I’ve been feeling conflicted about what to do with Prompt. The project has been chugging along for almost six months now. I have a lot of ideas and possible directions to pursue, but no clear path. In the midst of decision paralysis, I took some time off from working on the email-based community and went home to think about what my goals are, what I’ve been learning, and what I’d like to do next.

Problem-Solving
When I started Prompt, I wanted to help people who, like me, had a difficult time expressing themselves on the Internet in the age of social broadcasting. My hypothesis was that if you took away people’s identities from what they were writing, people would share more freely, and the merit of your words would be enough to connect with a stranger over the Internet. If you felt comfortable with what you’d written for Prompt, you could always post it under your real name on any number of social media platforms.

I also wanted to create something that showcased how I saw the world; a product that I loved, that other people could love, too.

Here’s what people have said about Prompt, from a feedback survey I sent out a few months back:

“It’s so different (in a good way) from conventional social media.”

“If the internet has to be a way to connect to people, this is a good way to do it.”

“All the random stories. It fulfills the same space as my long-lost lj obsession.”

“The randomness, diversity, and sameness of everyone.”

“I’m so pleased to have found you. Thanks for creating something so simple and intriguing.”

“The voyeurism.”

I’ve been surprised to find that people seem to like Prompt not as a precursor to blogging, but as an alternative. It’s a quick way to contribute content, and even if you’re not submitting something to Prompt, you’re perhaps thinking about the word or the phrase. In short, Prompt is entertaining, and useful when the Prompt happens to be what you want to write about. But I wonder if Prompt being somewhat entertaining and somewhat useful means it’s not doing a good job of either. So lately, I’ve been thinking about more ideas around how ideas get heard and spread, regardless of how many followers you may have.

Growth
Prompt has grown from 30 people to about 700 people in the past few months. Most people learn about it from friends or newsletter referrals. Prompt has been featured in several email newsletters, including Sarah Judd Welch’s Community.is, Laura Olin’s Everything Changes from The Awl, Thoughtful, and Wellesley Underground, my alma mater’s alternative alumnae magazine. Anywhere from 2–10% of the community will submit a response.

People have been encouraging me to grow the user base. I agree with this. I’m just not sure what would incentivize people to share Prompt with other people en masse. What I have been prioritizing more is experimenting with mechanisms that encourage users to spread the word, rather than doing a marketing push.

I have not figured this part out yet, but it is a more valuable puzzle piece than pushing for sheer numbers, especially since the function of Prompt won’t dramatically benefit with more people on it. Would increasing the number of users on Prompt enhance the feeling of being heard on the Internet? If the two were correlated, it would be fascinating. Maybe it would make a good discovery tool for content.

Community / Identity
About two months ago, I added the functionality to be able to send notes to other people’s responses, and I’d publish them, openly. I also allowed people to submit responses completely anonymously, through a Google doc.

In the beginning, I didn’t think I was building a community; I just thought that being able to see what other people who’d gone through a similar thought process would come up with would be interesting, and you’d feel less lonely as you tried to find the words to express yourself. But it turns out that despite being in an anonymous community, people want to respond and connect to other people.

The prompts that seem to resonate the most are the ones that ask you to write something about a memory. For example, “First Kiss” was wildly popular. I wonder if it’s because they are stories that are intimate and are different for every single person, are rarely talked about with friends. There aren’t a lot of places to explore nostalgia on the Internet right now, but everyone has stories to share and pass down from their past.

Recently, Prompt moved to Mailchimp, and for the first time, I’ve been able to see its open rates. Prompt is averaging 47% right now. At the same time, I’ve noticed that email fatigue is real; I’ve been getting one or two unsubscribes per week from people who’ve said that it’s just because they’ve been getting too many emails.

Now what?
Here’s what’s also decidedly un-fun: a dwindling savings account and the uncertainty of being able to make something that makes money. Last year, to support myself, I took on freelancing gigs that utilized my previous skills as a venture capitalist. This year, I’ve challenged myself to take on projects that would also help me be a better creator. I wonder how long that can last for. I wonder when I’ll have to get a full-time job.

I’ve been thinking about a few ways to experiment with Prompt. This week, Prompt has been running XOXO-themed prompts. Another experiment is to try sponsorships, which I tested at the end of August. I’ve also been planning to try building on top of other platforms where content already exists.

If you know someone who wants to sponsor a Prompt or have other ideas, reach out — I’m curious to hear your thoughts. And if you have suggestions on other experiments, or how you thought about some of the topics I’ve brought up, I’d love to hear from you.

This week, I’m heading to XOXO, a conference for people like me: people who make things for the sake of making things. I’m excited to learn from other people about what it’s like to make things, and to surround myself with other people who are deeply in love with the process. But I’m also curious to hear stories from other people about what it’s like to seek financial sustainability and what breakthroughs they’ve had as I go through this process as well. I guess I’m hoping to be inspired to go down a path, whatever path that may be.

P.S. If you’re also going to XOXO (or just happen to live in Portland) and want to talk in person over food on Saturday night, I’d love to meet. I made this Google form to gauge interest: XOXO Saturday Night Dinner

Edlyn Yuen is making things that help people feel heard on the Internet. You can find her at Orbital in New York City.