When Collaborating, Think Small

Scheduling is a nightmare. When trying to collaborate with my creative friends, I find that the hardest part is getting everyone in the same place at the same time in order to think actively about building a new project. Recently I texted my friend Aaron “when are you free to talk about our podcast?” and he listed all the 1.5 hour windows that he had available during the week. It was exciting and disheartening at the same time. I was happy that my friends have so much going on, but it made me unsure of whether or not I could realistically spend time making things with my peers.

I’ve tried abandoning the need to schedule by creating open Google Docs and Facebook groups for project ideation and chatter. Building these spaces was easy, but it was hard to get my friends to come back to participate. The internet is a notoriously distracting place, and it didn’t make sense for my friends to spend free time working on odd jobs when they could happily scroll through their feeds instead. I fall victim to this as well. I can barely keep up with all of the Facebook groups I am a part of. My Dungeons & Dragons Facebook group has jokingly named “The Group Connor Made Us Make Because He Can’t Read” because of how bad I am at keeping up with group chats.


My preoccupation is currently “How can I put together a team?” I don’t want my groups to feel like work, because my friends are all busy with work anyway. There is no reason to add another thing to your schedule when it a) doesn’t pay and b) isn’t fun. I do my best to show up to a weekly writing group in Seattle, which is nice. I see the same people almost every week, and even if we don’t talk that much, we still spend about two hours working on our writing projects in close proximity. It’s the closest thing to achieving what I want as far as a creative squad. I just sometimes wish that we were all collaborating on a project together.

Furthermore, I have dear, dear friends all over the United States. They can be found in Los Angeles, New York, Texas, Portland, the Bay Area, and elsewhere. I want these friends to also have the ability to help collaborate on projects with me, but these people are even harder to reach because their life cycles are alien to me. I have no idea what their work schedule is like, and I don’t know if they even have the time or interest to collaborate.

Now, while finishing the last bits of my yogurt, I think I am coming closer to a solution. Sustained, multi-day projects may be completely unreasonable to coordinate with friends. My most successful collaborations have been one-day projects. With my web series “Cooking w/ Connor”, the commitment is low for participants. We hang out, we cook food, we live stream it, we eat. When the stream is over, so is the project, and my collaborator doesn’t feel stressed about meeting up again or having to do any research or homework.


This is maybe one of my greatest shortcomings. I am very, very big-picture oriented and I always thing LONG-TERM when I want to start a new project. I have notes for creating a long-form TV series, my own media company, and a web app to track coffee consumption. A lot of the things I want to accomplish have many, many steps and will take a lot of time and work hours. I am currently realizing the answer for collaborations is to maintain these big visions while doing one-and-done projects with friends to add to the greater portfolio. It’s less pressure, less work, and yields more tangible results.

The podcast I’m making with Aaron has clear goals and deadlines. We’re only making five episodes, and we’ll be doing it as soon as possible with minimal editing and fine tuning. It’s a lean startup that has the primary focus of being achievable. Sometimes it almost feels physically difficult to wrangle my ideas into manageable chunks like this. I sometimes lose myself in thought when I am deconstructing my plans into tasks for the day and the moment, but this may be the only way to work with my friends at this time in my life (at least until I’m able to pay them).

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