How I'm Skirting the Rules

I’m Proving That Following Your Passion Can Be a Profitable Business Model

Anna Marlis Burgard's devotion to capturing America's islands through stories and photographs didn't exactly translate to a sustainable job at first. But through a little ingenuity and a few well-crafted pivots, she's been able to make it happen.

Photo Credit: Anna Marlis Burgard

As one of the nation’s premier creative directors, Anna Marlis Burgard’s unfailing instincts have been tapped for countless photography shoots, illustrated commissions and manuscripts at the world’s top publishing houses. Yet it’s the stories behind the printed pages that really capture her attention. “Experiencing ways of life that are free from rule books—free from set expectations—is a driving passion,” Anna says. For the past four years, she’s been tackling her most ambitious project: Documenting more than 100 of America’s 16,896 islands, interviewing the residents and photographing water-framed wonders from Martha’s Vineyard, Massachusetts to Kodiak Island, Alaska.

How did she score such a dream job? The short answer is, it wasn’t easy. Just like the coastal waterways she visits, there were a lot of twists and turns along the way. Here the Newport, Rhode Island resident describes the few crucial times in her life when trusting her inner knowing allowed her to find a way around impossible situations and birth a truly unique and independent life of her own creation.

I or my company is Skirting the Rules by swimming against the tide of conventional responsibility to create a brand that’s wholly authentic to my interests, skills and passions: Islands of America. It’s the first-ever narrative and photographic collection of river, lake and coastal islands across the United States.

A time when I found the possible (a creative solution) within the impossible (against incredible odds) was when I originally envisioned Islands of America as a big, beautiful book. I’ve been making books since I was a little girl, and have been in the illustrated book business for decades as a creative director and author. It’s how my brain is wired. I received a healthy offer from the publishing house I most wanted to work with, but the relationship went south very quickly, and the deal fell apart. It was a gut punch; everything seemed to be aligning exactly as I’d hoped, then suddenly, I had nothing in my hands. Or, so it felt at the moment. There I was with all of this content, and this significant financial investment. I had to reimagine what else this could be.

The first thing I needed to do was secure the intellectual property, since a number of publishing houses had reviewed the proposal, and it was only a matter of time before someone “borrowed” from it. So, I created the website. Then I needed to change my financial model, so began negotiating comped or hosted visits to the islands instead of paying for everything myself. I also needed income coming in, and had to start getting my content out into the world, so I initiated relationships with Atlas Obscura,, Yahoo! Travel and other outlets to publish articles about the islands. At the same time, I looked at all of my notes and photographs and built proposals for smaller book projects.

One of these, Shrimp Country: Recipes and Tales from the Southern Coasts, has just been published, and I’ve signed a second book that I’m now finishing the manuscript for. If that first book deal had progressed, I would have never built the website, written the articles, or considered the other book ideas. I would have been satisfied by fulfilling my original vision. The loss became a much bigger gain in forcing me to learn new, valuable skills that resulted in transforming a single book idea into a multi-platform brand, and transforming my idea of my own capabilities.

An example of how listening to my intuition has helped me is how it’s kept me away from dangerous people, after an early, hard lesson, and has led me through risks with big personal and professional payoffs. I’m struggling to think of a single moment, as it’s just how I live my life now.

I’m not sure where my strategic brain begins and my intuition ends or if they’re parts of the same thing. I suppose strategy kicks in after intuition says: Go!

My secret talent is having strangers, even those considered leery, open up to me—share their lives, their homes, their stories, their recipes, their time.

My biggest rebel move (or my biggest risk) was walking away from a frustrating six-figure job the week my mother died. My father had died of cancer two years before, and Mom was taken down by dementia. Both diseases lurk in the sap of our family trees, so the odds that one of us six siblings would be struck by one or both seemed sufficiently high enough that I felt compelled to leave the job and work on my own projects, to accomplish exactly what I wanted to while I was still physically and mentally able.

There are members of my family who found this to be incredibly irresponsible; the negative background chatter was disheartening. I didn’t have a plan when I quit, I just knew that ending every day angry, feeling cortisol and adrenaline coursing through my body, was not how I wanted to live. A couple weeks after the funeral, I revisited some of my personal writing projects and was inspired to begin my travels for Islands of America. I’ve now visited more than 100 islands; the website, magazine and web articles and books that I’ve both written and provided photography for have significantly expanded my skills and talents, and have shown me that taking a huge leap into the unknown can land you exactly where you want to be. My mother was a writer, and my father was a watercolorist and photographer, so ultimately I feel I’ve honored them by taking the risks.

A woman is most powerful when she is fueled by the strength of her convictions and deepest passions—when she aligns everything toward her vision.

A time I wish I’d listened to my inner knowing more was during my marriage. I had a naïve vision of what marriage was supposed to be based on my parents’ relationship, and when mine didn’t conform—which was clear as soon as the honeymoon—I didn’t know how to recalibrate, couldn’t see I needed to leave until it was too late to avoid tragedy. There were coincidences during that time that I read as signs that I needed to change course, so I knew, intellectually, that I shouldn’t stay if I was interpreting events this way, but I was psychologically frozen by the shame of what was happening to me, and couldn’t tell anyone—couldn’t find the strength to fight so soon after the big church wedding and overseas honeymoon.

The female disruptor who most inspires me and why is Eleanor Roosevelt. Despite her various heartbreaks and difficulties, despite ridicule, she accomplished a great deal that profoundly impacted many, and found ways to create space for herself even during her job as the First Lady, taking off on road trips without the Secret Service, etc.

My advice to my younger self would be it’s okay to ask for help; there are many kind, generous people who will gladly give their time and lend their expertise to assist you toward your goals. When I was younger, I had a stubborn pride about doing everything by myself after a few key people had proven to be unreliable. But being independent isn’t the same thing as needing to solve everything alone. Countless strangers and acquaintances have helped me in many ways, from hosting parties so I can meet members of their island communities to lending their cars and giving me a place to stay to work, and so much more.

My favorite life hack is taking a pajama day, or what I call a zero day: no obligations, nowhere to be, no digital devices unless watching a movie, no goals or ambitions other than recharging and being. (Typical of an introvert with an extravert’s job.)

What has been your most exhilarating Skirting the Rules moment? When my money ran out, but I knew a big check was landing in two days from a consultancy I took on to refill the coffers. I kissed the abyss, but survived and thrived. Knowing I was comfortable coming so close to the edge—but also knowing that my calculations were sound. I spent my last dollars on gas and tolls to visit a private island in New York. I remember feeling giddy on the Jersey Turnpike—it was an adrenaline rush, how close I shaved it. Prior to this I made decisions based on perceived safety. Now I was willing to lay it all down: I was, and am, all in.