8 min read

What We Get Wrong About Connection (And How I Hope to Change That)

Hey friends! Manny here. I am beyond stoked to announce that I've been invited to participate in OnDeck's Founder's Fellowship. Through the Fellowship, I aim to grow the experience I've been testing – Multitudes – as I immerse myself in a community of ambitious founders and technologists.

Here, I describe (1) the problem I'm solving – our inability to predict who we can (and can't) connect with; (2) how Multitudes offers a meaningful alternative to the existing tools we use to discover and connect with new people; and (3) share what people have been saying about the experience.  

The Challenge: Predicting 'Compatibility'

This past January, I enrolled in Seth Godin’s Creatives Workshop. Fully remote and spanning 100 days, the workshop challenges each participant to ‘ship' something – e.g. a story, a song, a reflection, an image – every day. With multiple creative projects in my large – but clogged – pipeline, I looked forward to what the workshop might offer in the way of helping me build creative habits that might help me bring them to the finish line.

What also attracted me to the workshop was the promise of creative community. Like many during the pandemic, I’d been struggling with vicious bouts of loneliness. A recent move to a new city and a breakup had only amplified that sense of disconnection. So I was hopeful that I would find others whose work might spark new relationships – and even collaborations.

The Creative's Workshop is for writers, designers, and artists who want to deepen their craft together. In Seth's words, "You’ll learn to find your voice, to do work that a professional can stand behind, to make a living while making a difference." 

In searching for connections, my initial impulse was to seek out individuals who had similar interests to mine. Did they read the same Murakami books, produce similar electronic beats, write about alternate, spiritually futuristic worlds?

After sifting through several profiles, I identified twenty or so candidates that I thought met these criteria. To further whittle the list down, I Googled their names, trawled their social feeds and websites to determine whether these individuals would be ‘worth’ my time.

Eventually, I arrived at a shortlist of ‘worthy' candidates who I then initiated contact with. We scheduled Zoom calls to discuss our various projects and the directions we wanted to go in. Even when the conversations went poorly, we made cordial promises to stay in touch. Because hey! We’re both writers. And writers should look out for each other, right?

I continued like this for the first three or four weeks until I received a message from a guy named Tim. From the brief search that I conducted, Tim and I appeared to have little in common. He was a white dad in his mid-forties with social and political affinities that seemed to lean on the conservative side with no creative talents that I could immediately identify; I was a single, multi-ethnic progressive who liked to believe that I possessed many talents.

Under normal circumstances, I would’ve ignored or declined his invitation to chat. But, like any skillful networker, Tim started his invitation by praising my work and expressing his admiration for it.

And I’m a sucker for praise.

On that call, my preconceptions of this man quickly unraveled . He was genuinely curious, asking incisive questions about my ideas and my aspirations for them; he listened with the attentiveness of a therapist, picking up things I’d things I’d said that he correctly identified as signs of insecurity. He grew excited when he heard me discuss my vision for a more connected world – and expressed how much he wanted me to succeed. By the end of our conversation, I’d grown teary-eyed not just at how deep we’d gotten in the hour we’d been talking – but by how wrong I’d been about him.

This trend – of connecting with individuals who didn’t match my ‘type’ – would continue for the rest of the workshop. In the ensuing weeks, I would connect with a therapist turned conceptual artist who channeled a shamanic energy she’d named ‘Snake’; a visual artist who created these natural installations that expressed a deep rootedness to the earth; a writer whose essays centered on her experiences with the tragic loss of her child.

If you were to ask me at the beginning of the workshop whether these individuals would be the ones I’d connect with – some of who I went on to produce an album of experimental music with– I’d have given you a firm and decided hell no.

And yet, it is primarily these people who I continue to remain in touch with – not those I sought out in the beginning.

This experience affirmed something that I’ve been suspecting for a while – we are terrible at predicting who we can (and can’t) connect with.

The Reason: A Static View of the 'Self'

Is it a stick? A rope? A brick wall? Or something else entirely...

I think the reason why we suck at predicting compatibility has a lot to do with how we view our selves. Like one of the six blind men observing the elephant, we tend to fixate on a fragment the ’self' at any point in time. The ’self', like an element in the periodic table, ought to hold stable properties – tastes, interests, general attitudes. Properties that form jagged, irregular shapes like unfastened puzzle pieces, pieces that we then use to predict whose pieces might be complementary to ours.

In the process of this holding on to this static view of the 'self', we forget just how much we change over time. And so much of that change happens through the relationships we have with the people we surround ourselves with – and what they bring out in us.

Surrounding myself with creatives who were sharing work everyday – even though we were all entirely remote and had never met in person – absolutely shifted my being. The pre-Creatives Workshop Manny was far more timid, judgmental; the post-workshop Manny, more accepting, sharing his work even when it felt imperfect or incomplete. (Three months, incidentally, is the same amount of time it takes for your skeletal structures to regenerate themselves.)

As Walt Whitman famously insisted in “Song for Myself,” each of us is a pulsing, breathing, beautifully contradictory multitude.

To reclaim the beauty of the multitudes we each contain, we need a way to break free of the prison of our fragments and meet one another as whole persons full of wonder unblunted by identity-template and expectation.

And that’s where so many of our existing tools we use to connect – like social networking sites or dating apps – continue to fall short. By centering the user experience around image-heavy profiles and content feeds, they reinforce these misleading and exhausting habits of labeling each other – ENFP, Researcher, Storyteller – and then using those labels to assess our ‘compatibility’.

Only, compatibility isn’t a precondition for connection; it’s the achievement of it.

Now, don’t get me wrong; I’m under no illusion that we can be compatible with everyone. But learn who we’re compatible with only when we’ve given people a chance; when we’ve allowed ourselves to open up to one another so that we might discover what a relationship with this person – romantic or otherwise – would be like. And, sometimes, be surprised at who we’re capable of connecting with!

Multitudes: "Blind Dates without the Posturing Bullshit"

In the past six months, I’ve been experimenting with a new way for people to connect – one that takes identity out of the experience. It’s fully digital, uses non-code tools (at the moment), and restricted to members of a defined community or cohort (for reference, I restricted testing to participants in the aforementioned Creatives Workshop).

I’ve been calling this experience, “Multitudes.”

Here’s how the experience works:

  1. Two people from the same community or cohort are randomly paired together. Neither of these individuals know that they’ve been paired; they only know that they belong to the same community.
  2. These individuals are assigned new identities – the name of a constellation – and united over a phone call where they only have access to each other’s voices. No visuals or LinkedIn profiles to bias them or set expectations.
  3. On the call, they are guided on a 30-minute conversational experience by Carla – a kind, curious, and socially clumsy robot – who sets the tone of the gathering, leads them through multiple sets of activities that invite reflection, sharing, and collaboration.
  4. After the call, both participants are given the option to choose whether to connect with their partner – or not. If both consent, they will then be given a channel to exchange contact information.
A (rough) infographic of the end-to-end Multitudes experience

Through 10 rounds and 70 sessions of testing with 48 unique users, I’ve played with a number of different features and configurations to the experience, including:

  • using voice modulation to mask gender
  • introducing live performances by artists at the end of the conversation (where participants have an opportunity to interact with the artist at the end)
  • the use of a human vs. a robot facilitator
  • personalized experiences in which participants had their writing read back to them
  • having participants blindfold themselves to make the experience fully immersive

There’s a ways to go to developing the experience, as well as exploring the contexts in which it can be applied (there’s a lot of enthusiasm about a potential application to dating).

But, I’m heartened by the overwhelmingly positive response I’ve received so far.
Here’s what people who’ve done it have been saying:

“I didn’t know what to expect in 30 minutes but that’s left me with a really warm feeling, so connected. Whether I had known it was by the end or not, I’m still thinking about it a few hours later. I thought this would be an app for extroverts who like talking and conversation, but I didn’t realize how powerful it would be for introverts. You have to finish this app. You’re really onto something!”
“That was the best introduction to someone in this workshop that I’ve had. The connection that Darci and I will have until the end of this workshop is priceless. The fact that we’re going to keep bumping into each other really helps…the expectation of future interactions builds a sense of having had a meaningful introduction. The connection was worth the awkwardness.”
“It was such a memorable, special experience that I would gladly try again. What struck me most was the connection it seamlessly created between 3 people even though one was a robot. You have figured out an effective new twist on human interaction.”
"It was exciting and heart-opening and fun - a lift in my day. I had the idea that I would like to do this regularly as a way of scheduling in connection and adventure."
"It was like speed dating, but deeper and free of posturing bullshit."
"It defies easy categorization. Intimate. An extreme sort of ice breaker. An amazing way to spend half an hour."
"It's like Clubhouse – only the equitable version."
"This is a way to connect at the level of humanity, that at the level of shared humanity and it's a space that is safe and controlled. And you have agency and your boundaries are always respected. As you can go as you know, far outside of control as you want to."
"It's just like, pure encounter. Pure fun. I don't have to be anybody. I don't have to hold space. I can play. And those are the things that stood out for me most was just like having fun when Carla would play music. Just like pure play and and not play like only in the silly sense, but yeah, in the creative sense, when do you ever get to do that?"
“It’s like a conversation in an art exhibition. It’s like I’m walking into a room that was setup in a gallery and this room is dedicated to this conversation and this whole experience."

I’m excited to continue developing this experience as part of the On Deck Founder’s Fellowship. The accelerator starts this Saturday – and boy, oh, boy, am I excited for the adventure that's about to unfold.

If you haven't been able to try out the experience yet (and you're curious), I am organizing testing sessions on demand. Hit reply to this post and we can set something up.