Amidst the swirl of holiday commitments—travel, gatherings, last-minute deadlines—there’s often a small pocket of stillness that opens up in December. A moment when the pace softens just enough for reflection to sneak in...

And when it does, an inevitable question emerges:
How did this year really go?

It’s tempting to measure your year in the most familiar way—by tallying what you accomplished versus what you didn’t, what got crossed off the list versus what lingered.

But I encourage you to take this opportunity to rethink that entire framework.

Because the way most of us evaluate our year isn’t just unhelpful—it’s fundamentally misleading.

What if the way we measure success is the real problem?

And, what if how you measure your year is shaping how you feel, and how you behave?

Dan Sullivan’s concept 'The Gap and the Gain' explains this beautifully.

Most of us measure our progress using The Gap—by comparing where we are to where we think we should be.

This ideal—future you, perfected you—is seductive. But it’s also a mirage.
As soon as you inch closer, it moves.
The brain creates a new ideal, and you instantly feel like you haven’t done enough.

This measurement style has real consequences:

• It blinds you to the progress you've already made.

• It keeps you feeling perpetually behind.

• It erodes motivation because the finish line never arrives.

• It reinforces perfectionism and self-criticism.

• It trains the nervous system to associate growth with inadequacy rather than satisfaction.

The Gap isn’t a mindset issue—it’s a measurement issue.
And measurement shapes behavior.

When you measure against an impossible horizon, you’ll always come up short, no matter how much progress you’ve made.

The alternative—the one that actually fuels self-trust, momentum, and satisfaction—is The Gain: measuring backward, against who you were at the beginning of the year.

This quiet shift changes everything.

What happens when you stop living by perfection and 'shoulds'?

Two universal roadblocks keep people stuck: perfection and 'shoulds'—both are symptoms of Gap-thinking.

Perfection says, “If I can’t do it flawlessly, it’s not worth doing.”
Shoulds say, “Do this because others do it—not because you want to.”

A moment that crystallized this for me happened during a lunch with one of the doctors at One Medical.
He was literally angrily stabbing his salad.
I asked, “Are you enjoying that?”
He sighed. “No. I’m eating it because I feel like I should.”

How often do you do the same?

That is the Gap in action.
And it’s precisely why change feels hard.

Behavior driven by pressure is brittle, and unreliable.
But, behavior driven by alignment—with how you want to feel, live, and function—creates staying power.

This is why I encourage my clients to anchor habits in want, not should:
Want creates momentum.
Should creates resistance.
And resistance rarely leads to consistent action.

Don’t go for a run because you should.
Go for a run because you want the clarity, relief, and sense of vitality it brings.

Don’t eat well because you should.
Eat well because you genuinely enjoy the steadiness and energy it gives you.

When you actually want or enjoy the behavior, consistency stops feeling like a grind and starts feeling like self-respect.

How can one meaningful shift create momentum for everything else?

Consider the family featured in The Wall Street Journal in August ’25.

Their shift was a big one: they removed ultra-processed foods from their home.

Let’s call it what it is—a major change for most households.
But here’s the brilliance: watch what happened:

• Energy stabilized

• Cravings quieted

• Moods lifted

• Sleep improved

• Meals became easier

• Food choices felt more intuitive

• The whole household experienced downstream benefits

This is the Gain operating at scale: One upstream shift creates a platform for lots of additional gains.

Their success wasn’t about perfection.
It was about changing the environment so healthier behaviors became the path of least resistance.

Measurement influenced behavior:
Instead of measuring what they were giving up (Gap), they began noticing what they were gaining—energy, ease, clarity (Gain).

And what you notice, you reinforce.
What you reinforce, you repeat.

How do small changes reveal progress you might otherwise miss?

Gains aren’t limited to big moves.
Consider something as simple as hydration.

Maybe you set a goal to hydrate more consistently.
And maybe you achieved a 30-day streak.
You felt clearer, more energized, more regulated.

Then life got busy. Schedules shifted. Your streak collapsed.

In the Gap, this feels like a failure.
“I lost it.”
“I can never stick with things.”

But in the Gain, a completely different evaluation emerges:

• Before this year, hydration might not have been on your radar.

• Now you’ve proven you can build the habit.

• You’ve experienced how good it feels.

• Your awareness is higher.

• Your baseline is permanently improved.

This is the essence of the Gain: Even imperfect progress is still progress.

And, measurement impacts behavior here too:

• When you see evidence of your capability, you’re more likely to resume.
• When you see evidence of your shortcomings, you’re more likely to stop.

As the new year approaches, what questions help you see your true progress?

With this reframing in mind, consider:

• How am I different today than I was back in January?

• What habits became easier—or more enjoyable—than they were before?

• Which actions created ripple effects I didn’t expect?

• What did I choose because I wanted to, not because I should?

• Where did I loosen perfection yet still move forward?

• What new baseline did I establish—even if imperfectly?

These are the questions that reveal your real growth.

Growth is often subtle.
It shows up in steadier mornings, fewer crashes, clearer boundaries, a calmer internal dialogue, or the simple fact that you now treat yourself with more care than you once did.

What definition of success is worth bringing into a new year?

Here’s the most grounding, liberating measure of success I know:

"It is being better today than you were yesterday, everyday!" —Mr. Frank Dick, OBE former director of coaching for UK athletics.

Not flawless.
Not ideal.
Just better.

And if that’s the direction you’re heading—even inconsistently, even quietly—you are already succeeding in every meaningful way.

TL;DR

• Most people assess their year using The Gap—measuring against an ideal they can never reach, which keeps them feeling behind.

• The Gain flips the lens: measure yourself against who you used to be, not an unattainable future version.

• Measurement shapes emotion → emotion shapes behavior → behavior shapes your life.

• Big shifts (like removing ultra-processed foods) create a platform for many smaller gains.

• Small shifts (like a hydration habit) count too—imperfect consistency still reflects a higher baseline.

• Ask questions that reveal growth, not shortcomings.

• Carry forward the simplest and most empowering definition of success: Be a little better than you were yesterday.