3 Tips for CEOs Who Want to Stage an Office Escape

It was June, 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 entrepreneur buddies and said, “Sign up for kite-boarding lessons. We’re going to Brazil!” I’d 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.

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 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 for only 15 minutes each week 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 came back completely recharged. 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 your own escape? Here are some keys that worked for me:

  1. 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.
  2. 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; and then get out of the way. They’ll make tons of progress while you’re away not getting in their way, believe me!
  3. 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 in to 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.

This post originally appeared in Octane, the Entrepreneurs' Organization Magazine.

David Hassell is a serial entrepreneur and CEO of 15Five, a software company focused on producing transparency and alignment in organizations through structured, efficient and effective communication practices. He recently served as President of the San Francisco chapter of Entrepreneurs' Organization and has been named The Most Connected Man You Don’t Know in Silicon Valley by Forbes.

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons.

Photo By: Simon Jardine

About David Hassell

David Hassell is a serial entrepreneur and presently Founder & CEO of 15Five, a SaaS company focused on helping individuals and organizations reach their highest potential. Hailed by Fast Company as the "15 Most Important Minutes of Your Work Week," 15Five creates an internal communication process that enables the most important information to flow seamlessly throughout an organization.

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