On Dream Jobs, Doing TV, and Pickpocketing Hippies

Last week I did some TV stuff for the Boston news show Chronicle, in  
which I brought them around to some “insidery gems” in the city and  
talked about what made the places cool and what I saw as trends in  
Boston style for men. This is hilarious on several levels, the first  
being that I actually am considered some sort of expert on anything,  
but the shoot was fun, and I probably used the words “authentic” and  
vintage-esque at least eleven times per scene on camera. Also, for  
your own future benefit–should you find yourself unexpectedly on a  
news show– do NOT eat a Sour Apple Blow Pop right before you’re  
supposed to go on camera. Multi-colored tongues are not “in” right now.

Anyway, I am on a severe and utterly close deadline for Boston  
Magazine right now. The story is there waiting for me to nail it, but  
I keep being occupied by small tangential pieces of said story, and  
only seem to be able to work between the hours of 2-4 AM, which used  
to be fine, but now makes it impossible for me to do my day job  
without falling asleep in Espresso Royale and leaving myself  
vulnerable to pickpocketing by some of the less chill, more nefarious  
looking hippies.

It also is taking me awhile to get back into writing in the long form  
after spending the last three or four months exclusively writing and  
editing pieces that fall in the 200 word realm. Freedom of (word)  
expression is a mixed bag, friends. You always complain about wanting  
to “write the way you want” and “in your voice” and truly make  
something “completely original” but then, when you’re finally given  
that chance, most likely you just sit there reading old issues of  
Esquire and praying that some sort of writerly osmosis will transfer  
their skills into your work while you watch Weeds.

With most of that said, I have a request. I want to know about dream  
jobs. The one writing job that you wish you could have. The more  
specific the better (don’t just say you want to write for Tiger Beat,  
say you want to be the senior editor, etc, etc, etc) and how you  
imagine that someone would get that job. I’ll reveal mine in the  
Commenting portion of the show and tell.

Luv to Luv,
to Luv Ya.

Timbaland and Magoo

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33 thoughts on “On Dream Jobs, Doing TV, and Pickpocketing Hippies

  1. Olivia

    I’ve always wanted to write one of those "Choose Your Own Adventure" books . . .

    Wow, Kevin, you must be my dream come true.

    Let the games begin.


  2. Valerie

    Senior Editor, Vogue Magazine
    Esquire, Staff Writer

    I’d love to have a Dorothy Parker-esque existence. Of course, you should totally be a member of the Algonquin Round Table. You could be my Robert Benchley.

  3. Christine

    OK, I have sailing experience AND would make a fantastic gypsy…Can I come on this seeing-every-corner-of-the-world-and-writing-about-it-expedition? I’ll bring the pencils and notebooks (I have a Staples addiction and I’m a teacher so school supplies make me high).

    I also think Master Yoda’s wisdom applies to these BIG dreams we’re revealing. "Do or do not. There is no try."


  4. Joanne

    Definitely would have an engine for those tricky harbor entrances.

    Silk Soy is my favorite chocolate soy milk, hot or cold. If hot, a little pumpkin spice added for a special treat. Silk Soy vanilla is good too. Or maybe, once again, I’m buying into all that marketing.

    Tom, you have to shoot for the sky! Dream big and if you fail, fail big. No falling into a middle American rut (unless of course, THAT is your dream). Yes, it is overwhelming to have more than one dream, or overlapping dreams, but how exciting! You won’t get bored, and your endless curiousity will keep you young!

  5. Tom

    Is this purely a sailing sailboat, or does it have a small backup engine? I’m good with engines.

    I’ve never actually had chocolate soy milk. Someone want to recommend a good brand?

    I’m with Joanne on the "live and experience the world" thing. I got a good bit of that traveling across the souther US last summer on a motorcycle. Going by car really is cush, even if it’s a total piece of junk car. You end up interacting with people more when you’re on a bike, too.

    If we’re going to dream here, and I mean really shoot for the sky, then I’d like to do all of this for a living: build kinetic sculptures, take pictures, write a book on how to swap a Cadillac 500 engine into a 60s/70s GM A-body, write fiction novels and short stories, build this car…this car it…it looks like a bug kind of…it’s…hard to call it a car, but that’s what it is, in my head, anyway. Oh, and play music, record another album.

    HOly s*** no wonder I feel overwhelmed.

  6. Joanne

    That sounds so fantastic! Very similar to what I want to do while traveling on our sailboat…get off the beaten path, hang with the real locals, immerse myself in foreign culture. The money isn’t the thing, it’s the freedom, the freedom to LIVE and experience the world. That’s one of the reasons I homeschool my kids, so we can pack up and go at anytime. Only once has that happened so far, but it was five months in the Bahamas, and it was fantastic. And see, if you travel by sailboat, you can take what you want with you (kids and pets, of course, and yes, chocolate soymilk in those little aseptic packages!) Tom, Genevieve, Jodie, I think passports are in order…oh, and I am a massage therapist, so I can do that, too.

  7. Jodie

    ha ha…you guys are crazy and I love it…tom you hit the nail right on the head w/ the chocolate soy milk…and vive you are more than welcome to join my gypsy clan…I’m accepting applications 🙂

  8. Kevin Alexander

    Chinese massages? Chocolate Soy Milk? Gypsies?
    I like all of this.
    And to answer une question, my dream job is to be a posh professor of creative writing, doing one workshop, one 20th Century American fiction class a semester, and having contributing editorships with Esquire and two other mags to be named later, AND doing book projects in the summertime, when the living is easy.
    This, friends, is Kev’s dream job. Just give me six years. I’ll totally be there.

  9. Genevieve

    Clearly Jodie will need someone to blog about it for her. She’ll need an entourage of fellow writers (hint, hint, nudge, nudge) because a gypsy doesn’t travel alone. She needs a band of gypsies to get Chinese massages and to drink coffee on glaciers in Alaska with her (nudge nudge, hint hint).

  10. Jodie

    My dream is to step on the soil of every country (yeah and this includes Antartica…) and to take fantastic pictures with a good ole 35mm camera, and to write about it. Some say this is slighlty gypsy-ish…but I don’t care. I want to watch the sun rise in Australia while drinking coffee and chatting w/ the locals, I want to drive a jeep through Africa, I want to get a massage in China, and visit the fish markets at 400am in Japan. I want to take pictures of the glaciers in Alaska, go to a Sigur Ros concert in Iceland, and cliff jump in Brazil…and do all of this while meeting amazing people, writing about it, and loving life….I don’t want to be rich, I just want to pay my bills…I can’t wait to do this….

  11. Ruthie

    I want to write cards. I can never find one that says exactly what I want, so I end up writing my own anyway. How in the world do you get started on something like that when none of the card companies, that I can find, accept outside submissions? I take that back – I found one that does, and am sending my first one in. We’ll see what happens. ;0)

  12. Tom

    I can’t say I was robbed of my dream, because it was more of a meandering ramble. Perhaps I was robbed of my rambling, which is probably a good thing. I have many interests pulling me in different directions right now, and trying to give them all their due is kind of messing up my head.

    I’m with Genevieve on the whole Marina/metal bands thing – write about them…if they’re still out there? They were everywhere in the 80s. I often tripped over a practicing metal band on my way to school on Wednesdays (it was their designated "day out of the cellar"), but I’ve not seen much in the way of straight up metal in the past ten years. Still, nothing ever totally dies, so there have to be boys and girls out their sharpening their six string axes and shaking their cans of Aqua Net Super Hold in preparation for a moment on stage.

  13. Genevieve

    You know, one of these days I’m going to have to actually act on one of my ideas. Kevin, what of your dream? Reem, being a cult classic author sounds like something to truly strive for, and Marina you MUST write about metal bands if they still exist anywhere other than on youtube videos. I’ve been finding ones I haven’t seen since I was 13. Joanne, we must have the perks but not so much on the soy milk. I say that because I drink soy milk. Tom, your dream post was deleted?! You’ve been robbed of your dreams LITERALLY! This is not cool, Tom. Not cool.

  14. Reem

    I have two dream writing jobs. I could take one or two at a time. The first is to travel and be able to gather enough information to write about different places and cultures.

    The second is to be an author with enough imagination to create a cult classic series where it’s all about one character with a bazillion storylines and plots. Wouldn’t it be nice to be the next Diana Gabaldon?

  15. Marina

    Well, apart from writing romance and fantasy books, I’d love to be a music/ cinema or literary journalist.
    Truly! I’ve always wanted to be a journalist, since I was all the way back in fourth grade. That’s what I’m doing now, the only set back is that I still don’t have clear which of the three options to pick. I’d love to write about music (and we’re not talking Britney Spears here, I’m talking metal music), or write about movies and their actors (in a professional sort of way, not crazy paparrazzi love stories), or be a literary critique.
    Time will tell, I suppose ^_^

  16. Joanne

    I am so there! And we can each have cool job titles. And perks, don’t foget perks. It will be very hip.
    (I found some chocolate soy milk in my fridge, it’s helping.)

  17. Christine


    I like your idea. Think of the marketability of a book that has a little something for everyone in it.

    Hollywood Herman,

    Your post made me think that perhaps I want to write a TV show because like commercials, you don’t see many good ones these days. I’ve got a big screen TV that I turn on, cruise through the guide, and then shut off to go read instead. What’s the point? And they always wind up canceling the shows I do like!


  18. Hollywood Herman

    I’d love to try writing commercials. I mean, think about it — you just don’t see many good ones these days. There seems like a real opportunity to do fun, game-changing stuff. I don’t know, maybe I’ve just been watching too much Mad Men….

  19. Tom

    My first post got wiped somehow. Fitting, as it contained no real answers.

    I kind of like Bill’s thoughts. Thanks for posting, Bill. I don’t know if that’s my dream job, but it certainly does sound a LOT more like what I’d rather be doing (note: I was an English/Journalism major who subsequently did office/project managing…ooh, the similarities are frightening!).

    As a true dream job it might be as a novelist of fiction. I haven’t really figured all this out yet, unfortunately. I’m just writing and seeing where it takes me. I’ve been told that if I keep doing the work, the results will take care of themselves. It’s the best strategy I have at the moment, and it’s working somehow…I think.


  20. Bill

    I kind of have my dream job now. After years of working as an office manager, but doing any writing project I could in whatever administrative job I had (I was an English major in college), I started to make the transition to editorial positions by first becoming a copy editor for a scientific publisher and then joining a nonprofit social services agency as their publications editor, now communications manager. I get to write for a variety of publications: newsletters, brochures, Web, etc., about the people we help, donors, volunteers. It’s something I genuinely enjoy.

    If I had the discipline, I’d love to write a novel and have it published.

  21. Genevieve

    Girls, do you realize that if combined our resources we would have travel, science, marriage & parenthood, history, teenage-interest, fiction, photography and creative non-fiction covered in one publication? We could call it Pangea, the super continent of intellectual interests. Plus, we should have chocolate coffee recipes.

  22. Angie

    My dream job is to write for National Geographic. I don’t want to write the articles about insects that glow in the dark and eat their own legs after mating, though. I want to write about other places and cultures and political realities, etc. In April’s magazine there was an article by Paul Salopek that I thought was really well done – it made me wish I could write like that (except I don’t want to be arrested in Sudan!). You can read it here, without the amazing photos:

    As for how to get the job … well, I imagine I’d have to actually write, which means I’m way behind! So far, my strategy is to badger the HR department into giving an editorial job. Not sure how well this is working…

  23. Joanne

    My dream job involves a whole lifestyle, and it will take money to achieve said lifestyle change. Remember when we were talking about environment influencing how you write? Well, in my dream…we own a bigger bluewater sailboat, maybe 40-50 feet, and it is not an older project boat, it is actually in good shape with all the equipment that we need so we don’t have to spend every waking moment fixing something, and we can travel where we want to on it, be it the Caribbean, Maine, the South Seas, or New Zealand. My four kids suddenly become more adventurous, self-sufficient, and never whine or bicker. Oh, and the 2 year old is potty-trained. We have the dog and three cats with us, too. We travel around from port to port having a grand time, living simply and fully, enjoying each sunrise and sunset, eating and drinking whatever we want and never gaining an ounce because we are so fabulously in shape from our lifestyle. Oh yeah, you asked about the job part. I write witty and thoughtful essays about travel, family, and sailing, and because they are so insightful and enjoyable to read, I am offered a column in Cruising World, and then become an editor-at-large. This turns into a multi-book deal. My name ranks up there with Fatty Goodlander, Larry and Lin Pardy, and other well-known sailor/writers. Oh, and my husband is able to give up his architecture work and become a photographer doing sailing and travel photos. Subsequently, we are asked to follow the Volvo Ocean Race around the world, writing and taking photos of the crews and their racing boats. Of course, all our expenses are paid.
    (I may have to spend the rest of the day contemplating this idea. I wish I had some coffee and some chocolate. OHHH, a mocha latte would be nice!)

  24. Cheryl Barker

    My dream writing job right now is simple–to be writing, revising, and polishing a book to meet the deadline of my yet-to-be acquired first book contract. Of course, I may panic when that happens and come up with another dream job 🙂

  25. Christine

    My dream writing job is to write young adult novels that will finally make me popular–in some form–in high school. I want to write books that make cheerleaders skip practice, nerds forget about quadratic equations, and anyone that falls between those two groups hungry for my next book. I want to be the kind of author that turns non-readers into chronic bookworms. Then, I want to travel around to schools and do writing workshops where I breeze in, do the workshop, inspire everyone within reach, and then breeze out without having to collect, correct, assess, collate, file, or grade anything. I want to do all this from a log cabin in the mountains by a lake somewhere.

    Too much to ask? Probably. But dreaming BIG is the only way to dream…

  26. Genevieve

    I know my dream won’t sound very exciting, but I would like to write books of creative non-fiction and travel around, doing readings, listening to other writers read their stuff, and drink an assortment of caffeinated and alcohol fueled refreshments with them afterwards. At the beginning of every conversation we would talk about books and writing but by the end we would quote Kevin Smith movies and do tricks with beer bottles. I don’t think I’ll be able to do this sort of thing until my kids are out of high school, but it will probably take me that long to get published anyway. So it works out.

    Oh and "With MOST of that said, I have a request?" Silly man. Take care of yourself and get sleep soon.