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.