I’ve lost count of how many Leichtturm1917 notebooks I’ve bought, only to fill three of their pages with ink from the pens I also purchased at the time and have subsequently misplaced.

For me, journalling never sticks. No matter how much I think I want to do it.

I love the idea of journaling for personal fulfilment, productivity, and development. But like so many things in life, the process is often far less enjoyable or addictive than it appears to be when you watch others doing it.

This issue extends into the digital realm; I’ve had the same problem making the brilliant Day One app stick for a long time.

But I’ve finally found a use for it.

My history with Day One

For the uninitiated, Day One is a digital journal. It’s available on the Mac, iPhone, iPad, and Apple Watch. It’s free to use and offers a beautifully simple approach to getting your thoughts and photos onto ‘paper’. There’s also a paid tier, which enables cross-device syncing, multiple journals, and a few other goodies.

Day One has won several design awards and earned its developer, Paul Mayne, a much-deserved fanbase. This culminated during the summer of 2021 when Day One was acquired by Automattic, the company behind WordPress.

I’m happy to say that little has changed since the acquisition, thus (hopefully) validating Mayne’s reassurance that he’d remain at the helm and continue to lead the same passionate team that has developed Day One over the last 10 years.

My personal history with Day One has been embarrassingly inconsistent. I was an early Day One adopter in 2011 and used it to journal my daily activities. That stuck for a bit, but a few too many skipped days led to me abandoning the app entirely.

Since then, I’ve dabbled with Day One, on and off. Most notably, I used it to journal the start of my YouTuber journey and began building separate journals for charting my progress, noting down random ideas, and keeping track of useful tidbits picked up during my research.

But still, it wouldn’t stick.

As it turns out, I was simply using it wrong.

My new business planner

I’m currently undertaking a rather serious bout of business planning. I have a lot of thoughts, ideas, and desires to get out of my head and onto paper. In the past, this would have prompted me to open a Word document or delve into Evernote. There’s nothing wrong with either of those tools, but it struck me the other day that my past business planning endeavours have usually resulted in me getting lost in formatting, toolbars, and relentless organisation.

What I needed was something that would encourage thought exploration; a tool that would give me a clean, uncluttered interface on which to build the future plans for my business.

Ulysses came close. But it wasn’t quite right; it feels like too much of a word processor (which is exactly what it is). Writing down the initial formation of my new business plan in Ulysses would therefore feel like I was embarking on a long-form blog post. Not ideal.

Then, it struck me: Day One had everything I needed. It’s designed to get all of that stuff out of your head and onto paper. The user interface is about as uncluttered as they come. Text formatting is consistent, easy, and benefits from markdown support. It even has that all-important ‘use me as you want – I’m your personal journal’ magic sauce.

I have no idea what’s in that magic sauce, but trust me, it exists.

In reality, Day One is nothing more than a simple text and markdown editor that enables users to organise entries within a simple file and tagging structure. It is basically a completely stripped-down, more attractive version of Evernote.

So, how am I using it to plan my business? It’s easy – I’m simply adding entries into Day One for all aspects of the business plan, be it the financials, long-term goals, partner research, or mission statement.

Because so much of the plan is intertwined between these different entries, I’m using tags to group them together. For instance, if an entry includes details on both YouTube channel planning and budget requirements, I can include a tag for each, thus making it easy to find everything related to those elements. This has proven to be a beautiful way of breaking up a business plan into separate journal entries and not being bound by one MASSIVE Word document which fast becomes unwieldily.

Using Day One for this task feels so natural and enjoyable.

But you probably have one question.

Will it stick?

You know, I think it might.

Admittedly, I’ve only been using Day One for this purpose for a few days, and I’m conscious that the novelty may wear off, but I’ve got a trick up my sleeve to counteract my pathetic commitment issues.

Over the last year, I’ve found that recurring tasks in Things has been my saviour. This isn’t an earth-shattering, unique discovery, but I have been surprised by how the presence of a recurring task on each day’s to-do list has forced me to make certain duties habitual.

I’ve applied this process to my business planning in Day One. Each day, Things reminds me that I need to spend half an hour or so working on my business plan. It’s going to work, too, because this is big deal – the result of this business plan could transform my future. Therefore, I have the will, need, and desire to meet that mini-goal each day.

And now, I have just the tool to make it enjoyable. Thank you, Day One!