Start The Year With This Mind-Opening Leadership Exercise

The Annual 3-Step Self-Awareness Checkup


a road leading towards a sunrise

Whenever the Gregorian calendar marks another trip around the sun, many people reflect on the year that’s passed and contemplate the year ahead. We find value in examining how we’ve lived our most recent year, presumably intending to live better during the next twelve months.


After a year as challenging as 2020, this seems especially apropos. But practicing self-reflection is certainly not new. Ancient texts such as Buddhist teachings, Marcus Aurelius’s Meditations, and the Bible all encourage regular self-examination. More recently, scholars recognize Donald Schön’s 1983 book The Reflective Practitioner as the hallmark of modern thinking on self-reflection, especially in a workplace setting.


Exactly Where Do You Think You’re Going?


Most people will skim this article, thinking, “Hmmm, those are some good questions” – and then do nothing more.


But great leaders aren’t like most people. They take the time to answer life’s hard questions so they can observe and steer their course. I often remind my executive coaching clients that with self-awareness comes perspective and choice. Without it, there is only habit and pattern.


It’s easy to get caught up in the rhythms of our modern world while focusing on hitting professional performance targets, getting promoted, or acquiring trappings of success. When this happens, we begin living unconsciously; we’re merely going through the motions.


The Annual 3-Step Self-Awareness Checkup


A life unexamined can lull us into thinking we’re achieving what we want. The problem? This type of unconscious living might help others reach their goals, but it’s unlikely to help you achieve your own.


On the other hand, regularly pausing to examine your life allows you to notice where you might be diverging from the life you want – and make any needed course corrections.


Take these three steps regularly to consult your life’s map and stay on track. After all, when you don’t, who knows where you’ll end up?


Step 1: Evaluate Your 2020 Self-Awareness


Over the years, I’ve come up with – and borrowed – a long list of questions for annual self-examination. Think of this abbreviated lineup as my “greatest hits” version.


With 2020 in mind, consider each question, write your answers down, and then decide what to do with your new consciousness:


  1. Outside of family, who impacted me most? How?

  2. What was the best decision I made?

  3. What was my biggest failure?

  4. What was the most loving service I gave?

  5. What’s my most significant unfinished business?

  6. How did I care for my emotional, physical, and mental health?

  7. How did my most cherished relationships evolve?

  8. How did my relationship with God (or the divine) evolve?

  9. What did I learn about myself?

  10. What word describes my overall 2020 experience?


As you write out your answers, you’ll naturally begin thinking about how you might improve in the future. Remember, with awareness comes perspective and choice, so when you take a good look at how you showed up last year, you’ll see opportunities to do better next time.


Step 2: Envision Your 2021


As you consider your opportunities to do better in the future, use the questions below to kickstart your thinking. Like the previous list, this one could also be quite long. Here’s a short selection to inspire you.


Thinking of 2021:

  1. What changes do I most want for myself?

  2. What am I willing to risk for those changes?

  3. What am I most looking forward to learning?

  4. How will I create more joy in my life?

  5. How will I improve my most cherished relationships?

  6. What will I say no to?

  7. Outside of my family, who am I most committed to loving and serving?

  8. How will I improve my relationship with God (or the divine)?

  9. How will I make the year matter?

  10. What’s my motto for the year?


Again, don’t just glance at these. Instead, block 90 minutes on your work calendar to thoughtfully write your responses to these two sets of questions. Yes, I said your work calendar – because that’s where official calendaring happens. I promise this work will make you better at your job, so skip the guilt.


To give this work the attention it deserves, it’s best (but not imperative) to do it in a single sitting. Whether you type or handwrite your answers, what matters is that you do it in a way that’s uncomplicated for you and in a place that’s easily accessible.


Step 3: Distill. Commit. Go.


Here’s the challenging part. It’s where the rubber hits the road – and where you’ll find the biggest payoff.

  1. Take your answers to the 2021 questions and write your top ten commitments.

  2. Rank those commitments in terms of importance to you.

  3. Double-check your rank order, then cross out the bottom five. A shorter list will improve your focus.

  4. Now ask yourself if you have both the resources and intention to follow through. If you answer no for any remaining commitment, take it off your list. You might have an even shorter list now. No problem.

  5. Start working on your commitments.


Pro tip: Share your final list with a buddy. Get them to follow the same process and create their commitments. Then schedule and regularly hold accountability calls to check your progress and encourage each other.


In Lewis Carroll’s 1865 book, Alice’s Adventures in Wonderland, Alice runs into the Cheshire Cat and asks,


“Would you tell me, please, which way I ought to go from here?”

“That depends a good deal on where you want to get to,” said the Cat.

“I don’t much care where—” said Alice.

“Then it doesn’t matter which way you go,” said the Cat.

“—so long as I get somewhere,” Alice added as an explanation.

“Oh, you’re sure to do that,” said the Cat, “if you only walk long enough.”


Alice doesn’t care where she ends up. But I suspect you do.


Getting where you genuinely want to be requires more than going through the motions. It requires opening your eyes, asking yourself the hard questions, welcoming your new perspective, choosing or adjusting your path, and then going for it – with commitment and accountability.


Book those 90 minutes now. I predict you’ll be quite pleased this time next year.