At his trial in 399 BC, Plato records his (soon to be condemned) teacher Socrates uttering the famous maxim:
“The unexamined life is not worth living.”
It’s a powerful idea, and I generally agree with it. However, the reality is that plenty of people, including leaders of all stripes, don’t actually do a lot of reflection or examination–and they manage to go on living just fine, thank you very much.
So maybe most of us believe the unexamined life is worth living, but I wonder if the unexamined leader is worth following?
It’s the philosophy minor in me that wants to rise to Socrates’ challenge. I’m convinced there’s a connection between our decision to reflect on our motivations, actions, and outcomes, and being a leader worth following.
Certainly, busyness militates against this kind of self-reflection. And we all have blind spots that make it hard to practice self-examination. So how do we do this effectively?
Strategies for Reflecting on Your Leadership and Life
There are all kinds of effective ways to reflect, journal, and process your life. One of the best ways, as alumni of LEAD 24/7 know, is to do so with a coach, taking regular dedicated time to process and learn from your experiences. I like to think of coaching meetings like the proverbial woodcutter who takes regular pauses to sharpen his axe, only to come back to his work even more energized and effective. Sure, you can continue to power through your work–but absent reflection and processing, you’re likely to become duller and less effective over time.
Another tool that I’m exploring for reflection at the opening of 2025, is the YearCompass. It’s a fairly comprehensive way to look back at 2024, and then to take the data and experiences of your year and begin to shape a helpful narrative around it.
After reflecting on the year behind you, the YearCompass invites you to envision the year ahead, taking stock of commitments or habits that you want to let go, and those you want to adopt. Here’s how YearCompass describes their tool:
YearCompass is a free booklet that helps you reflect on the year and plan the next one. With a set of carefully selected questions and exercises, YearCompass helps you uncover your own patterns and design the ideal year for yourself.
Learn from your mistakes, celebrate your victories, and set out a path you want to walk on. All you need is a quiet few hours and our booklet.
Not every question or prompt in the YearCompass landed just right for me, but I think the exercise overall has been a real win. I’ve written before about ABC goal setting going into the new year, and the YearCompass combined with intentional goal setting seems like a powerful 1-2 combo for reflection and planning.
Reflection to Become a Person Worth Following
One benefit of all this examination, is that it can help keep you indexed to the vision of the life you want to have at age 90. LEAD 24/7 alumni will remember the “looking back at your life” and “sweet spot” exercises. This yearly reflection (and coaching) helps to offer a kind of reset to ensure your life is in fact aimed in the direction of the leader and person you want to become when you look back at the end of your life. It can help you appraise whether or not you’re functioning in your sweet spot, and perhaps give you some ideas for moving more squarely into the center of that spot.
If this sounds like a lot of work, I think you’re right. It is. Or at least it can be if you haven’t developed the habit of doing reflection as a leader, and haven’t surrounded yourself (at some level) with others who are engaged in the same process. But the alternative to regular incremental changes through reflection might be to undertake a massive course correction later in your life and career. I can only imagine that this will be more disruptive and difficult, if indeed it’s possible.
So let me encourage you in 2025 to make reflection a more regular part of your rhythm as a leader. You’ll have to prioritize the balcony time to do this (check out some of Jeff’s great questions for reflection in that blog), but I’m convinced the payback in the short and long term is absolutely worth it if we are to become leaders worth following leading lives worth living.
Tools for More Regular Reflection
In case you’d like to make this kind of self-examination more regular, let me commend to you two newsletters:
- James Clear’s 3-2-1 Thursday newsletter always ends with a provocative question for reflection.
- Dr. Benjamin Hardy’s Friday journal prompts are thematic, and take about 10-15 minutes to work through.
How about you? Do you have a habit or rhythm of self-reflection? What tools or practices do you find most helpful? Share your thoughts and ideas in the comments.
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