You’re supposed to make a product to solve a pain point for someone somewhere. That’s why they’ll buy your thing in exchange for their cash money.
Well, that’s not why I made Tailor.
The writing group that changed how I work
My writing group: We’d meet at my house every two weeks. Everyone brought their writing tools (laptop, phone, paper and pencil). Some people brought their dogs. Some people brought snacks. We’d open with a discussion and go around the room: What’s everyone working on today? What are your intentions for the session? What do you want to get done?
Then we’d do a 25-minute sprint, quietly writing together.
When the timer chimed, we’d pause and go around the room so everyone had a chance to unpack: How did it go? How was your focus? Did you get your blog post done, Sarah? Did you start your short story, Bill? No judgment, just support.
I did some of my best writing in that group. My short stories “Assistance” and “Stone Test” both came out of that group. The format did something incredible for my brain.
The problem with strangers
But people move on and the group eventually dissolved (amicably). I’ve wanted to recreate that magic but there’s a pretty big obstacle for me: I have ADHD with comorbid rejection-sensitive dysphoria. Asking strangers to join my writing group? Terrifying. Sharing my writing with them? Nightmare fuel.
Nonstarter. Body doubling with a stranger was just never going to work for me.
But the format stuck in my mind.
- Stating my intention (“I want to write a short story today.”)
- My peers mirroring the intention back to me and asking clarifying questions (“Sorry, do you mean you’re writing the whole story today? Or you’re trying to start it?”)
- Focusing with the quiet presence of others.
- Unpacking how the sprint went (“I crushed it, I wrote 500 words!” or “Well, I got a few lines down I guess?” or “Bad, guys. I looked at my phone the whole time.”)
- Receiving support, encouragement, and most importantly the insightful questions that helped me home in on what was guiding my success or failure (“You said you didn’t sleep much last night, it’s not a shocker that you can’t focus” or “Is this story intimidating you? What if in the next sprint you just write the first sentence and that’s all?”)
- Then doing it all over again.
The deeper I went into analyzing why that writing group worked so well for me, the more ideas I wrote down. But I kept getting stuck on the strangers. Focusmate already does this well. But I just can’t see me putting myself out there to engage with a stranger. Maybe on my best day. But I don’t need that support on my best day. I need it on my mediocre day.
What if the presence didn’t have to be human?
So I asked: What if the presence in the room with me didn’t need to be human at all? What if an AI could hold that same space—present, quiet, accountable, supportive, and nonjudgmental?
So I reverse engineered the writing group, like any good nerd would.
The writing group had intentions. Tailor has the intentions backlog (your “to-do list”). The group stated our intentions to each other. Tailor walks through your sprint plan in natural language, capturing your hopes, goals, motivations. The group had the timer. Tailor has the timer. The group had collaborative unpacking. Tailor rejoins you after the sprint ends to talk through how it went. What worked well? What didn’t work so well? How would you rate your focus? How do you feel about it?
And, critically, my writing group peers remembered from session to session. “How’s ‘Stone Test’ going? Did you get through the emotional climax? I know that was rough to write.”
Tailor remembers, too. After each debrief, Tailor creates a memory card of your session for your review. Once you approve it (you can edit, annotate, or tell Tailor to scrap it and try again), Tailor archives that card. Over time, Tailor learns your patterns.
- “Hey, Tuesday mornings are typically great focus time for you. Do you want to tackle some deep work?”
- “You usually group your admin tasks on Friday afternoons—is this a good time to knock out those expense reports in your backlog?”
And, if the app works as intended,
- “Three months ago your focus was averaging a 3.2 but you’re up to a 3.7 average now. How does that feel?”
The writing group is gone. But Tailor is almost ready to share. If you’ve ever worked better with someone else present, then you already know why I built this. If this sounds like it’s for you, beta signups are open.
—Catherine