How to Pour your Soul in 300 characters or less

Insights from a collective connection and sharing experiment

I was, and still am, so proud of myself for starting this newsletter. Today, this email reached 667 people, which feels a little bit like magic.
Last year, I wrote seven IRrEGULAR LEtTERS.

Of them all, these two were most shared, liked, and commented on.

Learning, but make it scandalous!

We've been fed a lie. Practice doesn’t make perfect.

Researching and writing this newsletter challenged me and brought me immense joy. It's one of my favourite creative outlets, so I plan to explore it more this year.
Thank you for being here. 💛
As for 2025…May we all boldly follow our curiosity.

We shall not cease from exploration, and the end of all our exploring will be to arrive where we started and know the place for the first time.
—T.S. Eliot

Why ‘Pour Your Soul’?

As a community builder, I am often interested in how people connect. Why do some people “just click” and others don’t? Which factors enable meaningful connection? What are the minimum requirements for connection? What contributes to feelings of belonging and being seen? Which gathering formats lead to easier connection? Do togetherness and belonging feel the same? And I know for a fact that I am not alone.

Articles titled “We’re Still Lonely at Work” remain on the front cover of Harvard Business Review four years after the pandemic. In November 2023, The World Health Organization declared loneliness a "pressing health threat."

In the surgeon general’s advisory, loneliness is described as a state of mind: “a subjective distressing experience that results from perceived isolation or inadequate meaningful connections, where inadequate refers to the discrepancy or unmet need between an individual’s preferred and actual experience.”

During the last four years, researchers with Harvard Graduate School of Education’s Making Caring Common project have investigated the underlying causes of loneliness in America. They published their findings in October 2024 in a new report called Loneliness in America: Just the Tip of the Iceberg.

If you read it, you’ll find many interesting data points. One that captured my attention is that 73% of those surveyed selected technology as contributing to loneliness in the country.

Social media seems to be one of the main culprits. Several studies (University of Pittsburg, 2017; University of Michigan, 2015; Royal Society for Public Health, 2017) found that excessive or passive social media can contribute to feelings of loneliness and social isolation, leading in many cases to mental health struggles, especially for your people.

"We are more connected than ever, but we’re also more alone."—Sherry Turkle

I can’t say I am surprised. Social media evokes mixed feelings for me. It can inspire and drive me crazy at the same time. FOMO, comparison, feelings of inadequacy, mindless consumption, wasted time.

Yet sharing, in writing or verbally, carries the potential to create connection and belonging. We’ve all been attached to fictional characters in our favourite books. We all come across people who can shift the energy of our day for the better in a thirty-minute call. We all got that message that lifted us instantly.

So, what about social media gives us the ick sometimes? And what other ways of connecting online are out there?

When I launched this newsletter, I imagined it as a place to experiment and follow my curiosity. And this seemed like an excellent opportunity to do just that.

What is Pour Your Soul?

This first experiment started with a reflective exploration of the things we chose to share and why. There are arguments to share generously and arguments to keep stuff for ourselves, especially on social media.

What we choose to share and our first collective experiment

I tend to keep my private life to myself (as the name suggests 😆) and share as much as possible about my professional life.

What essence do you have that’s so sacred and precious that you don’t want to share it with the world?

I was curious to see what happens when we change the rules of the game and create a sharing container that is so different from social media. Would we share more? Less? Would we go deeper? Dare to be more vulnerable? More human?

Here are the new rules of the game for this experiment:

—Thirty strangers enter the experiment for three months and accept the invite to join a little tool called TogetherLetters;

—Every Friday, they receive an email prompting them to share a 300-character ‘update.’ There were no rules attached to what to share or how much.

—Every Sunday, those who contributed an update would receive an email with every single contribution from everyone else, with no option to reply or comment.

—Those not contributing an update don’t get the email and stay in the dark.

—The spiel repeats itself every week for three months, and then we come together online in a call to share our reflections using the unhurried conversation format.

That’s it.

Thirty people signed up, and the experiment started in September.

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Some reflections 💭

You’ll have to experience this yourself to know what it feels like. Below is a list of little and big reflections—my own and shared by the others during our unhurried reflection conversation.

300 characters is enough to pour your soul.
In TogetherLetters, we were constrained to 300 characters or less. When I first saw that, I gasped. ”That’s nothing! How can I share anything in 300 characters?!” While this was a struggle at the start, I am now in the moment where I rarely use them all. This constraint forces me to cut the fluff and distill the message to its essence.

Dive at your own risk.
There were no guidelines about what to share. Some shared deeply personal reflections that landed in the center of my heart and I will forever remember. Others chose to share about their work. We all got to experiment with the depth and the openness we were comfortable with. This also meant that every Sunday letter was a precious surprise.

The collective brain is real.
It was interesting to find each other not once but several times preoccupied with the same things. For a week, almost everyone wrote about the weather. Then, there were the elections, the need to rest and slow down, and creativity. It is fascinating to know that someone else on the other side of the world is struggling or motivated by the same things you are. This experiment undeniably confirmed that we’re not that different after all.

It creates an “altered space, a different reality.”
Someone else shared this, but I feel it strongly. Reading back our letters, the entries have something artistic, almost poetic, to them. Sentences have soul. Each letter triggers a strong emotional reaction. I cried several times reading them. Strangely, I felt every word as if it could have been my own. Isn’t it curious that sharing in a closed space unlocked more poetry than sharing on the never-ending scroll wall of social media? How come?

No expectation of virality shifts attention internally.
What we shared reached 20 people at most. There were no likes. No comments. No shares. Stripped of these dopamine-boosting rewards social media uses to feed our addiction, we found ourselves worrying less about how others might read our message and focusing more on what we needed to share. There was no need to put on a show. The words were less performative and more raw and honest. This led to a strong sense of feeling heard, although no one was ‘talking back.’

There is no take without a give.
No sharing, no reading—that is the rule. There is a beautiful fairness to it compared to social media, which gives us lurker privileges. As someone else explained: “I had to put in some work and reflect on what to share before I was allowed to read other people’s updates.” You cannot peek into someone else’s life unless you’re willing to expose some of yours.

Skipping felt painful until it didn’t.
I missed sending my update in time twice, so I received no Sunday email. The first time, I felt a massive wave of anxiety and FOMO. I had missed out, and there was no warm and fuzzy reward for me. That felt, weirdly, like a failure. The second time it happened, it was different. I chose not to share an update. I was overwhelmed and tired. There was nothing in my cup to share. It helped me realise the energy needed for meaningful connection and thoughtful reflection. It was also an exercise in giving myself grace and accepting that I shouldn’t force what doesn't come easy.

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The experiment was scheduled to close at the start of December. After our reflection sessions, we decided to keep it open, with no expectations from anyone to show up.

It’s January 10th, and we’re still showing up, sharing bits and pieces of our lives. It is still one of the highlights of my week. I am grateful for our little corner of the internet and all the emotions I feel because of these wonderful souls. THANK YOU.

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Where else could we experiment with such a format as learning experienced designers?

Without deep-diving into any of these, here is how this format or variations of it could be applied to social learning:

💡 Onboarding cohorts
Small groups of new colleagues share weekly updates on their onboarding experience during the first three months. This is a collective version of the usual “buddy system.”

💡 Weekly reflections for masterminds or action learning sets
A weekly update check for small groups that usually meet once every month to help them stay accountable and check each other progress between the sync sessions.

💡 Learning Mosaic
In a large-group learning cohort program or bootcamps, divide participants into smaller groups. Use this format for weekly reflection and sharing of “aha moments” as the learning journey progresses.

💡 Emotions in Leadership
During a leadership program, small groups share their emotions weekly as they learn by doing, learn new things about themselves, and apply the new tools and approaches they learn. Bring their insights to the sessions around emotional intelligence.

What other use cases do you spot? 🤓

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Closing today with another little collective experiment, and you are all invited! 🎨

Similarly, but different: Tune into your inner artist and draw something you see outside your window today with your finger.
You’ll need to draw something before seeing everyone else’s drawings.

As you engage in this one, I’ll leave you with a few reflection questions:
—What did this make you feel?
—Are there any preconceptions or limiting beliefs you’re spotting?
—Do you see any patterns in everyone else’s drawings? (If any—because no one might play along, in which case, the reflection question is: What’s holding me back from playing along this time?)

👨‍🎨 Click here to draw with your finger and lean into something new, potentially uncomfortable, today. 🖼️

Until next time, stay curious out there.✌️
Anamaria