6 ways people who were underestimated in school thrive later in life

Ever felt like you were the “invisible kid” back in school? Or maybe you were openly told you didn’t measure up, and you spent years thinking you weren’t cut out for big things.

I get it.

I remember being the awkward kid who never raised his hand in class. Teachers thought I was either disinterested or just plain slow to catch on.

But the funny thing about being underestimated is that it can plant a seed—the kind that pushes you to prove everyone wrong.

Over time, I’ve noticed that countless entrepreneurs, CEOs, writers, and thought leaders were, at one point or another, overlooked.

The reasons vary—from subpar grades to shyness or simply not fitting the mold. Yet years later, they’re the ones dominating boardrooms, shaping their industries, or making waves in creative fields.

So what’s going on here?

How do people who once fell under the radar in school transform into the kind of folks who lead, innovate, and inspire?

Let’s dig into six ways that individuals who were undervalued in school end up flourishing down the line.

1. They harness the power of “I’ll show you”

I’ve seen this pattern come up again and again: someone is told they’ll never amount to much, so they channel that frustration into sheer determination.

Call it the underdog mentality.

Ever notice how people labeled as “bad students” often strive even harder when they discover something they genuinely care about?

As Greg McKeown notes in his book Essentialism, “If you don’t prioritize your life, someone else will.” If you’re an underdog, you learn early on to set your own priorities—often out of sheer necessity.

That thick skin, plus a burning desire to show everyone what you’re capable of, can be a turbo boost for success.

2. They adopt a self-taught mindset

Remember those days when teachers dictated what you had to learn, and if you didn’t connect with it, you’d check out?

For people who found the standard school system stifling, discovering the world of self-learning can be revolutionary.

Back in my twenties, I was running a startup that forced me to pick up new tech skills faster than I ever had in a classroom. And it struck me how liberating it is to learn on your own terms.

When you’re free from the constraints of traditional education, you suddenly realize the incredible resources out there—online courses, webinars, communities of fellow learners.

As Cal Newport has pointed out, “A deep life is a good life.” He emphasizes focusing intensely on meaningful activities rather than skimming the surface.

People who were disregarded academically often gravitate to that deep, independent learning because they have to figure out things on their own.

They’re used to not relying on teachers to spoon-feed the material, so they dig deeper and teach themselves.

I’ve mentioned this before but it’s worth repeating: in the digital era, practically anything you want to learn is within reach.

If you were underestimated for struggling through standard textbooks, maybe you’ll thrive listening to audiobooks, checking out YouTube tutorials, or reading interactive guides.

That willingness to pick up skills outside a classroom can give you a serious leg up in today’s fast-evolving business world.

3. They develop a unique perspective

Sometimes, not fitting into the school system means you see the world differently.

Instead of thinking inside a rigid structure of GPAs and gold stars, you come at problems from angles others might overlook.

I’ve met software engineers who, back in the day, were told they “lacked focus.” Turns out they were simply bored.

Once they discovered hacking, coding, and building solutions online, they found that they excelled when tackling real-world challenges.

It’s that unique perspective that can translate into game-changing ideas. Because you’re not entrenched in the conventional approach, you’re more inclined to experiment and come up with original solutions.

As Charlie Munger has said, “Invert, always invert.” In other words, think differently. Flip problems around. Look at them upside down. This approach often comes more naturally to people who didn’t thrive under traditional teaching methods.

Their “weird” ways of thinking become assets, especially when launching innovative products or forging new business strategies.

4. They leverage empathy and personal connection

It might sound counterintuitive, but a lot of the “quiet ones” or those who felt sidelined in school learn the art of observation.

Instead of dominating discussions, they’re tuning in, watching body language, picking up on social cues.

Over time, this often leads to highly honed emotional intelligence—an invaluable skill in business, leadership, and life in general.

I once worked with a startup founder who admitted she had barely spoken in her high-school classes. She was terrified of being called on, afraid to say something “stupid.”

But in adulthood, she channeled her listening skills into building amazing client relationships. She understood customer pain points quickly because she truly heard what they were saying—something that made her stand out in a crowded marketplace.

Research supports that empathy can boost teamwork and conflict resolution. As noted by Harvard, leaders who show empathy tend to have stronger, more efficient teams.

That’s a big deal if you’re an entrepreneur or manager who wants to build loyalty and trust.

So if you used to be that quiet kid, don’t underestimate the power of those listening skills you developed while everyone else was vying for attention.

5. They learn to master resilience

Here’s a question: How often did you see top students crumble the moment they encountered a real failure?

Meanwhile, those who were used to failing or being criticized on a regular basis just took it in stride. The truth is, when you’re used to adversity, you become well-practiced at bouncing back.

Look at Jordan Peterson’s take on personal growth: “Compare yourself to who you were yesterday, not to who someone else is today.” If you start off at the bottom of the class, each incremental improvement feels like a victory.

People who faced constant rejection or skepticism early on naturally develop thicker skin.

By the time they’re running a business or climbing the corporate ladder, they’ve got this innate resilience that helps them handle challenges with a calm, problem-solving mindset.

I recall a neighbor who failed a math test so spectacularly in eighth grade that he became the class joke for a good while.

Fast forward two decades, he’s now leading a tech team at a major company. Every time his product launch flops or a project stalls, he shrugs and says, “We’ll fix it.”

Because failing big all those years ago taught him that life goes on—and success eventually follows those who keep at it.

6. They find mentors outside the usual channels

When people aren’t recognized or encouraged in school, they often seek guidance elsewhere.

Instead of a teacher or guidance counselor, they might turn to a local business owner, an online mentor, or an inspirational figure in their community.

I’ve personally sought out various mentors who weren’t tied to any institution—entrepreneurs who gave me practical tips, authors who wrote words that clicked, or even online communities offering real-world advice.

As Tim Ferriss once said, “You are the average of the five people you most associate with.”

If you didn’t get support within the confines of a classroom, you look for it in other realms, often finding mentors who can offer more tailored, experiential knowledge.

And it’s not just about business savvy. A great mentor can help you fill the gaps left by traditional schooling: negotiating, networking, dealing with failure, and so on.

When you’ve been underestimated, you learn quickly that waiting for the right teacher to swoop in and help you is pointless.

You have to actively seek out those who can broaden your horizons.

Wrapping things up, but it’s still a big deal…

Being underestimated in school can be tough in the moment—no doubt about it. But it can also be a huge catalyst for future success.

It pushes you to harness that “I’ll prove you wrong” energy, adopt self-learning strategies, see the world in unique ways, connect with people on a deeper level, build rock-solid resilience, and forge mentoring relationships that truly matter.

And guess what? All of these traits happen to be gold in the entrepreneurial and tech spheres, where creative thinking, human connection, and the ability to pivot on a dime are everything.

So if you ever felt like you were overshadowed in your school days, take heart: Those tough experiences might actually be your superpower.

Until next time, friends.