The Space in Between

By Dave Hassell, an EO San Francisco member and founder of 15Five, an employee communication software company.

It was 8 June 2011, and I was working on a new product called “15Five”— employee communication software based on an idea that allowed Patagonia founder Yvon Chouinard to take half of each year off to climb mountains and surf, all while in the midst of growing a wildly successful multinational company. Yvon’s story inspired me. I immediately called three of my closest EO buddies and said,

“Sign up for kiteboarding lessons. We’re going to Brazil!” I decided to put together a trip that combined my love of kiteboarding with my love of connecting. The idea was to get a group of amazing entrepreneurs together to spend 10 days downwinding along the Brazilian coastline, creating new connections, sharing ideas and having fun.

But a week later, reality struck. What was I thinking? I was bootstrapping my new company and working 100 hours per week how could I possibly take time off? I called my EO friends and told them that the trip was off. Thankfully, they wouldn’t let me off the hook, saying I was thinking about it all wrong. What was the worst that could happen? Wasn’t I building a product that was supposed to allow CEOs to do this very thing? They had a point.

Six months later, 15 of us embarked on the trip of a lifetime, spending an entire week bonding and soaking up the sun in beautiful Brazil. I even got to put 15Five to the test, checking in at work for only 15 minutes while I was away! When the trip was finally over, I returned home, excited to see how things went in my absence. As it turns out, I came back to a better company than when I had left. More importantly, I returned completely recharged, and I proceeded to have one of the most productive periods of my entrepreneurial career. I believe that life is as much about the time out of the office as it is in it. As Ferris Bueller famously said, “Life moves pretty fast. If you don’t stop to look around once in a while, you could miss it.”

I think we as entrepreneurs are so afraid to let go that we don’t allow ourselves the time and space to enjoy what really matters in life— great experiences with family, friends and loved ones. It’s that space in between the hours at the desk and on the computer that makes it all worth it, and it’s what fuels us so we can be truly great entrepreneurs.

Want to stage an escape? Here are some keys that worked for me:

  • Write down the worst-case scenario. Whatever you think might happen, it’s probably not as bad as you think. Your business WILL be there when you get back. As my friend Tim Ferriss (of “4-Hour Workweek” fame) advises, write out the worst-case scenario, followed by what it would take for you to get back to where you were before you left (i.e., time, money). You’ll likely realize that even the worst case is not as bad as you think, and that taking a break from it all is well worth the risk. I guarantee 30 years from now you’ll be reminiscing about that time away, and I doubt you’ll be thinking about how great it was to be at your desk, answering a slew of emails all week.
  • Trust your team. Your job as CEO is NOT to do everything. Your job is to maintain and communicate the vision; give your people the information, tools and resources to march toward it; then get out of the way. They’ll make tons of progress while you’re away not getting in their way, believe me!
  • Make it a Full Move. In the ancient Chinese game of Go, a single move that takes care of more than one objective is called a “Full Move.” Find a way to tie your adventure into your business. For me it was having the opportunity to really get to know and bond with some entrepreneurs whom I admire. You could travel to a city you’ve always wanted to visit, work from cafes and line up meetings with people you haven’t met by polling your LinkedIn and Facebook connections.


Fun fact: Dave used to own a business called “Kite Adventures” in Brazil.


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