This is the fourth in a series called “Friend of The Lily,” where we feature women we admire.

Whether you’re an avid cyclist or have never ridden before, you’ll find that Annalisa van den Bergh is impressive. With two 4,000-plus-mile cross-country cycling trips under her belt, she shows no signs of stopping. She has plans to go on tours around the world and is determined to find a way to integrate sustainable bike travel into her daily life. In fact, on Wednesday, she launched her new blog, Work from Bike. It’s not just a blog — Work from Bike is a mobile design studio on wheels. Van den Bergh plans to split her time between her home in New York and on the road, escaping to other places by bike. She’ll make stops long the way to work at coffee shops and hostels.

“There’s something so damn empowering in using your own energy to go from A to B,” van den Bergh says.

(Taylor Gorman)
(Taylor Gorman)

We caught up with van den Bergh through email to hear more about how she got into cycling, why she decided to bike across the country twice and her advice for embarking on a trip of your own.

The Lily: You’ve ridden your bike across the country twice, right? When were these trips?

Annalisa van den Bergh: I owe my obsession with bike touring to my late mother. In 2006 at the age of 14, she signed me up for a bike trip from Buffalo, N.Y., to Toronto organized by Teen Treks, an organization that gives teenagers the chance to go on self-contained bike tours. The larger than life idea of biking across the country had been something I was dreaming of since that first bike trip. So in 2008, I signed up for Teen Treks’ maiden cross-country bike trip from Seattle to New York City mostly following Adventure Cycling’s Northern Tier route. The group consisted of five teenagers and two leaders we jokingly called mom and dad who actually ended up getting married and now have two kids!

My second cross-country ride was this past summer from Yorktown, Va., to Seattle mostly following Adventure Cycling’s iconic TransAmerica Trail. I biked the first half with my friends Taylor and Erik. I loved traveling with them, but we had different paces. A little over halfway through the trip, we broke off, and they went ahead of me. I finished off the rest of my trip partially solo and partially with cyclists I met on the route — or as I like to call them, trail family.

(Annalisa van den Bergh)
(Annalisa van den Bergh)

TL: Can you tell us about why you decided to do this not once, but twice?

AB: For the most part, that 2008 trip was what ended up defining me. It was the highlight of my life and what I never got tired of talking about. Doing it again when I had the chance was a no-brainer and ended up being the decision I’ve ever made. In late 2014, my mother, who I was very close with, died from leukemia complications. I would have recurring flashbacks of her bedridden, breathing machine-dependent days in the ICU. Almost two years after her death, I was laid off from my job at Slate. My freer schedule and PTSD flashbacks of my mom in that nightmarish state made me want to take advantage of my own health and ability to take on adventure. It was a very cathartic way to honor her, too.

TL: Do you plan on doing this trip again? Or another trip of this magnitude?

AB: I will definitely be going on more tours around the world. I’ve found that cycling does wonders to my mental health. This trip has reignited my love for bicycle travel and my aversion to full-time desk jobs. Looking back, I’m so glad — and even thankful — that I was laid off. Because if I hadn’t been, I wouldn’t have been given the opportunity to sublet my apartment, bike across the country, and discover that this is what I want to do for the rest of my life. My New Year’s resolution was to find a sustainable way to make bike travel a more integrated part of my life. I’ve just launched WFB (Work from Bike), a blog and design studio on wheels. Cycling makes me too happy not to find a way to do it as much as possible. Also, life is short!

(Annalisa van den Bergh)
(Annalisa van den Bergh)

TL: How did you train for a trip like this?

AB: I did go on a few bike rides before the trip, but for the most part, my training was the first brutal week of the trip itself. The steep, sweltering Appalachians and Ozarks actually made the longer but more gradual grades of the Rockies a piece of cake!

TL: When you are not on a trip like this, how does biking fit into your daily routine?

AB: I live in New York City, so I actually avoid biking in the city because I find it dangerous — though it’s gotten much better. I save my pedaling for occasional bike rides outside the city.

TL: When did you first get into biking?

AB: Aside from that first 2006 Teen Trek, my father is Dutch so I suppose I was born with a fondness towards bicycles! I learned to bicycle at my summer house on Fire Island — a car-free paradise two hours from New York City.

(Annalisa van den Bergh)
(Annalisa van den Bergh)

TL: What was your favorite part of this trip?

AB: Somewhere in Kansas, Taylor and I got to experience the state’s famed wild weather. Dark skies loomed in the distance, and we couldn’t stop taking pictures. Before we knew it, we got caught in a massive, nearly horizontally-falling hailstorm. In an abandoned, tornado-battered town down the road, we frantically looked for shelter. To our surprise, the door to a pristine, mosaic-adorned church was unlocked. We let ourselves in, napped in the foyer, feasted on whatever was left in our food bags and texted our trail parents — a sweet retired couple also doing the TransAm named Doug and Donna that we had met in Virginia. They were about 30 miles back and stuck in the same storm — but to their misfortune, in a very leaky shed. We chuckled, soaked up our luck and when the skies cleared, got back on our bikes and were treated to strong tailwinds that completely pushed us to the next town. I remember that day well because not only did we have the wind at our backs, but we also crossed into mountain time, which gave us an extra hour of sleep. We were halfway through America and on top of the world.

TL: What was your favorite way to pass the time while biking?

AB: I listened to a ton of podcasts, which definitely helped with the monotony of the Great Plains. It was also great blasting music on my handlebar speaker (one of the best investments I’ve ever made) in the middle of nowhere. Biking is very meditative and the saddle is the perfect place to do some thinking — well, a LOT of thinking. I’ve found that I come up with my best ideas when I’m moving.

TL: Did you ever feel unsafe while on this trip? What did you tell people who were surprised you were doing it solo?

AB: I took as many precautions as I could and rarely felt unsafe. When I was on my own, I would never stealth camp and always made sure to camp in places where there were a lot of people around. The pepper spray I carried to fend off the infamous bike-chasing attack dogs in Kentucky also gave me peace of mind. I always wore a helmet, turned on my rear light, wore reflective material and a rear view mirror. The mirror was a lifesaver, and I wish I had bought it sooner.

(Annalisa van den Bergh)
(Annalisa van den Bergh)

You’d be surprised how many people looked out for me. Among countless deeds, a woman pulled over on one of the most dangerous roads I’ve ridden on and insisted she give my friend Steve and I a ride through the worst of it. I was never actually alone because even if I wasn’t physically cycling with someone, I had trail family in front of and behind me. We looked out for each other and were each other’s scouts. I’ve learned that you have to trust your surroundings and be vigilant. Bicycling can be dangerous but at the end of the day, it was all worth the risk because I was living my dream.

TL: What was your biggest challenge on this trip?

AB: As Taylor and Erik are naturally more competitive people than I am, I was usually the one in the back — in some cases hours behind them. Most of the time I was cycling solo and would regularly roll into camp last, which was frustrating for a while and one challenge I had to overcome. But I learned to hike my own hike and to accept my standing as the literal third wheel. I came to embrace my pace and solitude, took a ton of pictures and never had shame in walking my bike up a hill.

TL: I read that you have diabetes. How did that affect your routine while on the road?

AB: Shortly after my 2008 trip, I was diagnosed with Type 1 diabetes (T1D). For those who don’t know, this means that my pancreas, which is supposed to produce insulin — a hormone that turns food into energy — does not work. So I have to do all the work for it. There’s a ton of factors that affect blood sugar, but the main points to know are that exercising brings it down and eating carbohydrates brings it up. I use a continuous glucose meter (CGM) to monitor my blood glucose levels and always made sure to carry more than enough snacks on my bike. I’m thankful that I’ve always been an organized person because it takes a ton of discipline to manage.

I actually know Erik because we both have T1D, so it was great to have someone with the same condition who understands the irritations of this disease and whose CGM also annoyingly alarms at 3 a.m. It’s funny; a lot of what we did was dictated by our blood sugar. If my blood sugar was high, it was time to get back on the bike. If I was low, it was time for a second breakfast.

(Annalisa van den Bergh)
(Annalisa van den Bergh)

TL: How did you utilize your smartphone?

AB: Because I was doing what made me the most happy, I found that my iPhone was not the time-sucking vortex that it usually is. I posted to social media more than I scrolled through it. My smartphone was more functional than addicting. It was my savior when I got lost and what played music and podcasts as I rode past endless wheat fields.

TL: How did you decide to take portraits on this trip? How did you find the people? Who’s one person from your portrait series that you learned something from?

AB: One of my favorite parts of my previous bike trips was the people that I met. Riding a loaded bicycle draws a lot of stares, questions and admiration. [It] leads you to meet so many more people than you would driving a car. Inspired by those I’ve met on my past tours, I decided to make it my goal to take a picture of the people I met. The portraits that I took were almost entirely based on chance and mostly of people who approached me rather than the other way around. People always asked me what my story was, so I turned the question around on them. Every interaction was a possible portrait.

[The result], 4000 Miles of Portraits, stands as proof of the fact that despite what we hear in the news, for the most part humanity is kind. One subject who embodied this fact was Richard Ewart of Judson, Ky. Out of nowhere, I came across a sign that said, “CYCLIST REST STOP,” pointing to a vestibule in a grassy field. Underneath it stood a cooler with ice water, chocolate and face wipes, as well as a plethora of bike tools up for grabs. I met Richard as I rode out of the rest stop. “My wife Donna does most of the work; my job is to put out the ice water.”

TL: What was something unexpected you learned from this trip?

AB: I’d like to answer that with a quote from my T1D friend and Bike Beyond cyclist, Cassidy Robinson. “We are capable of unimaginable things that are quite literally possible.”

I’ve biked across the country before but deciding to do it again, turning that gut decision into reality, and doing it on my own was even more liberating than that first organized tour. Every time I opened Google Maps and saw how far that blue dot had moved across the country, I got goosebumps. I said it before and I’ll say it again. There’s something so damn empowering in using your own energy to go from A to B.

TL: What advice would you give someone who wants to do something like this?

AB: Pack light and pack things that have multiple uses. For example, your pan can double as your plate, and your sports bra can also be your bathing suit top. I ended up shipping about 20 pounds home.

Don’t rush; allow time to see the sights and meet the people around you.

Make it a habit to leave as early in the day as possible to beat the summer heat.

Go east to west; it saves the most beautiful part for last, it spares you the cruelest heat, and it mirrors U.S. history.

This kind of trip doesn’t have to cost and arm and a leg. Use Warmshowers — the Couchsurfing for bicycle tourists, sleep in churches and town parks, and stock up on cheap supermarket staples like tuna packets and canned beans.

If you’re hesitating, just do it. There’s no amount of planning that can really prepare you. You just have to jump in!