What should I do next, after Nextt? Since shutting down Nextt a few months back, I’ve asked myself this question many times.

It’s a strange place to be—between things.

And although it feels weird and a bit scary to be here, I’ve decided that I need to spend a little more time right now in between things. For the first time in a long time, I’m not myopically focused on the urgent needs of a start-up. I have the opportunity to think more deeply about what I should do rather than simply jumping at the first good opportunity that I see.

What’s next?

I feel blessed to be able to ask this question. I don’t want to be one of those people that does the same thing simply because; and then wakes up at 65 and says “well, I guess that’s that.” Like you, I want to make the most of my work and my life.

How will you measure your life?

Professor Clayton Christensen published a brilliant article in the Harvard Business Review a few years ago that addressed this question. The article got such response that also published a book on the subject. I would highly recommend both.

In the article, Professor Christensen encourages his graduating business students to set a clear strategy for running the most important business of all—their own lives. In order to do so, Professor Christensen argues that it is critical for each of us to set a clear purpose for our lives. Without a big picture purpose, it is impossible to make smart decisions about how you allocate the most scare resource you own—your life’s energy and talents. From the article:

Over the years I’ve watched the fates of my HBS classmates from 1979 unfold; I’ve seen more and more of them come to reunions unhappy, divorced, and alienated from their children. I can guarantee you that not a single one of them graduated with the deliberate strategy of getting divorced and raising children who would become estranged from them. And yet a shocking number of them implemented that strategy. The reason? They didn’t keep the purpose of their lives front and center as they decided how to spend their time, talents, and energy.

It’s quite startling that a significant fraction of the 900 students that HBS draws each year from the world’s best have given little thought to the purpose of their lives. I tell the students that HBS might be one of their last chances to reflect deeply on that question. If they think that they’ll have more time and energy to reflect later, they’re nuts, because life only gets more demanding: You take on a mortgage; you’re working 70 hours a week; you have a spouse and children.

I agree with Professor Christensen that you don’t often* have the luxury of thinking about these deeper questions. When I talk to college students that are about to jump into the working world, I often use the analogy of whitewater rafting. They are about to get into a boat with folks (their team, their company, their significant other) and push off into the river. And once they jump in, the current will sweep them up and their ability to maneuver the boat will be limited. They’ll be focused on avoiding rocks, holding on, and not capsizing. But once in awhile, they will enter a smooth patch of water, and they will have the opportunity to look around and decide which stream and which direction they want to go next.

I’m in one of those smooth spots now.   And I’ve realized that in order to take Professor Christensen’s advice, I need to get out of my day-to-day life. To take a step back and look at myself. Addressing these big questions is not easy (like this list of 10 questions from Alastair Humphries). And I know myself. I’m not going to do this hard work sitting at home.

Leaving on a jet plane

So I’ve decided to take a trip. My wife and son and I are heading south in January and won’t be returning until May, 2015. Most of this time we will be sailing up the Caribbean chain, from Grenada to our final destination in the British Virgin Islands. My college-aged daughters will be joining us for part of the trip too. I wish they could join us for the entire trip, but they have their own lives now. And this is actually one of the reasons I made the decision to take this adventure.

When I dropped off my daughter Maddie at college it hit me very hard that most of my job as her Dad was done. Sure I’ll be her Dad forever, but my job of raising and teaching and protecting her was probably +95% complete. This job that I loved was done. I felt the same way when I dropped my daughter Caitlin off for college the next year. Another job I can never do over. My son is turning 13 on this trip. I’m going to grab this chance to be his Dad, while I can. Adventures are an amazing way to bring your family together.

Selfie after our family canoe trip to the Wabakimi Wilderness–Summer 2014 

Follow Along

We plan to post updates regularly on this blog. And I’ll report back on how this sabbatical works for me. In many ways, the risk and unknown of this trip feels very much like embarking on a start-up. If you follow along, I hope that our adventure inspires you to step outside your day-to-day life occasionally to ask some bigger questions. To measure where you are and decide where you still want to go. It certainly doesn’t have to be on a sailboat, but I do think that getting outside of your normal routine, if you can, is key. My hope is that you too, can find what you were meant to do.

The two most important days in your life are the day you were born and the day you find out why.

Mark Twain

Thanks for reading.

 

*many people because of their circumstances never get this opportunity. Those of use that do, should not waste it.