Reflection Done Right: Turning Experience Into Wisdom

Hello, it’s Siri. Welcome to my weekly newsletter on managing your energy, time and head space for work that matters to you. I am an ICF Certified Coach, with more than 450 hours of client coaching. My coaching sessions are “advice-free zones” unless the client specifically asks for advice. So I offer my best insights, reflections, advice here, in this newsletter which is published every Sunday.

In this issue, we’ll explore how to embrace a reflective process that fuels growth, not guilt.


“We do not learn from experience… we learn from reflecting on experience.”

John Dewey

As the year draws to a close, many of my clients have entered coaching sessions in a reflective mood.  One of the most moving sessions I’ve had recently was with a client reflecting on how the year had unfolded. He was accustomed to self-moritification, post mortems and guilt as part of his “reflection process”. So it was with some trepidation that he approached the session.

This is familiar to many of us. Reflection often brings with regret, guilt, or a sense of loss at how things turned out. That’s because we typically reflect only when things haven’t gone as planned.

Our minds replay various scenarios:

  • I should have acted differently.
  • I should have stopped that conflict before it escalated.
  • I should have said no to my colleague’s request for help, which turned into months of extra work.
  • I should have seen the signs and realised the promotion wouldn’t come.
  • I shouldn’t have spent so many hours at work when I ended up getting fired anyway.

This isn’t reflection. It is regret, rumination and post mortem-analysis.

True Reflection

In physics, reflection refers to light bending back after hitting a surface – a mirror. It allows us to see an image exactly as it is. Similiarly, true reflection lets us observe things as they are. It is not about regret or guilt; it is about understanding, learning and changing.

Reflection, as a cognitive process, involves three key elements:

  1. Observation with detachment,
  2. Connection with oneself
  3. Curiosity about behaviour.

Let’s break these down with an example: reflecting on how my week unfolded.

1. Observation with detachment

“Observation is the greatest form of intelligence.” – Jiddu Krishnamurthi

To observe objectively, I track data. For instance, when I am reflecting on how my week unfolded, I reflect on how I spend time. I want to know whether how I’ve spent my time aligns with what I want to achieve and enjoy at work. Throughout the week, I track my time spent on various activities. At the end of the week, I compare the time spent with my plan.

With data, reflection is easier because it grounds the process in facts, first. The same principle applies to any area that you have chosen for your reflection. Ask yourself:

Do I have data on my actions related to this area?

Data helps to ensure observations are closer to reality and less influenced by our incomplete memories.

2. Connection with oneself

Reflection often stirs emotions – sometimes uncomfortable ones. Guilt, regret and overthinking when added to this mix can cloud the reflection process. It is important to be able to separate the emotions from thoughts, and stay present with the emotions arising from the process.

Here is how you can sit with these emotions mindfully.

  • Scan your body and locate where these emotions are showing up as strong sensations in the body.
  • Observe the nature of these sensations. Are they intense or subtle? Static or dynamic? Rising or receding?
  • Stay present to the sensations with curiosity.

Being present with compassion, helps the emotions to settle and brings in clarity. Thoughts separate and the underlying emotions surface. Connecting with yourself, settles the emotions and creates space for insight.

3. Curiosity about behaviour

The gap between intention and outcome is ripe for reflection process. For example, if I set a goal to exercise regularly. I start off strong exercising regularly, then start and then stop a few times and then as the year rolls to an end, I have stopped exercising. I can approach the reflection on this goal with curiosity:

  • I wonder what made me exercise regularly from January to March, and then again in May and June.
  • What was different starting July when I did not meet my exercise targets?

Curiosity helps us explore behaviour with compassion, instead of judgement. Instead of berating myself that this was yet another year when I failed to be disciplined about my exercise, I can identify patterns:

  • I woke up early from January to March that let me exercise for 21 minutes.
  • The Bangalore weather was very hot in April which made it challenging to exercise.
  • I was travelling in July and then fell sick multiple times later in the year which disrupted my routine.
  • I added a new exercise routine in August, which disrupted my existing routine and then I fell off the wagon.

This approach highlights what worked and what didn’t thus providing actionable insights for the future and choices in the present moment. Instead of judging the behaviour or the person, curiosity uncovers valuable insights.

A Simple Framework for Reflection

Next time you sit down to reflect, try this four-step process:

  1. Choose an area of your life or work to examine.
  2. Observe the facts as objectively as possible.
  3. Connect with your emotions and stay present with them.
  4. Examine your behaviour with curiosity.

Using this approach, my client uncovered valuable insights during our session. He realised where he had been flexible to life situations, and was able to see where he had been flexible and offered himself grace instead of berating himself for not meeting his goals perfectly.

Your Turn

What areas of your life are ripe for reflection as the year ends? How will you offer yourself grace and compassion during this process?

Siri, say 👋via email or LinkedIn