How do you decide what events, conferences or communities to invest your time, effort and money in?

When people ask me how I decide what groups to be part of the answer is simple: I thrive on being surrounded by interesting people, doing hard things.

This notion initially surfaced during casual conversations but quickly revealed its resonance.

Even event organizers where I participated echoed this sentiment, underscoring its relevance. That’s it. That’s why I’m here too, “Interesting People, Doing Hard Things.”

The Journey of Building Something New

Embarking on challenging ventures is exhilarating and isolating. Innovating and breaking new ground sparks excitement but also brings solitude.

Leading such initiatives means facing difficulties often alone, with others looking to you for answers. This duality of inspiration and isolation is a unique aspect of the entrepreneurial journey.

Building something new often feels like an ongoing experiment. There’s no established playbook to follow, and the path is filled with uncertainties. Yet, this is where the real magic happens—when you’re figuring things out as you go, testing hypotheses, and making course corrections in real time.

This dynamic, although daunting, is incredibly fulfilling. Every small victory feels monumental because it represents a breakthrough in uncharted territory.

However, the flip side is the loneliness that comes with it. When you’re doing something hard and new, there aren’t many people who can fully understand what you’re going through. Friends and family can offer support, but they might not grasp the nuances of your challenges.

This is where a community of like-minded individuals becomes invaluable. Finding others who are also engaged in difficult pursuits can provide the understanding and camaraderie that are often missing.

The Importance of Community

One of the most significant realizations I’ve had is the importance of community.

When I say “Interesting People, Doing Hard Things”, I’m not just referring to people that have achieved crazy success but more those that are passionate about why they are doing what they do. These individuals are often the innovators, the ones who are pushing boundaries and redefining what’s possible in their respective fields because they are so deeply engaged in the problems they are working on.

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One of my seminal experiences of such folks was in 2019 when I joined a Lund Learning Lab in Human Factors and System Safety hosted at Slack, and led by Dr. David Woods, Dr. Richard Cook, John Allspaw, Laura Maguire, Todd Conklin, Bob Edwards were some of the speakers.

The focus of the Lab was Resilience Engineering for Safety in complex risk-critical worlds. The event has the broadest mix of participants from surgeons to software reliability engineers, business executives to public health policy leaders all exploring the topics of high-risk, high-stakes situations. Dealing with unplanned, unintended consequences and creating adaptive capacity to deal with them.

As an active participant, I saw, learned and debated various viewpoints on difficult topics in safety and human factors. The mix of different domain focus and knowledge, yet similar questions and concerns enriched my learning experience considerably.

Being around such people is incredibly motivating. Their passion is contagious, and their experiences provide valuable insights. They understand the highs and lows, the exhilaration of breakthroughs, and the frustration of setbacks. In these circles, you find people who have faced similar challenges and can offer advice and support. This shared experience creates a strong bond and a sense of belonging.

The Power of Masterminds

A key strategy I’ve employed to surround myself with interesting people, doing hard things is joining masterminds. These are groups of individuals who come together regularly to share their challenges, successes, and learnings. A mastermind I attended in Monaco stands out as a particularly impactful experience.

This event coordinated by one of the best super connectors I’ve met, Emmet Keffe III, brought together a diverse group of about 70 individuals, including executives to chairpersons of massive Fortune 50 companies, venture capitalists, doctors, psychologists, business coaches, operators and entrepreneurs at various stages of their journeys. It was a melting pot of experiences and perspectives. Despite the differences in our career stages, there was a common thread of ambition and a desire to tackle hard problems.


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For me, as an early-stage entrepreneur, being in the same room as these accomplished individuals was both inspiring and humbling. They had achieved significant milestones in their careers and were now contemplating their next moves. Some were considering post-career ventures, while others were thinking about how to make a lasting impact in their industries.

Lessons Learned

One of the most valuable takeaways from these interactions is the importance of perseverance.

Many of the seasoned leaders shared stories of their early struggles, the moments when they faced significant obstacles, and how they overcame them. These narratives were a powerful reminder that success doesn’t come easy; it requires tenacity and a willingness to push through the tough times.

Another crucial lesson is the value of adaptability. In today’s rapidly changing world, the ability to pivot and adjust your strategy is more important than ever. The people I met in Monaco exemplified this trait. They were constantly learning, evolving, and adapting to new circumstances regardless of what stage of their life, career or overall journey. This mindset is essential for anyone doing hard things because the path is rarely linear.

Meaning and Mentorship

Building a strong network is another critical component of doing hard things. The relationships you form with interesting people can open doors to new opportunities, provide mentorship, and offer support when you need it most.

Networking is not about exchanging business cards; it’s about building meaningful connections with people who share your values and ambitions.

Mentorship, in particular, has been incredibly valuable in my journey. Having someone who has walked the path before you and can offer guidance is invaluable. They can help you avoid common pitfalls, provide perspective during tough times, and celebrate your successes with you.

Many of the executives I met at the mastermind become informal mentors, offering advice and support as I navigate the challenges of building my startup.

Accelerated Growth

Engaging in challenging endeavors not only drives professional growth but also significantly impacts personal development.

The process of tackling difficult tasks forces you to confront your limitations, push your boundaries, and develop a deeper understanding of yourself. It’s a transformative journey that shapes your character and hones your resilience.

Being surrounded by interesting people, doing hard things amplifies this growth. Their stories, experiences, and wisdom provide a rich source of inspiration and learning. You gain new perspectives, challenge your assumptions, and broaden your horizons. This collective growth is one of the most rewarding aspects of being in such a community.

Where Are You Seeking Interesting People, Doing Hard Things

Seeking out interesting people doing hard things has become my guiding principle for discovering valuable communities and events. It’s a way to connect with peers, gain insights, and find mentors.

This blog aims to share these experiences and the lessons learned from navigating the path of hard things, alongside extraordinary individuals.

The journey of building something new is filled with challenges and triumphs. It’s a path that requires perseverance, adaptability, and a strong support network.

By surrounding yourself with interesting people who are also tackling hard things, you create an environment where growth, innovation, and success are not just possible but inevitable.

In the end, it’s about more than just achieving your goals. It’s about the journey, the people you meet along the way, and the impact you make.

By embracing the challenges and seeking out those who inspire you, you can turn the hard things into opportunities for growth and success.

This is the essence of why I seek out interesting people doing hard things, and it’s a philosophy that continues to guide my entrepreneurial journey.