Leeward

By following her passions, Heather Lee crafted an adventurous life. Now she’s in Winter Garden, looking for more.

Remember back when you were a kid? You would just do things. You never thought twice about belting Blondie’s “Call Me” from the stairs in your mom’s sequin shoes. Or that doing backflips on your parents’ bed might land you in the ER with nine stitches. You never asked yourself, “Is this a good idea?” or “What could go wrong?” All you needed to know was, “Is this gonna be fun?” And the answer was always yes.

You didn’t debate the merits of kickball versus soccer in gym class. All that mattered was playing. (The bonus was seeing your name on top of the record board in the elementary school gym.) And you certainly didn’t care that your underwear would show when you practiced hip circles and cartwheels on the playground.

You simply wrote books and played tag and asked silly questions and pretended to slay the monsters hiding in the closet. There was no bullshit. If you liked something, you just did it. If you didn’t, everyone in a 10-mile radius would know about it. That’s kind of how I’ve lived my entire life. Passionate curiosity, excitement, and stubbornness leading the way. Sometimes it paid dividends. Other times, not so much. Either way, all my reckless yeses curated an unimaginable life.

Pen and Ink

Five-year-old Heather loved to make books. I would spend hours half-drawing, half-writing stories on mismatched sheets of stray paper and then bind them together with the same colorful, thick, twisted, puffy yarn I used in my hair.

Then in first grade, I discovered the library. After that, if I wasn’t playing sports—soccer, fast-pitch softball, indoor and outdoor track—I was reading. Voraciously reading. There was a constant stack of books on my bedside—Judy Blume’s Are You There God? It’s Me, Margaret, Tales of a Fourth Grade Nothing, and Blubber. (Also, much to my mother’s chagrin, Forever and Wifey.) L. M. Montgomery’s Anne of Green Gables series, and, of course, every single Nancy Drew and Trixie Belden. As I got older, my tastes moved into science fiction and fantasy, devouring J.R.R. Tolkien, David Eddings, Terry Brooks, Piers Anthony, Orson Scott Card.

Like the heroes in my favorite books, I said yes— albeit reluctantly sometimes—to most things that scared me. I said yes to sports and school plays, playing the oboe, and Girls State. I said yes to Honors classes, and AP classes, and study groups on Friday nights.

Gratefully, that witty pen, expansive vocabulary, and strong athleticism earned me honors in high school and in college. And no one, literally no one, was surprised when I decided to major in journalism at the University of Central Florida. And neither was anyone surprised when I decided—on a whim—halfway through my junior year, that one degree wasn’t enough. I doubled up on classes and layered photography into the mix. I wanted a career in magazines, and the best I could figure, journalism and photography would get me there.

No door, no problem: Taking photography to new heights in South Africa, circa 1999

Liquid Courage

And that it did. An internship at WaterSki Business magazine landed a job offer with WakeBoarding magazine. Within months of accepting, I was on a plane to Japan for a feature story I would write and photograph. First trip west of the Mississippi, first international flight, first time using chopsticks. It took me three days to get hungry enough to try tomago, unagi, and shabu-shabu, but those eye-opening flavors ignited a whole new passion for the culinary arts.

All told, I spent eight years with World Publications, the company that published WakeBoarding. But through the years, my role expanded to include WaterSki, Boating Life, and WindSurfing magazines. I loved everything about that job—the creativity, the youthful energy, and oh my god, the travel. World Publications turned a sheltered North Country girl into a globetrotting adventurer. For that, I will be ever grateful.

In between photoshoots and international flights, this new version of Heather devoured cookbooks and food magazines, transforming a girl who could burn water into a woman who hosted four-course dinner parties. I dreamt of becoming the next editor of Food & Wine. Or the next Food Network Star, whichever came first. Only, I had zero food knowledge. My watersports portfolio didn’t open a single door at Hearst or Conde Nast. So I did what anyone would do: I left my job and went to work in restaurants, the price of entry to The Culinary Institute of America.

Let me be blunt: Culinary school at 30 years old sucked. The cooking, the wine, the eating, that was fun. But chopping onions at 5 a.m. sucked. Snowstorms and blizzards in Hyde Park, NY, suck. Zero financial assistance sucked the most. So unlike most of my fellow students, in addition to the rooster-crowing alarm, I also clocked in at 5 p.m. on nights and weekends to fund this grueling experiment.

By the time culinary school ended, I was 25 pounds heavier, a Canadian shade of pale, and 9/11 happened. The city shut down, magazines weren’t hiring, and I was still a nobody to the Food Network. So I tucked tail, came back to Central Florida, and took a job with a caterer in Winter Park.

I lasted one holiday season. One. I call this chapter of my life Death by 10,000 chocolate chip cookies. Holiday orders and festive parties stacked upon one another causing staffing nightmares and morale wreckage. There were cots in the store room for sleeping. For six weeks I worked and

scooped and cooked and cried and slept on that cot, right up until I collapsed and was taken to the hospital with pneumonia.

Here’s the thing about passion: Sometimes it will lead you wildly astray. All the best intentions won’t be enough to make up for the colossal mistakes, and those are very painful lessons. Like every other choice in life, there is no way but through, no matter how hard it hurts.

Although Food Network Star wasn't in the cards, the love of food never ended. Private party, circa 2003.

Bitter Sweet Beginnings

Without a doubt, culinary school was a sidestep. An off-road adventure I’m grateful to have experienced, but definitely would not do again. However, it did throw open the doors to an exciting new decade.

After the catering disaster, I spent five years in Ocala, playing to my strengths—working in editorial, meeting incredible people. And when good friends launched a restaurant concept in Tampa, I leaped. The lure of a bigger city, closer to the water, too tempting. And with it came a new challenge to conquer: restaurant PR. I developed an eye for food photography and a flair for social media, that led to freelance work galore. Ten years ago, I made the biggest leap yet and stepped away from W-2 life for solopreneurship. Fast-paced, creative, and incredibly diverse, career-wise, I was thriving.

Here’s the thing about passion: Sometimes it will lead you wildly astray. All the best intentions won’t be enough to make up for the colossal mistakes, and those are very painful lessons.

Of course, the best yeses aren’t always glamorous. For all the delightful peaks there were dismal valleys. Falling in love with the wrong man in my 20s. Rather than accept that I made a mistake, I doubled down and bought into His Big Lie for four tragic years. There was a very public professional failure in my 30s that delivered a solid blow to both career and self-worth.

And most recently, a beautiful love story profoundly impacted my life in a much deeper way than any. other. single. event. in my entire life — good or bad. My husband of 12 years died by suicide two years ago.

If grief is the price of love, then I’m rich beyond measure, but the “why” still haunts me. I miss his lopsided smile. His laugh. His tenderness with our dog, Rylee. His effervescent joy for fishing. I miss his hugs. When I could stand next to him, tucked partly under his arm, and bury my face in his chest. Mostly, I miss what could have been.

Musee d'Orsay in Paris (2019)

But there is beauty in this season of grief, too. Beauty in finding resilience, leaning into my faith, and discovering new passions.

For many years, I looked for someone outside of myself for affirmation and acceptance. Finding my worth in “winning” and “awards.” And yet, this season has truly shown me that no one can see your big picture. Only you know the journey you’re on. Others can contribute, and you should absolutely surround yourself with smart people who lift you higher, challenge to you to be better, think bigger, push your boundaries.

But the truth is, even with wise counsel, all of my best decisions have come when I’ve turned inward, prayerfully leaning into what felt like the best move for me.

Fort DeSoto Sprint Triathlon (2016)

I know what a resounding yes feels like. It’s undeniable. It makes my heart rise up and beat a

little faster. I’m excited. And scared shitless. But I don’t have to convince myself to move forward. I simply know that it’s the right thing.

In October, that yes led me to Cortina d’Ampezzo, Italy, to hike the Dolomites. No hiking boots, no elevation experience, but I said yes. I said yes to switchbacks and blisters. I said yes to dinner with strangers, and yes to meeting up with a dear friend in Venice. I said yes to whatever bus or train schedule would get me to Croatia and, eventually, Albania. In November, saying yes to an art/yoga retreat I discovered on Instagram led me to dance under the full moon on a black sand beach of El Paredon, Guatamala, with a lovely tribe of beautiful strangers.

Canyoneering in Costa Rica

And most recently, I said yes when my good friend, Jamie Mark, called with an offer: “I have this magazine, and it could really use your touch …”

I have a feeling the best yes is yet to come.

Hello, Winter Garden! Will you help me get to know my new town?

I’m looking to say to yes to 52 new-to-me Winter Garden adventures. Harvesting honey at a bee farm? Paddleboarding a secret spot? Climbing the water tower at night? No idea is too big or too small. Send your best ideas to, heather@emagency.com, and tell me about a time when saying yes changed your life!