An unexpected lesson in managing expectations

  • January 3, 2022
An unexpected lesson in managing expectations

By Maddie Lee

I started my time at BoingBoing, “A Directory of Mostly Wonderful Things,” as an intern with co-founder Carla Sinclair in July of 2020. Initially, although I had the title of an intern, it felt more like a mentorship. She was very hands-on while still giving me free rein. 

BoingBoing features short posts that are a little niche. They aim to do everything with a sense of humor, mostly about politics, technology and art. I had the freedom to write about almost anything. How often do you get to do that? It allowed me to have a voice that I most likely would not have had anywhere else. 

Sometimes Carla would assign me a piece she thought might interest me or be good practice. We would workshop whatever I had been working on until it was good to go. I loved the freedom and having someone to work closely with me. However, things were a bit different when I switched to working with Mark, her husband and co-founder, at the beginning of this fall semester. 

With Mark, I realized I wasn’t going to have my hand held throughout the process. I honestly got a little bit nervous. The freedom I had became a bit challenging. The goal for the semester was to post something each week, and it seemed like it would be easy to meet that quota once I got my first pitch list approved. However, even putting together a pitch list was stressful. I stepped into the role of an independent contractor, rather than an intern, more than I had before. I tried to emulate the style of what the other contractors were posting. Adjusting to working in someone else’s style was a learning curve that I didn’t see coming. 

It made me slow down with everything I wrote and every article I pitched. I dedicated much more time to editing before sharing the first draft. While this process made me feel extremely slow, it became self-validating to submit a piece and have it posted with no edits made by someone else. I got into the rhythm of working independently, submitting the piece, then moving to the next–although once I got to the bottom of my list of viable pitches, I struggled to find that routine again.

A part of this is because of a lack of responsiveness I suddenly ran into. Neither Mark nor Carla had left me hanging before, so I supposed that the problem was with my pitches. I could get hold of Mark by phone and email, but it was always, “I’ll take a look later!” It became a bit frustrating to devote so much more time to coming up with ideas for new posts than writing them. By the time I got a response, the pitches had lost their timeliness. 

All other independent contractors have permission to post directly onto the blog. Since I did not, this left my hands tied for a while. In the meantime, if I wasn’t searching for story ideas, I would outline some that I already submitted that I thought would get approved. 

Eventually, Mark let me know the pitches weren’t the issue, that it was a lot going on at home he had to deal with. At this point, it was the last week of the semester. I hoped I’d be able to wrap up the semester with one more piece, although I didn’t end up having the time to post something. But because I can continue to write for BoingBoing at any point, I didn’t have an issue with this. Whatever I started can simply carry over into the break. 

I went into this semester expecting things to be the same as they were when I first started. I wish I knew that going into it with expectations would make it harder to be flexible. To have these expectations is like having your own puzzle and expecting someone else’s pieces to fit right into it. 

Overall, I have seen growth as a writer, despite not posting as much as I thought I would. The biggest thing I learned was how responsible you must be to hold yourself accountable. In school, our deadlines and grades hold us accountable. Working independently with an outlet like BoingBoing provides great flexibility for someone who values freedom. However, it is extremely important to prepare for the responsibility it takes to be your boss. 

Throughout my time at BoingBoing, both Mark and Carla have been extremely generous with their investment in helping me grow as a writer and journalist. BoingBoing has been a place for me to apply what I’ve learned from the School of Communication and Journalism with creative freedom and unconditional support.