Alternatives to Journaling for Founders

Ben Jones
OutStride Coaching
Published in
3 min readFeb 13, 2023

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I bring up journaling with the founders I coach and get one of two reactions.

Sometimes it’s “I love journaling”, but more often it’s a muted sigh: “I’ve tried it, but it just doesn’t work for me”

And that’s ok…! Journaling can be tough. Not everyone enjoys writing and it can be especially difficult when you’re writing about your innermost thoughts and feelings. The dopamine rush from checking emails is way more fun.

Journaling helps founders think

The larger the company gets, the less you will do and the more you will think.

Jeff Bezos famously said that he only expects himself to make three good decisions a day.

Good decisions require good thinking and journaling is one way to encourage good thinking.

Physical or computer journals. Both are great! — Photo by Thom Holmes on Unsplash

Alternative 1: Record yourself (and listen to it)

Instead of sitting down at your desk and staring at your computer for yet another hour, go for a walk and have a conversation with yourself.

What is it about X that’s bothering me so much?

The biggest thing holding back the co-founder team is _____ ?

By recording your answer you force yourself to put your thoughts in a human readable format. This is insanely valuable. Firstly you get them out of your head and secondly you have to put them in some kind of coherent structure.

Optionally, you can also listen back to your answer. I personally don’t do this that much, but I know some people who swear by it.

You might feel a little weird at first, but soon you’ll get used to talking to yourself like a crazy person. Remember, the world won’t think you’re crazy if you’re wearing AirPods!

Walking helps thinking — Photo by Victor Malyushev on Unsplash

Alternative 2: Explain to a neutral listener

Find someone in your life who is disconnected from your startup like a friend of family member.

Ask them to do you a favour. They are going to listen.

I have this really difficult situation with an investor…

There’s this guy who I hired and it’s not working out because…

You do not want their opinion. You do not want their input. They are simply going to listen and hear what you say. Their job is to be a speech mirror.

They are allowed to ask clarifying questions e.g. what do you mean by X, but that’s it.

Why is this valuable? Again, it forces you to put your words into a human-readable format, again with a real human involved! You can end the call by sharing any insights you had and… of course, thanking them!

Coaching + Journaling = ❤️

Hi, I’m Ben, a founder-turned-coach. I scaled my company to 130 people, raising over $70m in funding before stepping back to focus on coaching full time.

Now I support founders in 1-on-1 & group formats on topics like strategy, co-founder relations, and fundraising. Read more here.

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