My relationship with writing diary entries started as an unpleasant one. Mostly because diary entries were homework I received in school during summer break. Not only did I have to record each day (vs enjoy it), but also our teacher read these entries and graded us. I wasn't sure if I was judged for having a relatively lame summer break or for my writing. Overall what this exercise did to me was associate judgment with the practice of writing.
I started journaling when I became a full-time founder. This happened because most times I had thoughts and ideas that I wanted to process, and make space for new ones. I picked up journaling as a habit because I didn't want to burden my friends with all my thoughts. I only wanted to burden them with SOME of my thoughts.
I started writing judgment-free diary entries. I told no one that I would journal. I didn't have a ritual of questions I wanted to think about. I just had a pen and a blank notebook. I wrote whenever I wanted to. Whatever I liked. This brings me to Golden Rule #1 (and the only rule I know):
Write like no one is ever going to read it.
This has been one of the best things I did for myself. It rewired my brain to delete the feeling of judgment with the practice of writing and replace it with zen.
The toughest part about writing is building a habit around it. Before I share my tips on how to get started, I'll acknowledge that there are 2 kinds of people: 1. the ones that just want to get the task done (me) and 2. the ones that enjoy the process of organizing and building a structure (Dafni).
Here's our shortest beginner’s guide to getting started with journaling for both.
Getting started with journaling (category: I-just-do-it people)
Grab a pen and a notebook/ planner. Don’t start by over-engineering the concept and fall into the trap of maintaining digital notes.
Freely write your thoughts. Anything. Anytime. Don't overthink patterns or themes. Most of my daily entries are bullet points aka unrelated thoughts.
At the end of the week, read through all that you've recorded. Log your thoughts and feelings.
You'll slowly start enjoying the therapeutic exercise of confronting and processing your thoughts. Bravo! You would've finally written your funniest, happiest, gloomiest, scariest thoughts on paper. Now you can choose which ones you want to discuss with your friends, colleagues, family, or therapist.
If you struggle with free writing and want help in journaling with some structure, I invited Dafni from across the room to write the next section.
Getting started with journaling (category: I-love-to-organize people)
A task I find surprisingly fun and relaxing is organizing and curating. I can spend hours discovering new music and curating a playlist based on a specific mood or theme. I have trackers for my travels, my financials, even one for my plants to take better care of them (the newest in my collection).
When it comes to organizing my thoughts and notes, I aim to strike a good balance between structure and randomness. There is always an amount of serendipity to journaling and your notetaking system wants to make space for that serendipity. At the same time, I need to know how my random thoughts and ideas fit into the grand scheme of things. So, I group stuff together by theme or project and use different tags to make it easy to come back to them later (examples of tags: useful, inspiring, personal). This helps me go back in time and re-discover certain ideas and personal highlights. It also serves as a source of inspiration to discover what I want to write about next.
An important first step is to set up a digital notetaking system in one central space (mine is on Notion). Rather than spending hours structuring early on, pick a basic structure that works for you right now and iterate as you go.
A very popular method to build your personal knowledge management system is Building a Second Brain by Tiago Forte. With time, you will build your own second brain, or as I like to think of it, your own organized chaos of thoughts.
We're such fans of journaling ourselves that we take pride in various ways we've identified where it can be applied to your professional world (shameless plug to Wonderpath).
Reflecting on goals
Reflecting on action items/ milestones
Reflecting on feedback and advice
The core idea is, we get a lot of information and input every day and the only way to take it with you tomorrow and learn from it is by taking the time to process it.
I don’t want to convince you all to start writing because it'll make you more organized, happy, and zen. I want you to understand that journaling is a practice that you will do for the present version of yourself.
Happy writing for yourself!
PS: Our core job is building Wonderpath, but once in a while we’ll write here and share our learnings with you. If you’d like us to cover other topics in the ecosystem of co-founding write to us!
For more updates follow us on Twitter: WonderpathHQ, Dafni Chontou; Tanya Sharma