Digital Nomad Diaries: This Shoe Designer Juggles Fashion Weeks, Trade Shows and Travel
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Digital Nomad Diaries: This Shoe Designer Juggles Fashion Weeks, Trade Shows and Travel

What really happens when wanderlust meets work? Welcome to Digital Nomad Diaries, where we ask women to get real about the joys and challenges of remote work. Because even though this lifestyle is definitely a privilege, that doesn't mean it's not without its challenges and trade-offs.  

Name: Shilpa Iyengar
Age: 32
Industry: CEO and co-founder of Alterre, a sustainable shoe brand
Countries/Cities You've Worked From: New York, NY; Quogue, NY; Madison, WI; Idaho Falls, ID; Salt Lake City, UT; Billings, MT; Missoula, MT; Tempe, AZ; Denver, CO; Santa Fe, NM; Seattle, WA; Portland, OR; West Palm Beach, FL; Miami, FL; Potomac, MD; New Orleans; LA; Johannesburg, South Africa.
Places You're Working From Next: Boston, MA; Calgary; Costa Rica

Since we couldn’t travel internationally for a large part of the pandemic, we have worked all over the United States. 

We only live in one place for about a month or so, so we are always on the move! However, we do generally spend the winter in South Florida, and I’m always in and out of New York City for trade shows and fashion weeks. We also spend a lot of time in Potomac, MD, as my in-laws live there.

Shilpa Iyengar, co-founder of Alterre

When did you first start working remotely? Did the pandemic make this possible for you or were you way ahead of the game?  

My husband and I first started working remotely a few days before NYC effectively shut down because of the pandemic. We had gone to my in-laws’ house in Maryland for what was supposed to be a weekend, and that turned out to be four months! I only had enough with me from the office to finish up the designs for the next season, so it felt weird not having all of my reference materials. It was also hard to get into the groove of working without family distractions, since I had set up a makeshift desk in the dining room. I think it took a few weeks to get a good schedule together and implement standing weekly meetings over Zoom, but after those initial hiccups, I’ve loved working remotely. I find it a lot more productive than going into the office, although I do miss the social time I had with my co-founder, Harmony Pilobello. Those first months of the pandemic gave us the time to reorganize our business so we could shut down the office and go completely remote. We haven’t looked back!

What were the practical considerations of remote work? (Did you sublet your place, have to find a pet-sitter, make any arrangements with your workplace?)

We let our lease run out in NYC and put our whole apartment in storage. Our clothing is split between our two parents’ houses, and the rest is carried in suitcases with us. For the office, we closed it and donated a lot of our office furniture. My husband also closed his office. We had to partner with a fulfillment house to ship our orders and we keep the essential archive items in Florida where our business is based. It was a lot of work to set it up the way we have, but it bought our freedom!

    What was the time difference adjustment like? Do you pick your destinations with this in mind? 

    It gets a little confusing when scheduling meetings, but otherwise the time difference hasn’t been too much of a problem. I have gotten much better at specifying the time zone in all of my emails. But overall, we do try to pick places based on the time zone. We try not to be over three hours behind or ahead of our business partners, who live on the east and west coast.

    Shilpa Iyengar, co-founder of Alterre

    For you, what are the costs of working remote? (Rent, co-working space, flights). Would you say that this cost you more than working at home, less or about the same?

    Since we are fully nomadic, the costs of working remotely include lodging (usually Airbnb), car rental when needed, flights, activities (like national park visits) and our monthly storage in NY. It probably costs us the same as it did living in Manhattan full-time, but it’s great because we are getting to experience so many new places (and have much larger apartments). On the business end, we are definitely saving money by not having an office.

    Any unexpected costs? 

    Anytime there are travel hiccups like a storm or wildfire causing our plans to change, it’s expensive to re-book things at the last minute. Otherwise, I would say the biggest unexpected cost is the cost of carrying large suitcases with you everywhere. It requires renting bigger cars, using larger Uber/Lyfts and the added cost of check-in bags on flights.

    What are the best parts of working remote?

    The best parts are being able to explore more remote areas you normally wouldn’t visit in just a weekend, getting to really immerse yourself in the culture of a different city or town and just seeing spectacular sights. There have been some once-in-a-lifetime experiences, like being a part of a second line march into the French Quarter in New Orleans with Arcade Fire to wolves howling nearby in the cold darkness while gazing at the Milky Way in Yellowstone.

    What about the worst parts and frustrations? 

    The worst parts are having to constantly plan where you will live next while you are trying to enjoy the place you are currently living. It takes up several hours a week, so it’s all I really do any chance I get. The frustrations are trying to work family obligations or work-related events into the overall travel plan. Since you don’t live anywhere, one graduation party might extend into a week in that city because of the flights and lodging. It’s also hard to accept an event invitation far in advance because you never know where you will be living at the time.

    Shilpa Iyengar, co-founder of Alterre

    Did you find that you were fully able to enjoy being abroad while working? 

    Yes, I always fully enjoy where we are living. I maximize exploring the city in the evenings after work and try to live in places that are within a few hours drive of national parks or places of interest, so that we can do weekend trips.

    How does remote work affect your productivity? 

    I’m actually more productive than when I used to go into the office. Knowing that there is so much to explore, I have set more concrete work hours and am more motivated to finish everything that needs to be done as efficiently as possible. You don’t always get a full five work days in the traditional sense, but you make sure you get the same amount of work done in the time you have.

    With all of your experience now, what are your current thoughts on remote work? Would you do it forever/indefinitely? 

    I think it’s definitely how I see more people working in the future because having that freedom of how you spend your hours increases productivity and happiness overall. Although I will say I don’t think we'll keep moving around every month indefinitely. While it is amazing to have so many experiences, it is very tiring. We are actually planning on moving to Miami at the end of the year as a more permanent base, but we will continue to work remotely. I don’t know if I’ll ever want to work in an office five days a week again if I can help it!