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Lessons Learned Along the Way

Jami S. Oliver March 2025

My journey to becoming CEO of a law firm was far from traditional. I was raised in poverty with the challenges that come with not having enough—enough support, love, money, even food. Relying on church donations at times, my mom worked two jobs to support me and my three sisters. To afford food and clothes, I worked a paper route with my sister when I was six, which I continued into high school. These early struggles instilled in me a determination to succeed and to fight for those who, like my family, were often forgotten.

Embrace your background. My upbringing fueled my ambition and empathy for clients. Your background, no matter how humble, can be a powerful motivator. Lean into your story rather than away from it. Your experiences shape you into a more relatable, authentic advocate. This empathy has allowed me to connect with clients on a deeper level.

Cultivate a growth mindset. I was an avid reader at a young age. I devoured books like Think and Grow Rich by Napoleon Hill and Jonathan Livingston Seagull by Richard Bach before I was 10. These books exposed me to the principles of success, and I’ve carried those lessons throughout my life. Over time, I learned to embrace fear. I joined Toastmasters in my 20s because I was terrified of public speaking. That single act of courage led to an enormous difference in the courtroom and business meetings.

The lesson? Read widely, attend seminars, and seek mentorship. Never say no to a new opportunity to learn and grow. Every lawyer I know who is thriving embraces a growth mindset and faces their fears head-on.

Set clear goals and stay focused. I decided I would become a lawyer in elementary school and never veered off course. When my dad, a disabled Army veteran, joked that we needed a lawyer in the family, I took it seriously. The next day I asked the school librarian for books on how to be a lawyer and remained laser-focused on this goal through high school, college, and beyond.

The takeaway? Define your long-term vision for your career or firm. Set clear, achievable goals and revisit them often. Weekly check-ins with yourself and your team are far more effective than annual reviews. Clarity brings action.

Gain diverse experience. I’m grateful for my time as a law clerk at a personal injury and products liability firm. It’s where I learned from some of the best trial lawyers in the field. It’s also where I got insight into some aspects of running a firm. This foundational experience exposed me to the skill set I’d need to develop as a sole practitioner and, ultimately, as a CEO.

My advice? Don’t be afraid to ask for diverse assignments early in your career. Take on roles that are outside of your comfort zone. If you’re offered a chance to learn how to balance the books, take it. If you’re invited to interview and hire new staff, do it. You’ll need those skills when you’re running your own firm.

Embrace resilience and adaptability. By age 40, I was a single mom raising two girls. I’d been passed over for partnership at my firm for being “too young” and “naïve.” So, I went out on my own. I struggled to make enough money to pay the mortgage and cashed in coins to buy groceries. The weight of that responsibility could have broken me. Instead, it hardened my resolve.

Resilience is not a character trait you’re born with—it’s one you develop. There will be setbacks. Say “thank you” for them. They’re there to strengthen you. Every time one thing gets solved, something else often breaks. That’s just life. But if you learn to embrace challenges instead of cursing them, you’ll develop the mental toughness required to lead a successful firm.

Invest in continuous learning. I’m an English and writing major who became a CEO. I had to learn the business side of things the hard way. During COVID, I pursued a master’s degree in business from the U.S. Small Business Administration. I hired a law firm coach. I’ve studied everything I can about marketing, management, HR, and finance. I’ve learned that before you can delegate, you need to understand the process yourself. Never stop learning. Educate yourself continuously. Workshops, certifications, coaching—all of it matters. Growth is exponential if you remain a student.

Give back to your community. After losing my mother and one of my sisters to pancreatic cancer, I felt compelled to act. I serve as chair of the Columbus, Ohio, affiliate of an organization dedicated to fighting pancreatic cancer, where we raise awareness and funds for cancer research. We participate in our annual walk, giving back to a community that has given us so much.

Find a cause that you care about. Engage in community service or pro bono work. These are not just good deeds—they’re investments in relationships. Your clients will see that you care about the community and that you’re committed to more than just your practice.

Build a strong team and network. My law firm’s growth is not the result of one person’s work. Its success is built on a thriving, active network of women trial lawyers around the country. Our team’s shared values drive our firm’s momentum. We’re proud to be a women-led injury law firm, redefining what it means to be a woman trial lawyer.

Build a team that complements your skills and aligns with your vision. You can’t do it alone, and you shouldn’t try to. Collaboration isn’t just a buzzword; it’s a multiplier for success.

Stay true to your values. Even as my law firm has grown, we’ve stayed true to our firm’s motto: Confidence. Courage. Determination. Our commitment to these values is what draws clients to us. I’ve passed on cases that didn’t align with our values.

If you’re not clear on your firm’s values, take a day to define them. Use them as your compass. They will guide your hiring decisions, your case selection, and your leadership style.

We’ll always be committed to holding wrongdoers accountable and growing the firm to achieve that end. You can do this, too. Lean into your story. Use it to fuel your ambition, grow your team, and make an impact. Success is not a destination; it’s a journey filled with lessons, setbacks, and triumphs. Keep going.


Jami S. Oliver is the founder of Oliver Law Office in Dublin, Ohio, and can be reached at joliver@oliverattorneys.com.