I still remember it vividly. The call came after midnight on Sunday, Nov. 19, 2023. It lasted just over a minute, but it still managed to change my life. In so many words, I learned that I was not going to be podcast editor on The Daily Pennsylvanian’s 140th Board. Once my term as sports editor concluded the following month, my time in the DP’s leadership would be done.
Once the emotions had calmed down, I realized that I found myself at a crossroads. The time between that late Sunday night and the end of the semester were filled with deep personal reflection. Should I stay at the DP, an organization that had come to dominate my first five semesters? Or should I bid it farewell and attempt to chart a new course during the time I had left?
Ultimately, I opted for the former. And not only did I hang around, coming to meetings and writing here and there, but I also doubled down, joining new departments. I didn’t do it just because I felt that I had something to contribute to the DP. My decision to embrace my title of former sports editor came from a feeling that there was more the DP could give to me. My experience had been as much about learning as it had been about writing, designing, or editing. Class was not dismissed; I still had more room to grow.
In many ways, my journey to the DP — and my path to leadership within it — was quite conventional. I had been on the staff of my high school’s newspaper, rising to editor-in-chief after a stint as news editor. Several of my early mentors at Penn were involved in the DP, and I joined their departments. After one semester, I applied to be on the internal board of the DP and found myself as a deputy design editor. The summer after my first year, I wrote my first sports article. Just a few months later, I was elected sports editor.
These first three semesters were a whirlwind of learning and education. I was constantly in new circumstances and picking up new skills. I was surrounded by mentors whom I respected and who genuinely cared about my growth.
But as sports editor, I felt myself stagnating. I had more responsibility, more trust, and instead of having every piece of my work critiqued, I now found myself doing the critiquing. For a while, this felt nice.
But what went completely over my head is that my style — as a leader, an editor, and a colleague — wasn’t for everyone. A string of poor decisions nearly cost me everything. Though I didn’t realize it at the time, I now know that I didn’t do the best job as sports editor. The responsibility of the job and my quick accession to it fed my ego and gave me what I thought was confidence but now realize was cockiness. A quicker lesson to learn was that despite having achieved a position of power, I was nowhere near done learning.
People say that “failure is the best teacher,” and I couldn’t agree more. I missed being critiqued, having my work scrutinized, and being called out when I needed it. I also felt listless and trapped in my comfort zone, like I had stopped taking risks. This hunger for lessons motivated me to begin writing for 34th Street Magazine, which I have kept up throughout the second half of my Penn career, first as a staff writer and then in the Features section. The same need to expand my comfort zone influenced decisions I made outside of the DP, like deciding to write an honors thesis, a yearlong research project with many sources in a language I barely knew a word of before coming to Penn.
In January 2024, as I returned from winter break as a former sports editor, I began to see things in a new light. I continued my work, but my focus was on learning and improving, rather than the getting-by that characterized my attitude as an editor.
By having my articles edited, I became a better writer. By working on pieces about specific topics — from lacrosse recaps to Street features on bees, ChatGPT, and climate science — I learn about them. And seeing new leaders gave me a new perspective on leadership.
My time in the Copy department this semester sums up my new attitude. I was the most experienced person on my shift. I helped answer questions the other associates had, providing guidance on where to find box scores or whether an acronym should be spelled out on first reference. But I also received guidance from others on a litany of matters.
Despite being an associate and having a deputy editor to answer to, it seemed like we were all there for the same purpose: to edit articles and have fun along the way. The hierarchy seems to melt away in the face of mutual education. By now, most people I interact with at the DP are younger than me, but it doesn’t matter — regardless of age, we all have something to teach.
Now, in May 2025, as my time at Penn comes to a close, I know that I have learned a lot from my nearly four years in the DP. But only a tiny fraction of it came from self-reflection; most would not have been possible without a fantastic set of teachers.
Thank you to Matt, Esther, Eashwar, Alexis, Walker, Vivian, Sean, Valeri, Brandon, Lachlahn, and everyone else in the Sports department for pushing me. I will remember DPOSTM forever; from the first Sunday Shift PIG game to the last Tuesday GBM, my times in the department will remain core memories.
Thank you to Brittany, Sophie, Allyson, Julia, Charlotte, Laura, Asha, Garv, and countless others in Kopy for helping me learn about AP Style, showing me Studio Ghibli movies, and keeping me young.
Thank you to Norah, Catie, Naima, Hannah, Jules, Bobby, Chloe, and the rest of Street for enduring my pitches and letting me write everything from a 1,400-word diatribe on the Western genre to a visual story about greening Philadelphia lots.
Thank you to Abhiram, Derek, Weining, Jean, Lydia, Jackson, Chenyao, Sydney, and the rest of the Multimedia department for taking me in and teaching me how to embrace multimedia storytelling. I hope to one day be a fraction as talented as all of y’all.
Thank you to Isabel, Alana, Tyler, Collin, Lilian, Sophia, Insia, and everyone else in the Design department for allowing me to embrace my creative side and dealing with all of my harebrained ideas for back pages, photo essays, and beyond.
And last but not least, thank you to the various senior leaders of the DP over the years — Alessandra, Anna, Diamy, Emily White, Emily Scolnick, Jared, Jesse, Jonah, Josh, Imran, Walden, and beyond — for believing in me and providing me with models of leadership I will attempt to emulate, no matter what situation I find myself in.
Thank you to my family, friends, and professors for your constant support and giving me tough love when I needed it. I hope you understood why I could never do anything on Wednesday nights for two-and-a-half years, or why I showed up to Thursday classes a little more tired than usual.
Most of all, thank you to the 137 years of DPeople from before I showed up. You created a wonderful institution, of which I am a mere steward. I am grateful for what you have done to give me space to write, to design, to edit, and most of all — to learn.
CALEB CRAIN is a College senior studying history. He previously served as the sports editor on the 139th Board of The Daily Pennsylvanian, Inc. His email is ccrain@sas.upenn.edu.
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