Introduction

This blog post describes a continuous training you can do to incorporate Philosophy and contemplation in to your life.

Enjoy! (or at least look at your suffering more objectively)

The Schedule

Daily

Morning Meditation

What will you do today, fate permitting? Go through your day step by step. What opportunities and challenges you expect to face, and how will you deal with them? Practice responding to adversity with the mental resources and skills you have.
Read a short passage from one of your favorite philosophical works (Marcus Aurelius, Epictetus, Seneca, Modern Stoics, etc.).
Go into silence for at least five minutes. Just sit there and observe without judgement or analyzing.

The whole thing should not take too much time: ten minutes on a busy morning. On a weekend morning you can spend more time in silence, and also reflect on a question more thoroughly.

Throughout the day

Continuous attention and awareness of your thoughts, actions, speech and moral choices (Prosochē). Ask yourself often “Am I doing the best thing I could be doing, right now?”, and “Am I responding and behaving in the best way I can?”.
Self-retreat (Quiet reflective moment + reciting few useful philosophical maxims/quotes), use when needed.
Mindfulness Meditation.
Practice discipline and moderation (food, drink, physical exercise).

Evening Meditation

Go through the events of the day.

Ask yourself these questions:

“What did I do amiss?”
“What did I do?”
“What duty was left undone?”

Answer the questions honestly, and when possible, in writing. Keep your file private. Do not just list the stuff you did or did not do throughout the day, but reflect on how you did in regard to your philosophical practice, virtues, and your own goals in life.

Monthly or quartelry

Do the normal Daily routine (Morning, daytime, evening). If you can spare the time, do longer sessions than usually.
Review the events of the past month/quarter, plan the next.

Choose one of these tasks to complete, either in writing or in your mind.

Yearly

Values clarification.
Review the past year, plan the next.
Consider participating in the Stoic Week or a longer course.

Exercises

Here are some more exercises and reflections you can add to your pracitce routine. Take one, many or all. Add them to your daily, monthly or yearly reflections as time allows.

Choose one to three important things that you are going to work on tomorrow.
Journaling / Freewrite
The cosmological perspective (time / space).
Pick a Philosophical principle/maxim/quote; when planning your day, consider how can you employ that wisdom today in the situations that may arise.
Pick a Stoic Virtue; when planning your day/week, consider how will you use and display it in the situations that may arise.
Reading + reflection.
Contemplation of a Sage. What would a Sage do in my position now?
Reflection of a philosophical quote.
Mindfulness meditation
Reflection of the Virtues (Wisdom, Justice, Courage, Moderation).
Values clarification.
Desired vs Admired.
Reflection of a philosophical quote.
Reciting of helpful philosophical maxims.
View from above (see here).
Praemeditatio Malorum / Negative visualization (see here).
Memento Mori, contemplation of death.
Journaling
Freewrite