The Happiness Paradox: When We Don’t Feel What We “Should” Feel

What happens when you finally get the thing you wanted, and it doesn't feel the way you expected?

In this episode, George and Liz explore one of the strangest experiences in personal growth: the disconnect between achieving happiness and actually feeling it. If you've ever reached a goal only to wonder why you're not celebrating, or looked around at your life and couldn't figure out why it still feels off, this conversation is for you.

The Friend Who Didn't Know She Missed Him

Liz opens with a story about a friend we'll call Susie. She'd just started dating a guy who was perfect for her. Same kind of weirdo. Absolutely right match. But one day, Susie called Liz in distress.

"I just feel terrible."

"What happened? Did something happen with Mike?"

"No. He's great. I just can't shake this horrible feeling."

Mike travels for work a few days a week. So Liz asked the obvious question.

"Do you just miss him?"

Susie paused. "Oh god. Is that what this feeling is? This is terrible. Why do we even want this?"

She didn't know how to name the feeling. Once she did, she realized she wasn't miserable. She just missed someone she cared about. That's actually a happy thing.

This is the happiness paradox in action. The feelings and the facts don't align.

What Is the Happiness Paradox?

It shows up in a few different ways.

You might struggle to trust or feel comfortable in a new healthy relationship because vulnerability has historically meant danger. You might get the success you wanted but feel overwhelmed or even fearful of it. Or sometimes the thing you wanted shows up, and you don't even recognize it's there because you're so used to disappointment.

We expect that when we get the things we want, we'll meet those moments with joy. Arms wide open. Celebration. Instead, there's often a disconnect. A gap between what we've achieved and what we actually feel.

George put it plainly: "I fall prey to this more than some might think."

The Inbound Stage Story

George shares his own experience with this paradox.

In 2012, he set a goal: speak on the Inbound stage. In 2016, it happened. He got a breakout session at the conference. But instead of enjoying it, his brain immediately moved the goalposts.

"I wasn't able to enjoy the fact that this was happening. I even kind of, by default, moved it to, well, it's not the main stage. It's just a breakout."

He'd achieved exactly what he set out to do. And rather than pause to appreciate it, he found ways to brush it off. Chase the next thing. Minimize what he'd accomplished.

This pattern, he admits, has repeated throughout his career and personal life.

Why the Disconnect Happens

George breaks down several contributing factors.

External vs. internal motivation. We often equate success with external achievements like promotions, money, or recognition. Those can provide a temporary high, but they don't fulfill our deeper need for connection, purpose, or meaning. When we focus too much on external validation, we lose sight of the internal drivers that create lasting joy.

Values that don't align with what we're chasing. We go after things that society says are successful without asking if those things actually matter to us. When we achieve them, they feel empty because they don't connect with our deeper desires. "It's literally like we've been climbing a mountain only to realize it wasn't the mountain we wanted to climb."

Comparison culture. Social media bombards us with highlight reels. Bigger houses. Better vacations. More likes. Rationally, we know it's curated. Emotionally, it hits hard. "Suddenly, we feel like we're not enough, which is a terrible place to be when you're trying to not be stuck."

Liz's Big House That Felt Empty

Liz shares her own version of the paradox.

She was the girl in the half-million dollar house. Nice neighborhood. Dogs. Big backyard. All the boxes checked. And she was miserable.

One day, sitting in the backyard with her ex-husband, she blurted out: "Why does it feel like no one's lived here in a really long time?"

Without thinking, he said, "Because I'm not sure anybody has."

They both walked away from that conversation. It freaked them out. But it was true.

"Sometimes you end up with good people in situations that become toxic, that calcify. And sometimes that happens on an individual level where we chase the things that we think we're supposed to want, and we check all the boxes. And for some reason, the more happy boxes we check, the unhappier we get."

The Programming That Rejects Happiness

There's another layer to this. Sometimes you're actually getting the thing that's genuinely aligned with who you are. And you still reject it like a bad organ transplant.

Liz explains the psychology.

"If vulnerability has been something you've struggled with in the past, meaning you haven't felt safe to be vulnerable, you know what's gonna happen? You're gonna try to kill the baby. You're going to have a fight or flight response because that happiness is identified by your subconscious as a threat."

Your brain is trying to protect you from pain. But in doing so, it blocks the very thing you've been working toward.

This is why someone might finally get into a healthy relationship and immediately start looking for reasons to sabotage it. Or land the dream job and suddenly feel like a fraud. The fleshy paperweight in our brain is desperately trying to keep us safe from reexperiencing pain.

The Control Trap

George and Liz both admit to being control freaks. Most high achievers are.

We say things like, "I don't care how we get there, as long as we hit the outcome." But that's rarely true.

Liz lays it out: "When you have your fist clenched around an opportunity, you will never give it the oxygen to take a true shape. You will always be restricting it to a very specific form."

We get so hung up on the how that we miss the actual thing when it arrives. Because it didn't show up the way we imagined.

She shares a personal example. About a month ago, she had to let go of a relationship she'd been clinging to.

"I knew the moment I let go, my worst fears were going to be confirmed. It was a relationship that was only there because I was holding on. And the moment I released, it didn't disappear. It was already gone."

Painful. But necessary. Because that space had to be cleared for something else.

Why High Achievers Struggle Most

George digs into why this paradox hits high achievers especially hard.

Always chasing the next thing. Success becomes a moving target. Once we reach a goal or get close, we've already moved on. "This mindset makes it hard to slow down and appreciate the moment because in our minds, there's always something more to accomplish."

Perfectionism. We set incredibly high standards. Even when we hit milestones, we downplay success or zero in on what didn't go perfectly. "It creates a situation where nothing is ever good enough."

Fear of losing momentum. We worry that if we stop to relish achievements, we'll fall behind. So we tie our self-worth to productivity and output.

Comparison to other successful people. When everyone around you is winning, it's tough not to feel like you need to do more. "I'll never be Gary V. I'll never be Jay Shetty." That comparison overshadows the happiness we've actually earned.

George offers the antidote: "Sometimes you just have to realize the only thing I can be is the best George B. Thomas."

Liz Wakes Up to Her Own Life

Liz had a turning point a few weeks before recording.

She'd been telling herself the wrong story about her life. Sitting on the edge of her bed at 4 AM, feeling adrift. Forty-two. Not in the big house anymore. Dating again.

Then she stopped and described her circumstances as if talking to someone else.

"I'm living in an incredible studio apartment in the middle of the historic district of Annapolis. My neighbors are artists. My hallways are filled with canvases. If I want to go anywhere, I just walk downstairs to my favorite coffee house. I work for myself and I'm successful at it. I get to travel. I get to have incredible experiences."

She paused. "What exactly am I upset about? Because on paper, this is the thing I said I wanted. My freedom."

Nothing changed about her circumstances. But the veil of self-deception lifted. She'd been so busy feeling like something was missing that she hadn't noticed she was already living the life she'd designed.

How to Reframe When Feelings and Facts Don't Align

George offers several strategies.

Practice presence. We're often future-focused, always thinking about the next goal. But happiness lives in the present. Make it a habit to pause and take in current achievements. Reflect on how far you've come.

George has a whiteboard he refuses to erase. It says: "I've come a long way since 2013." He sees it every time he walks in and out of his office.

Redefine success on your own terms. Stop measuring by external markers. George doesn't care about titles anymore. "CEO, CMO. At one of my jobs, I was an inbound evangelist. What the hell is that? Right now my title is Chief HubSpot Helper."

When you align goals with what genuinely fulfills you, happiness becomes part of success rather than something you're chasing after.

Celebrate small wins. We often jump from goal to goal without recognizing the smaller steps. Those steps were probably Herculean efforts. If we pause to acknowledge them, we create a sense of ongoing momentum and satisfaction.

Connect your work to something bigger. External rewards alone don't sustain us. When efforts tie to purpose, helping others, making an impact, or aligning with values, there's a deeper fulfillment that keeps you grounded.

Stop Chasing the Butterfly

George pushes back on the very phrase "pursuit of happiness."

"If you try to chase a butterfly, it's almost impossible. But if you just sit there, many times it'll just land on you."

The pursuit implies something is missing. That happiness is out there, somewhere ahead, waiting to be caught. But the irony is that happiness is often already present. We just don't stop long enough to notice.

When You Need More Than a Worksheet

Liz brings up something important. Sometimes no amount of reframing or gratitude practice is enough.

"Kittens, if you have trauma that is making it hard for you to be happy or trusting or vulnerable, go to therapy. Meet with a professional. Sometimes there is no growth mindset worksheet in the world that is going to take the place of the fact that maybe you have trust issues because of stuff that happened a long time ago."

She's doing all the work on her own. Apps, systems, reflection practices. And twice a month, she meets with a therapist because childhood taught her some messed-up things about love and relationships.

George adds: "You could've had the best childhood on the planet. Life is still gonna life. It's not a bad thing to have somebody to talk to about it."

Think of it as hiring a strategic advisor. A niche expert for what's happening in your brain and why.

Quotable Moments

"We tend to tie our self worth to our productivity, to our output. And we kind of always are thinking that happiness will come if we just achieve just a little bit more."

"The irony here is that happiness is often already present in our lives. People just don't stop long enough to actually notice that it's freaking here."

"If you try to chase a butterfly, it's almost impossible. But if you just sit there, many times it'll just land on you."

"When you have your fist clenched around an opportunity, you will never give it the oxygen to take a true shape."

"Sometimes you just have to realize the only thing I can be is the best George B. Thomas."

Your One Thing

Liz's takeaway: If you related to any of this, you're not a weirdo. You're not broken. You're not alone. This is way more common than you think. This conversation wasn't about fixing you. You're wonderful just as you are. It's about bringing recognition to something most of us experience.

George's takeaway: Be able to answer the question: What makes me happy? And when you can truly answer it, don't just chase it. Sit in it. Imagine it. Believe it. If you can manufacture it in your mind and marinate on it and see it, then once you're doing the work, you've mentally been there. It becomes less of a chase and more of an understanding. And when you get there, just enjoy it.

Reflection Questions

1. If you described your current life to a stranger, what would it actually sound like? Would you be chasing something or already living it?
2. Are you climbing a mountain that you actually want to climb, or one that society said you should?
3. When was the last time you paused to appreciate how far you've come since you started?
4. Is there something you're clenching so tightly that you're not giving it room to become what it could be?

Ready to go deeper? Press play above and let George and Liz walk you through the full conversation. If you've ever wondered why success doesn't feel the way you thought it would, this one's essential listening.