Sofia Koutlaki chats with Simon Drew about a courageous choice.

Courage is knowing what you should choose, what you should avoid, and when to do neither.

diogenes laertius 7.92

When I heard Simon Drew speak at the Stoicon Women Courageous Paths to Flourishing online gathering on 1 October 2022, I knew I would love to speak with him. He had interacted with only one person in that small-group coaching breakout room – me –so it was remarkable that the universe answered: I did indeed get to have a free coaching call with him. It could not have come at a better time.

For the last two years, I have been publishing a monthly newsletter called Some Little Language. The October post had been due on the 8th, and, in the wake of the Iran unrest, I was driven to write about hijab. But the disturbing events in Iran made writing very hard. I felt there was a danger (real or imagined) of my writing being hijacked by either of the opposing sides for their own agenda, and my first impulse was to keep quiet.

On the other hand, keeping quiet was oppressive. I have been working on my own healing by speaking out on my needs and wishes. I felt it was important for me to stay courageous and speak my truth about something I felt so strongly about. Even so, I did not publish the post on the 8th. I felt like a coward.

This was the ethical dilemma I brought into the coaching call with Simon.

I am grateful for the space that Simon held for me. His calm and calming presence, his probing questions nourished by authentic curiosity, and his overall heart-warming energy opened up the opportunity to bring my ideas to light, sound them off a fellow Stoic and achieve some clarity.

Fresh from the Courage Conference, we recalled that Courage needs to be tempered by the other three Stoic virtues: Justice, Temperance, and Wisdom. Publishing the piece seemed like the courageous thing to do, but would it also be temperate, wise and just? We worked through my dilemma with this Stoic approach.

Writing and publishing my immediate thoughts and opinions might at first glance seem courageous, but we questioned whether it would indeed be temperate and wise. It certainly would not be just for my nearest and dearest, who might find themselves implicated in a situation not of their own doing.

The key lay in the act of publishing. I recognised that nothing stopped me from writing down everything I wanted to, put it aside, let it mature and revisit it later.

The coaching call with Simon eventually helped me to strike a balance, homing in on my own personal experience in Iran, and bringing in some insights from a recent conversation with a new Iranian friend. The longer piece on hijab will eventually be written when the time is ripe.

Our conversation with Simon then ventured into the commonalities between Stoicism and other religious and mystic traditions, all essentially being different fingers pointing towards one and the same moon. We agreed that the appeal of Stoicism in our times is its inclusivity and universality. The coaching call with Simon was an inspiring experience which I recommend wholeheartedly. I am grateful to Modern Stoicism and to Courageous Paths to Flourishing for this opportunity and I look forward to following more of Simon’s events at The Walled Garden.


Sofia Koutlaki (PhD) is a Greek writer whose academic trajectory traced a line through English literature, the Classics, and linguistics. She analysed Iranian politeness, face and communication and lived in Iran for 14 years. Now based in London, she explores memoir and life writing, and the influence of Stoicism, mysticism and other spiritual practices on personal development and wellbeing. She discerns our shared humanity in the commonalities of different traditions, and often questions beliefs (how do I know what I know?). She co-hosts a 52 Week Practice towards a Stoic Life at the Stoic Salon with Kathryn Koromilas, and publishes a monthly newsletter at Some Little Language.

If you’d like to work with Simon Drew, explore his coaching practice here.


Courageous Paths to Flourishing featured a 90 minute Coaching Courage session. Stoic coaches shared stories of courage and then led workgroups on guiding us how to coach ourselves to be more courageous. The coaches were Tim LeBonAndi SciaccaScott PerryLydia Scratch, Dr Matthew SharpeSimon DrewLinda BebbingtonNona Maiorano, and Katie Stidolph. We also awarded a number of coaching calls to participants.

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