Reflecting On Year One

Thursday, January 5th 2017

The Backstory

The idea for Jam Sessions came to me during a cross-country flight from New York to San Francisco. I was thinking about the projects that I was working on and trying to brainstorm ideas on how I could: make sure I was working on things that were useful, make meaningful progress that I could share and get feedback on, and ultimately maintain my motivations to see the projects through to completion. I was also thinking about how when I meet up with friends–and the conversation drifts to what we’ve been working on–the discussions are always inspiring and insightful, sharing techniques, tools, and technologies that each other can explore and apply to their respective projects. The only issue with these conversations are that they typically happened at a bar, over drinks. I’m always down for some drunken discussions, except those can tend to have negative impacts both on memory and motivation. I wanted to figure out a way to harness that same level of excitement and sharing, but in an environment that doesn’t have to result in a pounding headache the next morning, but in a place where that excitement can be harnessed and applied.

“What have you been jamming on?”

As I continued to explore ways to create these scenarios for sharing and support, I was reminded of a common question that my buddy, James Wahba, and I tend to ask one another when we meet up, “What have you been jamming on?” That phrase alone provided the spark and foundation for what this idea could be built upon, Jam Sessions. I pitched the idea to James who was immediately into it, and who fortunately runs a co-working space in NYC, Projective Space, where we could host the events. After a quick back and forth on when and where made the most sense within the space to host the sessions, and some brainstorming on the goals and format, this simple idea had matured into a full fledged plan. Now it was time to put that plan into motion.

The Goals

  • Create a productive space where people come together to share, work, answer questions, trade tips, provide feedback, and offer insights.
  • Increase personal motivation fueled by a social obligation to the group to see your project through to completion.
  • Build individual momentum by feeding off the inspiration of helping and getting help from people who are transforming their ideas into reality.
  • Provide an environment that is open to a diverse group of people and professions, in order to increase the number of outside ideas and broaden the topics of discussions and outside perspectives.

The Format

From the start we felt that it was important to create a format that provided as little structure as possible, but just enough to provide a solid jumping off point and a conclusion that offers a clear direction for each member to work towards in preparation to share their travels during the next meeting. The thinking was that by imposing just the right amount of structure you could repeatedly get things started quickly, but still leave enough room for discussions and topics to grow organically and unrestrained, resulting in a more engaging and inspiring event that is concluded with a focus.


During the first 15 minutes of each meeting, members introduces themselves, the project(s) they are working on, and what they would like out of the session. Whether that is time to simply focus on something they’ve been working on, pose questions to the group, reach out for feedback, or offer their time to help others.


The next hour and a half can be just about anything the members want. Whether that is to sit within the group and continue the discussions that were initiated during the introduction, jump out to a table where you can throw on some headphones and focus on what you said you were going to work on, or break out into separate groups to get feedback or huddle around a whiteboard to brainstorm ideas.


The last 15 minutes are intended for the members to regroup and share what each one got out of the meeting and what they plan to accomplish and share at the next session.

Learnings So Far

So far, so good. We’ve had 11 sessions at this point, starting in April of last year and running through December. When we initially started, the goal was to have a session every week, but that pace was a little agressive for a new group and didn’t offer much time to promote the next event. It also didn’t offer much flexibility when it came to scheduling sessions around vacations, holidays and peoples’ lives. So far once a month has worked out well, but I could see introducing a few non-standard events that are associated with the group, but strays from the standard format. For instance, workshops that are conducted on a single topic or show-and-tells where members can offer a deeper dive into their projects in order to get a greater level of feedback and help.

When I had originally envisioned the evolution of the group, I had thought that the number of people participating would have increased quicker than it has. Although, reflecting on it now I think that the slower growth of the group has been a good thing. The whole concept is still a total work-in-progress, and the smaller group provides more opportunities to mess up and refine the format, so if attendance does pick-up it should be a better experience for all involved. That, and the smaller group has allowed for people to get to know one another better, which will hopefully create stronger bonds amongst the members moving forward.

Not really a surprise, but something I thought could be resolved through proper messaging is the confusion about what the group is due to the name. When people hear “Jam Sessions”, they immediately think that is has something to do with music. I’d be down for a meetup where people bring instruments and jam together, but unfortunately that’s not the focus of this group. At least, not in its current state. I’m hoping that by making a few updates to the site design and messaging, we’ll be able to reduce that confusion, but we’ll have to see how that goes.

Another aspect that I didn’t foresee being a challenge is sticking to the format. Even with the small groups, it has been challenging to guide the discussions so that each member’s project/questions get covered. Since the format is very organic, stearing conversations back to the topics that were presented during the introduction can be challenging, especially when a topic pops up that a lot of members are excited about and want to dig into more. We’re working on ways to harness these engaged conversations, and still ensure that each member gets something out of the discussion that is relevant to what they are working on, but again, this is a work-in-progress.

Moving Forward

Ultimately, our goal is to figure out ways to continue to increase the value that members get out of each meeting. In order to do that, we’ll be focused on build stronger relationships amongst the members, creating more outlets for discussion and collaboration, and will continue to grow the community to increase the number of opportunities, insights, and perspectives.

Some ideas that have been discussed, but are still being explored on how best to introduce them or how their introduction could affect the dynamics of the meetings, is the possibility of either live-streaming or recording the meetings and distributing them via a podcast. I think the topics of discussion and the ideas that are shared during these meetings could be very enlightening and inspiring to a broader audience, but the thing that makes them so interesting is how personal and open the discussion are due to the intimacy level of the group. Opening those conversations up to a broader audience could have negative repercussions and result in people not feeling comfortable to share as much publicly as they had previously privately.

Another idea that was explored early on during the ideation of the group–but never realized–was an area that would allow members to share and showcase their project(s) and the progress they’ve made in a low-barrier format that is not as daunting as writing a blog post, nor overwhelming as building out a case study. A simple way to share progress, get feedback, and guage interest–similar to the initial intention of Dribbble, but not solely focused on design and open to more skillsets. I still think that idea has legs, but not sure the solution has presented itself. In the meantime, you can join our Slack channel and that has been working out pretty well to fill that void, allowing members to continue conversations started during the meetings and share progress along the way.

Shout Outs

Jam Sessions wouldn’t be possible without the support from James and the Projective Space community. If you’re a freelancer, consultant, soloprenuer or a member of a small team who is looking for an inspiring place to spend your days, Projective Space is the place for you. You can apply here for either a communal or dedicated membership.

And to the Jam Sessions community, I’m looking forward to the discussions, projects and progress that we’ll make through 2017. I’m so excited to see where we take this!

Want to get involved?

If you’re in the NYC area–or are just passing through–and are looking for an opportunity to meet some new people, share what you’re working on, reach out with questions or ask for feedback, and ultimately engage with others who are motivated, inspired and committed to pushing the ball forward, and helping others while they do, you should come and join us for our next event.

If you’re not in the NYC area, but this idea intrigues you, or you’re interested in starting a Jam Sessions group in your area, please DM me, @ryanhefner. I purposely built the site on its own platform so that it could be extended and expanded into areas well beyond New York City and include features that our unique to the group.