Conversations With People Who Have Sweet Jobs, Part One

The first installment in my investigation into the perks, pitfalls, and methods of entry into various coveted occupations.

Job: Freelance Travel Writer
Pro: Ken McAlpine

Honestly, who wouldn’t want to get paid to travel around the country, perhaps even the world, and write about it?

Here’s the rub: the travel writing industry has taken a huge wallop in post 9/11 years, as magazines have folded, made cuts to staff, or gone web-only, making it rather tricky for writers to land a full-time gig and a reliable paycheck. Which isn’t to say someone with enough drive and talent can’t make money, and one of the ways to do so is through good old-fashioned freelancing. (The avenue of New Media demands its own story.)

I called up an acquaintance I met through work, Mr. Ken McAlpine, for his perspective on the risky yet rewarding occupation. Ken graciously agreed to help me out, and offered some wonderful insight. A dedicated family man with over twenty years of freelance experience, he’s a seasoned pro who contributes regularly to pubs such as Sunset Magazine and takes the kids surfing whenever the waves beckon. A sweet perk of the job, no?

Since I don’t have a transcript of the interview, which loosely started out as one and melted into a more natural conversation, I’ll recreate and condense some of the highlights from memory and shoddy note taking. Hey, I never said I was a qualified journalist.

On his life before chasing assignments: “I was working at a small paper called the Ventura County Reporter. I always tell people it’s not a good idea to quit your day job and start freelancing because assignments won’t come streaming in right away. [Editor’s note: Oops…] I did stay at the Reporter, although it wasn’t too chancy to up and leave since the pay wasn’t that great anyway.”

On his first published stories: “I started sending stories in unsolicited, and my first piece to be published was a story on winter surfing in Surfer Magazine. [Editor’s note: not too shabby!] Then I wrote a first-person story that Sports Illustrated invited readers to submit, so I sent in a piece about trail running and rattle snakes, and that was how I first got in Sports Illustrated. Since then I’ve had about 25 pieces published there, but that first one was great to have under my belt while pitching editors elsewhere. I’ve written for Outside Magazine and other outdoor magazines; I tend to write about things I’m interested in, so yes, it’s often outdoor activity related.”

On the burden (or blessing?) placed on freelancers at the time: “Freelancers were usually given assignments that involved weird, quirky aspects; I once did a story on a one-legged climber…stuff like that.”

On the evolution of freelancing: “The biggest change actually is how short articles have gotten. [Editor’s note: You mean, not how the Internet has taken over? Interesting.] Before, you had space to craft a story, but now I think what magazines want, or what they think readers want, is quick information. Assignments seem to get shorter and shorter: 125 words on ‘eat here, stay here, drink here,’ and something’s being lost. You can’t really do a place justice in 125 words.”

On his other work: “I’ve had the chance to write a couple books, which gave me room to really tell the story I wanted, and the freedom to have a sense of humor, and to use language you can’t use in most magazines.” [Editor’s note: I think the dirtiest word Kevin in our interview was “heck,” so I’ll be on a close lookout for usage of questionable vernacular in his books.]

On PR professionals…and PR “professionals:” “Some PR people are good friends and send great ideas, and they don’t send too many. There’s one person who sends about four pitches a day, and it’s the kind of thing where, if I was Borat I’d be interested, but seriously, what the heck? … When a firm pays for a trip it can be a difficult and uncomfortable situation, especially when the experience isn’t a positive one. And I can’t lie about it. It’s not always rosy. But there are only a handful of negative reviews I’ve given. PR is actually a great function in that it brings to attention things you wouldn’t have been aware of otherwise.”

On the biggest perks and challenges: “My biggest perk is that I get to enjoy a great family life and have personal time. I was freelancing and working from home before both my kids were born, so I got to walk them to school each day, coach their soccer teams, take them surfing…Financial uncertainty is a drawback, and after 9/11 it was a struggle, but I’m very lucky. With my wife’s income as a schoolteacher, we were able to make it work. I’ve had the chance to travel the world, meet some amazing people, and I wouldn’t have done anything differently.”

On haters: “I would never discourage anyone from writing if they want to do it. Just follow your dreams.”