Why We Connect More Through Stories of Struggle Than Success

Over time, most of us learn to lead with the most successful parts of ourselves.

Our clothing. Our careers. Our titles. Our relationships. The stories we tell, or quietly live inside, that make our lives appear steady, structured, and under control.

There’s nothing wrong with looking polished or celebrating success. I think recognizing achievement matters, especially when it motivates us and keeps us moving forward. But there’s also a downside to constantly chasing perfection: people see where you arrived, but not what it took to get there.

Eventually, that creates distance.

When you only show what you want people to see, it becomes difficult for others to connect with you. To understand the “why” behind what you do and who you are.

It’s an important truth about personal growth: People may admire success and perfection, but they rarely see themselves in it.

What they really recognize themselves in are underdog stories.

The stories where someone questioned themselves. Failed. Changed. Started over. Maybe even failed again. The stories that feel human.

I’ve noticed that many people still view struggle, whether their own or someone else’s, as a sign of weakness. And while I understand where that mindset comes from, I also think it keeps people isolated.

No one has a perfect life, no matter how carefully they try to present one. We all carry things that have shaped us. We all have parts of our story that cost us something.

And when we speak honestly about those things, we give people the chance to stop looking at the image and start connecting with the person.

Why Do Perfect Stories Rarely Stay With Us?

Most of us want people to succeed, whether it's a friend, family member, acquaintance, or even a public figure. We naturally celebrate positive outcomes and often feel inspired by the people living them.

But it’s one thing to respect a story and another to connect with it emotionally.

Polished, uncomplicated triumphs rarely stay with us because they often skip the part that matters most: the emotional reality behind the success.

When a story jumps from point A to point C without hesitation, fear, or struggle in between, it can start to feel less like honesty and more like presentation.

Underdog stories are different.

They show the “messy middle.” The doubt before the leap. The fear behind the reinvention. The cost of deciding to keep going anyway, despite the fear or naysayers.

That’s the part people recognize. And it’s a lesson I learned firsthand.

For a long time, I lived a safe life. I knew how to succeed within it, and I also knew what parts of myself to keep hidden to maintain the respect I thought my silence had earned me.

But when I finally started sharing my story publicly, I realized people weren’t looking for a flawless version of me. They were looking for something real enough to connect with. And once they found it, they started sharing their own stories in return. Their struggles. Their fears. Their emotional burdens.

That’s the power of underdog stories. They give people the context and reassurance that success alone never can.

In the end, it comes down to this: Perfection creates distance, while vulnerability creates recognition.

What Is the Difference Between Looking Fine and Feeling Seen?

You can build a life that looks complete and still feel disconnected inside it.

For a long time, I projected stability. I built a successful, 31-year career. I was married with a baby on the way. I had a consistent, reliable structure in my personal and professional lives. I knew how to show up in the way people expected me to; in the way I expected myself to.

But looking fine is not the same as feeling seen.

To maintain the security I’d worked hard to create, I kept parts of myself hidden. And the more I avoided acknowledging that fact, the more exhausting it became to manage the version of myself that felt safest to show.

A lot of people live inside that tension longer than they want to admit. They stay composed, keep conversations surface-level, and avoid sharing anything too vulnerable. They become very good at looking fine.

But eventually, distance grows not only between who they are and how they’re living, but also between themselves and others. And that’s not without its consequences.

According to the American Psychological Association’s 2025 Stress in America survey, 50% or more of respondents reported feeling lonely and disconnected at least some of the time. As a result, many respondents began canceling plans, found it difficult to make decisions, and stopped taking care of themselves, among other reported behaviors.

That’s part of why underdog stories matter so much.

When someone shares something real, the conversation changes. People stop trying so hard to appear perfect and start connecting through honesty instead. Feelings of loneliness are replaced with feelings of support.

That doesn’t mean you need to share every detail of your life; vulnerability still needs boundaries. But there’s a difference between avoiding ourselves completely and showing up as a whole person.

And when we stop hiding all the time, we often realize just how badly other people need something real and whole, too.

Do Stories of Struggle Reflect Strength or Weakness?

One misconception I’ve seen repeated all too often is the belief that struggle equals weakness.

It’s something I think is ingrained from an early age. Sayings like “stay strong” or “keep a stiff upper lip” encourage people to create a tough outer facade and hide their vulnerabilities.

Heavy emotions become shameful. Discomfort is something to be judged and criticized. Vulnerability risks rejection. When authenticity is so uncertain, it’s no wonder many people prefer to hide their obstacles and quietly push through pain to protect themselves.

For a while, that can feel safe. Eventually, however, constantly managing appearances becomes exhausting and lonely.

But that’s not how I see emotional openness.

To me, making yourself vulnerable shows far more strength than pretending everything is fine. It takes self-awareness to acknowledge difficult emotions, emotional intelligence to understand them, and self-confidence to let others know the real you. It’s a point of view cultivated by my mom and grandma, amazing influences in my life who always reminded me that showing emotions and expressing myself were okay. As a result, doing so has always been natural for me, even if it catches people off guard.

And despite what many people fear, I’ve found that when telling underdog stories, most people understand more than we expect. 

It’s taken me some time to master myself, but I have some tools to start accepting your own story, including:

●      Learn to love the whole version of yourself.According to Verywell Mind, vulnerability starts with acceptance: discovering how to acknowledge all parts of yourself, rather than just the most socially palatable ones. When you learn to appreciate who you are, not just who you could be, it often becomes easier to share that person with the world.

●      Start writing things down. For many people, honesty begins privately. Journaling gives you space to process your emotions without judgment and discover the lessons behind your experiences.

●      Find a platform. You don’t have to begin by sharing your story with the people closest to you if that feels too close for comfort. You can test the waters among strangers on blogging sites or social media platforms first if that feels more manageable.

What Is the Problem With Performing Perfection?

 One of the biggest obstacles to real connection is constantly performing perfection. 

Many people spend years:

●      Hiding their struggles. Pushing down negative emotions can feel safer in the moment, but it’s not without its consequences. Recent research has found that when people conceal their emotions, feelings of anxiety and depression tend to increase over time.

●      Promoting their successes. Instead of sharing the whole of their experiences, they reveal only the curated, positive ones.

●      Trying to stay completely in control of appearances at all times. When people are afraid of being judged by others or are judging themselves, they often put in the work to seem as flawless as possible.

These behaviors are often rooted in fear, insecurity, or discomfort around the idea of being fully seen.

But no one has a perfect life, no matter how polished they appear.

The healthier route is to create purposeful boundaries, not entire walls. To learn the difference between privacy and performance. And to remember that struggle is something to work through, not something to bury.

 I still work on this each day, but I’ve found a few strategies that have helped me along the way: 

●      Pay attention to what you edit out. Notice the moments where you start to remove the “messy” parts of your story from your self-talk or conversations with others.

●      Allow yourself to feel uncomfortable. Real connection often starts with discomfort. Vulnerability can feel exposing because it is. But discomfort is not the same as danger, and it’s important to remember that most people won’t use the honesty of your underdog stories against you.

●      Rethink your definition of success. I’ve never measured success by titles or experiences. Those are things people earn over time, but they’re not who someone is. For me, success is much more about the impacts I’ve made in other people’s lives than the titles or achievements I’ve received. 

Can Shared Loss Build Deep Connections?

Some of the darkest moments in our lives can also be the start of something new.

One of the most meaningful examples of this in my own life came after my mom passed away. A close friend of mine had lost his own mom a couple of years earlier, and in the interim, we had slowly fallen out of touch. But he still reached out to me. We reconnected over our love for our moms, and the indescribable grief and loss we felt when they died. We sat with our feelings and opened up about them rather than rushing past them. 

That kind of shared struggle has built a bond that is very special to us both today.

A lot of people become uncertain around heavy emotions like grief. They worry about becoming a burden or making others uncomfortable, so they minimize what they’re feeling or avoid talking about it altogether.

But sometimes the most meaningful thing we can do is simply be honest about what hurts and stay present in the emotion and in the moment rather than avoiding the discomfort entirely. 

That’s another reason underdog stories matter. They remind people that they are not alone. That someone else has felt these same emotions. And, as past research has supported, in the midst of pain, fear, or uncertainty, these shared experiences and moments of vulnerability can lay the foundation for some of the deepest relationships. I’ve experienced this firsthand, and it’s incredibly impactful when it happens.

What Happens When Someone Shares Something Real?

I know how easy it is to stay at the surface level, sharing stories that feel distant and overly polished.

We tell ourselves it keeps us safe from external judgment. But whether we’re behind a camera, on social media, or in conversation, the persona we project isn’t the reality of who we are. Over time, people can feel that distance, and you’ll notice that once they do, it’s harder and harder to form any real connections.

When just one person shares something real, however, the energy of the entire room can change.

Defenses lower. Other people start to open up. Everyone finally allows themselves to exhale. And connections start to form.

 That’s something I experienced after I started sharing the parts of my life I’d carried privately for years.

People didn’t relate most to the parts of my life that looked put together. They related to the vulnerability behind it. The guilt. The anxiety. The confusion. The emotional complexity of trying to live honestly after years of silence.

By revealing the imperfections everyone can recognize, underdog stories encourage people to stop pretending they’re the only ones struggling. To finally say the things they’ve been carrying quietly for years. They show your listeners that you are trusting them with what you’re sharing. That you’re giving them a piece of yourself that should be treasured.

 It’s this honesty, more than anything else, that allows people to empathize on a different level, and to build deeper, more meaningful connections. 

Why Does This Matter in Leadership, Relationships, and Life?

 In both the world and the workplace, authenticity changes everything. 

Personally

 The strongest relationships are usually built through vulnerability, not image management.

 When you show up as your genuine self, people stop connecting with your mask and start getting to know the real you. Interactions become more meaningful, from discovery-focused back-and-forth conversations to deep discussions about your goals. Empathy deepens as people understand not just what you do but who you are underneath it.

 Eventually, the pressure to constantly manage how you’re perceived lessens. You’ll notice you stop worrying so much about saying the right thing and start to feel more comfortable simply being yourself.

 In short, over time, your personal life becomes all the more fulfilling.

 Professionally

The same thing applies in leadership.

People may respect the title, but they trust the person. Alignment starts when leaders feel human. When they communicate honestly and with context, it’s this that allows teams to connect more deeply, to perceive leaders as more relatable and reliable, and to understand the humanity behind the decisions.

But vulnerability alone isn’t enough. Trust also requires consistency. As an article by Purdue University’s Mitch Daniels School of Business argues, vulnerability lays the groundwork for employees to know and trust you, but it’s your actions in the aftermath, both in your day-to-day routines and in moments of crisis, that determine whether that trust holds.

Conclusion

Everyone’s carrying something.

A story they haven’t told. A fear they keep quiet. A struggle they minimize.

But the parts of your story you’re most hesitant to share are often the very parts that help someone else feel less alone.

That doesn’t mean every story needs to become public. And it doesn’t mean you won’t be afraid of receiving judgment when you tell it. But as my mom used to tell me, “No matter what, you need to remember they can’t take your birthday.”

It’s a saying I’ve carried with me for years, and one I take to mean that no matter what people think about you, they can’t take away who you are.

Underdog stories allow people to stop hiding behind carefully managed versions of themselves and start connecting through something real.

True vulnerability comes with the risk of being known. But it also creates the kind of relationships and life that perfection never could.