05/06
Progressive Explorer

Insatiable curiosity
Thrives on diverse perspectives

What is it?

When is it crucial in a company’s life journey?

Why founders fail

How to hone this skill

01
What is it?

An active imagination and a deep, insatiable curiosity that drives you to seek knowledge across various subjects, challenge conventional thinking, and embrace perspectives different from your own. You are not just eager to learn, but actively seek our individuals and ideas that disrupt your assumptions, challenge your beliefs, and force you to see the world from multiple angles.

02
When is it crucial in a company’s life journey?

This trait is crucial at every stage, but balance is key. In the early days, curiosity fuels creativity and innovation. But as the company scales, execution becomes the priority, and curiosity needs to be channeled in a way that enhances operational efficiency rather than distracting from it.

“As a teenager, I was obsessed with autodidacticism—the idea that you could just teach yourself anything. I also read a lot of biographies and became so intrigued by the interdisciplinary approach of legends like Buckminster Fuller and Da Vinci. Their genius lay in their ability to analogize across science and the arts and bring insight from one domain to another. In some ways, that’s what we’re trying to do at Sana as well.”

Joel Hellermark, Founder and CEO

“As you scale the organization, 2,000 employees, 22,000 corporate clients, I feel 70% of the work is around execution and executing better over time. So then screening all the markets and being curious about separate topics is such a rare and difficult skill.” Cesar Carvalho, CEO and Co-founder, Wellhub.

03
Why founders fail

This is not about learning in the traditional way, reading the same books and listening to the same podcasts as everyone else or quoting famous investors on XYZ. It's about finding knowledge and insights in new areas. There is a real humility in the desire and curiosity to acquire learning and knowledge from the less expected places. It means listening to diverse voices who are potentially boring or uninteresting to you to acquire a different view. “I'm looking for all the ways in which I could be wrong”. Tony Haile, Filament.

“I have five to ten conversations a day with customers, with investors, all with different perspectives. That's how I explore. I explore by talking.” Manny Medina, CEO and Co-founder, Paid.

You also need to create a culture where this sort of learning is encouraged. “Harnessing the unique skills of different individuals is essential for maximizing your chances of success,” says Markus Halttunen, Advisor and Co-founder of Small Giant Games. “However, for this to work, the culture needs to be supportive and foster psychological safety – something that typically originates from leaders and founders. A true learning culture can thrive only if the founders are open to opposing views and willing to explore new ideas."

04
How to hone this skill

  • Topline: Embrace discomfort as the key to progressive exploration

    Progress isn’t found in safe zones; it’s found in the places that make you uncomfortable. Growth comes from engaging with ideas, people, and perspectives that challenge your beliefs, force you to rethink your assumptions, and sometimes bruise your ego a bit.


  • To be a true progressive explorer, you must embrace the discomfort of hearing hard truths and seeing your blind spots not as threats, but as tools for reinvention and breakthrough innovation.

  • Manny Medina
    CEO and Co-founder, Paid

    “The learning happens when you are operating at the edge of your abilities. [...] The best founders are always at the edge of their ability at all times. Super curious. Always open.”

  • The most transformative insights often come from unexpected places – critics, failures, industries that seem irrelevant, or even voices you dislike. Detach from your need to be right and approach these moments as a scientist seeking truth in unexplored territory.

  • Cesar Carvalho
    CEO and Co-founder, Wellhub

    “I have two coaches: one is a leadership coach, and the other is a top U.S. CEO – he's completely different than I am. I've never met someone who thinks as differently as him. He doesn't get into the details of things; he looks at the broad picture, forms his opinions, and shoots forward. And that's exactly what I need, because that's probably my biggest blind spot”

  • Reframe discomfort as your compass for growth

    Thought trap: "Listening to opposing views makes me doubt myself."
    Reframe: "Doubt is a sign that I’m exploring new territory – and that’s exactly where progress begins."

  • Thought trap: "Why would I take advice from someone who doesn’t understand my work?"
    Reframe: "The best insights often come from those who see things I can’t. Their distance gives them clarity I may lack."

  • Topline: Embrace discomfort as the key to progressive exploration

    Progress isn’t found in safe zones; it’s found in the places that make you uncomfortable. Growth comes from engaging with ideas, people, and perspectives that challenge your beliefs, force you to rethink your assumptions, and sometimes bruise your ego a bit.


  • To be a true progressive explorer, you must embrace the discomfort of hearing hard truths and seeing your blind spots not as threats, but as tools for reinvention and breakthrough innovation.

  • Manny Medina
    CEO and Co-founder, Paid

    “The learning happens when you are operating at the edge of your abilities. [...] The best founders are always at the edge of their ability at all times. Super curious. Always open.”

  • The most transformative insights often come from unexpected places – critics, failures, industries that seem irrelevant, or even voices you dislike. Detach from your need to be right and approach these moments as a scientist seeking truth in unexplored territory.

  • Cesar Carvalho
    CEO and Co-founder, Wellhub

    “I have two coaches: one is a leadership coach, and the other is a top U.S. CEO – he's completely different than I am. I've never met someone who thinks as differently as him. He doesn't get into the details of things; he looks at the broad picture, forms his opinions, and shoots forward. And that's exactly what I need, because that's probably my biggest blind spot”

  • Reframe discomfort as your compass for growth

    Thought trap: "Listening to opposing views makes me doubt myself."
    Reframe: "Doubt is a sign that I’m exploring new territory – and that’s exactly where progress begins."

  • Thought trap: "Why would I take advice from someone who doesn’t understand my work?"
    Reframe: "The best insights often come from those who see things I can’t. Their distance gives them clarity I may lack."

Topline: Embrace discomfort as the key to progressive exploration

Progress isn’t found in safe zones; it’s found in the places that make you uncomfortable. Growth comes from engaging with ideas, people, and perspectives that challenge your beliefs, force you to rethink your assumptions, and sometimes bruise your ego a bit.


To be a true progressive explorer, you must embrace the discomfort of hearing hard truths and seeing your blind spots not as threats, but as tools for reinvention and breakthrough innovation.

Manny Medina
CEO and Co-founder, Paid

“The learning happens when you are operating at the edge of your abilities. [...] The best founders are always at the edge of their ability at all times. Super curious. Always open.”

The most transformative insights often come from unexpected places – critics, failures, industries that seem irrelevant, or even voices you dislike. Detach from your need to be right and approach these moments as a scientist seeking truth in unexplored territory.

Cesar Carvalho
CEO and Co-founder, Wellhub

“I have two coaches: one is a leadership coach, and the other is a top U.S. CEO – he's completely different than I am. I've never met someone who thinks as differently as him. He doesn't get into the details of things; he looks at the broad picture, forms his opinions, and shoots forward. And that's exactly what I need, because that's probably my biggest blind spot”

Reframe discomfort as your compass for growth

Thought trap: "Listening to opposing views makes me doubt myself."
Reframe: "Doubt is a sign that I’m exploring new territory – and that’s exactly where progress begins."

Thought trap: "Why would I take advice from someone who doesn’t understand my work?"
Reframe: "The best insights often come from those who see things I can’t. Their distance gives them clarity I may lack."

Self-coaching techniques

  • Turn resistance into curiosity

    Ask yourself: “What’s one perspective I’ve resisted because it feels uncomfortable or wrong? What would happen if I treated it like a hypothesis to explore?”

  • Practice detaching your ego from the process

    When confronted with critique or uncomfortable ideas, remind yourself: “This isn’t about me – it’s about finding the best path forward. My job is to explore, not defend.” and “If I step back from my emotions, what value can I find in this perspective?”

  • Tony Haile of Filament recommends Rapoport’s rules for constructive disagreement:

    1. Restate the other person’s argument clearly and fairly.

    2. List points of agreement.

    3. Mention what you’ve learned from their perspective.

    4. Then, and only then, offer your counterargument.

  • Short-term focus

    This week, seek one perspective that challenges your current beliefs. Approach it with curiosity, not judgment, and reflect: “What’s one insight here that I hadn’t considered?”

  • Long-term growth

    Make a habit of seeking discomfort as a signal for growth. Regularly expose yourself to ideas that challenge your assumptions and view them as opportunities to refine your vision. Over time, this enables you to find progress in unexpected places, adapt to new challenges, and lead with humility and curiosity.

    You can also build formal systems around it:

  • Cesar Carvalho
    CEO and Co-founder, Wellhub

    “I created a special New Ventures team. Their only job is to be the company's moonshot R&D. I give them enough rope to run and they come out with bold ideas. I don't think this is going to come from teams 100% focused on execution. It's harder for them to be constantly screening the market for opportunities.”

  • Turn resistance into curiosity

    Ask yourself: “What’s one perspective I’ve resisted because it feels uncomfortable or wrong? What would happen if I treated it like a hypothesis to explore?”

  • Practice detaching your ego from the process

    When confronted with critique or uncomfortable ideas, remind yourself: “This isn’t about me – it’s about finding the best path forward. My job is to explore, not defend.” and “If I step back from my emotions, what value can I find in this perspective?”

  • Tony Haile of Filament recommends Rapoport’s rules for constructive disagreement:

    1. Restate the other person’s argument clearly and fairly.

    2. List points of agreement.

    3. Mention what you’ve learned from their perspective.

    4. Then, and only then, offer your counterargument.

  • Short-term focus

    This week, seek one perspective that challenges your current beliefs. Approach it with curiosity, not judgment, and reflect: “What’s one insight here that I hadn’t considered?”

  • Long-term growth

    Make a habit of seeking discomfort as a signal for growth. Regularly expose yourself to ideas that challenge your assumptions and view them as opportunities to refine your vision. Over time, this enables you to find progress in unexpected places, adapt to new challenges, and lead with humility and curiosity.

    You can also build formal systems around it:

  • Cesar Carvalho
    CEO and Co-founder, Wellhub

    “I created a special New Ventures team. Their only job is to be the company's moonshot R&D. I give them enough rope to run and they come out with bold ideas. I don't think this is going to come from teams 100% focused on execution. It's harder for them to be constantly screening the market for opportunities.”

Turn resistance into curiosity

Ask yourself: “What’s one perspective I’ve resisted because it feels uncomfortable or wrong? What would happen if I treated it like a hypothesis to explore?”

Practice detaching your ego from the process

When confronted with critique or uncomfortable ideas, remind yourself: “This isn’t about me – it’s about finding the best path forward. My job is to explore, not defend.” and “If I step back from my emotions, what value can I find in this perspective?”

Tony Haile of Filament recommends Rapoport’s rules for constructive disagreement:

  1. Restate the other person’s argument clearly and fairly.

  2. List points of agreement.

  3. Mention what you’ve learned from their perspective.

  4. Then, and only then, offer your counterargument.

Short-term focus

This week, seek one perspective that challenges your current beliefs. Approach it with curiosity, not judgment, and reflect: “What’s one insight here that I hadn’t considered?”

Long-term growth

Make a habit of seeking discomfort as a signal for growth. Regularly expose yourself to ideas that challenge your assumptions and view them as opportunities to refine your vision. Over time, this enables you to find progress in unexpected places, adapt to new challenges, and lead with humility and curiosity.

You can also build formal systems around it:

Cesar Carvalho
CEO and Co-founder, Wellhub

“I created a special New Ventures team. Their only job is to be the company's moonshot R&D. I give them enough rope to run and they come out with bold ideas. I don't think this is going to come from teams 100% focused on execution. It's harder for them to be constantly screening the market for opportunities.”

Next:
Transparent Self-awareness