Every journal prompt on this site was written by somebody else. That is the normal arrangement: a stranger supplies the question, you supply the answer, and the question is the part you are not expected to produce.
Derek Sivers has kept a daily diary for over twenty years, and his entire method is the opposite. He writes his own question, answers it, and then sets about attacking the answer.
The Only Living Subject in This Series
Almost everyone profiled on this site is dead, and every one of those profiles has the same hole in it. We can read what Leonardo or Darwin or Nightingale wrote, and we can see how they organised a page, but not one of them ever explained why. The method has to be inferred from the artefact. Sometimes that inference is solid and sometimes it is a guess with good manners.
Sivers – a writer and musician, best known for founding and later selling the music distributor CD Baby – is the exception, because he is alive and he publishes the explanation himself. His article Benefits of a daily diary and topic journals, dated 28 January 2019, sets out the whole practice in his own words. At that point he had been doing it, in his phrase, for “20+ years”. That article is now itself seven years old.
So this is the one entry in the series where we are not reading the notebooks of people who kept them and reconstructing a method. We are being told.
The Daily Part, in His Words
His instruction for the daily diary is almost aggressively plain:
Every day at some point, just open up this diary, write today’s date, then start writing.
And what to write:
Write what you did today, and how you are feeling, even if it seems boring.
The last four words carry the weight. Everything else in that sentence is standard advice; “even if it seems boring” is the part that makes the practice survivable, and it is the instruction most journaling content quietly omits because boring does not sell.
Notice what is not there. No prompts. No structure. No word count. No morning or evening requirement. After twenty years of doing it, the instruction he gives is: open the file, write the date, go. That is worth sitting with if you have ever abandoned a journal because you could not meet the format you had set yourself. The people who keep it going for years rather than weeks tend to have stripped the requirements down, not built them up.
His stated reason is also unfashionably simple:
You’re doing this for your future self.
The Line That Justifies the Whole Thing
If I had to reduce Sivers’ case for journaling to one sentence, he has already done it:
You can’t trust distant memories, but you can trust your daily diary.
That is not a sentiment. It is a claim about a specific failure of human memory, and it is the reason the boring entry is worth writing.
Your memory of 2019 is not a recording. It is a story, assembled after the fact, edited to fit how things turned out, and it feels exactly as vivid and reliable as a recording would. That is the problem: there is no internal signal that distinguishes a remembered fact from a reconstructed one. A dated entry written on the day is the only document you will ever have that was made before the editing started.
Which means the entry that felt pointless at the time – the one where nothing happened and you wrote three lines about the weather and a mild irritation at work – is doing the thing the interesting entries cannot. It is establishing what ordinary actually looked like. If you want a sense of the range, what other people’s entries actually look like is mostly this: unremarkable days, recorded anyway.
The hardest part of journaling is not starting. It is the stretch where the entries are boring and you cannot see the point of them, which is exactly when the record is being made. I write a short email about the parts of this that do not fit on an inspirational graphic. You can subscribe here.
Topic Journals: One File Per Recurring Argument
Alongside the daily diary he keeps a second kind:
For each subject that you might have ongoing thoughts about, start a separate “Thoughts On” journal.
His reason is that it puts his past and present thinking on one subject in the same place, so he can see how a view of his changed over time.
This is the cheapest structural improvement in the whole article, and it is worth being clear about why it works, because it is not a writing technique at all. It is a filing decision. A chronological diary scatters your thinking on any one subject across years of unrelated days, which means you can never see the sequence. Put the same entries in one file and the sequence becomes visible – including the parts where you contradict yourself, which are the interesting parts and which a date-ordered journal reliably hides.
You do not need to write differently to get this. You need one extra file.
The Actual Technique: Answer, Then Attack the Answer
Here is the part I think is genuinely his, and the part that quietly criticises a lot of what this site publishes.
I answer with my initial thought first, but then question it afterwards with skepticism, and consider different perspectives.
Two moves, and almost all journaling advice stops after the first one. A prompt gets you a first thought. It is designed to. The implicit theory is that the first thought is the valuable thing, dredged up from somewhere honest, and that writing it down is the whole exercise.
Sivers treats the first thought as raw material. It is the input, not the output. The work happens when you turn on it.
An illustrative example of the shape – constructed, not from anyone’s journal:
Should I take the contract?
Yes, obviously. The money is good and I have nothing else booked for March.
But. “Nothing else booked” is not the same as “nothing else coming”. Last time I filled March in January I turned down something better in February. And is the money good, or is it just more than zero? Against what? If I say no, what would I actually do with those three weeks, and would I do it?
The first answer took four seconds and was already fully formed before the pen moved. Everything useful is downstream of the word “but”. That is a different act from responding to a prompt, and it is much closer to working a decision out on paper than to any prompt list, including mine.
Which raises the awkward question I have been circling. This site publishes a great many prompts written by somebody else, and I still think they are useful, particularly for anyone who freezes at a blank page. But they train the wrong half of the skill. They make you good at answering. Sivers’ claim is that the thinking happens in the interrogation, and he puts it about as strongly as it can be put:
Almost all the thoughts I have on any subject are the result of writing in my diary and journals, then questioning myself.
Not some of his thoughts. Almost all of them.
Plain Text, and Why He Bothers to Say So
One more thing, which sounds like a technical footnote and is not:
It’s a standard format not owned by any company. It will be readable in 50 years on devices we haven’t even imagined yet.
The site’s existing comparison of writing by hand or on a screen treats this as a two-way choice, and Sivers is pointing at a third axis that neither side of that debate covers. A paper notebook is readable in fifty years by default. A note inside a subscription app is readable for as long as that company exists and chooses to let you export. Plain text is the digital option that behaves like paper.
If you write digitally and you accept his premise that you are doing this for your future self, the file format is not a nerdy detail. It is the whole delivery mechanism.
Still Revising It After Nearly Thirty Years
The last thing worth noting is that the practice is not finished. In February 2026 he published a short piece on using a private journal to internalise a new viewpoint – a five-step sequence he calls Strengthen, Clarify, Plan, Picture and Prepare, built around fill-in lines like “Here’s how this will help me: _” and “Here’s how I’d explain it to a stranger in ten seconds: _”.
The steps themselves are not the point. The point is that someone roughly three decades into a daily practice is still changing how he uses it. There is no version of this where you get it right and then simply maintain it.
The One Thing to Try
Tonight, write a question at the top of a page. Any real one.
Answer it. You will have the answer immediately, because you already do.
Then write the word “but” and keep going for another five minutes.
That second paragraph is the technique, and it is the only part of this that most people are not already doing.
If you like methods traced to the person who actually uses them, rather than repeated secondhand, that is what my newsletter is. Short and occasional. You can subscribe here. And if you would rather have the whole daily practice laid out in order, I teach a course on it over on Udemy – a little over 36,700 people have taken it, which still surprises me.
