In the early years of Airstream Life magazine I was often asked by people how I was “so lucky” to get the job I have.  To tell the truth, there wasn’t much luck involved.  It was a matter of necessity meeting inspiration.  I quit a perfectly good job in another industry because I was burned out, and stared out the window of my home office for a month trying to figure out what to do next.

No brilliant ideas came to mind, so I began working up a list of criteria for the next thing I wanted to do.  It was December, and our 1968 Airstream Caravel was sitting out in driveway, waiting out the gray winter gloom until it could be de-winterized and used again.  (See photo at right of three-year-old Emma and I shoveling the snow off our deck on a typical December afternoon.  We were doing this so that I could fire up the outdoor grill.  Such are the lengths that we would go, in order to break the monotony of winter.)

I thought back to the brilliant few weeks we had enjoyed with the Caravel in the summer, traveling all over the northeast states and Quebec, and I decided that the first requirement of my next job would be that I’d have the ability to keep using the Airstream frequently with my wife and toddler.

This seemed utterly unrealistic but brainstorming isn’t the time to be realistic.  So I plowed on to the next criteria:  I wanted a job where I would be my own boss again, where I could have the opportunity to write creatively, and which I could do from anywhere. Publishing felt like a good path to achieve all of this, but my publishing experience up to that point was strictly business-to-business newsletters of the deadly boring variety. If I were to re-enter that industry I wanted to publish something that I wanted to read.  All of this led to the eventual concept of Airstream Life — a dream job where I could travel (nay, would be required to travel) via Airstream and have the freedom that comes with being my own boss.

But anyone who runs their own business knows it’s not as easy as that.  Making a living, managing employees, and balancing work & life are just a few of the huge obstacles that confront any small business owner.  It was a long time before Airstream Life was a financially viable business, and even today the unforeseen challenges and hassles continue to pop up on a regular basis.  The dream was achieved in some ways, not in others, but overall I feel like we did OK.

One of the decisions I made early on was to have no employees. Everyone who works for Airstream Life is part-time contract, and they all have other jobs or clients (or are otherwise retired).  I like this model because I can work with people who are truly self-motivated and need little management, and I can pick the very best people from nearly anywhere in the world and connect with them via the Internet.

The flip side is that it is sometimes difficult to replace those excellent people when they inevitably move on. This past week my assistant notified me that she was going to be leaving effective June 1, for personal reasons, and so my search for a replacement began.  She was highly overqualified for the job, but that only meant that the job was done superbly, and so I’ve been talking to some more highly overqualified friends in hopes of finding a similar replacement.

One of them was interested in talking to me about the job, and we set up an appointment for last Sunday afternoon.  Jokingly, she said, “I’m not dressing up for the interview,” to which I (also jokingly) replied, “No?  At least wear some fishnet stockings — sexual harassment is part of the job, you know.”

“Good thing I have my law degree,” she shot back.

And that’s one of the many reasons I like hiring very experienced people.  They aren’t afraid.

I’m also looking for some new contributing writers.  One of the magazine’s most popular columns, “eBay Watch” has finally come to an end as the long-time author has decided to stop writing it.  I’ve got a new concept for a buy/sell commentary column in mind, but haven’t yet found just the right person to write it.  Anyone who is obsessive about scouring eBay, Craigslist, and other online sites for all types of Airstreams and Airstream-related items is invited to send me an introduction letter.

The last person I am seeking to replace is myself.  Airstream Life has been the dream job that I wanted, but after seven years of running all aspects of the magazine, it feels like time for a change.  I would like to gradually ease out of the Editor’s position and just act as Publisher from now on.  Tom Bentley, a long-time contributor to the magazine, is stepping up to take over part of my job, as Associate Editor, and I certainly hope that he (and perhaps another Editor or two) will take on more responsibility in the future.

Replacing one’s self is probably the hardest hiring job ever, but also one of the most necessary for an entrepreneur.  Once you’ve got things going well, you can stay in the captain’s chair forever or seek new challenges.  But if you stay in place forever, you run the risk that the business will never transcend you.  I want Airstream Life to continue after I’m gone (whether working on another project, retired, overseas, or dead, whichever comes first!) so I need to get serious about obsoleting myself.

Beside, I’m not one to sit still.  With Alumapalooza and other projects taking up more of my time, I am happy to let someone else enjoy the Editor’s position under my guidance, and eventually with very little oversight. Don’t expect to see me disappear this year or even in 2012, but when I do eventually fade out, send me a note of congratulations because I’ll be happy I succeeded at my most challenging task.

Airstreams are superb travel vehicles, optimally designed to make exploring geography with exceptional comfort.  But they are good for something more than that.  I often meet fellow travelers who use their Airstreams for exploring a region that only they can reach: inside their own mind.

So many of us are just a little bit weird by conventional assessment.  We eschew the normal travel pattern by avoiding airlines and hotels, we haul our children and pets to quirky places, and we often are accused (sometimes with frank admiration) of having an “alternative lifestyle” by virtue of being free-booting and happy to take a chance once in a while.   That last characterization is a bit of a broad brush, but I’ll accept it because I’ve come to realize that “alternative lifestyle,” although a loaded term, is another way of saying we live where the wildflowers grow.

That’s where the interesting stuff happens.  You get a little more room to roam around when you bend the rules and conventions of straightlaced society. We meet people all the time who admire the traveling lifestyle, and they generally fall into two groups, those who have done it too and get the concept, and those who are firmly in the center of the fairway and happy to admire the wildflowers from afar.  It takes all kinds to make a world, so I’m not implying that any one group has it right or wrong, but it is interesting to me to see what choices and options have opened up to us simply by virtue of releasing ourselves from the conventional bonds of society and taking a chance that something good might happen.

It really doesn’t take much to broaden your life. Last night we were talking with one of our overnight guests, a writer who is going to take his Airstream across the country to find raw material for his next book. Along the way, he’ll discover new friends and interests.  Heck, he has already and he hasn’t even left yet.  I am looking forward to reading what he has gleaned from his travels.  He’s launching on a massive cross-country expedition but there’s just as much value in taking the Airstream off to a quiet spot in the woods for a couple of days to re-connect with yourself.

I also think its interesting to see how generally-accepted social boundaries change when you take people away from their routine and put them into a campground for a few days. Suddenly people are feeling freer, and you can see it in their dress, their speech, their relaxation of personal rules, what they eat, how they decorate, and from a thousand other little cues.  Nearly everyone comes away refreshed, and a few (like us) come away with a determination to stay out in the wildflowers as long as possible.

“I’m fixing a hole, where the rain gets in,

and stops my mind from wandering …”

My plan for the summer includes a few trips like that too.  I want to do more writing and come up with new ideas for the coming years.  The first step is to “fix the holes” and stop the rain from getting in, and travel is great for that.  Deep in most people’s minds are the thoughts that we haven’t had time to process, and the ideas we never gave a chance.  There are also often old hurts and energy-sapping memories that can be better vanquished with a change of scene.  There are inspirations waiting to be born, and viewpoints yet to be conceived.  Once you clear out the detritus of daily life, who knows where you will go next?  Perhaps an “alternative lifestyle” is waiting out there for you–even if it’s only a change of perspective.