The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Sales/Women in Sales Leadership
Women in Sales Leadership artwork

Why Winning Feels Empty

Women in Sales Leadership · 2026-07-23 · 18 min

0:00--:--

Key moments - from our scoring

Substance score

23 / 100

Five dimensions, 20 points each

Insight Density6 / 20
Originality4 / 20
Guest Caliber5 / 20
Specificity & Evidence5 / 20
Conversational Craft3 / 20

Amy Evans, a sales leadership coach with 25 years at companies like Salesforce and ADP, addresses a common trap among high-performing sales leaders, CEOs, and founders: hitting major goals but feeling nothing. The episode examines why this happens through the lens of neuroscience and behavioral psychology, drawing on concepts from Dan Sullivan and Dr. Benjamin Hardy's "The Gap and the Game," as well as Tal Ben-Shahar's research on the "arrival fallacy." Evans explains that high achievers typically measure themselves forward against an ideal future state (gap thinking) rather than backward against where they started, which creates a perpetual sense of inadequacy. The brain is neurologically wired for the dopamine hit of pursuit, not arrival, making actual achievement feel anticlimactic. Evans presents the antidote: measuring backward to recognize progress, reframing your worth beyond production metrics, and adopting a weekly practice of documenting three wins. This framework helps leaders combat burnout and the hedonic treadmill effect while maintaining ambition.

Key takeaways

  • →High performers experience goal-achievement emptiness due to gap thinking - constantly measuring forward against ideals rather than backward against starting points - rather than personal failure.
  • →The brain releases dopamine during pursuit, not arrival, which is why hitting goals feels anticlimactic and the high wears off almost immediately upon achievement.
  • →Measuring backward (comparing current state to where you started) rather than forward (to where you want to be) triggers fulfillment and provides the perspective needed to acknowledge real progress.
  • →Your worth is not tied to your production output or hitting your number; it's rooted in self-love, how you contribute to others' growth, and giving yourself credit for the journey.
  • →A practical weekly practice of writing down three wins trains your brain to feel energized and fulfilled by progress, not just the final destination.

Topics in this episode

Sales leadership coachingGap thinkingArrival fallacyDopamine and pursuit psychologyBackward-measuring performanceThe Gap and the Game (Dan Sullivan and Benjamin Hardy)Weekly wins practiceNeuropsychology of achievementSelf-worth tied to productionBurnout prevention for high performers

Questions this episode answers

Why does hitting a major sales goal or target often feel empty or anticlimactic?

The brain is neurologically wired to release dopamine during the pursuit and chase, not upon arrival. When you actually achieve the goal, dopamine drops sharply, creating a physiological letdown. Additionally, high achievers typically measure forward against an ideal future state rather than backward against where they started, so the win never feels like enough.

What is gap thinking and how does it contribute to burnout?

Gap thinking is constantly focusing on the gap between where you are and where you want to be, rather than acknowledging progress made. This creates a perpetual sense of inadequacy and never allows you to arrive or celebrate, keeping you on an endless treadmill that accelerates faster and faster, eventually leading to burnout.

What does measuring backward instead of forward mean in practice?

Rather than measuring your current state against your ideal future goal, measure your current state against where you started - whether that's the beginning of the year, when you took the job, or when you started the company. This provides perspective on actual progress and accomplishments, allowing you to feel more fulfilled.

What is the arrival fallacy and how does it affect goal achievement?

The arrival fallacy is the belief that hitting big goals will deliver lasting happiness. Research shows it doesn't - the happiness is fleeting and the high wears off almost immediately because achievement becomes forgotten and the dopamine peak drops after arrival.

What is the specific weekly practice Amy Evans recommends to combat empty wins?

At the end of each week, write down three wins - three things you did well or where you made progress, whether in work or personal life. This trains your brain to recognize and feel fulfilled by progress along the journey, not just final destinations.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

6 / 20

The episode surfaces two real psychological constructs (gap thinking/gain thinking from 'The Gap and the Gain' and the arrival fallacy) and a dopamine explanation for post-win deflation, but these are presented at surface level and buried under heavy repetition and motivational filler. Very few ideas per minute that a B2B operator wouldn't already know.

high achievers stay unhappy because they measure forward against an ideal, an ideal instead of backward. M against where they began
dopamine picks, it peaks, I should say, when you're chasing in the chase, in the hunt, we are hunting this thing down and it, that is the dopamine peak and it drops when you actually get there

Originality

4 / 20

The episode is almost entirely a paraphrase of two existing books (Dan Sullivan/Hardy's 'The Gap and the Gain' and Tal Ben Shahar's arrival fallacy work) with no original synthesis or contrarian reframing. The host explicitly acknowledges she is summarising others' research, and adds nothing structurally new.

I'm going to read you the paraphrasing that comes straight from this book. So I get it exactly right
there's this, um, gentleman named Tal Ben Shahar, and he's from Harvard and he's written about this arrival fallacy

Guest Caliber

5 / 20

This is a solo episode with no guest; the host has a legitimate practitioner background (Salesforce, ADP, 25 years in sales), but the episode itself functions as a coaching monologue and demonstrates no deep operator-level insight that validates that seniority.

after 25 years of selling and leading inside of companies like Salesforce and adp, I help people who own their number grow their business and themselves at the same time
I coach CEOs, founders and sales leaders

Specificity & Evidence

5 / 20

The only concrete references are two named books/researchers and a brief personal origin story (Atlanta, pre-med degree, debt); there are zero named companies, client outcomes, sales metrics, or B2B case studies. The actionable recommendation ('write three wins') is generic self-help advice.

I moved to Atlanta, I didn't know a soul almost 30 years ago and I had a degree in pre med and I had a job in nonprofit where I was barely able to pay my bills
Dan Sullivan, Dr. Benjamin Hardy...one of the core ones that gets to this topic is called the Gap in the Game

Conversational Craft

3 / 20

There is no conversation - this is an uninterrupted solo monologue with significant repetition, throat-clearing, and motivational padding. No questions are posed or challenged, no pushback exists, and the same points are restated multiple times without adding depth.

And I'm so glad you're here. Thank you for being here. Thank you for pressing Play.
We're never gonna stop striving to hit the number. That's the job. That's what we've signed up for.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

feel13number10life10goal9journey9progress8back7high6worth6happened6three6ways5measure5achievement5credit5started5

Episode notes

In this one I'm naming something almost every high achiever feels and nobody says out loud. You hit the number, maybe the biggest of your career, and instead of elation you feel a whole lot of nothing. The win washes right over you and you're already onto what's next. I walk you through why that empty feeling isn't a flaw, it's a thinking trap, what the research on the gap and the gain and the arrival fallacy actually says about it, and the one simple practice I give my CEO and founder clients to start feeling their wins again. Key Takeaways: - Measuring progress backward against your starting point provides true perspective. - Celebrating small wins weekly can boost fulfillment and energy. - The brain is wired for dopamine hits during pursuit, not achievement. - Hitting a goal provides a fleeting high, not lasting happiness. - Reflecting on your journey helps reduce burnout and gap thinking. - Self-worth is rooted in contribution, not just numbers.

Full transcript

18 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Tell me if you've been here, you hit your number for whatever number it is. And maybe it was a big one, maybe it was the biggest one of your career, maybe it was the biggest one in the whole company, the history of the company, or maybe it was one that was just really unbelievably difficult to get to and you got there, you won and you feel nothing. You feel empty inside. And then honestly you're straight on to like, what's next? What do I need to do next? What's the next goal that I've got to achieve? And if you've ever won something really, really big and felt so empty or just, I don't know, this. Anti climax, if you will, it's anticlimactic. Stay with me because this empty feeling is not that there's something wrong with you, it's really a thinking trap and once you start to see it, you cannot unsee it. And I'm so glad you're here. Thank you for being here. Thank you for pressing Play. If we haven't met, I'm Amy Evans. I coach CEOs, founders and sales leaders. And after 25 years of selling and leading inside of companies like Salesforce and adp, I help people who own their number grow their business and themselves at the same time. Here's what you're gonna get out today. Number one. Why winning can oftentimes make us feel empty inside. Even after the victory. It should be huge. We should be celebrating. But eh, ah, there's a whole lot of nothing that anticlimactic feeling too. The ways that you can start to measure your life. In a way there's, there's ways that you can measure your life. M2 There are two ways that you can really look at your life. And I've been reading and learning and studying about this. I'm sharing with you what I have learned. There's two ways that you can look at your life. One that actually allows you to feel the your wins and let them fill you up and make you feel fulfilled with what your accomplishments are. And third, I'm going to give you something you can truly use which is a practice you can use to actually begin to let those wins sink in and start filling back up your energy bucket if you will. Because when we're constantly going on to the next thing, it's like we accomplish something and then we throw it all away and we've got to begin again. It's kind of the nature of the beast. But there's a way mentally you can get better at it and get stronger at it. So stay with me to the end. I'm going to tell you why this is something really important to work on and think about and some of the mindset challenges that you can overcome with it. Because what the payoff is is putting yourself in a position to reduce the feeling of burnout, to reduce feelings, emptiness that can come with goal achievement. So here's what, what we'll get into. Number one, this concept of you win but you don't feel it or it doesn't feel like a win and the win just kind of passes right through you. We've been here, especially if you've been a sales leader, you're a revenue leader, you're a CEO, you're a founder. The minute the customer or the prospect says yes, you feel that jolt, that of uh, yes, we got it. And of course it's like you're, you're not quite finished with the race because you still have to get ink on paper, right? We all know what the reality of that is. And then you fight through that next battle. You fight to get the battle of yes, we're going to do it or yes, we're winning or yes we're hitting the number and then there's always a little bit more extra. And it's almost like that wind hits you and washes right over you and you don't ever allow it to really hit you and be with you so that you can absorb it, celebrate it. This is not because there's something wrong with you. It's because of, uh, how we are built as high performance. This is something that's a known, studied thing. And there are two ways to look at performance in your career and even in your life. It works in your life too. Because I don't know a single person who hasn't arrived at a birthday and said, oh, I thought I'd be further along by now. When in reality, if your 10 year old self saw you and what you've actually done, what you've actually been through and what you've actually accomplished, your 10 year old self would be pretty freaking amazed by you and who you are. But that's not how we think, that's not how we've been trained to think because it's really, really core human psychology. And I'm going to share with you what I've been learning about it and how to make it easier for you. So we're living in this world where founders, CEOs, sales leaders, you all, it's every goal, the goal post is always Moving the finish line is always moving, right? There's always the next quarter, there's always the next year, there's always the next whatever. And so there's never a chance to truly arrive and have that moment of elation and of celebration where we say, I just did something huge. We just did something huge. And to let it actually get in, get into your mind, get into your heart, get into your body, get into your identity of absorbing that winning energy. And this is an, uh, idea of when you live this way, the other way that we're accustomed to, which is like the goal is ever moving. Like, you finish, you finish one month or one quarter, one year, and you're back to zero again, right? It gets you in this trap of this gap thinking. You're thinking about the gap. There's always a gap between where you are and where you want to be, where you are and where you're going, where you are either financially in your own personal life or business wise in the metrics that you're looking at, revenue, sales, what have you, whatever your KPI is. So we're living in this place of constant gap thinking where even when there's progress and there are steps along the way towards your path to achievement and victory, there's still not this feeling of giving that progress any credit. And what's fascinating about progress is progress is, and making progress is one of the core human needs that we have. It's, it's one of our definitions of success, not just getting to the goal or hitting the number, but are we making progress? And if you're not giving yourself credit for progress, it's common. And here's what you can start to think about and do about for it. So I'm going to give you some information. This is the research I've read. I've read some books by Dan Sullivan, Dr. Benjamin Hardy, if you've heard of these guys, they've got several books out there. But one of the core ones that gets to this topic is called the Gap in the Game. And I'm going to read you the paraphrasing that comes straight from this book. So I get it exactly right, which is they say that high achievers stay unhappy because they measure forward against an ideal, an ideal instead of backward. M against where they began. And the research, this whole book gave it to you in two seconds. The research really says you've got to measure backward against where you started versus where you are now. And when you do that, it gives you perspective, true perspective, and can allow for some of that Fulfillment to arrive again in achievement and hitting these numbers and acknowledgement of yourself and your self worth, of the journey, because it's the journey that makes it so worthwhile. Nobody acknowledges the journey though, right? They're only looking at the bottom line. They're only looking at the numbers. So when we think about the journey, there's this arrival fallacy that maybe you've heard of and I'm going to share with you. So there's this, um, gentleman named Tal Ben Shahar, and he's from Harvard and he's written about this arrival fallacy. And it's this belief that hitting these long, these big goals, that anytime you hit a goal that it delivers happiness. Oh, come on. We know that's not true. It might be for a minute, it might be for an hour, it might be for a few days that you're happy or you're proud of the team and you're celebrating, you're winning. But it's not a long lasting happiness because ultimately that achievement of whatever that goal was, that number was you were chasing, it melts away because we forget it. And that high really wears off almost immediately. And like I said, it's, it's, you can almost get the high before the actual win occurs because at the minute you see we're gonna win, we're gonna get there and you have that realization of victory or achievement, it's fleeting. And when the victory actually occurs, it's even less rewarding. So there's this arrival fallacy. So when our brains are on pursuit, I do a lot of looking at brains and how, um, neuropsychology affects how we think, it affects how we sell, it affects how we lead, it affects how we have our relationships. And it touches every bit of the areas that are required for you to be successful in your life and in your business and in your company. Right? The brain on pursuit, our brains are re, are wired for the chase, right? Our brains are rewired, are wired for dopamine hits and dopamine picks, it peaks, I should say, when you're chasing in the chase, in the hunt, we are hunting this thing down and it, that is the dopamine peak and it drops when you actually get there. So there is a, um, physiological explanation for why it's anticlimactic when we actually achieve a goal and get there, right? We're literally built and wired in our brains to feel let down when we achieve something. And I don't have to tell you, but maybe you already know like this, the cost can wear on you. The cost that happened for me and for a lot of people around me is you can go at this pace for a while. You can do the striving, you can do the, you know, constantly going back to zero without pausing or giving yourself a moment to reflect and acknowledge what you came, what you, where you came from and, and where you actually arrived and giving yourself credit and energy to replenish yourself for the journey. What happens is burnout. You feel like you're just on a treadmill, a never ending treadmill that keeps getting turned up faster and faster and faster and you never actually get there. That's this gap thinking and what's really to compact that is this thinking that we all have for high performers, is that our worth, like who we are, what we're worth as a human being is tied to our production and our output and that worth sets back to zero on a regular basis. Ouch. No wonder we're tired. No wonder we're all tired. So you're always in this race to get your own self approval of yourself. Right? And this, this really drains energy so, so much. I have information that will help you. Okay, this is what you do about it. M in looking at, there's either you can live in the gap, which is the I'm not there yet, or you can look at that journey, that journey along the way of what actually happened. And so taking to points in time. This is the data. If you take points in time and measure backward, okay, how what happened at the beginning of the year, what happened two years ago, what happened when I started this company, what happened when I started this team, when I started this job, where were we versus where we are now? And getting some time perspective allows you to feel more fulfilled and give yourself true acknowledgement for what you've actually achieved. By the way, it adds to part of your stories that you're going to tell to anybody who wants to know about you, your leadership, what you've done in your career, what you've accomplished. It always begins with the uh, where things were when you showed up versus where you are now. And you can take the show up moment that you're measuring back to as far as you want. For me, I take it back to I moved to Atlanta, I didn't know a soul almost 30 years ago and I had a degree in pre med and I had a job in nonprofit where I was barely able to pay my bills and I had credit card debt, I had student loan debt. I uh, pretty much the only thing I owned was a bunch of debt. And I showed up and from that time period until now, I learned how to sell. I put myself through graduate school, I paid off all my debts and loans, I bought my first home, I bought a second home, I had children. I, you know, was able to afford a lifestyle that I never would have dreamed of when I was that young. When I first started my career, I was able to save and invest. Like I'm talking, put yourself into the, all the things that you've actually accomplished. Now, this isn't to make ourselves feel better so that we don't have to keep striving anymore, but there's something that we have to do to abate that and soothe the. You're not good enough. And your worth is only tied to your number because your worth is tied to how much you love yourself, how much you love other people, how much you're contributing to other people and their growth and development. And the way to get access to that is to look back in time at, uh, what actually has occurred, what you've actually achieved, and give yourself some credit to do that one practice you could choose to take on and that I coach my high paying coaching clients and my CEOs and founders to do is at the end of every week, write down three wins, three things that were successful, could be in personal life, could be in your work life, could be in the business. There are three things that made progress this week for you in something that you did well. And of course acknowledge the stuff you're working on. Right? We always have stuff we're working on. So that's the opportunity that lies in front of you, is to get perspective. Take an opportunity this week, this Friday, Saturday morning, before you forget it, write down what you accomplished, three things that went well, three wins that you had, and then even three things that you're working on, you begin to train your brain and get in this habit of being fulfilled by the journey. We're never gonna stop striving to hit the number. That's the job. That's what we've signed up for. But getting yourself in a place where you can feel energized, joyful, fulfilled by the journey that you are on, that's the game that we're all playing. If you enjoy today's conversation and you'd like to send it to a person, if you are thinking of somebody that you know while you were listening to this today, send this over to them, give them this gift of this information so they can learn what you just learned. And if you want to reach out to me, my DMs are always open on LinkedIn. Come find me at amyevans. And meanwhile, go be the leader you know you are. You're stronger than you know you are. And I'll see you next time.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • How Multi-Threaded Selling and Building the Closing Strategy From First Contact Drives Revenue GrowthThe B2B Revenue Executive Experience · on Sales leadership coaching87 / 100
  • Beneath the Surface: Selling to Emotions, Not Just Logic with Ash KhalekPillar Talk · on Sales leadership coaching87 / 100
  • THE #1 THING YOU CAN DO TO GET YOUR TEAM OUT OF THE B-PLAYER TRAPSales Leadership & Management Show · on Sales leadership coaching57 / 100

More from Women in Sales Leadership

All episodes →
  • Energy Management Beats Time Management39 / 100
  • Why Change Feels So Scary43 / 100
  • Part 2: When You Out-Earn Your Husband46 / 100
  • Part 1: The Leadership Habit Killing Your Relationship49 / 100
  • Why You're Never Starting From Zero45 / 100
Explore the best B2B Sales podcasts →
All Women in Sales Leadership episodes →