My buddy Sean Fioritto has been craving a community of likeminded people in Chicago for a while, and he’s been struggling to find it.

Around 2 months ago, he met Monica Guzman. Sean tells me that Monica specifically reached out to him because she was ALSO feeling isolated and wanted to meet more people like her.

Like Sean, Monica was looking for more ways to connect with likeminded people who she wouldn’t have to explain herself to, who might actually understand the challenges and aspirations of running a solo business.

They started talking. And talking more. And talking more.

Sean had recently hit a kind of breaking point, and drafted a blog post, a rallying cry of sorts.

Before hitting publish, I gave Sean just a little bit of coaching and sent him a preview release of my new audiobook “The First Ten“. He pressed the button.

In just a matter of days after making his post public, Sean and Monica went from isolated entrepreneurs to taking their first steps to building the community they’d been craving in Chicago.

But wait. I can practically hear you thinking to yourself…

“Chicago has coworking spaces, right? Why create all of this noise? Just go there! Problem solved.”

Well hold your horses.

Sean goes to one of those coworking spaces.

In fact, he’s tried several. Monica was on the hunt for a coworking space, too. But there was a problem.

As Sean has described it to me, the problem is that for most of the people inside the coworking spaces he’s tried and settled for, the offer is little more than a low-cost, low commitment office that lets him get out of the house. He didn’t want more services or facilities to be more productive. He didn’t need nicer furniture to be more comfortable or even free coffee to be productive.

Without any context or sense of community among the members, it’s just a bunch of people being lonely together. The loneliness problem doesn’t actually go away.

“I rent a coworking space, but we barely know each other. There’s no way that spontaneous collaboration will ever happen there. Nothing surprising could ever come out of that place, and it only makes me feel a little less lonely.”

As a quick sidenote, ugh, I hear stuff like this way, way, way too often. It makes me mad. Maybe worst of all, I hear it from frustrated members, but I hear it even more often from coworking space staff who can’t figure out why their members come in every day and sit in complete isolation from each other. They’re not sure what to do. They worry if they’re doing something wrong. If that sounds like you – check out my challenge below and email me. I want to help.


Back to our dynamic duo, Monica & Sean.

They both wanted people to have a friendly conversation with, to push each other to be better in the way that great coworkers and teammates do.

I know first hand how this feels, because I needed the exact same thing 10 years ago before I started the Indy Hall community.

And Sean learned, like I did 10 years ago, that he wasn’t alone.

Sean learned something that too many coworking space founders (and their teams) learn far too late, if they ever learn at all:

For a lot of professionally creative and independent people, “space” isn’t the most valuable problem you can help them solve.

As Monica told Sean: “Community is more important than the space, community is the point.”

Working alone sucks, but loneliness isn’t cured by a room. Too often, in fact, space becomes a distraction that allows the loneliness to perpetuate.

Loneliness is best cured by inviting people to do something together. It’s really that simple.

You might notice that Sean and Monica’s first events don’t look like the typical events that have become the default at so many coworking spaces. Nobody’s on stage. There aren’t any sponsors, or even a promise of free food and beer.

And that’s not an accident.

Sean has been listening to our playbook, and has been supporting Monica to put together a first event that I see as exceptional on three particular fronts:

  1. Keeping the event low impact and casual – it’s absurdly easy to plan and execute, which means Sean & Monica can focus their efforts on inviting people to join in instead of being distracted by speakers, sponsors, and lots of other unnecessary “event defaults”.

    Think about community building as more like “hanging out with a purpose.”

  2. This invitation is clearly written by a person. Take a look at the last event promotion you sent or received. I always tell my team to imagine if you used that same tone or voice to invite your best friend to your birthday party. Would they actually want to come, or would they tell you to loosen up?  

    Instead of a buzzword-laden agenda, Monica and Sean host this event with a tone that talks more about the people who would be there and what they care about instead of what they do. While crafting the invite, Monica chose to talk a _little_ bit about what kinds of jobs people might have, but she brilliantly chose to focuses MUCH more on common interests, values, and identities to invite diversity. At the same time, the invite makes it clear who this is for, and what you can expect (and subtly, what not to expect too).

    I might go so far to consider this style of invite an “advanced community building move” but she’s executed if beautifully.

  3. This last one is a little bit counterintuitive, so stay with me!

    Think about the difference between dinner party where you can get a chance to meet everyone, vs a giant house party where you probably wouldn’t break away from your existing friends. It’s absolutely brilliant to be keeping these initial gatherings small and intimate. Far too often, an event success is gauged by headcount.

    Instead, Monica guided them to make choices that will encourage and invite people to get to know each other.

    This choice makes a far more effective community building event (where the result is people actually forming relationships) and builds a stronger foundation for future growth of the community.

    Note that they could have increased the headcount when the first event filled up. In fact, Sean admits he would have gone that way if Monica hadn’t talked him in this direction. He told me:

    “When Monica scheduled a second meeting, at first I was like, ‘huh? why?’ and then it dawned on me that we could actually focus on making friends that way, which is the entire point. The reason my little slack community exists is because we started with a core group of friends. Monica is a smarty.”

    It’s worth noting that they also could have set that second session up a few days later or even the following week. And they can always adjust going forward. Minor tactical choices like this matter a lot less when you’re making smart strategic choices like the rest of them.

    But the point is that this intentional choice to keep it small will let them focus on priority #1, which is building the community core that’s missing elsewhere. Smarty indeed.

You can be a smarty, too.

You can put this into action too, whether you run a coworking space already, are working towards opening one, or are an enthusiast who wants to build a stronger community.

Here’s the first couple of steps to get you started:

  • Think about who you’d want to invite.

    Ask yourself: What kinds of things does this community already like to do? Might they like to do it together?

    Keep it simple and casual, but give people something to look forward to. Remember, more like a dinner party, less like a giant house party.

    e.g. sharing food and drinks are an easy choice (pot luck dinners rule), playing games like Sean, Monica and their crew, checking out something new in your neighborhood, going to a museum…almost any kind of group activity is fair game so long as it’s relatively easy for new people to join in.

    And avoid putting people on stage unless it’s for karaoke night.

  • Pick a date, pick a time, and pick a place to invite them to do that thing. Remember, the goal is a small event where people can actually get to know each other. It can be really helpful to choose a place where the size of the venue helps keep your headcount down.

    Quiet bars and cafes are great. Don’t pick somewhere that people will need to shout across the table the whole time.

    If you DO operate a coworking space, don’t use your own space as the venue. Remember this is for doing something together, not showing off your space. Besides, you’ll have an easier time getting to know people when you aren’t thinking about the operational details of your space.

  • Put it out there. Keep your invitation personal. Personal invites go a long way, and there’s a very good chance that you already know people who want the same thing as you (or at least know someone else who might).

    And if you’re nervous, remember that this is low stakes, especially compared to signing a lease. If only a few people show up, this event can still be a success because you’ve completely re-calibrated the goal towards maximizing conversations instead of maximizing headcount.

Got it? Good!

Alex’s Challenge: Do it in the next two weeks.

My challenge to you is to give this a shot in the next two weeks. Yes, two weeks.

If you take more time than that, you’re guaranteed to overthink it.

There are tons of things you THINK you need to do, but don’t. Focus on the fundamentals, like Sean did. And like I did.

If you decide to take me up on this challenge, and organize something like this in the next two weeks, reply to tell me what you’re going to do.

Yes, I’m serious!

I want to hear about it. Shoot me an email and tell me where you are (city/country), a little about your community, and what your community building event is going to be.

And afterwards, send me pictures! I love seeing pictures of communities coming together. They totally make my day 🙂


Want more step-by-step guidance? I’ve got your back!

IHW audiobook image

For the next 2 weeks, my new audiobook “The First Ten” is on sale for $10 off to celebrate it’s launch!

Check out the free sample chapters to get a taste, and pick up a copy now so you can listen to over the next two weeks while you’re getting ready to do your community building event. 

Chapter 3 and 6 in particular are PACKED with more stories and lessons about what makes a great community building event, with even more examples for you to draw from.