Journaling — how and why I keep a daily diary

Whether you call it journaling or reflection or writing a diary, I think of them in the same way: making time to reflect on your day, and keeping a record of what you did and how you felt.

I’ve been keeping a daily diary for years, and it’s one of the habits I’m most pleased to have maintained.

Journaling for memory

I can point to almost any day in the last few years and learn what I did, how I felt, and understand what was on my mind.

Every now and then, I’ll compare my current day to the same day one or two years ago. I’m frequently amazed at how issues and challenges that seemed insurmountable rapidly fade away into distant memories, or are completely forgotten until purposefully being resurfaced.

It’s a good reminder to keep my current fears in check.

Journaling for self-awareness

Journaling has enabled me to become considerably more self-aware.

I can see patterns of behaviour, consistency in what causes me to have a good or a bad day, and an awareness of what makes me excited or anxious.

I have learned how exercise, diet, and weather affect my mood. I’ve learned how creativity and socialising and alone-time affect me in different, and unexpected ways.

Journaling for thought development

Something I often need to remind myself is that journaling can be an incredible way to process my thoughts.

When I’m overwhelmed or stressed, it can sometimes feel like there is no good path forward. I could become frustrated or waste hours in an unproductive state fretting over my next move.

Journaling can sometimes feel like a cheat code for escaping this sense of overwhelm. If I can detect the feeling then I’ll try to find a quiet moment to write what’s on my mind in my journal.

Sometimes, just writing out all of the things worrying me is an incredible shortcut to clarify what’s bothering me, and can help me prioritise what’s most critical.

If I’m really stressed about a situation, I’ll attempt to answer some templated questions that will pull more thoughts from my mind. Often, framing a difficult decision with the question of “What’s the worst possible outcome?” can be enough to make progress.

Resources for journaling

Apps and resources that have helped me over the years:

Apple Notes — one of the most underrated apps on the iPhone. I used Notes to maintain a daily journal for over a year. It’s often the fastest way to jot a thought down.
Apple’s Journal app — for over a year Apple has offered a Journal app, with helpful hints and automatic suggestions. I love that it’s “moment” based rather than day based.
State of Mind on iOS — at a similar time to rolling out Journal, Apple introduced a method for logging your state of mind to Apple Health. You can set up reminders and a widget on your Lock

Where do you find inspiration to write?

Every so often, I feel at a loss when trying to figure out what to write about.

I frequently feel uninspired and lacking in ideas, so I will go weeks, possibly months without writing.

But there’s a great source of material I haven’t turned to enough: questions.

Whenever I speak at an event, or meet another founder, or really, anyone, I’m usually thrown a question of some sort.

I’ve started to note these questions down, as they’re the perfect starting point for topics to write about.

I’ve found that writing answers to questions I’ve been asked has three valuable advantages:

1. Writing addresses my frustration

If I had more time, I’d have written a shorter letter. — Blaise Pascal

When I’m asked a question, typically I must think on my feet.

Occasionally, that works OK. But sometimes, about 2 minutes after I’ve answered the question, I’ll realise I had something better to say on the topic.

There’s no rewind, or “edit” button for live conversation.

It can be incredibly frustrating!

By retrospectively writing an answer to questions I’m asked, I can address my frustration by giving a better answer.

2. Writing helps form better answers

I find writing to be a fantastic way to clarify my thoughts.

It forces me to consider something on a deeper level. The act of writing can crystallise a topic for me.

It’s correlated to the way I like to learn: if I must teach someone about something, it will absolutely force me to learn more about that thing.

I’ve often found that teaching others is the best way to teach myself, but it always feels like cheating!

3. Writing multiplies my impact

I’d like to think another benefit of turning these questions into written articles shared here, is that I can be more helpful to you, the reader of this blog.

When I have a chat with a friend, or when I am fortunate enough to speak at an event, I often think “gosh I wish that was recorded, the conversation could have been very helpful for more people.”

A wonderful thing about writing is it tends to last a lot longer than audio or video. It’s easier to find via search, and can more easily be edited to bring it up to date.

Some questions I have written answers to

Some questions I need to write answers to

Why are you building an email marketing tool, when it’s one of the most crowded markets you could possibly enter?
What’s driving you after so many years to keep doing GoSquared?
How have your values influenced your decisions and lifestyle recently?
What advice do you have for someone starting out on their own startup journey?

Do you have a question for me? Please

The crippling fear of hitting “publish”

“I am always doing that which I cannot do, in order that I may learn how to do it.” — Pablo Picasso

I’ve been feeling it increasingly — I’ll put a tweet together, a short article, maybe even a visual piece of work. I’ll be feeling pretty good about it, and then the time comes to hit “publish”…

That’s when the fear creeps in. What if this is rubbish? Is this going to offend someone? Will it be misunderstood? Will people judge me for it?

It’s been enough to make me undo all my work and not hit publish on countless occasions.

I know I’m not alone on this — even the best feel it to some degree whenever they’re about to publish their work.

I keep trying to tell myself, though: don’t let it stop you.

Usually, the worst thing that happens is no one cares. Everyone looks the other way and gets on with their lives.

No one cares as much about you and your work as you do.

With that in mind, I urge you (and my future self) to overcome that fear next time by hitting publish. It’s the fastest, most effective way to learn, iterate, and improve.