Having Your Dreams Crushed Can Work For You

The story of how not getting my dream job was the best thing that ever happened to me.

I spend a fair amount of time managing student expectations. Statements such as “well, a 4.0 might be a little ambitious,” “while the White House would be lucky to have you intern for them, I suggest you send out at least one other application,” and “it really isn’t possible to take 23 credits, do law review, and have a part time job” are not uncommon in my office.

Law students show up to win. If they come to law school with a goal of getting a specific job or working in a specific field, they can become singularly focused on that objective. In order to help take some of the pressure off them, I often share my personal story of not getting my dream job. I think it is a pretty good story, I usually both laugh and cry when I tell it. More importantly, my students walk away feeling a little less need to be perfect and give themselves more permission to try different things. I hope it does the same for you.

My story

I’m the kind of person who always has to have a plan. I thought I couldn’t go to law school until I knew exactly what I wanted to do when I graduated. At some point, I decided I wanted to be a prosecutor. And I clung to that decision for dear life for three years. Every internship, every class, and every networking event was geared towards that goal.

3L year came around and I — you guessed it —  only applied for post-grad prosecutor positions. Six of them to be exact. A few rejected me right off the bat. Three invited me for in person interviews. Two for second round interviews. And, one for the elusive third and final interview. At this point, I could not have been more confident I was going to get the job. Back then, the rumor was that the third round interview was a mere formality.

I mean they wouldn’t bring you to meet the district attorney himself if you weren’t going to get the job, right? Besides, I had a high level reference with a personal relationship with the district attorney. I also nailed the interview. I walked out of it on top of the world. I stopped worrying about finding a job and turned my attention back to pretending to prepare for classes (what? I was a 3L!).

How I found out I didn’t get the job was pretty terrible in and of itself. I was on a, wait for it, date. I had been dating this guy for a while and we were actually headed to dinner where I would meet his parents for the first time. But, I digress.

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We were on the train on the way to the restaurant when I  got a text message from my mom: “you got a letter from the district attorney’s office.” I knew it was bad news. I’d heard it a million times. Call good. Letter bad. But, I had to be sure. I told her to open it and text me a picture. There it was, in black and white, “we regret to inform you.”

I was devastated to say the least (not to mention pissed that I had to spend the rest of the night pretending to be happy). There was no plan B. Also, it was February of my 3L year. I didn’t have a single application pending anywhere else. I felt like a complete and utter failure for not accomplishing my goal. They next day, with swollen, red, and puffy eyes, I set out to find something else to do after graduation. I literally applied to everything and anything I could possibly find. The good thing about having my dreams crushed was not having any fear of rejection. In some ways, my sadness made me brave. I applied for things I would have previously felt inadequate for or unqualified to do.

Ultimately, I received and accepted a year long fellowship at my law school practicing immigration law. When I started, I had absolutely no clue what I was doing. And I absolutely loved every second of it. Crammed in a tiny room with 4.5 desks,  (guess who sat at the half a desk all year) I created relationships with four of the most important people in my life today. I was thrown into the deep end of practicing law and didn’t drown. I realized I was capable of so much more than I ever thought. I met my former business partner and decided to open a law firm (wait, what? This was NEVER the plan). And ultimately, I hung around the school long enough for them to hire me as an adjunct professor, which allowed me to uncover my true passion and calling: teaching law students and bar exam takers the skills they need to succeed.

I wouldn’t have had any of these experiences if my “dream” had turned reality. Maybe my life would be just as good. But, it wouldn’t be the same. I loved owning my own business, appreciate the friends I’ve made, and thoroughly enjoy the work I do with students every day. I can’t imagine not having done these things or not knowing these people.

Lessons learned

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I now realize that I made two huge mistakes back then.

The first, was not really understanding why I wanted to be a prosecutor. In retrospect, what attracted me most to being a prosecutor was that I would have the opportunity to help and serve people. I had a very narrow view of “service” at this point in my life. If I had been really clear on my “why” (as Simon Sinek would put it), I would have understood my real reason for wanting to do the job. This would have allowed me to be rigid about my goals, helping and serving, but flexible about how to get there, job choice.

The second, was tying my personal self-worth to the outcome of getting a specific job. This concept is so crucial to surviving in the legal profession. The fact is, it wasn’t personal. I was qualified for that job, and I would have been great at it. There were a lot of applications and many factors to consider. The important take away was that their personal needs and opinions were not an actual reflection on my abilities or self-worth.

For the record, my story isn’t unique. One 2011 grad, who is happily employed at a small firm, says:  “You’ll get rejected for most things. I applied to 50 big firms, 300 clerkships. I got rejected from most, I’m still waiting to hear from a few, safe to say I probably didn’t get them.”

A dear friend and mentor of mine set out to save the world as an environmental lawyer. She now proudly displays her environmental law certificate on the wall of her law school academic success office, a job she took after practicing adoption law, and not environmental law, for a bit. She is excellent at her job and impacts the lives of hundreds of students each year. I still think she is saving the world, just in a different way than she imagined.

I am not telling you to stop going after your dreams. I’m not telling you to stop planning and setting goals. The point is for you to understand that if “the dream” doesn’t happen, your life, or career, is not over. Maybe your plan will end up perfectly executed. But, I almost hope it doesn’t. Because, what is waiting on the other side might be so much better.


Kerriann Stout is a millennial law school professor and founder of Vinco (a bar exam coaching company) who is generationally trapped between her students and colleagues. Kerriann has helped hundreds of students survive law school and the bar exam with less stress and more confidence. She lives, works, and writes in the northeast. You can reach her by email at info@vincoprep.com.