Writing a book in four months

Never sit down to write cold

The physical copies of Timeboxing arrived from Penguin Random House this week. It felt nice, of course, to see them, hold them and smell them. I even started reading it for a little while but I found myself just looking intently for typos (unsuccessfully, I might add), so I stopped.

The book’s arrival was a big moment for me. The project has successfully produced a physical cuboid of 300 printed, paper sheets. 

It made me reflect on that project and how the book came to be. It didn’t take very long. So perhaps if you’re one of the 80% of people who think they have a book in them, this might encourage you. (And if you’re more interested in shorter writing endeavours, such as 1,000 words, here’s a shorter story.)

What happened

Penguin got in touch with me just over a year ago (Nov 2022), having seen a viral TikTok video which used my name and a HBR article I’d written. We talked for a while and signed the deal at the end of January. I then wrote the first draft of the book over four intense months — Feb through May. A gentler period of editing followed and lasted until September. Since then the focus has been on promotion. 

A detailed plan

I was brand new to all this so I asked a friend who works in publishing. She advised me to write a very good, very detailed plan. Such a document would obviously help convince the publisher that you will write a good book and agree terms. It will also help you to write a good book. 

The first draft of my plan was not great. It was short, missed some key book pitch sections and lacked rigour and detail. So I decided at the start of the Xmas holidays last year to do the best pitch I reasonably could. And I did so by timeboxing that 3-week break meticulously. The outcome was a detailed plan of 10,000 words, including an intro to the timeboxing concept and why it matters, some stuff about me and why I’m well-placed to write it, and a 250-word chapter synopsis for each of the 24 chapters I had in mind.

Chapters as chunks

The chapter synopses were indeed invaluable when it came to writing out the full book.

Short chapters help maintain momentum for the author, writing, as well as for the reader, reading. I also had lots of experience of one- to two-thousand-word essays, writing for publications such as HBR and the weekly newsletters at Filtered. So this felt familiar and feasible: I had 24 short essays to write. I could meet my contracted deadline with Penguin by writing one chapter a week. 

When I sat down to write, I never started cold because I always had, at the very least, a 250-word synopsis. In most cases, by the time I came to write the chapter, I’d also have some additional ideas that had occurred since I’d submitted the pitch doc. 

Not starting cold was how I avoided (and how I avoid) writer’s block. Cold starts make blocked writers.

Routine

Of course, there was a routine — a series of timeboxes — behind the writing of a book about timeboxing. Specifically:

Monday evening. For an hour I’d read through my synopsis + additional notes as they were, rough and raw. Sometimes this would prompt a little research and anything I found that seemed relevant I’d paste into my Google doc. 

Thursday evening. Having had 3 nights' sleep since refamiliarising myself with the chapter material, I was in a good headspace come Thursday to turn the rough and raw material into structured bullet points (most chapters consisted of three or four sections). This usually flowed nicely and I got it done well within the hour I’d timeboxed for it. 

Saturday morning. I generally felt energised to write the chapter and got up early — at 5 or 6am. I timeboxed 15 minutes for the intro, 30 or so for each section (depending on how long it was), 15 mins for the conclusion and 30 mins to read it through and make a first set of edits. Monday & Thursday’s groundwork prepared and warmed me up for this Saturday morning writing session. I’ll state it again as it’s such an important idea for timeboxing and writing: I never sat down to write cold. I’d then go for a 5km run, a couple of further thoughts would usually occur, and I’d add those in on my return. I’d then share the doc with my mum (who was my first editor throughout the book-writing process) who’d give it another set of suggestions many of which I’d incorporate (usually the next day). I think back of those Saturdays very fondly.

The benefits of timeboxing are mostly thought of in terms of the timeboxes themselves — how focused, deep and high-quality those sessions can be if they’re well-planned and executed. Of course, that’s true but the longer periods in between scheduled timeboxes are important too. The diffusive, subconscious thinking that goes on during a run or a sleep or in a shower if you’ve seeded your mind with the right kinds of information and inspiration can be special. That’s why the routine above included a couple of nights’ sleep between each session. 

Momentum

I started well. On the Friday evening before that very first Saturday morning session I was out with some friends. There was a lot of fun going on that night but I tore myself away early, with more than a tinge of regret. I kept that sort of discipline throughout the four months. That, combined with the routine described above, meant I stayed ahead of the schedule. This way, it seemed like the work I was doing was getting me further ahead rather than catching up from behind. That felt positive and proactive. I was also aware that with timeboxing as the subject matter, I’d look daft if I didn’t meet or exceed agreed deadlines.

On average, I got six chapters done each month, rather than the four estimated. The book consists of four parts (BELIEVE-PLAN-DO-OWN) and I had an idea early on that if I could get a whole part done each month, things would be well. That’s what I did. It did entail some sacrifice. During holidays I’d get up before the rest of the family and implement a compressed version of the above routine. On a 2-week holiday in Costa Rica I got four chapters done, on a short business trip to the US I did three (including two on the flights each way) and two skiing trips yielded five further chapters. Half the book was written on vacation. But since the writing was a joy and writer’s block was kept at bay, it barely felt like a sacrifice.

In the end, I was able to hand in the 45k word draft, distributed over 24 chapters, on 29th May 2023, several months ahead of the contracted schedule.

Timeboxing, the book, written. Timeboxing, the practice, vindicated.