I have a Google Doc that’s 47,000 words long. It has no title. It’s not organized. Nobody has ever read it, and nobody ever will.
It’s where I think.
Not journal entries exactly — those are in a separate notebook. This doc is where I work through problems by writing about them. Business decisions. Client situations. Ideas that won’t leave me alone at 2 AM. Strategic questions I can’t answer in my head but can somehow untangle on a screen.
I started it three years ago, after reading something Joan Didion wrote: “I don’t know what I think until I write it down.” I thought it was a nice quote. Then I tried it and realized it’s not a quote — it’s a description of how thinking actually works.
The Problem with Thinking in Your Head
Here’s what happens when I try to solve a problem by thinking about it. I loop. The same three considerations circle around each other endlessly, like a carousel that’s impressive the first time but maddening by the fifth.
Should we hire a content strategist or outsource? Well, hiring gives us more control. But outsourcing is more flexible. But control matters because quality matters. But flexibility matters because our needs change. But quality. But flexibility. But—
The loop doesn’t resolve because it’s not a loop. It’s a tangle. And tangles don’t untangle themselves through repetition. They untangle through structure. Writing provides structure.
When I write about the hiring decision, I’m forced to do things that thinking alone doesn’t require. I have to put the considerations in order. I have to give each one a paragraph, which means I have to actually develop it beyond a half-formed instinct. I have to see where one argument ends and another begins, which often reveals that two things I thought were separate are actually the same thing, or that something I assumed was a minor factor is actually the crux of the whole decision.
Writing is slow in a way that thinking is not. And that slowness is the feature, not the bug. The speed of thought allows you to skip over gaps. The plodding pace of writing forces you to fill them in.
My Process, Such as It Is
I don’t have a formal writing practice. That phrase — “writing practice” — implies a discipline I haven’t achieved. What I have is a habit that I do most days but not all days, usually in the morning, usually for about twenty minutes.
I open the doc. I write whatever is on my mind. Sometimes it’s a specific problem: “The Prodeal engagement isn’t working and I need to figure out why.” Sometimes it’s more amorphous: “I’ve been feeling stuck and I’m not sure what’s causing it.”
I don’t edit as I go. Editing and thinking are different activities, and doing them simultaneously sabotages both. I write badly and keep going. Sentence fragments. Half-baked assertions. Contradictions that I’ll notice later. The point is not to produce good writing. The point is to externalize the contents of my head so I can see them.
Usually, somewhere around word 400, something clarifies. Not always — some mornings the doc gets another 600 words of unresolved mush and I close it feeling no clearer. But more often than not, the act of writing surfaces something I didn’t know I knew.
Last month, I was writing about why a particular client relationship felt off. I’d been attributing it to a personality clash. But as I wrote, I realized the real issue was that we’d never established clear success metrics. The personality stuff was a symptom. The missing metrics were the disease. I wouldn’t have seen that without writing, because in my head the personality narrative was too vivid and too satisfying to see past.
Writing to Share vs. Writing to Understand
These are two different activities and I think conflating them is why most people don’t write more.
Writing to share — blog posts, articles, social media, this essay — requires craft. Audience awareness. Structure. Editing. A beginning, a middle, an end. It’s a performance, even when it’s honest. You’re shaping the thinking for someone else’s consumption.
Writing to understand requires none of that. It can be ugly. It can be circular. It can be wrong. It’s not for anyone. It’s the textual equivalent of talking to yourself, and it’s just as useful and just as socially unacceptable to admit to.
I think a lot of people avoid writing because they assume all writing is the first kind. They picture a blank page and think: I need a thesis. I need an argument. I need this to be good. And the pressure of that expectation kills the thinking before it starts.
The 47,000-word doc has no thesis. It has no argument. Large portions of it are embarrassingly bad. But it’s where some of my best decisions were made, where my clearest thinking happened, where problems got solved not through brilliance but through the mechanical act of converting thought into text.
Why Founders Should Write More
I’m not saying every founder needs to publish a blog or build a personal brand through content. That’s a separate argument with separate merits. What I’m saying is that every founder should write as a thinking tool.
Running a company generates an enormous amount of ambiguity. Strategic questions that don’t have clear answers. Personnel decisions that involve competing values. Resource allocation under uncertainty. Product direction when the market is shifting.
Most founders handle this ambiguity by talking about it — with co-founders, advisors, team members, mentors. And talking helps. But talking has a weakness that writing doesn’t: other people respond. They offer opinions, reactions, suggestions. Sometimes that’s exactly what you need. But sometimes you don’t need input — you need output. You need to know what you think before you absorb what others think.
Writing gives you that. Twenty minutes alone with a document, before you’ve asked anyone else, before you’ve been influenced by anyone else’s framing. Just you and the problem, rendered in sentences that force you to be specific.
I’ve made several major business decisions by writing about them first and only discussing them after. The writing didn’t give me the answer every time. But it gave me a clearer question, which made the subsequent conversations far more productive.
The Journal
Separate from the Google Doc, I keep a physical journal. Moleskine, unlined, because I like the anarchic energy of writing without horizontal rules telling me where to put words.
The journal is more personal. Less business, more life. How I’m feeling. What I noticed. Small observations from the day that don’t fit in any productive category but feel worth recording.
I write in it maybe four times a week. Short entries, usually. A paragraph or two. Sometimes a full page when something big is happening.
The value of the journal is different from the value of the doc. The doc is for solving problems. The journal is for noticing patterns. When I read back through old entries — something I do every few months — I see themes I couldn’t see in real time. Recurring frustrations that point to structural problems. Recurring sources of energy that point to where I should spend more time. Gradual shifts in what matters to me that were invisible day-to-day but obvious across six months of entries.
Last year, reading back through the journal, I noticed that every entry from a certain three-month period mentioned feeling disconnected from creative work. I’d been so focused on operations and client management that I hadn’t written a single piece of original content. The journal showed me the cost of that drift — not in business terms, but in personal terms. I restructured my week to protect creative time. The change was small. The impact was large.
The Resistance
I understand the resistance to writing. It’s slow. It feels indulgent. When you have forty things to do, sitting down to write about your thoughts feels like the forty-first thing, not the thing that makes the other forty easier.
And there’s a vulnerability to it. Putting your real thoughts on a page — even a page nobody will read — means confronting them. It’s easier to keep the thinking vague, swirling, undefined. Vague problems feel manageable because they’re shapeless. The moment you write them down, they take form, and form can be uncomfortable.
But that discomfort is the whole point. The problems exist whether you write them down or not. Writing just makes them visible. And visible problems are the only kind you can actually solve.
What I’d Tell You
If you’re not a writer — if you’ve never kept a journal, never written for yourself, never used writing as anything other than a communication tool — try this.
Tomorrow morning, before you check email, open a blank document. Write for fifteen minutes about whatever is taking up the most space in your head. Don’t structure it. Don’t edit it. Don’t think about whether it’s good. Just get the thoughts out of your head and onto a screen.
Then close the document and go about your day.
Do it for a week. See what happens.
I’m not promising clarity. I’m not promising that writing will solve your problems. But I’m reasonably confident that by Friday, you’ll know something about your own thinking that you didn’t know on Monday. And that’s worth fifteen minutes.
The 47,000-word doc isn’t going anywhere. It’ll be 50,000 by the end of the month. Nobody will ever read it. That’s what makes it the most useful thing I’ve ever written.