Malcolm Gladwell has spent a lot of time dissecting the stories of high-achievers and underdogs.
In his books like Outliers and David and Goliath, he explores why certain people manage to triumph despite limitations like lack of resources or brutal competition.
But have you ever wondered what exactly sets these individuals apart on a day-to-day level?
It’s not just about raw talent or being in the right place at the right time—though Gladwell acknowledges that timing can matter.
More importantly, people who beat tough odds maintain habits that strengthen their focus, resilience, and sense of purpose.
Over time, these daily routines compound, leading them to success when others might fall short.
I’ve come across plenty of determined people in my own journey—from launching startups in my 20s to meeting other entrepreneurs who’ve defied expectations.
While their backgrounds vary, they all seem to embody the practices Gladwell highlights in his work.
Below are five habits that Gladwell points to when explaining how underdogs can make it big. See if any resonate with you—and if not, consider adding them to your daily lineup.
1. They invest time deliberately
The 10,000-hour rule may be Gladwell’s most famous concept, and while it’s sparked debate among experts, the idea still stands: mastery comes from consistent, focused practice.
People who succeed against the odds don’t just dabble in something; they go deep. They carve out substantial time for their craft, honing it day by day.
But here’s the catch: it’s not just about clocking hours.
As noted by Gladwell, “Practice isn’t the thing you do once you’re good. It’s the thing you do that makes you good.”
In other words, these individuals don’t wait for some magical breakthrough before dedicating themselves. They’re at it even when they’re still rough around the edges, not getting immediate results.
This principle applied big time when I was building my first startup. I had to learn the nitty-gritty of marketing and user growth strategies, and it felt like an uphill climb.
But my daily routine of testing new ad campaigns, analyzing user data, and tweaking my approaches eventually paid off.
I wasn’t seeing rocket-ship growth right away, but a few months in, I noticed subtle improvements. That momentum kept me going.
If you want to beat the odds, schedule regular time to refine your skills or knowledge in a particular area.
Gladwell isn’t saying you should never rest. Rather, he’s pointing out that success rarely lands on those who treat practice as an afterthought.
It’s an intentional process, spread across months and years, that develops your hidden potential.
2. They embrace small wins as fuel
If you’re fighting from the bottom, it’s easy to feel overwhelmed by how far you have to go.
But according to Gladwell, underdogs thrive by celebrating the small milestones. Tiny successes might seem insignificant, but they accumulate into big gains over time.
This is backed by experts like professor Teresa Amabile and researcher Steven Kramer, who have noted that recognizing even minor progress can be a powerful motivator.
You don’t need the entire puzzle solved to feel a sense of accomplishment; seeing a single piece click into place can spark enough momentum to tackle the next challenge.
Gladwell himself emphasizes in The Tipping Point that big transformations happen when seemingly small factors align.
The same holds true on a personal level. If you close your first modest deal, reach a small but meaningful follower count on social media, or secure a minor collaboration, those wins show that your efforts aren’t in vain.
Even if you’re not playing in the major leagues yet, these early victories demonstrate your capability—so you keep going.
When I was scaling my startup, I’d track the tiniest improvements in user engagement—like a 1% rise in click-through rates.
While it didn’t sound impressive at first, those incremental gains hinted at a formula that was working.
Recognizing the importance of these baby steps gave me the energy to handle the next round of experiments.
If you’re feeling discouraged, look for that sliver of progress. Odds are, it’s already there, waiting to be celebrated.
3. They turn adversity into creative solutions
In David and Goliath, Gladwell dismantles the assumption that bigger and stronger always wins.
The underdog advantage often lies in the ability to innovate around constraints. People who succeed against formidable odds tend to be resourceful, turning shortcomings into unique strengths.
A classic real-world example is how small startups often outmaneuver large corporations.
They might not have the budget or the massive team, but their agility lets them pivot and experiment in ways that bigger players can’t.
Gladwell says underdogs frequently rely on ingenuity—like the biblical David who used a sling instead of traditional armor—to overcome obstacles that seem insurmountable.
If you find yourself at a disadvantage, ask, “Is there a different angle I can take here?”
Adversity doesn’t automatically mean defeat. In Gladwell’s view, it can also be the perfect environment for innovation.
Rather than dwelling on what you don’t have, look at what you do have—and how you can maximize it in a way others might overlook.
4. They stay curious and open to new perspectives
Gladwell’s entire writing career hinges on asking unconventional questions and turning widely accepted truths upside down.
Whether exploring why some professional hockey players have birthdays in the early months of the year (Outliers) or dissecting how certain social phenomena reach a tipping point, he consistently emphasizes the importance of curiosity.
People who exceed expectations similarly maintain an open mind, always hungry for new ideas.
They don’t cling rigidly to old methods just because they worked in the past. They experiment, research, and learn from unexpected places.
Because they’re open to feedback—even if it stings—they can pivot faster than those stuck in a single viewpoint.
Gladwell notes that true growth often comes from looking beyond our comfort zones. If you’re curious about how to do something better, you’ll naturally search for unusual tactics, mentors, or technologies.
5. They focus on meaningful goals (beyond just winning)
One of the things that often goes unnoticed in Gladwell’s analysis is that successful individuals usually have a deeper motivation than just “beating” somebody else.
They’re not purely addicted to competition or chasing money.
There’s a genuine sense of purpose behind their daily actions, whether that’s serving a community, pioneering an innovation, or telling a story they believe needs to be told.
In Outliers, Gladwell points out that remarkable achievements are rarely the product of a selfish, short-term outlook.
They come from a blend of passion, commitment, and the belief that your work can influence the world in some positive way—no matter how small.
This purpose fuels them through the low points when external rewards (like money or recognition) haven’t materialized yet.
Personally, whenever I got bogged down chasing vanity metrics—like trying to outdo a competitor in user count—I’d lose steam fast.
But if I pivoted to focusing on how my project could genuinely help people, my motivation skyrocketed.
That sense of higher purpose made it easier to swallow the tough times and keep pushing.
When you anchor your goals in something meaningful, you’re less likely to quit. You’re also more likely to attract supporters who share your vision.
In a world filled with endless distractions, having a deeper reason behind your hustle can be the ultimate differentiator.
Wrapping up
Malcolm Gladwell’s insights remind us that success in the face of adversity is rarely a matter of chance.
The people who beat the odds do so by dedicating themselves to deliberate practice, celebrating small wins, innovating under constraints, staying curious, and grounding their efforts in a mission that truly matters.
If you’re feeling like the underdog right now, remember that you don’t need every advantage handed to you.
A few targeted daily habits, repeated consistently, can gradually reshape your trajectory.
Whether you’re building a side hustle from scratch, aiming for a promotion at work, or tackling a personal passion project, these habits can give you the edge you need.
Try weaving these practices into your routine. Maybe you block off an hour for focused skill-building, or you start actively looking for creative solutions every time you face a budget or resource limitation.
Perhaps you take five minutes each day to reflect on small wins or reconnect with the deeper purpose behind your goals.
Over time, they’ll add up in ways you might never see coming.
Until next time, friends.
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