December 8, 2025 • 10 mins
The Moment I Realized I Was Measuring My Success All Wrong - The GAP and the GAIN
Feel like you're never doing enough even when you're crushing it? In this transformative episode, Cindy Gordon reveals why high-achieving entrepreneurs feel constantly behind and how to shift from measuring against impossible horizons to celebrating actual progress. Inspired by Dan Sullivan's gap and gain concept, discover the neuroscience of success measurement.
In this episode, you'll discover:
- Why you feel behind even when you're winning (the measurement trap)
- The neuroscience of measuring backward vs. forward
- How gap thinking triggers stress while gain thinking creates momentum
- The 3-question Entrepreneur's Gain Journal that changes everything
- Why comparing to others poisons your actual success
- How to shift from "I'm behind" to "I'm progressing" identity
- Specific practices to make gain thinking your default
- The progress paradox: why celebrating gains helps you achieve goals faster
Perfect for: Overwhelmed entrepreneurs who never feel like they're doing enough, high achievers stuck in constant dissatisfaction, and anyone measuring their worth against moving finish lines.
Key insight: "You're not behind. You're not failing. You're just measuring wrong."
Join 1,500+ entrepreneurs learning gain thinking through Cindy's weekly Reality Check newsletter, and discover how Growth Collective members celebrate progress daily for just $1 a day.
Resources mentioned:
- The Entrepreneur's Gain Journal
- Weekly Gain Practice Framework
- The Growth Collective Membership
- Reality Check Newsletter
Stop living in the gap. Start living in the gain. Your progress is already remarkable - you just need to see it.
🎯 You don't have to figure this out alone! The Growth Collective is your $1/day business support community with weekly office hours, strategic frameworks, and entrepreneurs who get it. Less than your coffee, more than a mastermind. Details at https://exclusivelycindy.thrivecart.com/the-growth-collective/
💡 Don't forget to subscribe for more quick productivity tips for overwhelmed business owners and female entrepreneurs!
💌 Join 1,400+ entrepreneurs getting exclusive overwhelm solutions and productivity strategies straight to their inbox - sign up now! https://cindygordon.myflodesk.com/countmein
Connect with Cindy Gordon - Reality Check Method Coach for Overwhelmed Entrepreneurs:
- Website: ExclusivelyCindy.com
- Instagram: https://www.instagram.com/exclusivelycindy/
- YouTube: https://www.youtube.com/@cindygordon
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
I wanna share something thathappened last week that shifted
my perspective just a littlebit.
I was having a terrible day, youknow, the kind where nothing
feels like enough.
I had landed a new client,finished a project ahead of
time, and got some amazingfeedback from my growth
Collective members.
But all I could think about washow far I still had to go to
(00:20):
meet.
My yearly goal.
Then I called my mom to checkin.
She has been dealing with somemobility issues lately.
She was frustrated that shecould only walk to the mailbox
and back and kept comparingherself to her friend who was
still very, very active.
And I heard myself say, mom,literally two months ago, you
(00:40):
couldn't even get to the frontdoor without help.
So look at how far you've come.
And then it hit me.
I was giving her the advice thatI wasn't taking myself.
Hi, I'm Cindy, and you arelistening to The Overwhelmed
Entrepreneur, and today we aretalking about why you are
feeling like you're never doingenough, even when you're
crushing it, and moreimportantly, how to shift from
(01:01):
measuring it against theimpossible horizon to
celebrating how far you'veactually come.
So here's what's happening inyour brain, and this was
inspired by Dan Sullivan'stransformative work on how high
achievers measure success.
We're all stuck in what we callthe measurement trap.
You set a goal, you work yourass off, you progress, and
(01:24):
instead of feeling accomplished,you immediately look at how far
you have to go.
The horizon keeps moving, thefinish line keeps shifting, and
you feel like you're failingeven when you're winning.
Does that sound familiar?
This happens when we measureforward against our ideals
instead of backwards againstwhere we started.
We are living in the gap betweenwhere we are and where we want
(01:47):
to be instead of living in thegain of how far we've come.
So let me reality check thiswith you with actual numbers
from one of my clients.
Samantha came to me about sixmonths ago, completely
overwhelmed and making about$3,000 a month, working at least
60 hours a week, and had zerosystems.
Today she's making about$8,000 amonth working just a little bit
(02:10):
less than before, so about 40hours a week.
She has two contractors andactually is taking the weekends
off.
But when we talked last week,she was frustrated.
Why was she frustrated?
Because her goal was 10 KAmonth.
She was so focused on that twogrand gap that she couldn't see
the five grand gain.
(02:31):
She couldn't see that she almosttripled her income while cutting
her hours by a third.
This is what measuring forwarddoes to us.
It makes us miserablemillionaires, literally not
millionaires yet, but you getthe point.
We achieve amazing things, butyet still feel like failures.
Here's what's actually happeningin our brain, and understanding
(02:55):
this changed a lot for me.
When you measure against yourideal, that moving horizon, your
brain registers it as a threat.
You're constantly in a state ofnot enough, which triggers
stress hormones, killscreativity, and ironically makes
you less productive when youmeasure backward.
You acknowledge the gain, yourbrain releases dopamine, you
(03:17):
feel accomplished, you feelconfidence, you create momentum,
you actually become more likelyto reach that goal because you
are operating from abundance andnot scarcity.
It's not woo woo.
This is neuroscience, and it'swhy some entrepreneurs seem to
effortlessly grow while othersgrind themselves into the
ground.
So how do we actually shift fromthe gap to the gain?
(03:40):
Here's the practice that I'vedeveloped and it's something
that we explore in differentways during our Growth
Collective office hours.
And if you are not in there yet,you need to be.
The mindset.
Shifts alone are worth it.
Every Friday before you plannext week, write down three wins
from the current week.
Not what you didn't finish, notwhat could have been better, but
three actual wins.
(04:02):
Here's the key.
Make them specific andmeasurable against where you
were and not where you're going.
A bad example, made progress onmy website.
A good example wrote five pagesof website copy when last month
I couldn't even write one.
Bad example.
Got a few new clients, goodexample, signed two new clients
(04:24):
at my new rate when, threemonths ago, I was afraid to
charge half that.
You see the difference there,measuring backward against your
starting point and not forwardagainst your ideal.
Let's talk about theparticularly toxic version of
gap thinking, comparing yourprogress to others.
This is especially brutal in theage of social media where
(04:45):
everyone's highlight reel lookslike their everyday reality.
You see someone celebratingtheir first six figure month,
and suddenly your best monthever feels like a failure.
You see someone's perfectmorning routine and your
perfectly functional morningroutine feels inadequate.
The thing is, as you're not justmeasuring against your own
(05:05):
moving horizon anymore, yourmeasuring.
Everyone else's carefullycurated success stories last
week in my email community, bythe way, it has over 1500 other
entrepreneurs who get weeklypractices, tips, tricks, and
strategies.
The link is in the show notes ifyou want in.
(05:26):
Someone replied back and saidthat they felt like a failure
because they only grew by 40%this year while someone in their
mastermind grew by 200%.
Think about it, 40% growth andthey felt like a failure.
That's gap thinking poisoningactual success.
But don't worry, I replied andcelebrated the heck out of them
(05:48):
because that is worthcelebrating.
The deepest work here isn'tabout changing how you measure.
It's about changing who youbelieve you are.
When you live in the gap, youridentity becomes, I am someone
who's behind.
When you live in the gain, youridentity becomes someone who
makes progress.
This shift changes everything.
(06:09):
It changes how you show up foropportunities.
It changes how you price yourservices.
It changes how you talk aboutyour business.
It changes how you feel at theend of each day.
I used to end each day with amental list of what didn't get
done.
Now.
I end with three gains from theday, same day, same tasks,
completely different experience.
(06:30):
If you wanna deepen this concepta little bit more, here is a
practice for you.
Grab a journal and every nightthis week answer these three
questions.
What are the three business winsfrom today, no matter how small.
Question number two, how istoday's version of me better
than last year's version?
And the final question to answeris, what problem do I have now
(06:53):
that I would've loved to have ayear ago?
That last one.
It's powerful.
Like I'm overwhelmed with clientinquiries.
The past you would've killed forthat problem or you are
overwhelmed is I need to hirehelp.
That's awesome.
That's a growth problem, not afailure.
One of my clients realized hercurrent problem of needing a
(07:15):
bigger email system would'vebeen a dream scenario when she
had 12 email subscribers.
Now she has over 3000.
That's gain thinking.
Here's something a little bitcounterintuitive.
When you stop obsessing aboutthe gap and start celebrating
the gain, you actually achieveyour goals faster.
(07:35):
Why is this?
It's because you're operatingfrom confidence and not
desperation.
You make better decisions.
When you feel successful.
You attract betteropportunities.
When you radiate achievement.
You have more energy when you'renot constantly disappointed.
It's not about lowering yourstandards, it's about
acknowledging your progresswhile you pursue potential.
(07:57):
Think about it.
Would you rather work withsomeone who's constantly
stressed about not being enoughor someone who's excited about
their growth journey?
Your energy attracts or repelsopportunity?
Let me give you some specificways to shift from the gap to
the gain this week.
So in the morning, a little bitof morning reflection instead of
(08:17):
starting with your to-do list,start with yesterday's wins.
When it comes to client calls,begin by sharing a recent win
before diving into challenges.
How about your email signature?
Maybe add a win of the week tokeep yourself accountable in
your team meeting.
Start with gains beforediscussing the gaps and social
(08:38):
media, how about sharingprogress posts and not just
milestone posts?
The key is making the gainthinking your default, and not
something that you remember youhave to do.
Every entrepreneur you admire,every success story you see.
They all started behind whereyou are now.
The difference isn't talent orluck or resources, it's that
(08:59):
they've learned to see andcelebrate their gains while
working towards their goals.
This week I challenge you to dothree things.
Write down 10 gains from thelast 90 days.
Share one of your gains publiclyand start a simple gain journal
with just three wins each andevery night.
If this resonated with you andyou want to go deeper, I would
love for you to join my emaillist link in the show notes.
(09:22):
And consider joining the GrowthCollective where we practice
gain thinking together everysingle week in our community
office hours.
You have already come so farfurther than you realize, and it
is time to start seeing it,celebrating it, and using it as
fuel for where you've going.
Until next time, this is me,Cindy, reminding you that when
(09:44):
everything feels urgent, nothingreally is, especially when
you're measuring backwards andseeing all the ground you've
already covered.
And remember, you've got this.
Speaker (09:56):
Thanks for spending these few minutes with me today.
Remember, overwhelm isn'tpermanent.
It's simply your brain's way ofsaying pause and take a little
reality check.
If this was helpful, you'll lovemy weekly email tips where I
share the systems that keep meand hundreds of other
entrepreneurs on Track Link inthe show notes.
If you got value in today'sepisode, please share it with
(10:17):
another entrepreneur who needsthat reminder.
If you're loving the show, I'dbe so grateful if you could
leave me a quick review.
It helps other overwhelmedentrepreneurs find us.
Make sure you hit subscribe soyou never miss your weekly dose
of clarity.
For more resources and toconnect with me, visit
exclusively cindy.com.
Until next time, remember you'vegot this.
I wanna share something thathappened last week that shifted
my perspective just a littlebit.
I was having a terrible day, youknow, the kind where nothing
feels like enough.
I had landed a new client,finished a project ahead of
time, and got some amazingfeedback from my growth
Collective members.
But all I could think about washow far I still had to go to
(00:20):
meet.
My yearly goal.
Then I called my mom to checkin.
She has been dealing with somemobility issues lately.
She was frustrated that shecould only walk to the mailbox
and back and kept comparingherself to her friend who was
still very, very active.
And I heard myself say, mom,literally two months ago, you
(00:40):
couldn't even get to the frontdoor without help.
So look at how far you've come.
And then it hit me.
I was giving her the advice thatI wasn't taking myself.
Hi, I'm Cindy, and you arelistening to The Overwhelmed
Entrepreneur, and today we aretalking about why you are
feeling like you're never doingenough, even when you're
crushing it, and moreimportantly, how to shift from
(01:01):
measuring it against theimpossible horizon to
celebrating how far you'veactually come.
So here's what's happening inyour brain, and this was
inspired by Dan Sullivan'stransformative work on how high
achievers measure success.
We're all stuck in what we callthe measurement trap.
You set a goal, you work yourass off, you progress, and
(01:24):
instead of feeling accomplished,you immediately look at how far
you have to go.
The horizon keeps moving, thefinish line keeps shifting, and
you feel like you're failingeven when you're winning.
Does that sound familiar?
This happens when we measureforward against our ideals
instead of backwards againstwhere we started.
We are living in the gap betweenwhere we are and where we want
(01:47):
to be instead of living in thegain of how far we've come.
So let me reality check thiswith you with actual numbers
from one of my clients.
Samantha came to me about sixmonths ago, completely
overwhelmed and making about$3,000 a month, working at least
60 hours a week, and had zerosystems.
Today she's making about$8,000 amonth working just a little bit
(02:10):
less than before, so about 40hours a week.
She has two contractors andactually is taking the weekends
off.
But when we talked last week,she was frustrated.
Why was she frustrated?
Because her goal was 10 KAmonth.
She was so focused on that twogrand gap that she couldn't see
the five grand gain.
(02:31):
She couldn't see that she almosttripled her income while cutting
her hours by a third.
This is what measuring forwarddoes to us.
It makes us miserablemillionaires, literally not
millionaires yet, but you getthe point.
We achieve amazing things, butyet still feel like failures.
Here's what's actually happeningin our brain, and understanding
(02:55):
this changed a lot for me.
When you measure against yourideal, that moving horizon, your
brain registers it as a threat.
You're constantly in a state ofnot enough, which triggers
stress hormones, killscreativity, and ironically makes
you less productive when youmeasure backward.
You acknowledge the gain, yourbrain releases dopamine, you
(03:17):
feel accomplished, you feelconfidence, you create momentum,
you actually become more likelyto reach that goal because you
are operating from abundance andnot scarcity.
It's not woo woo.
This is neuroscience, and it'swhy some entrepreneurs seem to
effortlessly grow while othersgrind themselves into the
ground.
So how do we actually shift fromthe gap to the gain?
(03:40):
Here's the practice that I'vedeveloped and it's something
that we explore in differentways during our Growth
Collective office hours.
And if you are not in there yet,you need to be.
The mindset.
Shifts alone are worth it.
Every Friday before you plannext week, write down three wins
from the current week.
Not what you didn't finish, notwhat could have been better, but
three actual wins.
(04:02):
Here's the key.
Make them specific andmeasurable against where you
were and not where you're going.
A bad example, made progress onmy website.
A good example wrote five pagesof website copy when last month
I couldn't even write one.
Bad example.
Got a few new clients, goodexample, signed two new clients
(04:24):
at my new rate when, threemonths ago, I was afraid to
charge half that.
You see the difference there,measuring backward against your
starting point and not forwardagainst your ideal.
Let's talk about theparticularly toxic version of
gap thinking, comparing yourprogress to others.
This is especially brutal in theage of social media where
(04:45):
everyone's highlight reel lookslike their everyday reality.
You see someone celebratingtheir first six figure month,
and suddenly your best monthever feels like a failure.
You see someone's perfectmorning routine and your
perfectly functional morningroutine feels inadequate.
The thing is, as you're not justmeasuring against your own
(05:05):
moving horizon anymore, yourmeasuring.
Everyone else's carefullycurated success stories last
week in my email community, bythe way, it has over 1500 other
entrepreneurs who get weeklypractices, tips, tricks, and
strategies.
The link is in the show notes ifyou want in.
(05:26):
Someone replied back and saidthat they felt like a failure
because they only grew by 40%this year while someone in their
mastermind grew by 200%.
Think about it, 40% growth andthey felt like a failure.
That's gap thinking poisoningactual success.
But don't worry, I replied andcelebrated the heck out of them
(05:48):
because that is worthcelebrating.
The deepest work here isn'tabout changing how you measure.
It's about changing who youbelieve you are.
When you live in the gap, youridentity becomes, I am someone
who's behind.
When you live in the gain, youridentity becomes someone who
makes progress.
This shift changes everything.
(06:09):
It changes how you show up foropportunities.
It changes how you price yourservices.
It changes how you talk aboutyour business.
It changes how you feel at theend of each day.
I used to end each day with amental list of what didn't get
done.
Now.
I end with three gains from theday, same day, same tasks,
completely different experience.
(06:30):
If you wanna deepen this concepta little bit more, here is a
practice for you.
Grab a journal and every nightthis week answer these three
questions.
What are the three business winsfrom today, no matter how small.
Question number two, how istoday's version of me better
than last year's version?
And the final question to answeris, what problem do I have now
(06:53):
that I would've loved to have ayear ago?
That last one.
It's powerful.
Like I'm overwhelmed with clientinquiries.
The past you would've killed forthat problem or you are
overwhelmed is I need to hirehelp.
That's awesome.
That's a growth problem, not afailure.
One of my clients realized hercurrent problem of needing a
(07:15):
bigger email system would'vebeen a dream scenario when she
had 12 email subscribers.
Now she has over 3000.
That's gain thinking.
Here's something a little bitcounterintuitive.
When you stop obsessing aboutthe gap and start celebrating
the gain, you actually achieveyour goals faster.
(07:35):
Why is this?
It's because you're operatingfrom confidence and not
desperation.
You make better decisions.
When you feel successful.
You attract betteropportunities.
When you radiate achievement.
You have more energy when you'renot constantly disappointed.
It's not about lowering yourstandards, it's about
acknowledging your progresswhile you pursue potential.
(07:57):
Think about it.
Would you rather work withsomeone who's constantly
stressed about not being enoughor someone who's excited about
their growth journey?
Your energy attracts or repelsopportunity?
Let me give you some specificways to shift from the gap to
the gain this week.
So in the morning, a little bitof morning reflection instead of
(08:17):
starting with your to-do list,start with yesterday's wins.
When it comes to client calls,begin by sharing a recent win
before diving into challenges.
How about your email signature?
Maybe add a win of the week tokeep yourself accountable in
your team meeting.
Start with gains beforediscussing the gaps and social
(08:38):
media, how about sharingprogress posts and not just
milestone posts?
The key is making the gainthinking your default, and not
something that you remember youhave to do.
Every entrepreneur you admire,every success story you see.
They all started behind whereyou are now.
The difference isn't talent orluck or resources, it's that
(08:59):
they've learned to see andcelebrate their gains while
working towards their goals.
This week I challenge you to dothree things.
Write down 10 gains from thelast 90 days.
Share one of your gains publiclyand start a simple gain journal
with just three wins each andevery night.
If this resonated with you andyou want to go deeper, I would
love for you to join my emaillist link in the show notes.
(09:22):
And consider joining the GrowthCollective where we practice
gain thinking together everysingle week in our community
office hours.
You have already come so farfurther than you realize, and it
is time to start seeing it,celebrating it, and using it as
fuel for where you've going.
Until next time, this is me,Cindy, reminding you that when
(09:44):
everything feels urgent, nothingreally is, especially when
you're measuring backwards andseeing all the ground you've
already covered.
And remember, you've got this.
Speaker (09:56):
Thanks for spending these few minutes with me today.
Remember, overwhelm isn'tpermanent.
It's simply your brain's way ofsaying pause and take a little
reality check.
If this was helpful, you'll lovemy weekly email tips where I
share the systems that keep meand hundreds of other
entrepreneurs on Track Link inthe show notes.
If you got value in today'sepisode, please share it with
(10:17):
another entrepreneur who needsthat reminder.
If you're loving the show, I'dbe so grateful if you could
leave me a quick review.
It helps other overwhelmedentrepreneurs find us.
Make sure you hit subscribe soyou never miss your weekly dose
of clarity.
For more resources and toconnect with me, visit
exclusively cindy.com.
Until next time, remember you'vegot this.
Popular Podcasts
Las Culturistas with Matt Rogers and Bowen Yang
Ding dong! Join your culture consultants, Matt Rogers and Bowen Yang, on an unforgettable journey into the beating heart of CULTURE. Alongside sizzling special guests, they GET INTO the hottest pop-culture moments of the day and the formative cultural experiences that turned them into Culturistas. Produced by the Big Money Players Network and iHeartRadio.
The Joe Rogan Experience
The official podcast of comedian Joe Rogan.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.