Jeena Cho

Sex & Money: Fail, Fail, Fail. Rinse and Repeat

In talking about sex and money, a common theme that comes up often is failing or the sense of being a "failure." This comes up in the context of being good enough - being a good enough mom, being a good enough lawyer, being a good enough wife, the list goes on. When I work with my clients, there's a lot of shame, guilt and embarrassment around debt, as well as personal finances.

For most of my life, I was completely focused on being successful. I expected nothing short of perfection from myself. If I didn't get an A, if I didn't get a flawless comment on a writing assignment, I'd beat myself up for "failing." If you're like me and anything short of perfection is defined as failure, I challenge you to rethink this.

Fear of failure was my primary motivator in life - I went to college then law school because I had to be "successful." In reality though, being driven from this place of fear of failure is damaging to your sense of self because we all fail - at some point in our life.

My first big failure in life was failing the New York State bar exam. You can read about it here. 10 years later, I can see now that this event wasn't a failure at all. Yes, I failed the exam but it opened up so many opportunities in my life. Had I passed the NY exam, I would've never left. I wouldn't have ended up in CA and I wouldn't be where I am.

Failing the bar also offered something that's priceless, which is that it helped me exercise my resiliency muscle.

All of us have the ability to become more resilient. We can do this by meeting challenges and so-called "failures" with an unshakable faith in ourselves.

Since the bar exam, I've had many other "failures." I was turned down for jobs, I failed to land clients, and I lost boyfriends. I've also received not so glowing reviews of my work, and sometimes missed cases in my legal research. Despite all of these "failures" I've also had many successes, including building a successful law practice, publishing a book, winning cases and receiving glowing review of my work.

Without failures, there would be no successes.

What I know now, that I wish I knew earlier in my career is that the faster I can bounce back from failures, the quicker I can reach success. I no longer have a debilitating fear of failure. Failures - mistakes, not having the desired outcome, unexpected mishaps - it's all part of life. I've always found it interesting that in other industries, failures are simply lessons. In the design field, for example, it's common to make dozens of prototypes. With each "failure" you learn, improve, and repeat the process. Can we view our own so-called failures as stepping stones to success?

Frequently, I see lawyers consider themselves as "failures" for not producing the "right" results. However, in any given case, there is so much that's beyond the lawyer's control - the case law, the facts, the judge, the opposing counsel, and opposing clients. Sometimes, our own clients fail to cooperate. Given the limited amount of control we do have, is it reasonable to expect to win every case? Or hold yourself out as a "failure" if you don't get the desired outcome?

I'd like to suggest that we reframe failing as learning opportunities. In fact, failure is healthy because it means you are taking risks and making an effort. The trick is to learn from each experience, bounce back as fast as possible, and move on. This comes with practice, time, patience and a whole lot of compassion for yourself.

Jeena Cho is a San Francisco bankruptcy attorney with JC Law Group PC. She’s working on her second book, The Anxious Lawyer for the ABA. Jeena also teaches classes on Mindfulness and Meditation for Lawyers. You can email her at or follow her on Twitter @jeena_cho.


Cameron Rhudy

Hi Jeena, I agree with you 100%. And I think you make a really good observation about other industries.  As lawyers, we expect to get it right the first time, all of the time. But that is not true of a lot of other professions, in which it is expected that mistakes will be made and that it is part of the process. It really is important that we show ourselves some compassion and then take what we have learned and move on. Thanks! Cameron


Great article. And in what I do, working with lawyers who are looking to leave law behind, the opposite of being perfect is the most helpful. Lawyers looking for a career change need to, and will, make mistakes. And making mistakes is actually just another way of saying “trying things”. Our need for perfection as attorneys can get in the way of our desire to leave the law. Thanks for the post! Casey Berman

Courtney Gabbara

I love this post. I think the advise you are providing is universal to all men and women at all levels of their legal profession. I also agree that the sooner we learn to accept our “failures” as learning experiences, the sooner we can find our true potential. I often times sell myself short before I even know how I did. I pick at the smallest details and if they’re not perfect, hold it against myself for longer than I’d care to admit. Thanks for posting this! I think you did a fantastic job discussing something not many people feel comfortable sharing/admitting. Courtney

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