We’re reaching that time of year where many of us take a step back and ask the same question: “Was this a good year?” But how do you measure a good year – and should you even try? 

The Obsession with Measuring Success

Conventional wisdom tells us that what gets measured gets managed. It’s the mantra of productivity, leadership, and self-improvement.
We track performance, set KPIs, measure progress – all in the name of growth.

And yes, measuring can be motivating. Seeing progress can inspire action and build momentum.

But measurement also has its shadows.

Rethinking How To Measure a Good Year

Not Everything Worth Measuring Can Be Measured

In leadership and life, some of the most meaningful things resist measurement.

Intelligence:

We often reduce intelligence to a test score. But as Sir Ken Robinson said, we shouldn’t ask “how intelligent are you?” but rather “how are you intelligent?” True intelligence wears many faces – creative, emotional, entrepreneurial — and no single test captures it all.

Wealth:

Money is a poor proxy for richness. Some of the wealthiest people live in quiet misery, while others with little lead rich, free lives. “Rich” might just be who you are, not what you have.

Achievement:

Booker T. Washington once wrote: “Success is to be measured not so much by the position that one has reached in life, as by the obstacles overcome while trying to succeed.” The best achievers aren’t always at the top — they’re the ones who’ve travelled the furthest.

Personality:

As someone accredited in personality profiling, I know how valuable these tools can be. But I also know their limits. As Marcus Buckingham says, “There are galaxies inside of us.” No profile can capture a person’s entire universe.

The Best Measures Are Often Intuitive, Not Quantifiable

After many years of facilitation, I’ve developed a love-hate relationship with feedback forms.

The love part? Insights can help you grow.

The hate part? Even flattering feedback can feel hollow if it misses the essence of the experience.

My truest measure comes from within:

  • Did I try something new, even if it failed?
  • Did I see eyes light up with recognition?
  • Did I tell a story that landed deeply?

That’s the feedback that matters.

As I told a friend recently: “If you think you slept well, who cares what your watch says?”

The Trap of Comparison

One of the greatest flaws in how society measures what a ‘good year’ is, is that we often think we need to compare ourselves to others.

But growth and position are not the same thing. You can win and not grow. Or come last and grow immensely.

Rethinking How To Measure a Good Year

Rethinking What Makes a Good Year

So, how do you know if you’ve had a good year?

Traditional ways to measure a good year might look like this:

  • Did I make money?
  • Did I meet my goals?
  • Did I win?

But you can tick every box and still feel flat.

Try measuring your year’s success differently. Ask yourself instead:

  • Did I grow in wisdom?
  • Did I change my mind about something?
  • Did I connect with wonder — the moon, the stars, the rain?
  • Did I show kindness?
  • Did I make myself a little uncomfortable in pursuit of something worthwhile?
Rethinking How To Measure a Good Year

The Real Measure of Success

A lot of the tools we use to measure the success of our year are powerful, but incomplete if used on their own.

Balance your scorecard with what can’t be quantified: curiosity, kindness, awe, and joy.

In the end, I personally don’t want to live my life as a set of accounts or performance reviews. I want to live it as a blend of measurable progress and unmeasurable joy. That’s the kind of year I want to have – and the kind worth striving for.

If This Reflection Resonates With You…

Book a CAFE Life workshop where we explore the art of reflection, resilience, and leadership that goes beyond the scoreboard.

These sessions create space to pause, reconnect, and redefine what success means for you and your team.

Find out more or book your team session here.

Rethinking How To Measure a Good Year