Stoic Self Reflection – Learnings from 5 Years of Weekly Practice

In this article, I am outlining how the key lessons learned and insights gained from practicing stoic self reflection weekly for over 5 years consistently and some of the benefits you might gain from it too if you start the practice. I am also linking my free to download weekly reflection template; the one I created and use personally for my weekly stoic reflection practice.  

Stoic Reflection Questions You Can Use in Your Own Weekly Stoic Reflection

Based on the weekly stoic reflection template, I am taking somewhere between 5-30mins (depending how I feel) writing a stoic reflection every week with the following structure.

These could as well be used as stoic daily reflection questions for example. The key is to simply find your own rhythm that works best for you. All I am aiming for with this article is to inspire you to do your own personal version of this. Only you yourself know whether doing this practice is right for you as well as in what cadence you wanna do it. This could be anything from annual, monthly, weekly to even daily. I found the weekly rhythm to be the sweet spot for me personally.

Short summary of the week

Quick summary of events, where I might have travelled, where I am writing the reflection from. This could simply be something like the following real examples from my reflections:

• “calm weekend as I was kinda tired from work; busy workweek and really enjoyed seeing x friend again” as well as 
• “Crazy week, got promoted and am writing this reflection from Japan; travelling a lot lately for work – just got back from San Francisco last week!” or 
• “Holy shit; I got my first sale on my new side project mypassion.ai”
• “Probably did the most stupid mistake ever this week and still thinking about this stupid thing xxx” 

Did I experience anger? envy? lust? Why did the week’s events upset me? What could I have done to avoid getting upset?

This is mostly related to triggers I am noticing in daily life. Less about things to improve on myself. The goal here is to better understand myself by asking myself what triggered me during the week and why this has done so. I am asking myself questions like: 

• Why am I triggered by this one colleague calling me out in a meeting? 
• Why was I a little upset about this and what can I learn from it? 
• How can I become a more reflective person, more at peace with a similar situation in the future?
• Why did this trigger something in me and likely won’t really trigger most others?
• What can I learn about myself from this? 

What failures have you overcome? Where can you improve? What has disturbed my inner peace?

• What can I improve
  • What has disturbed my inner peace this week? What have I not done well that does not align with mz values that is not to happen again? What chage in my daily habits might be necessary to prevent this from happening again and having more inner peace? 
  • I used to be very self critical, especially at work, but it is important here not to be harsh with yourself
  • Could be as little as, sending that message to my mom when being abroad

3 things I am grateful for

Gratitude simply always reminds ourselves to be actually grateful, especially for the smaller things in life. No rocket science, but as usual, simple consistent practice at least weekly makes a big difference. I used to do this practice daily in my morning routine as a stoic morning reflection as well as a quick stoic evening reflection before going to sleep. 

However, personally, I am not always following a strict morning routine as I don’t like to be too strict on myself either. We don’t just want to end up as self-improving machines forgetting to live life along the way, do we?

• I was so happy about and am so grateful about my friend x who reached out to me after a long time 
• I am grateful for my tasty morning coffee
• I am so grateful to be able to write this reflection at my cozy and warm home right now

What goals did I achieve?

Professional life

Based on the goals I set for myself in a professional context such as lifelong (self) education and up-skilling, passion projects or side projects I am working on as well as some noteworthy achievements in my main job or business.  

• Making progress on my passion projects and having reached my goal of publishing 1y blog post / week
• Having read 2h this week 
• Certain achievements at work, having delivered a project with positive feedback or new clients and revenue milestones in the business

Private life
What little steps, baby steps and also bigger goals have I achieved this week to celebrate? Privately, such as 

• going to the gym twice, regular sport 
• Having meditated 3x times this week 
• Etc. 

State of mind and thoughts

What is on my mind right now and what are my thoughts? Writing about this in an unstructured way helps me get more clarity on the key topics that kept my mind busy this particular week. I am also using this writing for clarity reflecting on key life events and bigger decision I made or I am about to make.

Example of The Stoic Reflection “Thoughts” Section 

This is an actual example excerpt of this unstructured section. This is literally the section pulled out of my personal stoic reflection to give you an authentic example on this. 

“I do believe life operates in cycles, kind of like a rollercoaster. Sometimes it goes up, sometimes it goes down. I do believe as long as we are willing to reflect on the down phases and try to really get the lessons life tries to teach us during these phases, life will always go up again. 

That is the ultimate spark of hope. It means when times are worst, it can only get better. It also teaches humility to be grateful when times are great because worse times may just be around the corner again. 

While at a societal level, as explained in the famous book “Sapiens by yuval noah harraris” history unfortunately tends to repeat itself but at least on our own personal level at least we can learn lessons during the down phases, the necessary and unavoidable tough times in life, potentially taking a hard decision to change the circumstances that got us into this down phase in the first place. 

We can come out stronger, prepared for better times life has yet to offer – based on this philosophy. In hindsight, I do believe when we go through much struggle life is testing whether we are ready for the next chapter and tested whether we actually are ready to get to the next level in the game of “life”. I am.”

Stoic weekly reflection Based on Principles from Seneca, Aurelius & Co

These reflections are based on Seneca, Aurelius among other well-known stoicists. Mostly the book A Guide to the Good Life: The Ancient Art of Stoic Joy among others from well-known stoic philosophers such as Seneca’s letters and Marcus Aurelius’s meditations mainly inspired this approach. 

Conclusion

The stoic weekly reflection was and still is one of the most powerful tools I use to sort of do a regular “self therapy” every single week by looking into myself, by being honest with myself about the positive as well as negative situations life throws at me, and by better understanding my inner intellectual and emotional state. 

This allows me to zoom out, look at life from the bigger perspective, what actually matters in the bigger picture of things, and to use life’s, sometimes little, sometimes big, daily struggles as a tool to listen into myself and improve continuously emotionally, spiritually and philosophically.

Stoic self reflection allows me to stay grounded and humble. It also is a tool that allows you to go back in time and reflect on your “state of mind” from months or years before to see how your character and mind evolved – especially in phases in which we struggle; when life challenges us the most. 

I encourage you to give it a try to start reflecting weekly on whatever questions are most relevant to you. You can use the same or totally different questions, and reflect on the topics that are most important to you personally. 

All I am sharing in this article is simply inspiration from my personal use. The only person knowing what is right for you, what the right questions to reflect on are, is yourself.

Stoic reflection improved my decision making in private and professional life and has a colossal positive impact on my life. I can only think of continuous learning and reading, regular sports and meditation being routines of similar value as a weekly stoic reflection habit. This can have the same impact on you. You just need to give it a try and you can easily get started today by using the free weekly reflection template.

Book & Reading Recommendations

• A Guide to the Good Life: The Ancient Art of Stoic Joy – William B. Irvine. 
• Letters from a Stoic – Seneca
• Meditations – Marcus Aurelius