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journal app that asks you questions

2 October 2026 · 5 min read

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the short version

journal app that asks you questions. underway is one.

it asks out loud, about your work. it hears your answer. then it asks what a person would ask next. you talk for about three minutes, whenever suits you, and a few minutes later there is a numbered episode.

it is a build-in-public diary, so the questions are about what you are building, not your whole life. it works on the web today. the iPhone app is on the App Store too.

what a journal app that asks you questions should do

a prompt gives you the same question whatever you said yesterday.

the site puts the problem in one sentence: "Most tools give you a prompt and a record button. Underway asks, hears your answer, and asks what a person would ask next."

so the test for a journal app that asks you questions is simple. does it ask something that depends on what you just said? a prompt cannot. a prompt does not know you skated past the number.

the site's heading for this: "The interview is live, not a form."

it asks out loud

"A spoken question, like someone across the table. Not a card to read."

that matters more than it sounds. a card is something to read. eyes down, one hand full. you answer a voice, not a screen. the site's line for the phone in your hand: "It asks out loud. You answer a voice, not a screen."

it hears what you said

this is the part a form cannot do. "After each answer it decides: dig into the number you skated past, or move on. No script."

the example card on the site shows one. you say you lost two customers and carry on. it picks that up: "You said you lost two customers over it. What happened?"

it digs in, moves on, or stops.

it knows when to stop

"About three minutes of you talking, then one last question about what comes next. It stops while you still have something to say."

the interview card reads "about 3:00, never past 5:00". that is the whole commitment. about three minutes of talking, whenever suits you.

it never starts from nothing

a blank prompt asks the same thing whatever happened.

underway reads your day first. the site: "You never start from nothing. It reads your day and asks about what happened." you connect what you use (calendar, GitHub, your meeting recorder and more, all read-only) or add a voice note or a screenshot yourself. it proposes what the episode could be about. you pick.

it asks about what you said last time

this is the part that makes it more than one good question.

"Underway keeps a private memory of your series: what you said you’d do by Friday, who Carlo is, that cash has come up three weeks running."

"So each interview picks up where the last one stopped."

the live site shows a real one, asked in episode 1 of the founder's own series, Building Underway: "So what happened when you watched Episode 0 back?" the site's comment on it: "A real question, not “what did you do today?”"

so no, it is not the same questions every day. the site answers that directly: "No. It starts from a plan, then listens: after each answer it digs in, moves on, or stops. It remembers the series, so it asks about the thing you said you’d decide by Friday."

you control the memory. "Read, fix or delete anything it remembers. Nobody else sees it."

voice, camera or screen

"Camera, voice or screen. Choose each time."

the interview is the same either way. voice only makes an audio episode, and the site says how it sounds: "Tap Audio and answer with your voice, from the sofa, the car or a walk. The questions stay in, so it sounds like an interview, not a voice note."

if you would rather someone else asked, the site's one line is: "Underway can host, knowing your company and what you said last time. Or someone else asks: a co-founder in the room, or a guest joining by a link."

what stays yours

the questions are not picked by what did well. the honesty list: "We never let “what performed well” decide what you get asked."

and recording and posting are two choices. "Every episode stays private until you send it, and most people start that way."

what this is not

it is not a form with fields to fill before you press record.

it is not a piece to camera you script first. the site's answer to the script worry: "It's an interview, not a piece to camera. It asks, hears you, and asks the next thing."

it is not a general journal for everything in your life. it is a diary about your work, made by interview.

faqs

is this a journal app that asks you questions, or a form?

it asks out loud and decides the next question from your answer. "The interview is live, not a form."

is it the same questions every day?

no. it starts from a plan, then listens. it remembers the series, so it asks about the thing you said you would decide by Friday.

is it a guided journaling app?

people do search that phrase. underway is a build-in-public diary, and the guide is the interview: asked out loud, one question at a time, about the thing you picked. you answer. it listens, digs in or moves on.

is it an ai that interviews you?

that is how some people search for it. what it does is what this page describes: it asks out loud, hears your answer, and asks what a person would ask next.

do i have to be on camera?

no. camera, voice or screen. choose each time. voice only is still a numbered episode with the questions kept in.

how long does it take?

about three minutes of talking, whenever suits you. never past 5:00. the episode is ready a few minutes later, with nothing to do unless you want to drop a line.

does it work on my phone?

it works on the web today. the iPhone app is on the App Store too, and you sign in with the same account. screen sharing stays on the web.

does it cost anything to try?

three episodes free, no card.

where to go next

the app walkthrough, step by step: /founder-video-diary-app.

how talking compares to writing: /video-journaling-vs-writing.

what a first episode looks like: /first-episode.

a real series, in the order it was filmed: /series/underwayrich.

one line for the series

a journal app that asks you questions, and then asks about the answer. about three minutes, whenever suits you.

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