Gather Your People

How to check-in with your friends, colleagues (and yourself)

Selected slides (published with consent) from a subset of our members’ collective 2019 State of the Orbital talks. Thanks to our speakers for sharing updates: Archie Archambault, Katie Smillie, Michael Grinich, Bailey Richardson, Ida Benedetto, Kevin Huynh, Nikki Sylianteng, Amy Reeder, Andrew Badr, Casey Gollan, Christina Xu, Cole Krumbholz, Jeremy Canfield, KC Oh, Alex Fisk, Anne Libby, Ben Smyth, Chris Choyce, Edlyn Yuen, JB Rubinovitz, Labib Rahman, Marc Brown, Randy Brown & Kirk Fernandes, Cordelia Yu, and LiJia Gong.

We just wrapped up the early 2019 State of the Orbital— a biannual, semi-private ritual where our members deliver short talks covering:

  • what they’ve been working on over the past six months
  • what they’ve learned
  • how they’re doing
  • and what’s coming up next for the rest of the year.

The events are open to members and their invited guests, but we don’t advertise externally because they’re not intended to be performative experiences (i.e. content marketing fodder for Orbital). Rather, they’re effectively a mid-year personal and professional review.

This round, 30 members (including myself) participated. We spread the talks out over 7 separate events across February and March to make it easier to accommodate anyone who wants to participate.

Why we do this

Many of our members are solo practitioners—freelancers, entrepreneurs, remote employees, people exploring career options—or have multiple projects outside of their formal job. Given that, they often lack a regular cadence of review and reflection. There’s always more work to do and it’s all too easy to just keep grinding away.

The problem is that if you’re not reflecting, you’re not learning. And if you’re not learning, it’s quite easy to get stuck or to find you’re working on the wrong thing.

So, the State of the Orbital serves as a forcing function for everyone to collectively come up for air: my job is to create the time, place and structure (a set of optional prompts and 25 minutes), and to gather the audience.

All our members need to do is to set aside time to think, create their presentations, and show up. Some folks spend 20 minutes on their presentation, others spend hours. The process works in either case.


The outcomes are much like what you’d expect.

For the presenters, most of the value comes just from preparation itself. Often people realize that they’ve actually gotten quite a bit done over the past six months. Sometimes, they realize that they’ve been operating under assumptions that are no longer true and need to course correct. Reflection is like sleep—you need it but you tend to only appreciate it after you’ve had it.

The audience gets a lot of out of the exchange as well, too. The event provides an opportunity for folks to gather and an efficient way to learn from each other’s stories, lessons and challenges. But more importantly, they learn how they might be helpful to each other, which is a necessary catalyst for enabling the community to build connections amongst themselves of their own accord.

How to run your own State of the [blank]

Whether you’re part of a community of independent creators, freelancers, or you just want to get your group of friends together, here’s how I’d suggest you do it:

  1. Pick a Saturday 2–4 weeks out. (You could poll everyone, but honestly it’s easier to just pick a date and see what happens.)
  2. Define your constraints and prompts.
  3. Send invitations to 5 of your friends.

Here’s what our outreach email looks like:

Hi folks,

As we’re now solidly into 2019, I wanted to invite y’all to share an update with the members on where you’re at and what your plans are this year.

If you’re interested, let me know your availability below and I’ll follow up to confirm.

Questions to consider:

  • how you are spending your time?
  • what did you learn last year?
  • what do you want to get done in the next 6 months
  • what are some of the decisions you need to make?
  • is there anything you’d like feedback on?

As before:

  • Suggested Format: 10 slides, 25 minutes total for talk + Q/A
  • You’re welcome to invite your friends to listen, but please don’t invite your Twitter followers.

Please respond by Wednesday, February 6th. Then, I’ll confirm dates and send out announcement/invites next Thursday.

If you have questions, LMK!



On the day of the event

As the host, here are the things you should keep in mind:

  • Create an easy experience for folks to introduce themselves. I like to have everyone respond to a simple poll (e.g. last great breakfast) to warm up the room. It gives everyone a turn to say their name and get used to the sound of their voice in the room, which helps it feel more like a gathering of friends and less like a piano recital. Don’t just assume people know each other or are as ready to dive in as you are. Fun over formality.
  • Set the tone. Repeat the reason why we’re all here, and recap the prompts and constraints. Set clear guidelines around behavior. For instance, we clearly state that the information shared should not find its way back to Twitter. (For reference, here’s the deck I use to kick off the event.)
  • Manage the clock. Make it easy for people to manage their allotted time. We setup an iPad in clear view of the presenter so they know exactly how much time they have.

That’s it!

By far, this is my favorite Orbital ritual. We’ve intentionally built a community of people who have a wide range of interests and who do very different work from each other. And so, it’s a real privilege for all of us to be able to get a glimpse into each other’s stories, lessons and challenges when we can.

What I’ve also learned through doing this over the years is how important it is to be selfish in designing community rituals—otherwise they’ll never happen.

Fundamentally, my willingness to run the State of the Orbital is because I want and need a biannual checkpoint for myself. I’ve found a way to include others in the process, largely because it’s just a lot more fun to do it that way.

If this were solely a service I was providing for the benefit of others, it wouldn’t be sustainable. I would feel like a laborer rather than a dinner party host. As such, limit what you do to simple, finite, manageable acts, such as setting a date, creating the space and setting constraints.