Let's be clear: human beings are designed to seek pleasure. There's an instinctual reason that sleep, sex, and exercise feel good. Vacation time brings joy. Even America's founding fathers understood we're not put on this world solely for work: Thomas Jefferson replaced "life, liberty, and property" with "life, liberty, and the pursuit of happiness."
So if vacation brings happiness why the hell do Americans get two weeks of vacation? And why the hell do we feel guilty when we take that vacation? Why do we stare at our iPhones while sitting on the beach? Why do we make "just this one work call" on a Saturday afternoon? When friends ask, "how are you?" We reply, "Busy." Why? Busy isn't a state of mind, it's an admission that we've f-ed up our priorities and can't handle our lives and spend our precious little time on this planet doing what we "should do" instead of what we "love to do". (Sidenote: "should" is the most self-guilt inducing word in the English language. Strike it from your vocab this right second.)
But I digress. Imagine that you could take two MONTHS instead of two weeks. If you're enslaved to your salary or enslaved to your startup -- I've experienced both -- then this concept is unfathomable. But if you can design a business that supports your lifestyle rather than a life that revolves around your business then you can spend two months on sabbatical each year doing whatever fulfills your soul. I've chosen to study boxing in Cuba, go kitesurfing in Polynesia, and visit college friends while traveling cross-country in a campervan.
After nine years of studying financially free entrepreneurs, I cracked the code. If this could help your life and business, I would be honored:
1. Hire people smarter than you
Why would you want someone doing a function in your company that you can do better? You'll just enable their mediocrity at the expense of your time. In my real estate company I'm a mediocre project manager (PM). So I hired and trained a killer PM. My job is to only set goals and vision while he manages builders, budgets, and timelines.
2. Better yet, find a partner
Friend and mentor Doug Fath ran two real estate companies in parallel: development and lending all while traveling through South America and Africa. How'd he pull it off? He found business partners with complementary skillsets and created a clear division of labor using the Profitable Partnerships technique. This both leveraged his time to run two businesses and freed his time to travel for two months.
3. Empower, don't enable
This expression came from Doug as well. Within months of hiring our 24-year-old PM I left to the DR for the winter while he gut-rehabbed a massive Boston triple-decker and turned it into luxury condos. Had I stayed in Boston I would've enabled him by answering trivial questions. Instead I empowered him to make decisions on his own. Did he make mistakes? Tons. But those mistakes educated him in a way I never could and the business is stronger for it.
4. Never fault first-time mistakes
Tony Robbins says, "it's only a mistake if I don't learn from it." Never, ever fault a teammate the first time they make a mistake. Make it a teachable moment. When our new construction supervisor handed a plumber a $10K check before starting work and the plumber ghosted, it stung. The supervisor broke our cardinal rule of "ahead on work and behind on payments." I wasn't angry but he was mortified and in the years since he's never made the same mistake.
5. Always fault repeat mistakes
I have all the patience in the world for new mistakes but zero tolerance for repeating the same mistake. Repeat mistakes mean the teammate isn't learning and A-Teams have no room non-learners.
6. People don't run businesses, systems run businesses
If you actually run your business and you go away, then the business no longer runs. But if you create systems to run your business while recruiting and leading an A-Team, that's when magic happens. Andre Annicq, serial entrepreneur and father of my MIT roommate, sailed the European coast with his family each summer, stopping in at ports to check in on his executive team. He taught my roommate, "a great leader makes himself redundant."
7. Set boundaries when you're away
Once you complete Steps 1-6 it's time to pack your bags. The first time I left on a multi-month trip, I was so scared the business would implode that I tethered my phone to my board-shorts and perpetually spot-checked the team. Not only was I an enabler, I was a disruptor. During the last sabbatical I instead turned off email and Slack and said, "I'm available for Skype calls on Mondays, otherwise only contact me in emergencies." We had zero emergencies because the A-Team handled their business.
Will your business grow faster if you take two weeks instead of two months? Maybe. And can you do it with a VC-backed startup? No way. Trust me, I tried. But if you recruit an A-Team, train them to run the systems you've built, and empower them to make decisions without you then your business will revolve around your lifestyle. Pack your bags and take a two-month hike.