By Esther Mann

Dear Esther,

After college, I really wasn’t sure what I wanted to do with my life. I had pretty good grades and plenty of options, but no clear vision for myself professionally. My father suggested that I go to law school, saying that even if I don’t enjoy law, it would still serve me well in any profession or business that I would ultimately choose. I thought that was pretty good advice and I followed his suggestion.

During my second year of law school, which I didn’t love all that much but trudged through anyway, I started dating Chavi. Chavi comes from a family of professionals. Her parents, siblings, and even her grandparents are all professionals. Chavi was in dental school at the time, and the fact that I was in law school definitely made me a good fit for her family, though of course we had so much more in common and we eventually fell in love. But regarding my future, it was a given that I would graduate law school, hopefully get a good job with big law, and that would be that.

All that came to pass, except that I was never really feeling it. I was just going along with the program, doing well enough to secure a good job and letting life move me along, without any real excitement. I think my biggest mistake from the start was that I never told Chavi how much I was not enjoying law school. Or if I did say anything, I guess I never said it with tremendous conviction. After all, who loves school all that much? She also complained about the pressure she was feeling, but she did feel excited about being a dentist. I never felt excitement. On the contrary.

Right now I’m in my third year as an associate attorney and I’m miserable. To give you an idea of just how miserable I am, several months ago I came down with COVID; I was very sick for a few weeks and could not work. I was actually thrilled to be sick and get a pass from the grind I was in. Happier being sick than dealing with my job—I think that says a lot!

I recently spoke to a guy I was friendly with from work and shared with him how much I hated what I was doing and how depressing I found it. Basically, his response to me was that everyone there pretty much hates the work, the hours, the pressure, etc., but that it is what it is and I should just put my head down like everyone else, enjoy the great salary and whatever other perks are involved, and do what I have to do. He made it sound so simple. But for me it isn’t. I’m miserable. I dread getting up in the morning; I feel resentful and totally unfulfilled.

And the worst part is that I’m afraid to talk to Chavi about how I’m feeling, especially since I don’t really have a specific Plan B. I’m afraid she’ll think I’m some sort of loser who can’t handle the pressure. She can sense that there is something up with me, because she sees that as time goes on, I seem more and more unhappy and withdrawn. I’m not the happy-go-lucky guy she married.

I’m feeling so stuck and frightened about my future. Where do I go from here? Regarding law, I feel like I’ve deceived Chavi from day one. That’s a long time for deception. I feel trapped, alone, and hopeless. How do I begin to straighten out this mess that I’ve created for myself?


Dear Stuck,

“Oh what a tangled web we weave, when first we practice to deceive.” This famous quote, written by Sir Walter Scott in 1808, is as relevant today as it was way back then. Not to accuse you of being a deceitful individual, but often in life, even minor omissions of our truths can eventually snowball into major deceptions. And the longer it goes on, the harder it becomes to unravel.

Your desire to meld into Chavi’s “professional family” from the get-go is understandable. You certainly weren’t lying to her when you told her you were in law school. However, you failed to share with her your unsettled feelings about your future, leading her to believe that you were on a secure path toward becoming a lawyer. Mind you, many people in law school who are totally gung-ho about practicing law wind up running for their lives after a year or two of actually practicing law. So either way, you still could have been at the crossroads you find yourself at presently. The only difference is that you would have had a partner to lean on during the difficult journey you’ve been experiencing. Had you originally mentioned to Chavi that you were not sure where your future would take you professionally, you could have freed yourself of any feelings of dishonesty. And more importantly, perhaps Chavi would have been able to help guide you toward some interesting possibilities.

But for now, all that is water under the bridge, and here you are, preferring COVID over law. That says it all. I think you know that the first thing you need to do is speak to Chavi. I’m guessing that she’s been worried sick over your behavior and may even be relieved to learn that your depressed mood is related to your professional life rather than something way more serious.

Marriage is a partnership. Ideally, it’s two people coming together and helping one another out, through thick and thin, without judgment, but rather with understanding and compassion. In your letter, you made no mention of Chavi lacking in ways that would keep her from being there for you. Maybe you need to give Chavi a lot more credit and assume that she loves you for reasons way beyond your law degree. You’ve been married for a while already; hopefully, you’ve forged a tight relationship that will serve as a strong foundation, enabling the two of you to work through this particular setback. Trust me, couples overcome much worse bumps along the way.

Your next order of business is to try and figure out the right career path for you. Are you still as clueless about your career options as you were when you entered law school, or has time, maturity, or life experience given you enough hints to point you in the right direction? Maybe you’ve even thought about certain options but never bothered exploring them because you felt totally locked into law and didn’t see the point in wasting any time investigating them.

I’m guessing you’re still quite young. Many people don’t find themselves professionally until they are much older. Some people wind up trying a number of different career paths until they finally hit the jackpot. The point is that once Chavi has your back and you begin to open yourself up to all sorts of possibilities, the rest will follow. You are a smart guy who knows what hard work looks like. Now you just need to channel those skills in the right direction. This is not the time to feel defeated. You’ve only just begun!


Esther Mann, LCSW, is a psychotherapist in Hewlett. Esther works with individuals, couples, and families. Esther is presently offering phone, Zoom, and FaceTime sessions. She can be reached at or 516-314-2295. Read more of Esther Mann’s articles at


Please enter your comment!
Please enter your name here