Re-Entry—It Isn’t Just Hard On Astronauts

We are back.

Just a few short weeks ago Sarah, Jimmy and I stepped off the boat that had been our short term home and began a 22 hour journey from Tortola, B.V.I., that included a ridiculously dangerous taxi ride, a ferry ride involving the rescue of a capsized sailboat, two long flights, and a 1AM drive from Milwaukee to our home in Waunakee, WI.

The Journey Home Begins


The Last Picture of the Trip


We are back. Back to pets, unopened mail, and lawn mowing. Back to bills, budgets, expectations, responsibilities and goals. Back to friends and family. Back to feeling normal. But also feeling really abnormal, like we used to live here.

Happy Reunions 


But Missing This . . . .


Yes, re-entry has had its ups and downs. Right now, I’m working hard to distill what I’ve learned from the experience and translate it into the next phase of my life’s work.

In other words, I’m asking myself “what the hell do I do now?”

Entrepreneurship, in many ways, is about freedom. Freedom from gatekeepers and bosses. Freedom to pursue something in which you are passionate. Freedom to pick and choose opportunities. Freedom to make yourself into something that you design.

So I’m using my experience as an entrepreneur to help me address this strange freedom that comes from stepping outside of your regular life.

And one of the first lessons that keeps sticking in my head comes from this great list of from the VC Fund First Round:

Choose Must.

There is a difference between what you should do (or could do) and what you feel that you must do. Here’s how Elle Luna describes that question in the First Round piece:

Elle Luna quit her dream job at the peak of success. She left Mailbox before it was acquired by Dropbox because she wanted to create art. Over the next year, the talented designer behind Uber‘s mobile app and Medium painted, traveled to Bali, and launched her own textile venture, The Bulan Project. Most importantly, she emerged with a lesson that applies to everyone: ‘There are two paths in life: Should and Must. We arrive at this crossroads over and over again. And each time, we get to choose,’ says Luna. Should is how others want us to show up in the world — how we’re supposed to think, what we ought to say, what we should or shouldn’t do. Must is different. Must is who we are, what we believe, and what we do when we are alone with our truest, most authentic self.’ The hard thing about Must? It’s a daily practice and a recurring choice. The good news? You arrive at these crossroads again and again, and you always get to choose. Here’s how Luna did it

This “must” question isn’t easy to answer. But as I consider it, I keep reminding myself that finding satisfaction and joy and meaning from life doesn’t come from lazy things like sitting around drinking beer all day—or from hard things like selling your soul to make more money so you can buy more material possessions (or sit around drinking more expensive beer all day). That stuff just doesn’t last.

And I also remind myself that the “must” career question shouldn’t be a completely selfish one. It also has to work for my family and fit with the “must” responsibilities that I have as a husband and father.

Jeff Goins, in his new book “The Art of Work” makes this point brilliantly with the following quote from Jackie Robinson

A life isn’t significant except for its impact on other lives.

Exactly.  Here’s hoping that we can all make an impact that matters.  And that you are able to make the freedom to ask these questions too.

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