Well, my typing sounds better than my singing, so let’s go with this: This past Saturday, I returned from a month in Hawaii, having spent most of the time on Oahu and some on the Big Island. I don’t sleep on golden pillows, so how could Alice and I take off for (and more tellingly, pay for) a month on a tropical island? (And yes, there were mai tais.)

For the same reason we previously stayed for long periods in the Bahamas, Panama, Mexico and Hawaii once before: freelancing.

The freelancing life can often be a scramble, particularly if you do a fruit salad of contract work like I do. I do B2B and B2C copywriting, edit books (both fiction and non), write essays and journalistic pieces, and travel articles too. I’ve never been able to narrow my work to a niche—something that’s undoubtedly affected my income—because my interests are broad. My writing palette has too many colors, and I find that pleasing. More pleasing yet is that, with the glories of the Internet, my office travels with me. As does Alice’s with her.

Thus, when we read of a house-sitting opportunity on some golden isle, and the setting and the situation fits, we go for it. Most of the time we still work close to our regular schedules, using that Franklinesque early to bed, early to rise admonition. But we get to rise in places like Hawaii! And there’s plenty of time to play, in such places where the play is often plentiful.

Sometimes the Freelancing Life Offers No Gravy At All

But I don’t want to downplay the occasional downers of being a contract worker. You do have to deal with social isolation—if you have a water cooler, you’re usually the only person to lurk around it. Some freelancers I know like to go to coffee shops or other public places to work, but that’s never appealed to me. I like the silence, which gives me plenty of head space in which to fret. And I can always go from my Airstream office in the yard to pester Alice in the house when I need some companionship.

You also have to be comfortable with marketing yourself, and with rejection. I send out a lot of article pitches, and often don’t get a response. A long while back I used to steam about that, but really, what’s the point? I just send more pitches. I still don’t hear back from many, but I’d guess I’ve had at least 40 and maybe 50 paid articles published this year. Here’s one that was in the latest Writer’s Market on one of the themes of this piece, Writing From the Road.

You also have to be comfortable with fluctuating income. As I said, no golden pillows, but I do have socks. I’m not breaking any banks (or breaking into banks), but I’ve been doing this, with a short corporate-writing break, for 25 years, and I’m still here.

But Sometimes the Gravy Is Very Good

I first sketched out above some real benefits of a freelancing life, but here are a few more:

Control: for the most part, you get to choose for whom you work, and what you work on. Sure, freelancers sometimes take on projects that are dull or tedious, but you really do have the choice to say no. And to say yes!

Choice: speaking of choices, they are vast in the freelancing realm. You can work for large businesses and small, you can sell products from your website or a place like Etsy, you can work at 3am if you are a night creature, you can use your expertise to design an online course, you can write books in your downtime, you can take online courses to spruce up your old skills or learn new ones. Choice and control are kissing cousins, but having lots of each is positively positive.

Exercise: one of the choices I make is to exercise every work day. Might be a hike, might be a bike, might be a stroll on one of the many picturesque slough trails in our area. Or if the weather is lousy, a ride on the recumbent bike inside. Many people think that exercise is a tedious chore, but for me, so much the opposite: you get to move the legs, move the blood, see some sights, change your perspective. And maybe eat a larger lunch because you did all those things. I always look forward to the mid-day exercise break, and it’s something that most office workers don’t get a chance to easily do.

Naps: what’s better than a short nap after exercise and lunch? And better yet, on the orange plaid of our ’66 Airstream? I rarely actually go to sleep, but the 20–25 minutes of hazy glow make for a more focused afternoon.

So, freelancing: there might be a pimple or two, and some days the clouds race in, but most of the time, the face and the weather are fine.

Vin Scully and the Voice in Your Head

I must mention a delightful coincidence that came from the Hawaii trip: I got to hear Vin Scully, the legendary voice of the Dodgers, announce his last six games. In the 60s, growing up in Southern California, I was a baseball maniac. It’s not that I simply played baseball a lot (in the streets at home, in Little League, in public parks), but I read bunches of baseball biographies, memorized statistics—even the heights and weights of players. My brother and I would spend hours pitching a tennis ball to each other in our driveway against the back gate. (We used a tennis ball because I’d broken so many neighborhood windows with hardballs.)

I loved baseball, and more so because I heard a voice in my head while I played, declaring my glory on the field. The voice I heard was Vin Scully, the announcer for the Dodgers for SIXTY-SEVEN YEARS. Sixty-seven. Because I’d grown up with Vin, I thought all baseball announcers were like him: sunny, smooth, always ready with a story that no one had ever heard or told before. A great, boundless lover of the game, but never a “homer” for the Dodgers. It’s almost impossible to express what warmth and human connection came through the radio from this modest guy—he was baseball’s easy-spoken orator, an open-hearted genius behind the mic.

There’s a quote from the writer William Dean Howells about Mark Twain that says, “Emerson, Longfellow, Lowell, Holmes—I knew them all and all the rest of our sages, poets, seers, critics, humorists; they were like one another, and like other literary men; but Clemens was sole, incomparable, the Lincoln of our literature.” Vin Scully was the Lincoln of baseball announcing. It was a profound pleasure that I happened to be in Hawaii to listen to the last of his games, when since moving from Southern California forty years ago, I’d hardly heard him at all.

Vin, you lazy guy, you’re only 88, why not go a few more?

That was a gift from the freelancing life as well—Vinnie, wishing us all a pleasant evening, wherever we are, forever.

[Note: the gracious folks at Invoice2Go, who make simple-to-use invoicing applications for freelancers and the like, are going to excerpt some of this post on their site for a helpful infographic on freelancing tips. Check out their stuff if you have invoicing needs.]