Skilled Reflection

Keep a skilled eye on yourself.

Project maintained by skilled-reflection Hosted on GitHub Pages — Theme by mattgraham

Every session

Whether it’s your first session or not, here is what you can expect when you show up to a Skilled Reflection session.


We’ll probably wait five minutes for people to show up.

The organizer will go over room guidelines:


The organizer will introduce the theme with some brief context. Both are intended only as guidance, and to be re-interpreted in a way that is relevant to yourself.

For example, one previous session was focused on the idea of studying for a test. For this theme, the organizer suggested how a “test” can be any important goal or event one is preparing for, and the exercises should be reinterpreted as appropriate.


There are usually 3 - 4 writing prompts that cover approximately 45 minutes. The organizer will introduce them in turn, with specific time limits, and intentions.

An initial 1 - 2 prompts are warm ups. They are short, and intended to get you to define the things you’re interested in exploring. For example, in the first session, participants were asked to spend 4 minutes making a list of 4 goals they would be most happy to achieve in the next five years.

The next 1 -2 prompts are “content”. The general guidance for these prompts is to write something that will be useful for you tomorrow, and the next day. Instructions to yourself.

time and word limits

These limits work together to encourage a balance between reflecting on a the quality of a decision (thinking and revising ideas) and making decisions (writing).

Some examples:

  1. a prompt with 1 minute limit and 50 word limit is meant to get you to free write with minimal restrictions on quality of thought.
  2. a prompt with 4 minutes and 40 word limit is meant to encourage revision of your ideas, and more careful selection of your words.

redefining the prompt

much like the initial suggestion to reinterpret a prompt to fit your own needs, re-evaluation of what the prompt means to you, should occur throughout the writing. This is especially true for the “content” prompts.

Not only should you re-evaluate what the prompt means to you, but you are encouraged to redefine the prompt so that it is MORE meaningful to you. Let it become something else.


Prompts can be difficult. Prompts and topics are designed intentionally, to encourage you to think about complex parts of your current living experience, with the goal of bringing clarity.

We can resist a prompt (and be inclined to redefine it) because we would like to avoid doing difficult but necessary work, or because we are simply not equipped to processs this in the moment. An example of the latter might be that the prompt triggers an emotional experience.

You are encouraged to stop or change the prompt in a way that works for you. If you do not want to stop the exercise altogether, bring your attention to yourself, the person who decided to show up today. What is it that person is ready to think about right now, and work on? Go with that prompt.

wrap up

The organizer will reserve five minutes at the end of the session for a light discussion. The purpose of the discussion is to offer an opportunity for closure on the experience for those who would like it. Sharing is always optional. An organizer may direct a question at you, and the intention is to ensure that everyone has a chance to participate. You will not be required to reply, and the organizer will know to move on politely if you choose to not reply.


The true value of the session is best achieved by thinking about this part the most, throughout. How is your future changed, by taking one hour to show up? Hopefully, you have written some reminders and instructions, that will make tomorrow helpful. Save and revisit them. The exercise is designed so that you could repeat the entire process on the same document.

my first virtual exercise

If you can’t wait for a session, feel free to email us for a conversation, or jump over to “Self 250” to try one at home.