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Working Remotely: A Digital Nomad on a U.S. Road Trip

20-minute read

The idea of working remotely came about when I stumbled upon Remote Year—a startup that organizes a year of travel throughout the world for 100 people. As I scoured through the site, my mind began firing at the thought of myself—someone who, as the Brand Design Manager of Poppy Barley, spends 95% of her time on a computer—zipping around the world, working from any place I could find and being inspired by vibrant new cities. However, a full year away from the tight-knit team that makes Poppy Barley happen every day was not something I was able to rationalize (or fund!). But the seed had been sown.
Once I discovered that my S.O., Kevin, would be able to take a leave from his job and was intrigued by the prospect of finding some creative space for writing (he’s a musician), there was really nothing to lose. All I needed was an internet connection and my laptop, and all he would need was his guitar. I broached the idea and discussed options with Poppy Barley's founders, Kendall and Justine, to arrange a combination of work and travel for a more appropriate amount of time. Luckily for me, they are both avid travellers and incredibly supportive of our team getting out to explore the world. I began formulating a plan that would make me easily accessible to the team and still able to work on major product launches, campaigns and company activities, but ultimately a plan that would allow me to have an amazing adventure. #PoppyBarleyPassport, here we go!

A route less traveled

Kevin and I had a number of travel ideas, but landed on a road trip through the United States. Neither of us had done a major road trip before or visited much of the US, and we had this romanticized view of hitting the open road, CRV packed to the brim with our belongings and seeing where the wind blew us through this massive country. Well… the wind blew us exactly where I mapped out. :) With this being a remote work adventure, I was admittedly nervous about not being able to connect with the team, expectations not being met or work suffering. My main goal was to ensure that this was a positive experience both for me AND Poppy Barley. So I mapped it all out to the day, and we stuck to it. See our route below:
US Road Trip 2016
There’s something very different about driving for travel rather than flying. The world seems so much more accessible—you have your own vehicle, you can go where you want, stop when you want and see what you want. You're on your own timelines and the pace slows down; you have so much time to think and talk and BREATHE. It opens up possibilities and makes it feel like taking a major two month trip isn’t such a big deal afterall. When you're doing something so regular (driving) with someone so familiar, it sort of takes the nerves, or fear, right out of it. It allowed us to be spontaneous and free, with ample time to explore. Can you imagine anything better? Just a hop over the border and you’re in an entirely new country. It was so easy. The customs officer was even friendly (he just took our oranges… apparently no citrus can go across)! But to be clear. IT TAKES A LONG TIME. The drive down to our main goal city, Austin, where we spent a full four weeks, was a bit painful and numbing. Five straight days on the road, getting to a hotel in the early evening for a hot tub and dinner, and waking up to hit the road again the next morning (after our free breakfast, of course) became quite exhausting. But it all sort of blurred together and we definitely had our laughs and fun along the way. What helped our long drive down the most was listening to the podcast, Serial. I didn’t fall asleep once! (And I’m a huge car sleeper, totally relaxed by the constant lull of the car engine and the warm sun.) Highlights of our drive to Austin include the fields upon fields of wind turbines in Montana; the adorable shop owner in Sheridan who sneakily followed us in his car because he saw us peering through his vintage music store window on our way to dinner (“I’ll be open at 9am!!”); wandering through the magnificent red rocks of the Garden of the Gods in Colorado Springs; and spotting roadrunners as they bolted across the highways of the vast New Mexico deserts (Beep! Beep!). Wind Turbines in Montana - How to Work Remotely - Poppy Barley

The wind turbines of Montana

Garden of the Gods in Colorado - How to Work Remotely - Poppy Barley

The Garden of the Gods in Colorado Springs

Keep it weird

Austin, oh Austin. You are such a wonderful city. Described as a “blue dot in a red state,” Austin could not be more eclectic, friendly and active. We found an Airbnb “Austienda" just south of SoCo and were thrilled to discover its proximity to great shopping, restaurants, coffee shops, bars and everything you might need. Arriving in late, we wandered around the corner to the closest place for food to discover a huge open patio at Opal Divines with three women singing an acoustic set. What a welcome! Austin, Texas - How to Work Remotely - Poppy Barley

A view of downtown Austin, Texas, floating on Lady Bird Lake

Austin is really set up quite like our hometown, Edmonton, with a beautiful river valley running right through it, separating downtown from the south side and bursting with runners, cyclists and dog-lovers. We would bike along “Lady Bird Lake”— a reservoir in downtown Austin—which was always bustling with water activities, from kayaking to paddle boarding. South Congress is a main strip running the north to the south, packed with countless vintage, high-end and odd-ball knick-knack shops, along with cafés, food trucks and, of course, PATIOS. I would have to say that Austin might be the Queen when it comes to patios. They all have vintage, twinkly lights and could not be more inviting. We found ourselves sitting on a busy patio absorbing the heat and sipping on a cold beer more often than I’d like to admit.

Our "Austienda" Airbnb in South Austin

My first (or maybe third) order of business in getting to Austin, however, was to find a coworking space. In hindsight, I wish I had been more organized with a space to walk into right when we arrived, as I spent the first week and a half trying to get settled in a spot. It’s so hard to tell what will be the right “fit” from a few photos online. Working out of coffee shops and our Airbnb to start was fine, but the difficult thing was being able to have video calls in privacy—all the background noise in coffee shops doesn't make for very productive team meetings. After feeling awkward in a University library (I clearly didn’t belong, as a tutor questioned “are you a student?!”...urgh) and driving Kevin a bit crazy as I sat in our Airbnb working all day, I finally discovered the perfect space in East Austin called Urban Co-Lab — “A shared work community for urban innovators.” It was bright, they were friendly, they had coffee and a conference room that I could take calls in. Yay! Urban Co-Lab, Austin, Texas - How to Work Remotely - Poppy Barley

My workspace at Urban Co-Lab

The D'Orsay Flat at Urban Co-Lab in Austin, Texas - How to Work Remotely - Poppy Barley

The arrival of my new D'Orsay Flats in Ivory Snake and Black called for a photoshoot!

Kevin @ Radio Coffee & Beer, Austin, Texas - How to Work Remotely - Poppy Barley

The devil on my shoulder while trying to work at Radio Coffee & Beer

I worked for four weeks, Monday through Friday, just like I would in Edmonton. We launched two major collections—The Stardust Collection and The Desert Collection — and The Perfect Handbag in Brown. The difference was, every time 5pm hit, Kevin and I would be out exploring. Our Austin after-hours experience involved diving into the insane crowds and blaring music of SXSW, though we eventually discovered, after some discussion with in-the-know locals, that you can find tons of free music and a not-so crazy scene at the unofficial “West of the Fest” down 6th. We found ourselves lounging and soaking up the sun at Barton Springs, a 3-acre natural swimming pool in Zilker Park. We frequented a coffee/beer/patio hangout called Radio Coffee & Beer, which provided a convenient transition from afternoon work to happy hour and would have outdoor movies on Wednesday nights (we saw “O Brother, Where Art Thou?” on a perfect warm evening). The Bat-watching Sunset Cruise was truly a sight to behold as we watched 1.5 million bats fly out for their nightly feeding. (Did you know that bats can only drop into flight?!). Our best meal—perhaps of the entire trip—was at Geraldine’s, which offers a “bat’s eye-view” above Lady Bird Lake, live music, cocktails and small plates—every bite can be described as the best thing I have ever tasted (Kevin’s words, actually). From Geraldine’s you can stroll over to Rainey Street, which is a long row of old restored houses that have been transformed into lounges, patios, cocktail bars and live music venues, all decked with twinkly lights and teeming with Austinites. SO cool. His & Hers Poppy Barley shoes in Austin, Texas - How to Work Remotely - Poppy Barley

Our His & Her Poppy Barleys: The Vancouver Chukka in Black and the now sold out Modern Mary Jane in Ruby Red

The Wet Secrets playing at SXSW in Austin, Texas - How to Work Remotely - Poppy Barley

Watching Edmonton-based band The Wet Secrets kill it at SXSW.

Barton Springs, Austin, Texas - How to Work Remotely - Poppy Barley

Barton Springs—a 3-acre natural swimming pool in Zilker Park

Radio Coffee & Beer Wednesday night movie in Austin, Texas - How to Work Remotely - Poppy Barley

Watching "O Brother, Where Art Thou?" at Radio Coffee & Beer.

SoCo bridge in Austin, Texas - How to Work Remotely - Poppy Barley

Onlookers gathering on the South Congress Bridge to watch the bats fly out at sunset

On the road again

Trips to Dallas, Fort Worth and the unexpectedly beautiful San Antonio (the river walk is stunning!) filled our weekends. And before long, our time in our little hacienda in Austin came to a close. The next month, we would SERIOUSLY be on a road trip. April saw more vacation time than the first month, as we would literally be off the map—living out of suitcases and squishing in work time where and whenever I could. I was able to stick to my schedule laid out with Justine and Kendall the majority of the time, but there were some unavoidable shifts that led to random late nights in hotel rooms or tethering on the road to make things happen. All worth it in the name of adventure! My full-time job began to squish into more part-time hours, which had its stresses and worries, but I became incredibly good at switching on and off. Work time involved smoke smoldering off my laptop keys as my fingers worked faster than they’ve ever worked. My job also became very production-oriented as the team needed things from me ASAP when I was online and would have to have meetings and make decisions without me (sad face!) as my personal life took the front-seat—a very weird feeling! All I can say is that the Poppy Barley is an amazing team of do-ers and improvisors. I am SO lucky to have had these wonderful people support me in my adventure, embracing the extra pressures on their own work that I know it caused, and being so flexible to just get what needs to get done, done, and still be those happy faces I saw weekly on Google Hangout. I will be forever indebted to their kindness and positivity! Dallas, Texas - How to Work Remotely - Poppy Barley

The insane overpasses of Dallas

Chisholm Trail, Trompe L'Oeil Painting in Sundance Square, Fort Worth, Texas - How to Work Remotely - Poppy Barley

Chisholm Trail, Trompe L'Oeil Painting in Sundance Square, Fort Worth, Texas

The D'Orsay Flat and Perfect Handbag in Fort Worth, Texas - How to Work Remotely - Poppy Barley

My fab new D'Orsay Flats and The Perfect Handbag in Fort Worth, Texas

From Austin, we headed for Phoenix for a few days where we relaxed in the heat by the pool and took a hot air balloon ride over the Sonoran desert. Driving north to the Grand Canyon we camped under the stars at Mather Campground and spent the day strolling along the South Rim of the canyon. No picture will EVER capture the magnitude and jaw-dropping brilliance of the Grand Canyon. I felt as though I were on a treadmill and a backdrop was scrolling beside me. It went on FOREVER and was so impressive. From there, we went for three days to Vegas where my sisters and friend joined us for some pool-side fun and nightlife! We also saw Jerry Seinfeld do standup—if you’re looking for an hour and a half of crescent-moon-filled laughter, try to see him! Vegas was flashy and expensive, but when you’re with some of your favourite people in the world floating around the pool (and shark tank!) laughing, you really can’t complain. Hot Air Balloon in Phoenix, Arizona - How to Work Remotely - Poppy Barley

Getting ready to take off in a hot air balloon in Phoenix, Arizona

Hot Air Balloon in Phoenix, Arizona - How to Work Remotely - Poppy Barley

Hanging out in our balloon basket

Hot Air Balloon in Phoenix, Arizona - How to Work Remotely - Poppy Barley

7,000 feet up!

The Grand Canyon, Arizona - How to Work Remotely - Poppy Barley

The South Rim of the Grand Canyon

LA, San Francisco, Portland, Seattle — up the west coast we went for an unforgettable journey. If I was to tell someone what kind of road trip to take after doing this, I would say fly into LA and rent a car to drive up the Pacific Coast Highway to San Francisco and on to the Oregon coast. You’ll hit so many beautiful spots winding up the coast, higher and higher with the bright blue ocean as far as the eye can see. Massive cliffs and jagged rocks with crashing waves below, as you watch old convertibles zip down the often nerve-racking roads without a care in the world. The views of Big Sur, the silence of the Red Woods, the sand beneath your toes. People write novels about this stuff. It’s art. Red Rock Canyon, Las Vegas, Nevada - How to Work Remotely - Poppy Barley

Our humble steed in Red Rock National Park, Nevada

To save you the play-by-play of our journey back to Canada, here are my most memorable activities and favourite spots by city:

LA / Calabasas

- Santa Monica Pier (obvs!) - LACMA (The Los Angeles County Museum of Art) - Zinqué—Wine and tapas on Melrose! - Corner Bakery Cafe in The Commons of Calabasas—great breakfast and remote work spot; this is supposedly a good celeb-sighting spot, though we never saw any. Santa Monica, California - How to Work Remotely - Poppy Barley

The end of Route 66 on Santa Monica Pier

Pacific Coast Highway

- Big SurNepenthe, Julia Pfeiffer Burns State Park, The Henry Miller Memorial Library - Pacific Grove, Monterey and Carmel — lovely seaside towns to bike around; check out Cannery Row - Fort Bragg—Glass beach; Cafe Del Mar great organic restaurant for breakfast, lunch or dinner. - Gold Beach—small resort town with fabulous beaches, delicious meal at Spinner’s Seafood & Chophouse - Trinidad Memorial Lighthouse—cute little village by the sea - The Redwoods—we went to Humboldt Red Wood State Park and strolled through the Avenue of the Giants. - Drive thru-tree Big Sur, California - How to Work Remotely - Poppy Barley

Big Sur. No words.

Big Sur, California - How to Work Remotely - Poppy Barley

Having a beer at Nepenthe

Glass Beach in Fort Bragg, California - How to Work Remotely - Poppy Barley

Exploring the coastline of Fort Bragg

Glass Beach in Fort Bragg, California - How to Work Remotely - Poppy Barley

Glass Beach—pieces of sea glass that are a result of dumping garbage in the ocean until 1967 (I know, terrible). The pieces have been broken down and smoothed by the crashing waves over time.

Trinidad, California - How to Work Remotely - Poppy Barley

A Trinidadian with the Trinidad Memorial Lighthouse.

The Redwoods, California - How to Work Remotely - Poppy Barley

Weaving from coast to Red Woods and back again.

The Redwoods, California - How to Work Remotely - Poppy Barley

Humboldt Redwood State Park.

The Redwoods, California - How to Work Remotely - Poppy Barley

Driving through Chandelier tree at Humboldt Redwood State Park. It was tight!

San Francisco

- The Trident—cross the Golden Gate Bridge to Sausalito for lunch - California Sunset Cruise under the Golden Gate Bridge - Fisherman’s Wharf —take the tram from Union Square - Top of the Mark for a cocktail and 360 views of the city - The Saloon—one of SF's oldest Blues bars and DEFINITELY a dive, but such a great dance-party. Go at midnight… with friends. Alcatraz, San Francisco, California - How to Work Remotely - Poppy Barley

Sailing by Alcatraz on a sunset cruise in San Francisco

The Golden Gate Bridge, San Francisco, California - How to Work Remotely - Poppy Barley

The Golden Gate Bridge, San Francisco

Sausalito, California - How to Work Remotely - Poppy Barley


Sausalito, California - How to Work Remotely - Poppy Barley

Enjoying the sun after lunch at The Trident in Sausalito.


- Hubers for Spanish Coffee—they literally light your coffee on fire at the table - ¿Por Que No?—these tacos are to die for. To die for!! - Kenny & Zukes for Brunch - Portland Saturday Market


- Poppy—this rivals my previous comment about Geraldine's being the best food on our trip - Chihuly Glass Garden - Capitol Cider for Open Jam & Games—we played UNO and saw an amazing Brazilian jazz band - This Airbnb—homemade granola, chickens in the garden and a bottle of wine?! Great hosts. The Space Needle, Seattle - How to Work Remotely - Poppy Barley

The Space Needle and an installation of Chihuly Glass Garden in Seattle.

Home again, home again

13,000 kilometers, 10 states and a lifetime of memories later, Kevin and I drove back into Edmonton in one piece. Coming back to work on Monday morning felt a bit unusual, but I was excited to return after feeling quite disconnected from everyone and my PB life in the last few weeks. It was refreshing—refreshing to go of course, but just as refreshing to come back. I missed working closely with the team and have realized how important our face-to-face interactions are, but I’m also so thankful to be able to have taken such an unbelievable trip and still be able to work through it all. If this trip has taught me anything, it’s that most of the time my work/life balance is off kilter and I let my job take over my thoughts when I should be occupying my mind with LIFE. Your thoughts need a break from work too! To be able to completely take your mind out of work, and look at the world in a new way—a grab the bull-by-the-horns, get-out and explore kind of way—is something that seems to fade as you get into your regular routine and day-to-day comforts. So, my goal post-amazing-remote-work-experience is to not let that excitement and vitality fade. To use my evenings and weekends and the flexibility of a career that allows me to work from anywhere wisely—while still giving all I can to build the Poppy Barley brand, and the company.

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The Harley Heeled Sandal Ankle Size Guide

How To Measure:
The Harley Heeled Sandal: Take a tape measure and wrap it around your foot, right below your ankle bone as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 26 cm
5.5 26.5 cm
6 27 cm
6.5 27 cm
7 27.5 cm
7.5 27.5 cm
8 28 cm
8.5 28 cm
9 28 cm
9.5 28.5 cm
10 28.5 cm
10.5 29 cm
11 29 cm
11.5 30 cm
12 30 cm

The Esther Heeled Sandal Ankle Size Guide

How to Measure:
The Esther Heeled Sandal: take a tape measure and wrap it around your ankle, above the ankle bone, as that is where the strap will sit (see product imagery and fit video for a visual demonstration). This measurement is based on the last adjustment point on the strap.

Size Strap length will accommodate an ankle measurement up to the size below
5 23 cm
5.5 23 cm
6 23 cm
6.5 23 cm
7 24 cm
7.5 24 cm
8 24.5 cm
8.5 24.5 cm
9 24.5 cm
9.5 25 cm
10 25 cm
10.5 25.5 cm
11 26 cm
11.5 26 cm
12 26 cm

Belt Sizes

Natural Waist Measurement Typical Jean Size Belt Size for High‑rise Pant Belt Size for Mid‑rise Pant Infinite Belt Size
23-25" 23/24 26" 28" 1
25-26" 25 28" 30" 1
26-27" 26 30" 32" 1
27-28" 27 30" 32" 1
28-29" 28 32" 34" 2
29-30" 29 32" 34" 2
30-31" 30 34" 36" 2
31-32" 31 34" 36" 2
32-33" 32 36" 38" 3
33-34" 33 36" 38" 3
34-35" 34 38” 40" 3
36-37" 36 38" 40" 3
38-39" 38 40" 42" 4
40-41" 40 40" 42" 4
42-43" 42 44" 46" 4
43-44" 43 44" 46" 5
44-45" 44 46" - 5

Sizing Note: For the most accurate fit, measure around your body where you plan to wear the belt. Choose the closest belt size to that measurement.

Belt Diagram Accent Belt and Complement BeltThe Accent Belt, The Polished Belt and The Complement Belt size measurements start from the beginning of the leather to the middle hole.

Belt Diagram Infinite BeltThe Infinite Belt size measurements cover the entire length of the leather.

Belt Measuring Guide

Belt Measuring Guide

A - High-rise style:

If you plan to wear your belt around your natural waistline, wrap a measuring tape around the narrowest part of your midsection. Then, add 3” to determine your high-rise belt size.

B - Mid-rise style:

If you plan to wear your belt lower than your natural waistline, you will require a dierent size. If you have a particular pair of bottoms you intend to wear your belt with, wrap a measuring tape through the belt loops while in a relaxed position.

When wearing your belt in your preferred style, it should fasten in the middle hole. The belt will relax with wear allowing you to cinch it tighter, as needed.

If you plan to wear the belt in both the high and mid-rise styles, you have two options:

  1. Select your high-rise style and fasten it more loosely when worn in the mid-rise style.
  2. Select your mid-rise style and fasten it more tightly when worn in the high-rise style.