Podcast: The Most Courageous Thing I Ever Did
Podcast Title: The Most Courageous Thing I Ever Did


I stopped practicing law, and it was the most courageous thing I've ever done. Recognizing that I wasn't a fit for the system and that the legal system wasn't a fit for me allowed me the freedom to change my life.

Asha B. Wilkerson

Episode Summary

In this conversation, Asha Wilkerson shares her journey of leaving the legal profession and finding her true calling. She discusses the courage it took to make the decision and the struggles she faced while practicing law. Asha talks about the pressure and fear of making mistakes, as well as difficult client situations. She explains how she transitioned to a virtual law practice but still felt anxious and overwhelmed. Eventually, she realized that practicing law was no longer in alignment with her life and made the decision to change. Asha encourages listeners to seek life coaching and embrace change to find joy and live a regret-free life.


  • Recognizing when a career is no longer a fit and having the courage to make a change is essential for personal growth and happiness.
  • The legal profession can be stressful and anxiety-inducing, with constant pressure to perform and fear of making mistakes.
  • Difficult client situations and the inability to help everyone can take a toll on mental health and well-being.
  • Transitioning to a different practice area or finding a new career path can bring relief and a renewed sense of purpose.

Timestamped Summary of This Episode

  • 00:00 Introduction and Courage to Change
  • 02:06 Accidental Journey into Law
  • 03:00 Struggles and Stress of Practicing Law
  • 05:04 Transition to Virtual Law Practice
  • 06:01 Pressure and Fear of Mistakes
  • 07:49 Difficult Client Situation
  • 09:25 Constant Anxiety and Procrastination
  • 10:52 Feeling Miserable and Fear of Failure
  • 11:22 Taking Action and Making Changes
  • 12:40 Admitting Law is No Longer in Alignment
  • 13:30 Finding Joy and Embracing Change
  • 14:13 Encouragement to Seek Life Coaching
  • 14:42 Healing and Living a Regret-Free Life

Resources Mentioned:

Connect with Asha:

Asha Wilkerson (00:14.338)
Thanks for watching!

Asha Wilkerson (00:21.658)
I stopped practicing law and it was the most courageous thing I’ve ever done. Recognizing… What? So slow still. I’m sorry.

Asha Wilkerson (00:43.254)
I still feel super slow.

Asha Wilkerson (01:08.755)
I stopped practicing law and it was the most courageous thing I’ve ever done. Recognizing that I wasn’t a fit for this system. It’s too slow.

Asha Wilkerson (01:43.938)
I stopped practicing law and it was the most courageous thing I’ve ever done. Recognizing that I wasn’t a fit for the system and that the legal system wasn’t a fit for me allowed me the freedom to change my life. I always tell people that if I could accidentally become an attorney, I was that one. As a kid, I just knew that I was going to be a teacher or maybe a forensic psychologist. I loved law and order.

But not for the attorney stuff. I loved Dr. Wong because I was so fascinated with understanding how and why people did the thing that they did fast forward a few years. And I found myself applying to law school to see what would happen. I had participated in a summer law program in college, but only because of a lack of funding that eliminated my job was I able to attend a pre-law summer program. After completing the summer program, we received free LSAT test prep.

So I got to studying and took the exam. I applied to UC Law San Francisco, which was UC Hastings back then. And I got an early decision right before Thanksgiving. It was settled. I knew I was going to go to law school after attending college. Even back then, I was a firm believer in just try and see what happens. Ultimately, I decided.

Asha Wilkerson (03:00.026)
Ultimately, I decided that going to law school over pursuing more education to become a teacher would give me the best foundation to do a variety of things. Fast forward a few more years and I’m sitting in my own law office in downtown Oakland wondering how much longer I was going to keep this up. I’d had some success but it was hard fought and costly, not just financially but costly of my time and mental health.

Asha Wilkerson (03:55.254)
I was doing noble work, but it was definitely risky. And I very quickly realized that I couldn’t help everybody who deserves help. Wanting to save the world and being unable to help most people who walked through the door became stressful. Plus I hated the antagonistic system that we have in America. Everything was a fight and it took years to resolve matters by design. My anxiety was spiking. I was constantly worried that I’d missed a deadline or that I would mess something up in a case and potentially lose it for my client.

I was afraid to disappoint my clients even if the law wasn’t on their side because I wanted nothing more than to help them. And since they had come to me asking for help when I couldn’t do it, I was devastated. This stress turned into sleepless nights, lights.

Asha Wilkerson (04:44.79)
This stress turned into sleepless nights, persistent worry, and exhaustion. Although I wanted the phone to ring because that meant I had potential clients, I was terrified of the phone ringing because I didn’t want to fight with opposing counsel. I didn’t want to get bad news and I didn’t want to deal with my clients’ emotions, even though they were very valid.

Instead of recognizing that I wanted to quit the profession altogether, I decided to try something new. And I turned my brick and mortar law practice into a virtual law practice working from home. A few months after I vacated my downtown office, I noticed that I was still anxious when the phone rang on one hand, I was grateful for the emails and phone calls because that meant I can make some money. But on the other hand, I felt like the pressure to perform, to help everybody and to not mess anything up was just too much.

Asha Wilkerson (05:53.438)
Now, I know a lot of people feel pressure to perform, but let me explain what it felt like for me.

As attorneys, we’re licensed by the state bar and we have a standard level of competence and performance that we must hit for every case. If somebody believes that we may not have acted competently, they can make a complaint to the bar and we’ll be investigated. And when I say anybody, I really mean anybody, whether they’re a client, former client, opposing

of a random person off the street. If they feel like we’re not performing well, they can call the licensing board and an investigation into our alleged incompetence will be initiated. This is the definition of you can’t mess it up.

Asha Wilkerson (07:49.898)
Right after I started practicing independently, I took on a client that I thought I could help. It turns out the medical experts didn’t support the theory of the case and without the support of the medical experts, you can’t win. So I gave her the very tough news that I had called five or six different experts and they all stated that what she experienced was not caused by the doctors, she was suing. I explained that without a doctor in the same field stating that her doctor’s actions fell below the standard of care, there was legally no way we could win.

I recommended dismissing the case so that she wouldn’t lose it. And she didn’t like my recommendation. I understood, but I also let her know that I was unable to bring a frivolous lawsuit or my license would be at stake. That meant I was not able to advance a lawsuit that I knew had no likelihood of winning because it was a waste of time and money for her, the court, and the opposing party. I asked her to let me out of the case so that she could do what she wanted and maybe find another attorney.

And do you know that this lady wouldn’t let me go? I had to petition the court to be relieved as counsel and when my former client showed up, she told the judge that also.

Asha Wilkerson (09:05.57)
I had to petition the court to be relieved as counsel. And when my former client showed up, she told the judge that although she didn’t want me on the case anymore because I didn’t want to be there, she didn’t want to let me go because she hadn’t found another attorney yet either. After listening to both sides, the judge issued an order relieving me as counsel. Thank God.

After that experience, I was in a constant state of low-grade, work-related anxiety. I carefully selected cases, but I was always afraid that I would find out some information in discovery that would lead to the case falling apart. Then breaking up with a client was much harder than breaking up with a boyfriend because so much was at risk. I wanted to help my clients, but I was also afraid I’d end up in another situation like the one I described above where a client…

Asha Wilkerson (09:56.234)
I wanted to help my clients, but I was also afraid I’d end up in another situation, like the one I just described, where a client, against all reason, would refuse to heed my legal advice. I started procrastinating on my work projects. I started avoiding phone calls and relying…

Asha Wilkerson (10:15.41)
I started procrastinating on my work projects, I started avoiding phone calls, and replying slowly to emails, and I found myself dreading sitting down at my desk each morning. I had a roommate at one point in time, and after he would leave from work, I’d either get back in bed, or I’d take an afternoon nap, but I’d make sure I would get up

and sit at my desk again before he came home to pretend like I’d been working all day. After a couple of months, I realized that I might be depressed, and at the very least, I was miserable. At one of the worst…

Asha Wilkerson (10:52.83)
And one of the worst things was that people on the outside thought I was doing so well because I was running my own law firm. They thought that I must have been smart and a real go-getter to be so young and successful. I felt like I was lying to the world but I didn’t know how to tell the truth. And the truth was I was miserable. And I was afraid that if I kept going, I was going to make a mistake that I couldn’t come back from. But I was also afraid that if I quit, I’d fail at life. Dramatic? Sure.

But the fear was real. Eventually I decided that I needed to take some action and change things. I switched my practice area from plaintiff-side litigation to advising business owners. Then I added business law to the menu to compliment employment law. I inventoried my skills and I remembered that I loved teaching and started hosting workshops for business owners. I also offered to provide advice and counsel to small businesses to keep them out of trouble so litigation wouldn’t become an issue.

I went back to school and I earned my MBA to serve my clients better while at the same time applying to full-time teaching positions and paralegal programs in the Bay Area. Eventually I landed one and decided to make the leap away from full-time attorney to full-time educator. Making this shift felt like a lifeline had been extended. For a while,

Asha Wilkerson (12:13.33)
Making the shift felt like a lifeline had been extended. For a while, my law practice and teaching overlapped, but after a couple of months, I was able to hit pause on my law practice and decide whether I really wanted to give it up or if I just needed a break. Ultimately, I decided to give it up. But it was a decision that I made over a period of years. I kept trying to tweak the practice to make it fit me, and with each tweak, it would get a little better, but it was still a major stressor.

Eventually, I had to admit to myself and to the world that practicing law was no longer in alignment with my life. A small part of me was embarrassed about what my colleagues would think, and a larger part of me was worried about disappointing my family. After all, I was the first person in my family to become an attorney, and I knew it would have made my Civil-Rights-Activist grandfather very proud if he was still living.

But I also knew that I could no longer ignore what I was feeling inside and that I had to build a life I actually wanted to participate in. After quitting law, I moved into business coaching and now I’m a healer and a life coach. I could see this 10 plus year journey as a waste of time since I’m no longer using my degree, but instead I know that every iteration of my professional life was a shift I needed to make to find more of myself.

I had to start healing the parts of me that strove to make everybody else happy. I had to heal the parts of me that were afraid to speak up and say, no, I don’t like this. I had to strengthen the courageous parts of me so that I could switch lanes without seeing the finish line. I also refused to be one of those people who went through life miserable, only because they were too afraid to see what other possibilities existed.

I went from professionally optimistic to professionally miserable to leaving the profession altogether. It took me a while, but I decided that it was worth it to pivot and find joy, or at least something that was more enjoyable than what I had been doing. So if you’re feeling stuck where you are,

Asha Wilkerson (14:13.638)
if you’re feeling resentful for the life you have now, if you’re ready to make a change, but aren’t quite sure where to start and what to do, I encourage you to talk to me about life coaching. Sometimes all you need is one person in your corner who will give you permission to explore while also holding you accountable so you can reach the goals you’ve set for yourself. Head to ashawilkerson.com/coaching to book a life coaching inquiry call. And remember it’s because I’ve healed

that I’ve been able to repair old relationships and start new ones from a different perspective. It’s because I’ve healed that I’ve been able to leave expectations behind that no longer serve me. It’s because I’ve healed that I’m currently living my dream life out loud with no regrets.


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Ep 15 From Stuck to Thriving: Recognizing When It’s Time to Move

Feeling stuck in life? In this episode, Asha Wilkerson explores how to recognize when it’s time to make a change. She discusses the signs of toxic environments, stagnation, and cultural misalignment, sharing personal insights from her own move to Portugal. Tune in to learn how changing your surroundings can reignite your motivation, creativity, and overall well-being.

Ep 14 Have You Asked Yourself What You Really Want Lately?

Ep 14 Have You Asked Yourself What You Really Want Lately?

Join Asha Wilkerson as she delves into the importance of knowing and pursuing your deepest desires. Through real-life client success stories, Asha explores how uncovering and expanding your vision for what you want in life can lead to profound personal growth and fulfillment. If you’re ready to break free from old patterns and discover what truly lights you up, this episode is for you.

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