✨ Celebrating the Gain: An Empowered Way to Close the Year
🎧 Prefer to listen? Click above for my audio version! 🎧
Earlier this year, I read The Gap and The Gain by Dan Sullivan and Dr. Benjamin Hardy.
The concept is radically straightforward, yet nuanced and sometimes challenging in practice.
Here’s the heart of it:
Our culture quietly trains us to measure progress by looking forward – toward a constantly shifting ideal, a future version of success that we haven’t reached yet. When we live like this, we’re measuring from a place of lack. We’re in the GAP.
But when we measure progress backward – from where we started to where we are now – we step into the GAIN. And that shift leads to more clarity, confidence, and freedom right now, not someday.
“The only way to measure the distance you’ve traveled is by measuring from where you are back to the point where you started.”
— Dan Sullivan
This framework is especially powerful for high-achievers, perfectionists, and anyone who tends to move the goalpost the second they accomplish something. (Sound familiar? You’re in good company.)
I’ve been using this tool all year. There have been days where I can feel myself sinking into the GAP – too focused on what I don’t have, what isn’t going as planned, or where I still feel behind. But being able to name that limiting thinking as “the GAP” has helped me create distance, regroup, and shift back into a more grounded, empowered perspective.
And it has reliably supported my well-being and sense of progress during a topsy-turvy year.
And so, with the end of the year fast approaching – a season that tends to stir up a lot of comparison, urgency, and resonant choruses of “I should be further along by now” – I want to offer you the same tool.
This isn’t about resolutions or reinvention.
It’s about recognition.
Let’s take some of my favorite exercises from the book and walk through it together.
Step 1: Define Your “Personal Success Criteria”
Before you look back, take a moment to anchor into your own version of success.
Because without this, every reflection becomes another comparison trap.
Grab a piece of paper and finish this sentence in 10 different ways:
“I know I’m being successful when…”
Your answers might be emotional, relational, health-related, financial, creative, or tied to boundaries or joy. There’s no right or wrong.
This becomes your personal success criteria – your internal compass for what’s actually working in your life and what to keep leaning into.
Step 2: Acknowledge the Gains
The book includes a plethora of incredible reflection questions and exercises – and I highly recommend diving in if this resonates. (I’m not affiliated with the book in any way… just a fan!)
Here’s a simplified version that works beautifully whether you’re a business owner, an executive, a parent, an artist, or anywhere in between.
🎯 Part 1: Look Back 12 Months
What do you now know that you didn’t know a year ago?
What habits, boundaries, or systems strengthened this year?
What did you say “no” to that the older you would have said “yes” to?
What did you handle this year that a past version of you couldn’t have?
⚡ Part 2: Look Back 3 Months
What progress have you made that deserves more credit?
What surprised you (in a good way)?
What’s one thing you’re proud of – even if no one else saw it?
Step 3: Apply This to Your Money Life
This is where the GAP and GAIN framework becomes truly transformative.
I’ve seen way too many people stay on the sidelines of their finances because they feel embarrassed – ashamed of what they “should have done,” or worried an advisor will judge them.
But here’s the truth:
Your past money decisions aren’t failures.
They’re data.
And data is useful!
Using the reflection questions below, look at any money experience from this past year:
What worked – even if the situation felt messy?
What can you learn from this experience about what you don’t want?
What will you do differently in the future because of this experience?
What about this experience are you grateful for?
Alignment rarely comes from big leaps.
It comes from small, grounded adjustments rooted in self-awareness. Staying in the GAIN allows us to look at actions or efforts that didn’t result in the intended success and still find valuable and useful information to help us get closer to what our definition of success really is.
We can’t be afraid to fail.
There is no failure if we use those lessons to inform our future self.
A Final Reflection to Close the Year
As we wrap up the year, my hope is that you give yourself the gift of perspective – not the polished, performative kind, but the honest acknowledgment of how far you’ve come, no matter how big or small.
The resilience you’ve built.
The boundaries you strengthened.
The lessons you weathered (and the ones you earned).
The ways you kept going, even when it was hard or uncertain.
Because when you honor the GAIN – instead of the GAP – you step into the new year already grounded, already successful, and already aligned with who you’re becoming.
You start your year already free.
And that is the most powerful starting point of all.
Share the Love & Give A Gain
In the spirit of community and giving, consider offering this same gift of perspective to someone you care about.
Tell a friend what you’ve seen them grow through this year.
Reflect a strength back to a colleague who doesn’t give themselves enough credit.
Celebrate a small win your partner, sibling, or friend barely noticed.
Sometimes we can’t see our own gain until someone mirrors it back to us. Your acknowledgment might be the exact encouragement someone needs to end their year with more compassion, confidence, and clarity.
Recognition is powerful when we practice it internally – but it becomes transformational when we share it.
