video diary prompts that carry on from your last entry

video diary prompts work best when they come from your last entry, not from a list. a list asks what you're grateful for, what made today different, what you're avoiding. it's fine on day one. by day ten you've answered all of it, the camera is on, and you're staring at it with nothing to say.

a diary that keeps going is a story, and a story carries on. the best prompt for the next entry is the thing you left open in the last one: the decision you hadn't made, the customer who hadn't replied, the number you were waiting on.

underway now works that way from the very first entry. after episode 0, the questions for the next episode are written from what you said in it. after that, from the last one you finished. this piece is about why that matters, what changed in the app on 16 october 2026, and a few prompts to borrow if you're starting from nothing.

why most video diary prompts stop working by week two

the prompt lists on page one are written for anyone. that's their strength and their problem. a prompt that fits everyone can't know that you spent yesterday rewriting your pricing page, or that you said you'd hear back from a supplier by friday.

• they repeat. there are only so many ways to ask how you feel today, and the answers start to repeat too.
• they ignore what you already said. every entry starts from zero, so nothing builds from one to the next.
• they ask for reflection, not story. a viewer can follow a thread across entries. they can't follow a gratitude list.
• they put the work on you. you still have to pick a prompt, and picking is the part that kills the habit on a busy day.

the fix isn't a longer list. it's a prompt that knows where you got to.

video diary prompts written from what you said last time

when you set up an episode in underway and don't pick a topic, type a note or tick anything from your day, the questions are written from your last finished episode. before your first numbered episode, that's episode 0, the intro where you said what you're building, who it's for and what you're setting out to do. after that, it's the newest episode you've finished.

the setup says so plainly. the button reads set up with questions from episode 0, or from whichever episode came last, and the summary before you record says carrying on from that episode. the questions pick up what you said there and ask where it went next, one question for each thing, asked in order.

the old standard set of questions, the one that asks how today started and what you worked on, is now only for someone with nothing finished yet, and the fallback if writing the new questions fails. that matters most at the moment people are most likely to quit: the first episode after the intro. you've just said something real about your business on camera, and the next thing you hear should show it was heard.

after your first entry: three notes on today

once episode 0 is made, and before you record episode 1, today shows three short notes written from what you said in it. they sit under noticed, below the record button and your progress.

• a well done, naming what your episode 0 was about.
• a topic for episode 1, in your own words, with two ways in: talk it through with your co-host, or answer questions on it. not this one drops it at no cost.
• one connection worth adding: a tool you mentioned, or somewhere your episodes and shorts can go out. never a guess at a tool you didn't name. connect, or not now.

talk it through with your co-host opens the setup on the co-host, camera on, with the topic chosen. answer questions on it opens the interview with questions written on that topic. either way you're one press from recording something that follows on from what you already said.

if a couple of hours pass and episode 1 still hasn't been recorded, the same notes arrive as an email from rich, underway's founder. it's the same content, not a nag, and you can reply to it. if you'd already had the general what to film in episode 1 email, this one isn't sent as well.

what to film: pick up to three topics and go

what to film is back on today. it's the list of topics underway has found in your episodes and your day: threads you left open, things that changed, things you said you'd do. from the episode after episode 0 it sits under your progress and noticed.

pick one, two or three. each one you pick lights up and is numbered in the order you chose it. then one yellow button: film this, or film these 2, or film these 3. it opens the setup with all of them chosen, the first one leading, and the questions are written from those topics.

for your first five episodes what to film is open by default, on today and on the setup screen, where it has a yellow line round it so it's hard to miss. after that it folds away and remembers whether you opened it. it's never required. you can still record with nothing picked, and then the questions carry on from your last episode, as above.

when your last entry is still being read

topics used to be found some time after an episode's file was made. now the reading starts as soon as you finish an episode, and the topics usually arrive within a few minutes.

if you open the setup before that's done, it tells you so rather than showing an empty list: the episode is still being read, topics from what you said in it appear once it's done, and you can record now, because the questions still come from that episode. nothing waits on it. you never have to sit at a loading screen to keep your streak.

the co-host picks up where you left off

the ai co-host is the live conversation in underway, the one that follows up and digs in rather than asking set questions. it now carries on from your last episode too.

if you start a conversation without picking a topic, it opens by picking up something you said last time, in your words, named so that someone watching cold knows what it's about. if you did pick a topic, the topic still opens. it also knows the threads you've left open across your episodes, and offers them if you ask what to talk about. it doesn't read the list out at you.

this applies to ordinary co-host episodes, on camera or voice only, on the web and the phone. the intro conversation for episode 0, and a season's opener, still start from the beginning, because there's nothing before them to carry on from.

video diary prompts from a list vs from your last entry

a list isn't worthless. it's a decent way past the first blank screen, and some people like the calm of a fixed question. but if the point of your diary is to document something you're building, the next question should come from where the build got to.

a few video diary prompts to borrow if you're starting cold

if you're not using underway, or you're about to film your very first entry, these are the shapes that tend to carry on well into the next one. each one leaves something open on purpose.

• what are you building, and who is it for? say it the way you'd say it to a friend, not a pitch.
• what problem does it solve, and what do those people do instead right now?
• where does it honestly stand today?
• what's the hardest part at the moment?
• what are you setting out to do next, and by when?
• what did you decide today that you might regret?
• what are you waiting to hear back on?

the last two are the ones that make the next entry easy. whatever you're waiting on is the first question next time: did it come back, and what did it say?

how to keep a video diary going

the hard part of a video diary is rarely the camera. it's deciding what to say, every time, on a day when you're tired. a prompt that carries on from last time removes that decision. you press record and answer a question about something you already care about.

underway counts episodes, not days, so a gap doesn't leave a hole in the numbering. it tracks a streak against the commitment you chose, and a pause protects it when you're away. you film whenever suits you: morning, lunchtime, after a meeting. and when you finish, it cuts the episode, names it, and starts reading it for the next set of topics.

where to go next

if you haven't filmed a first entry yet: how to start a video diary.

the app that asks the questions, in full: a journal app that asks you questions.

topics for a build-in-public series: build in public ideas.