When you’re sitting there in a cubicle, daydreaming about breaking out on your own, the wish list usually goes something like this:

Chuck the job and flee all the noise and nonsense. Maybe to a serene place in ski country. Check.

Work for big-name clients who want you. And on relatively classy projects. Yes.

Take a lot of vacations. Places like, oh, Iceland, Italy, Morocco. Okay.

Have the spare time to write a book, build a blog, go hiking whenever. Check.

Oh, and have a spouse who is also freelance, and also has time for all of the above. Double check.

Laura Silverman, freelancer

That, a tad over-simplified, describes the life that Laura Silverman has crafted for herself, as a self-employed writer in creative marketing.

She works out of a 1935 cedar-shingle cottage in woodsy Sullivan County, New York two hours above New York City, with her husband, independent producer and cinematographer George Billard, who, says Laura, has never held a conventional ‘job’ in his life.

Throughout her career, she has alternated between freelance copywriting, and stints as an employee at companies like Bergdorf Goodman, Coach Leatherware and Saks Fifth Avenue. She only succumbed to the staff jobs when clients seduced her with things like benefits, bonuses and regular paychecks.

But always, within a year or so, the work would get stale, the office politics would suck the energy out of her, and she’d pack up to go freelancing again.

This time Laura says she has gone independent for good.

I was so intrigued I pestered her for an interview by email. (Which she delayed for a week because, well, she was on vacation in LA. Lucky stiff.)

Your mix of writing work? Clients?

LS: I work in the fashion and retail worlds quite a bit. Current clients include Target, Cole Haan, Sephora, and Interface/FLOR. Projects range from print and TV advertising to brand positioning and online content.

I also do a lot of work on naming and positioning projects for start-ups. [See samples of her work here.]

What draws you to working on your own?

LS: I’d say it’s the “free” in freelance that’s most appealing. And, as a writer, I work best when I can go back to my cave and ruminate. Also, I can really make the most of my time, working when I choose.

Not to mention that two or three weeks of vacation annually does not suffice for me.

Compared to working in staff jobs, are you better off freelancing? Or not?

LS: Overall, I have done as well or better financially when working freelance. And I’ve been better off both creatively and psychologically, without a doubt.

How does it work to have two freelancers, two die-hard independents under the same roof?

LS: It means we can travel a lot together. In the last four years we’ve been to Iceland, Morocco, Italy, Turkey, India, Vietnam, Cambodia and Laos.

We’ve discovered that it works best for us to have separate work spaces. Working together at home can lead to a lot of naps!

You say that freelancing enabled your life in the woods. How so?

LS: Had we been tethered to jobs in the city, we could never have moved to our place in the country, plain and simple. We still make the two-hour drive into New York at least once a week, but up here we get to live in nature, our cost of living is lower, and it affords us an isolation that really supports our work.

What is a typical work day?

LS: I work a lot. I’m a morning person, so I’m up early. My day is a mix of working on my novel, working on my blog, and working for clients. Plus snowshoeing or hiking, cooking, gardening and other domestic projects.
Laura Silverman in Venice. She works a lot. Vacations a lot.
Any downsides to working solo? Any irritations?

LS: This past year, cash flow was a challenge. Clients seemed to think it was perfectly OK to wait 90 days before sending payment. I used to hate dunning people, but now I don’t have a problem with it.

I work for MONEY, so why should I feel ashamed to ask for payment? As for doing work I’d rather not do, one of the best things about being freelance is that you can always say no.

Side projects?

LS: I am actually working on my first novel right now. I hope to finish it this year. Who knows where that will take me? I would like to think that it will lead to more.

And I just launched my blog — gluttonforlife — in December (although I was accruing posts for several months prior), so I’m not really sure where it’s going yet. It’s truly a labor of love, a way for me to share my passions with others. Initially, it took quite a bit of work to set up, but now it has an easy rhythm although I’m trying to post every day. It’s really a joy.

As a ‘serial freelancer’ what would you suggest to those thinking about going out on their own?

LS: Have a clear idea of how you’re going to support yourself. Really envision the life you want to have; write it out on paper even. Then put together a little nest egg, enough to get through a couple of months, should you need it. This is a psychological bolster for you, too.

Then take the leap. It may sound hokey, but I believe that the universe rewards risk. Getting through hard times means really accessing your creativity: find new clients, discover new avenues for your work, maybe even create an additional revenue stream by exploiting something else you do well.

Where to find Laura Silverman

Web: bylaurasilverman.com

Blog: Glutton for Life


Post-game commentary

– As idyllic as this all sounds (well, it’s idyllic to me, anyway) I’d bet Laura would admit there are days when things ain’t so pretty. Clients want the moon, the words won’t come, a check is late, the internet is down. Whatever. The key is, when you can see a pond out your front window, and you’re in charge of your own fate, the crap is a whole lot easier to take.

– Laura Silverman is good at what she does. She writes enviably well. Check out her work. She has a touch for the world of Tiffany and Sephora. She isn’t trying to be all things to all clients. She does what she does.

– She has built a network of people who know her, trust her, understand what she does. You don’t accomplish that overnight. But you can always start today.

– Laura Silverman works. And hard. What she creates doesn’t spring full-blown from the spigot.

– She devotes time to side projects that may or may not result in anything, but do lift the soul. That is always a good thing.

All photos by George Billard.