Have you ever met a person whose story leads you to truly think about your life and all the things you believe to be true? I was at a conference a few months ago and met a person who is considered by many to be the most connected person in Silicon Valley. He's also an extremely successful entrepreneur.

Yet what inspired me most was his story. More specifically, his mindset captivated my attention. I was drawn to the unique way he lived his life. His outlook was based on two ideas that you rarely hear in the startup world: serendipity and surrender.

The person I'm referring to is David Hassell. He is a serial entrepreneur and founder of 15Five. His goal is to fundamentally change the relationship between companies and employees. In the new paradigm he espouses, companies thrive by supporting their employees in becoming their best selves.

His socially focused ambition is inspiring, yet his story is what I want to discuss. I interviewed Hassell to better understand how serendipity and surrender created success and happiness in his life and how we can embrace that mindset in our own lives.  

Hassell's story illustrates the ways serendipity and surrender can lead to big breakthroughs in your life and career. After his story, consider the five tangible ways you can incorporate this philosophy into your life.

Making and trusting a bold move

Hassell ran a successful AdTech company in his twenties - living in New York City and running the rat race. He grew frustrated with the speed of New York and the sense of disconnection it created in himself and others around him. He listened to a friend and took an unplanned trip to Brazil.

"I got introduced to kiteboarding by a Brazilian friend while living in NYC, and was immediately hooked," said Hassell. "After working on my Adtech startup for nearly 7 years, I felt like I needed a break to get some perspective, so I flew to Brazil to help that same friend start a kiteboarding adventure travel company. I was still working remotely on my company back in New York. Kiteboarding quickly became my passion. I also enjoyed the slower pace of life that allowed me to feel like I was really living. While it was hard to admit, I knew this lifestyle was a better fit for me than New York."

As serendipity would have it, one of his first kiteboarding students was a notable entrepreneur from Silicon Valley. After a few conversations with this entrepreneur, he realized that he was stubbornly clinging to the idea of making his Adtech startup work.

He came to the difficult conclusion that in order to live the life he wanted, he had to let his startup go. He did just that, and focused on kiteboarding full time. He had no idea where it would take him - and that's the whole point.

"Kiteboarding didn't make me a lot of money, but it created this great period of my life where I felt rejuvenated," said Hassell. "It paid enough for me to live in Brazil and go on adventures and it was extraordinarily fun. Most importantly, I learned how to let go and become comfortable with the unknown."

Serendipity guides us into our next chapter

Hassell surrendered to the experience and trusted that things would unfold exactly as they needed to unfold. While still living in Brazil, he felt a calling to move to the Bay Area. When he arrived, Hassell only knew one person. He wanted to meet more people. So he leaned on kiteboarding.

"I made friends with the local kiteboarding community," said Hassell. 'I started a kiteboarding company just as it became the hip thing to do. Soon I was networking with some of the most influential people in tech."

Hassell loved meeting new people and so he took it to the next level. He became president of the Entrepreneur's Organization (EO) chapter and hosted regular dinners with inspiring entrepreneurs and leaders in Silicon Valley. It all came from his passion to create a community of bright and inspiring people.

Following that passion for meeting people has led Hassell to build one of the deepest and most influential networks in the Bay Area. In fact, Forbes called him the most connected person you don't know in Silicon Valley.

5 ways to embrace serendipity and surrender

In his famous commencement speech at Stanford University, Steve Jobs mentioned how you cannot connect the dots looking forward. Yet, many of us (myself included) try to control all the dots or we try to connect them beforehand. 

Just like Jobs, Hassell challenges us to surrender into trust and allow the dots to connect themselves while you focus on your passions.

Here are five ways to add more serendipity to your life:

  1. Say "yes" - If you don't try new things, or you don't say "yes" to new opportunities, you won't allow serendipity to create opportunities that you never expected. You need to be open to doing something you wouldn't normally do and do it without judgment.
  2. Get comfortable with the unknown - It's not easy at first, yet getting comfortable with the unknown is like jumping out of a plane. You're terrified when you get to the door, but after you jump, it's pure bliss. Start small and build up to the leap of faith that might be in your future.
  3. Learn to let go - Hassell moved to Brazil just to kiteboard and seven years later he's kiteboarding with some of the leading venture capitalists and tech CEOs in San Francisco. You can't plan that. Let go, follow your passions and allow things to unfold.
  4. Don't over schedule your life - Consider leaving more room in your schedule for serendipity. If you're always booked up and always running too hard, then there's no room for the magic that takes you in a new direction or accelerates your growth.
  5. Let go of what isn't serving you - If you tune into the things that aren't serving you, and examine your attachments to the meanings behind those things, you can let them go and create the space needed for amazing new things to show up in your life.

Final Word

When you consider the power of serendipity, you realize that it's a gift that arrives when you create the space for it to happen. The hardest part is making the bold moves to create that space without proof that the serendipity will come. In my experience, surrendering has always allowed things to unfold in ways that are better than I could have imagined and better than if I tried to control them in the first place. Consider how you can add a little space and serendipity in your life and watch what happens. You're likely in for a nice surprise.

Published on: Jan 23, 2018