Episode 63: Second Choices, Lasting Wins

What if the doors that didn’t open were pointing you to the ones you actually need? We share a candid look at how “second choices” shaped a meaningful legal career and a steadier mind. Along the way, we unpack the hard skills and soft wisdom these detours forged. 

If you’re navigating a season of Plan B—schools, cities, jobs—this story offers both compass and company. Learn how to turn placements into laboratories for growth, use discretion without abandoning standards, and build a life that crisscrosses opportunities instead of clinging to a single path. Subscribe, share this with a friend who needs a reframe, and leave a review with your best “second choice” that turned out right. Your detour might be someone else’s roadmap.

Find out more at https://www.linkedin.com/in/emilystedman/.

Transcript

Mission And Mental Health Framing

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Welcome to the Grace Period, where we get real about attorney mental health and well-being and pull back the veil on the high-stakes world of big law. I'm your host, Emily Logan Steadman, a commercial litigator, partner, and someone who believes there's always room for a little more grace, even in a high-stakes profession. On the Grace Period, I share real stories from my own journey and invite you behind the scenes of big law, beyond the bellable hour, to talk about what it means to stay human in a demanding field. Whether you're a lawyer, a legal professional, or someone trying to find your footing, this space is for you. Let's pull back the curtain, start the conversation, and find our grace period together. Disclaimer, the views and opinions shared on this podcast are mine alone and do not necessarily reflect those of my firm or any organization. This podcast is for informational and entertainment purposes only. It is not legal advice, and listening does not create an attorney-client relationship. Today, I want to talk about second choices. After high school, my life became a series of second choices. As a senior in high school, I was dead set on attending UVA, the University of Virginia. I had long admired Katie Couric. During the Today Show series highlighting where its hosts went to college, Katie showed us UVA and I was hooked. But I did not get in. I was waitlisted. I'm not patient. I'm very decisive. So to me, waitlisted was a decision. So I said, see ya, and went to my second choice, Wake Forest University. Wake was tough for me, socially and academically. I had lived in my K-12, small but diverse public school district bubble for a long time. Wake, a small liberal arts college full of brilliant and often wealthy students, shook me. The lack of diversity was like reverse culture shock. One of the deepest, most transformative experiences of my life is attending public school from kindergarten through high school. From kindergarten on, my elementary, middle, and high schools were diverse, racially diverse, socioeconomically diverse, intellectually diverse. I knew others who lived radically different lives than me. That taught me kindness and empathy. That taught me how not to be racist. That taught me the value of teams and experiences where people of all types share their views and opinions. At Wake, I didn't fit in easily and I no longer excelled at school, despite my work ethic. It was a reality check and a wake-up call. So I focused on goals, on building my resume. I became a resident advisor. I joined a sorority. I rose through the ranks of that sorority, first as director of a new member class and then as president. While I was a resident advisor, they made a rule. RAs could not serve as leaders of their sorority or fraternity. They could not be president. Well, in my world, that just wouldn't do. So I wrote an email email to the director of student life asking for permission to run for sorority president president. I outlined all the reasons it made sense for me to take this chance, and I explained all the reasons I could do both for at least one semester. The director of student life granted the exception, and I won that election. Our sorority, not my first choice sorority, was in flux the entire time I was a member. Leading it was not easy, but through that process, I learned how to motivate peers, how to set goals with a group and check in on progress and hold people accountable. I also learned that deference to mentors is not always a good default. Our sorority advisor decided, during my term as president, to hold fast and true to GPA requirements for sorority leadership. This meant I, in quotation marks, had to address head-on the GPAs of several sorority sisters who held executive roles. This included both my little sister in my sorority and my roommate. With the advisor pushing me, I explained to them that if their GPAs did not improve, they'd lose their titles, their roles in the sorority. This meant that eventually I, again in quotation marks, had to remove them from their roles. I don't think back fondly on that time, on that decision. I see now that I could have pushed back on the advisor. I could have exercised some discretion, not just for those two sisters who meant a lot to me, but for everyone. Discretion is important in life. Yes, I firmly believe in treating everyone fairly. I understand that when lines are drawn in the sand, when metrics and other qualifications are set, someone is always on the other side of that line. Someone, even sometimes myself, who is otherwise deserving of being on the other side of that line, of a promotion of whatever is on the other side of that line. And yet, sometimes discretion is appropriate. Why? Because that's simply how I would want to be treated. Another second choice in my life, moving to Phoenix, Arizona after undergrad. I learned about Teach for America in high school. As a product of public schools, I believe in a quality public education for all, regardless of where you're born, what zip code you live in, or your area's property taxes or other socioeconomic markers. Teach for America's mission resonated deeply, and I made it a goal to get accepted come senior year of college. The problem? Leading up to 2008, TFA was a prized postgrad resume builder. It was incredibly difficult to get into, and I honestly wasn't certain I'd make the cut. Fortunately, one year while serving as an RA, my building manager, a graduate student who lived in the dorm with us, was a TFA alum. She helped connect me with other alumni and showed me what it would take resume-wise to be qualified. I also connected through my summer camp with an alumni who coached me on how to make the most of my TFA interview, a grueling full-day interview consisting of group exercises, teaching a lesson to peers, and a one-on-one interview. At the same time, I took the LSAT. I hated that process. I hated the study classes, I hated standardized tests, and law school became my fallback. If I got into TFA, I would go no matter where they sent me. I still remember the interview day. For my lesson, I taught non-cardinal directions. I pretended that in a prior lesson we had learned north, south, east, and west. And today we were gonna learn about their cousins, Northeast, Southeast, Northwest, and Southwest. I made it interactive and had magnets to use on the whiteboard where I drew a compass. And I did my lesson first. So we were in a small group setting, and I knew if I watched my groupmates give their lessons, I'd second guess everything I did and I would try to incorporate their goodness into my lesson. That's never a good thing. A month or so later, I ran into my building manager. She congratulated me, but I didn't know what she was talking about. And then it hit me. I must have been accepted into Teach for America. Why didn't I know? Well, and it's funny how memory stays with us. I had dropped my phone down the side of under my bed and not had it with me all day. This was 2007. PDAs and smartphones were just becoming a thing. If I didn't have my laptop open or my email open, I only got basic SMS text messages. So I ran upstairs in the student union, busted open my email on the communal computers. Yes, this is how old I am, and I saw the acceptance email. I then sprinted back to my sorority dorm room to grab my phone and call everyone who would listen to me to tell them that I got in. And of course, I set my AOL instant message to I got into TFA. Back then, you could rank every location of TFA as in highly preferred, preferred, or I will not go there. I was a Spanish major, so I picked a couple places as highly preferred where I knew there'd be a Spanish-speaking population: Colorado, Phoenix, and the Rio Gran Valley. I also listed, I believe, South Dakota. I really thought I could survive in a very rural area. I knew I didn't want to go to a big, big city, and I shouldn't have been surprised when they assigned me to Phoenix. I hated Phoenix. Colorado was my first choice, or Denver was my first choice. It wasn't as big of a city as it is today. But they sent me to Phoenix, and again, I hated it. I did not like desert living one bit, but I loved teaching fifth grade. I loved it. I still think about my students and all the lessons they taught me about resiliency, humor, and unconditional love. I became a real adult because of them, and I became a better human because of them. At the end of my two-year commitment to my school, I knew that I did not want to stay in Arizona. Although at first I had committed to staying a third year, I had serious doubts. Arizona was just not the place for me. It was also the Great Recession. And even for teachers, that meant that I was not guaranteed to find another teaching job. So even though I had been avoiding law school, I said to myself, you've always considered law school. Why not go now? And if you hate it, you can move home to Atlanta and teach the rest of your life. I'll say this: working before law school and knowing I had a backup plan if law school didn't work out are two of the most significant reasons I think I did well in law school. Law school also wasn't hard. Compared to the challenges my fifth graders faced, being a law student seemed like a breeze, like an absolute privilege. That perspective gave me a leg up in law school. I'm convinced of that. But I didn't get into my first choice of law school. Despite my dislike of Arizona, at first I applied to Arizona State University. Then, very, very cliche and stereotypically, I went to the movies to see the blind side. The opening scene I still remember a grassy knoll or hill, students heading into their private school dressed in khakis and collared shirts, a perfect image of the South. I missed it, and I decided right then and there to apply to law schools back there, closer to home. My heart was set on the University of Georgia, somewhere I'd purposely not gone for undergrad, but had always loved. But I also refused to take the LSAT a second time, and my score was just meh. So I didn't get into UGA. I don't honestly recall why why I applied to Ole Miss and not say Alabama or Tennessee, which were even closer to home, but I did. And when I got in, I called people who went there for undergrad andor law school. Not one person had a negative thing to say about it. Not one. Everyone raved about Oxford, Mississippi, and Ole Miss, so I enrolled. The day I called my parents to tell them I was going to law school, they were in DC. Why? To participate in the ceremonial swearing in to the Supreme Court bar. They answered my call while at brunch and I gave them the news. Elated is an understatement. As I hung up, I heard them joking about ordering a bottle of champagne to celebrate my decision. The thing about second choices is this. They are what you make of them. I made the most of my time at Wake. I made the most of my time in Phoenix for Teacher America, and I made the most of my time at Ole Miss. I also made the most of my clerkship in Wisconsin after law school. Wisconsin wasn't even on my radar. I never thought I'd end up there after law school. It would have been easy to become bitter or regret not getting any of my first choices, but I believe that would have been wasted energy. Instead, I took the opportunities as they came, took full advantage of the opportunities my second choices presented along the way, and I built a life and a network that now crisscrosses the country. As a kid, I never imagined where I'd end up. I had a gut feeling I'd leave Georgia, but I had no clue that journey would take me to North Carolina, Phoenix, Mississippi, and then Milwaukee, Wisconsin. It's been 13 years since I moved to Wisconsin, and I'm still shocked that I'm still here. But that's what happens when you make the most of things. Life surprises you. So if you're living a life of second choices, this is what I encourage you to do. Make the most of them, lean in, take the opportunities as they come, and use them as stepping stones to build the life and career that you want, and likely one that surprises you too. Thank you for joining me on this episode of the Grace Period. Remember, you don't have to choose between your well-being and your ambition. By setting boundaries, building supportive habits, and giving yourself permission to pause, you can thrive in law and in life. Until next time, take care of yourselves and each other. That is the path to our grace period. Disclaimer The views expressed here are solely my own and do not represent the official policy or position of my firm or any organization. This podcast is for informational and entertainment purposes only, not professional or legal advice. It does not create an attorney client relationship.