reflect badly. But that bottleneck prevents growth.
So I teach clients how to stop grading papers—and more importantly, how to shift their mindset so they can build systems that allow them to trust their team.
Mark Graban:
I want to come back and talk more about systems and what it means to have a systems-driven firm. But first, I find it fascinating that, back in 2011, when you went virtual, you had people telling you it was a mistake. It just meant they were making a different prediction. You thought it would work. They didn’t. And it turns out, you were ahead of the curve.
Davina Frederick:
Right. I’ve always been a bit of a maverick—and sometimes too far ahead of the curve. I try things and have to learn the hard way. But for me, going virtual was about being really honest about what I needed and wanted. I had gotten good coaching around that, and I had personal factors going on that shaped my decision too.
Unfortunately, I’ve had a lot of naysayers—some close to me. People who are afraid for you often say hurtful things. But at some point, I had to stop asking for advice and just get quiet. I had to listen to that small voice inside and figure out what I wanted. Everyone has ideas: “You should practice in this area, you should become a speaker…” but when you’re multi-talented, that can get confusing. You get pulled in different directions.
So when I had to choose between practicing law or going all-in on coaching, I had to really think about what brought me joy and what the long-term benefits were. I had to shut out the noise and trust myself. It’s not easy. We love and respect our people, but sometimes you have to make decisions based on your own inner voice.
Mark Graban:
Yeah. Sometimes the mistake is putting too much weight on others’ opinions instead of going with your gut—or at least going out and testing your idea. If it doesn’t work, you adjust.
Davina Frederick:
Exactly. And you will make wrong decisions. That’s part of it. In all the years I’ve run different businesses, I’ve made plenty of mistakes. But every single one teaches you something about yourself—if nothing else.
Mark Graban:
Yeah, it does. Making a mistake doesn’t mean you’re a bad person, or a bad entrepreneur, or a bad lawyer.
Davina Frederick:
Right. If you’re not making mistakes, then you must be an alien—or divine—because everybody makes mistakes in life and in business.
Mark Graban:
And I think if you’re not making mistakes, then you’re probably not doing anything new. You’re not taking any risks—not even intelligent ones. We don’t want to be reckless, but even smart risks can lead to mistakes. As we talk about on the podcast all the time, the key is to learn quickly and adapt—rather than repeating or doubling down.
Davina Frederick:
Yes! And I’m always talking to my clients about that too. One thing I had to learn—and now teach—is that the longer we stay stuck in our feelings about a mistake, the more it harms us and our business.
Take hiring, for example. A lot of women lawyers I work with are terrified of hiring another lawyer. They’ll hire staff, but they stop short of bringing on another attorney. And that’s really what you need to do to scale.
I’ll ask, “Why haven’t you hired?” and they’ll say, “Well, I hired someone X years ago and it didn’t go well.” And I’ll say, “Okay, that person has moved on. They got another job. They’re living their life. But you are still stuck, letting that one experience hold your firm back.”
That’s a mindset issue. Instead of analyzing the mistake and saying, “How can I do better next time?” people say, “That went badly, I must be terrible at hiring. I’m never doing that again.”
And I tell them: imagine if you had applied that logic to dating. “Oh, that first person was awful. I’m never dating again.” Most of us wouldn’t be in the relationships we’re in if we thought that way.
Mark Graban:
Right. That kind of thinking reflects a fixed mindset. People say, “I’m not good at that,” instead of saying, “I’m still learning that.” Carol Dweck’s work on growth mindset is so important. Just because you made a hiring mistake doesn’t mean you’re bad at hiring. It just means you need to learn and improve.
Davina Frederick:
Exactly. And for women law firm owners especially, that fixed mindset is often tied to perfectionism and what I call the “good girl” syndrome. We got good grades, passed the bar, did everything “right,” and now we expect that same kind of gold-star reward system to apply in business.
But when you run your own business, there’s no one to please but yourself. You have to decide what you want. And that terrifies some people.
They’re used to following rules. In business, there are no clear right answers. There’s only your best decision in the moment. And high-achieving women get stuck—they’re paralyzed by trying to find the “right” answer. They analyze and analyze, but don’t act. It’s analysis paralysis.
Mark Graban:
And as you said earlier, in law school you’re trained to analyze, to see both sides. So when it comes time to make business decisions, that mindset can get in the way.
Davina Frederick:
Exactly. So I teach my clients: there’s no right decision. There’s only your decision. And then you make that decision right—by committing to it, learning from it, adjusting as needed. But don’t let indecision stall your growth.
Mark Graban:
Yeah. So Davina, tell us more about what it means to be a systems-driven firm. I know you work mostly with women lawyers, but I think the ideas apply broadly to other professional services too.
Davina Frederick:
Right. So first, I think a lot of people conflate systems with automation. When lawyers tell me, “I need better systems,” what they often mean is, “I need better software.” They’re thinking about case management tools. But systems are really about how we do repetitive tasks the same way every time—or as close to the same as possible.
So if something is done repeatedly in your business, you should have a process—a written process. Most business owners say, “Oh yeah, I have a system for that,” and I say, “Is it in your head or on paper?” Because if it’s only in your head, it’s not a system. You can’t scale unless other people can follow your process without needing you to explain it every time.
It could be written, or a video, or audio—whatever suits your team’s learning style—but it needs to exist outside of you.
For example, in a law firm, a common system to build is around marketing. A lot of lawyers say, “Most of my business comes from referrals,” which is great—but that also means you’re dependent on other people’s goodwill. What happens when that referrer retires or moves or passes away?
You need a systematic way to generate new business—ads, content, a podcast, outreach—that works without your constant involvement. For some, that might mean building a team that knows how to carry out marketing steps each month. For others, it’s about documenting a repeatable process so it actually happens consistently.
Mark Graban:
Yeah. As an industrial engineer, when I hear “system,” I don’t think software—I think of how the work is done: the structure, the standards, the process. Systems help make the work more consistent and help people succeed.
And what you’re describing reminds me of a classic operations failure mode: inspection at the end versus quality built into the process. You described “grading papers”—where the leader checks everyone’s work before it goes out. It’s inefficient, and the leader becomes the bottleneck.
Davina Frederick:
Exactly. And I tell my clients: stop grading papers. If you’re doing all your own work, and then everything your team does gets stacked on your desk, you’re stuck. So instead, I teach a process where you meet with your team member for 30 minutes a day—they bring their questions, you give feedback verbally, and they take notes.
That, combined with checklists and written procedures, builds confidence and trust. Over time, they have fewer and fewer questions. But if you’re just redlining documents or fixing them yourself, they don’t learn. They just accept your changes and move on—there’s no absorption.
Your role as a business owner should evolve from being the doer to being the teacher and mentor. You want to teach your team how you think—how you make decisions—so they can start thinking that way too.
We often underestimate the depth of our own knowledge and experience. We assume people know what we know. But if you haven’t taught it, you can’t expect them to do it your way.
Mark Graban:
Yeah, I think a good coach—or a good leader—ensures quality by giving feedback and explaining the why, instead of just fixing something or telling someone what to do. Because otherwise, you end up fixing the same problem again and again.
Davina Frederick:
Right. There’s a great book I recommend called The Power of a System by John Fisher. I’ve never met John—he’s a personal injury attorney in the Northeast. But I ask a lot of my clients to read that book even if they aren’t in personal injury law.
The way he wrote it is brilliant. He basically sat down and wrote it like he was writing to his team. So every section is framed like: “In this firm, we do this. You have the authority to do that. Here are your tools. Here’s why we do it this way.”
And that’s the part I love most—he always explains why they do it that way. That’s what builds buy-in. When people understand the reason behind a system, they’re more likely to follow it and apply critical thinking. Otherwise, they’ll just say, “This is dumb,” or “We’ve always done it that way,” and miss the point.
One great example he gives is about closed door time. He tells his team that he has blocks of time where he shuts the door and focuses without interruption. And he explains why: because he needs uninterrupted time to think and work deeply. He even says, “You can take closed door time too,” if you need to focus.
It’s not about being rigid. It’s about communicating standards, tools, and expectations and the rationale behind them. That kind of culture creates accountability and clarity.
Mark Graban:
I love that. What you’re describing is just good thinking—whether it’s from law, engineering, or healthcare. In hospitals, for example, nurses are often interrupted during medication rounds, which leads to errors. Some places have adopted visual tools—like bright vests or sashes—that say, “Do Not Disturb, Medication in Progress.” It’s a signal to protect their focus.
You still need people to respect that boundary, but it’s a systems-based solution to prevent mistakes—not just telling nurses to try harder.
Davina Frederick:
That’s such a good example. I need one of those smocks at home when I’m packing for vacation—because if my husband talks to me while I’m trying to pack, I forget everything!
You mentioned engineering earlier—I actually worked for an engineering firm during part of my marketing career. I was a technical writer and helped them write RFPs for government contracts.
That world is extremely systematic. We did a lot of Florida Department of Transportation work. There were quality standards, documented processes, and consistent systems across projects. Everything had to meet certain specs and follow a defined process.
That experience really influenced how I think about business now—even though I’ll never be as systematic as an engineer. I’m more of a visionary. I like having people around me who manage the details. I’m what I call an “80-percenter”—I get things 80% done, then want someone else to finish the last 20%.
But applying that mindset—knowing that systems matter—has been critical for my coaching and for helping my clients grow law firms that don’t burn them out.
Davina Frederick:
Since the pandemic, we’ve seen so many new tools created for lawyers. I’ve got clients running successful firms in all kinds of practice areas, fully virtual, with distributed teams. I have one client who does family law—her entire team works remotely from their home offices.
When you have remote employees, systems become even more critical. You can’t just yell down the hall to “grab this file” or answer a quick question. You have to be intentional in how you communicate, delegate, and track work. That’s where systems shine—they give structure to distributed teams.
Mark Graban:
Yeah. Well, Davina, thank you so much for being here today. Again, our guest is Davina Frederick—Wealthy Woman Lawyer is the phrase to remember. Be sure to check out her podcast and her website. I really appreciate you sharing your core “favorite mistake” story. You shared several others too, but I especially appreciated the lessons and the great advice about becoming a systems-driven organization.
I try to be a systems-driven podcast!
Davina Frederick:
You are—it went very smoothly. I appreciate you having me here. I’ve really enjoyed this. I love talking shop. I love talking about business and mistakes and what we can learn from them.
Honestly, I think one of the most powerful tools for personal growth is owning your own business. You really learn so much about yourself in the process. So I’m grateful you gave me the opportunity to share.
Mark Graban:
Thanks again, Davina.
Davina Frederick:
Thank you, Mark.