Journaling – The Stoic Method & App

I downloaded Stoic from the app store this week to try a different approach to journaling and this review is based on the 7-day trial period before the paywall kicked in.

You’ll see from my other post (The Power of the Daily Journal) that I believe journaling is very important to leading a successful life (however you define it), but the challenge is that it can be very open-ended. I use Day One, but the current version does not prompt you with questions like the old Day One Classic used to. You can define your own prompts, but having something come at you unexpectedly makes you think outside the box and get some perspective.

That’s why I thought I would give Stoic a try. It’s billed as a ‘mental health tracking app’ and since a lot of my posts here centre on this area, it seemed more relevant to my way of operating than an open-ended tool on a day-to-day basis. And, if you’re like me when it comes to facing your fears, this app applies stoicism to managing stressful situations, fear and negative emotions by providing a structured Q&A process to help guide you through the darkness. Doing the work is essential.

The Stoic Mental Health Tracker

Here’s the sales pitch: Stoic can help you live a happier and more tranquil life. you will learn stoicism philosophy and how to cope with stress. Get your daily mental health tracker companion for mood tracking, journaling, meditations, and reflection. It analyses your emotive influences and gives you insights on how to be happier and more productive.

Stoic App – Elegant Graphics Too

My Experience with the App

I started reading The Daily Stoic at the beginning of 2019, also recommended by Tim Ferriss (more from him here), though tailed off with my daily readings as I often do with long-term commitments (I’ve always been a starter, less a finisher). Something in the prose resonated with me and, having been accused of being more like Spock from Star Trek at times, maybe this is my more logical choice of philosophy for my life. So I took the plunge and started journaling with the app.

Like many apps today, stoic operates on a subscription model and asks you to sign-up for a 7-day free trial with an annual subscription of £30 per year thereafter.

It follows a classic journaling template with a morning session, an evening session as well as a number of exercises which you can do when you want but which are also selected as part of the morning or evening routines. I break down the morning and evening sessions below so you get an idea of how it plays out, plus a summary of each of the 7 different exercise types. There’s a quick rundown on the settings and a mention of the statistical analysis that the app promises (but you don’t get to see in the free trial). After that, I’ll sum-up my thoughts.

Morning Session

The first thing it asks you to do is to give a memorable title to your day. I found this curious because at the start of the day it’s hard to know where it’s all going. Maybe over time, you become better at directing your life, but I would find it more useful to be able to edit this at the end of the day so you could title it with something like a key lesson or event.

The app then gives you a quote for you to reflect on, a little slice of daily wisdom. Here was my first quote – a lesson in good manners. You can customise which types of quotes to include from Stoicism, Buddhism, the Tao and the Bible in the settings.

“Remember to act always as if you were at a symposium. When the food or drink comes around, reach out and take some politely; if it passes you by don’t try pulling it back. And if it has not reached you yet, don’t let your desire run ahead of you, be patient until your turn comes. Adopt a similar attitude with regard to children, wife, wealth and status, and in time, you will be entitled to dine with the gods. Go further and decline these goods even when they are on offer and you will have a share in the gods’ power as well as their company. That is how Diogenes, Heraclitus and philosophers like them came to be called, and considered, divine.”

~ Epictetus

It asks you 4 simple binary-style questions to get a feel for what it will offer up next.

It then asks you a random question to make you think about where you are and where you are going. You can modify this or set one or more of the default questions to appear every day if there’s something you want to work on more specifically. Usually, this is open-ended and reflective; classic journaling.

It then offers three exercises for you to do. This seems to be based on your answers to the first 4 questions, but you can choose none or all of them (the latter is what I assume the app wants you to do).

Overall you could spend 30-40 minutes on your morning session with this app (depending on the exercises it recommends), though I had imagined it would be more of a 5-10 minute session. However, many successful people suggest you spend 30 minutes to an hour in the morning reflecting on what’s important, so this app certainly drops you into that mindset.

One important point to note is that you should click the “finish morning routine” button at the bottom once you have completed as many of the exercises as you want to ensure your inputs are saved.

If 30-40 minutes sounds too long, check out my own morning and evening journaling templates and system.

The Exercises


There are (better) stand-alone apps for this like Pause, as well as being built into many other mindfulness apps such as Calm, Insight Timer and Headspace, but the implementation here is pretty straightforward and you can choose between relaxation and focus. I found it less beneficial here due to the nature of the graphics (black and white are not as soothing as the softer tones and edges used in the other apps) plus it only runs for 1 minute so you may need to re-run the timer. Also, the second time around (in relax mode) the counter inside the rounded square which inflates and deflates didn’t seem to match up to the actual movement which was very distracting. I’m sure this is a bug the devs will fix.


Swirly circles and a background sound ranging from fire to wind to rain to leaves. Fairly basic and you can set the length of your meditation session, but I prefer more developed apps like Insight Timer and Calm, or using one of the guided meditations from people such as Gabrielle Bernstein.

Fear Setting

This is a tough one. It takes a good 30 minutes to work through the questions (see also Tim Ferriss’ video here for more insight) but it is incredibly powerful – as long as you take the courage to act on the insights you gain. The final step in the process – the consequences of inaction – make you realise that almost any action is preferable to inaction and should spur you on to greater things.


This is actually Negative Visualisation. It is a technique that focuses on thinking about the negative outcomes in your life. The idea is to contemplate what you own or have achieved and visualise your life without the things we take for granted. It is intended to help remind you how lucky you are and better appreciate the things you already have. According to the app it takes 10-20 minutes unless you end up contemplating the fundamental meaning of existence whereupon it could take a few hours!

It’s a specific technique for appreciation, and there are other methods out there.


The app asks you a question and then asks if you think your response to the question is in any way skewed by one of a number of standard biases. Simple stuff, but it can make you pause and realise you have a tendency to see things not as they may be.


You get to pick an area to journal about such as your thoughts on the daily quote, planning your day, gratitude, a summary of your day, future dreams, milestones, freewriting, fear setting, etc.


The app picks one of the many quotes and then asks you to write about it.

Evening Session

The evening session plays out much as the morning one did, but the journaling aspect of the app is more reflective and allows you to select a particular focus, from free-writing to reviewing your fear settings, to gratitude and others.

Settings Deep Dive

There is a setting in the app that switches on therapy mode which seems to switch off the ability to do the morning and evening routines as well as a whole bunch of settings (like the ability to refer the app, send feedback, etc). Not really sure why though as it doesn’t seem to be explained anywhere.

Other settings are pretty standard and include adding a PIN to lock the app (though touch/face ID would be a nice upgrade), the option to integrate with Apple’s Health app/ecosystem (I presume for the meditation/mindfulness options), options to choose which of the four quote topics to include (Stoicism, Buddhism, Tao and the Bible) as well as the ability to change the app’s icon (black/white, white/black, pride).

Statistical Analysis

There is a section which starts to analyse your responses and build trends over time to provide better insight into your progress. There is also an option here to authorise integration with the Health App, but the kicker is that the analysis doesn’t start until 14 days of data has been gathered. While I appreciate you need a good data set to be able to produce tangible analysis, it’s a shame the app only gives you a 7-day trial so you don’t get to see how the analysis works unless you pay for a year’s subscription. Facepalm!

Overall Thoughts

I like the idea of the app. It’s a more directed form of journaling that helps you address things like fears which hold you back, as well as help put things in place to move you forward. It’s very well thought out.

Other systems, like the High-Performance Habits Planner, the Best Self Journal, et al, all embody these elements but – for the newcomer – may seem like overload. They can feel like jumping from the slow lane to the fast lane in an instant. While they are perfectly valid, they take a lot of discipline to fully embrace (I know, I have both journals without a single entry) because your inner self isn’t fully aligned to what they are able to deliver. You will struggle to get from where you are today to where they can take you tomorrow.

Sometimes you need a little more help, a little more guidance and a little more time to work up to what they offer, and that’s where an app like Stoic can come in. Download it, try it out for 7 days. You might start to move your own life into a higher gear.

Will I Use It?

While I think the app is great if you don’t already have anything in place, or if you find nothing is working for you, I won’t be taking out a subscription.

The reason is that I already have the book The Daily Stoic, so just need to have the same discipline to pick that up first thing instead of a smartphone/app combo that our brains seem more addicted to. I can do the same reflection and journaling based around the ideas in the app (or any of the other journals I have) plus bring in the exercises on a more regular basis (for example meditation 3x per week, fear-setting every month, etc). It’s a little more manual but, maybe I am coming round to the physicality of the printed journals and the benefits that the trainers and coaches espouse to putting a real pen to paper!

Also, I prefer to have a more fixed morning and evening routine, something that is more sandboxed in time so I know beforehand how much time to allocate. Timing is key.

My daily schedule can be all over the place and being presented with a “you’ll need about an hour or so for this morning’s routine” or “today will only take about 10 minutes” based on an arbitrary line of code in the app leaves me less in control than I’d like. The longer exercises (visualisation, meditation, and fear setting) are something I’d prefer to plan a chunk of time for outside of this morning/evening session and not bundle into morning and evening sessions.

UPDATE: Just after I published this piece I found a new journaling app called Jour (iOS only at the time of writing). It’s typography and design style is much more relaxed and sets you up nicely with 5-10 minute morning routines. It’s early days and the team will add the evening routines shortly. It extends the idea of exercises with ‘Journeys’ which are guided exercises (like fear setting which is already included), so you can pick an area you want to focus on and work through this in parallel with your daily routines. It seems to blend the idea of journaling with apps like Calm and Insight Timer by building a library of Journeys to help you with things that may be blocking your success. It looks very promising and I will update you on this app in due course.

Are you a student of stoicism? Have you tried the Stoic Journaling app? Let me know in the comments below and get the conversation started.

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