Meet Jenny Shen

Team Re.Now
Published in
4 min readAug 17, 2018


We asked our mentors a few questions on location independence, inspired by the famous ‘Proust Questionnaire’. Their answers have been compiled in this series of blog posts. Through these windows into their lifestyle, we hope to discover more about them and what drives them to be untethered.

Jenny Shen is an independent UX/Product Designer at Toptal, specializing in travel and localization. A public speaker, mentor and consultant, she has been a digital nomad since 2013.

Are you a remote worker, digital nomad or both?

I’m certainly a remote worker — 100% of my work is remote, and I consider myself a digital nomad too. I work remotely full-time and once a month I travel to other places for conference speaking or a workcation and I take my work (laptop) with me.

Photo by Drew McLellan

What has been your biggest challenge when working remotely/as a digital nomad?

Convincing clients (mostly from Europe or Asia) that remote workers are as just as, if not more, efficient than people who work on-site. Now I’ve kind of gave up on convincing people, and just focused on working with clients who understand remote work and can work with someone remote.

Luckily, companies like Buffer, Hanno, Realtimeboard and ReNow advocate for remote work with stats and real case studies. I’m hopeful that this situation will improve and soon we will no longer have to convince anyone. In the near future, remote work will be “normal”, or even the norm.

What do you wish you’d known when you started out as a digital nomad/remote worker?

Working and traveling at the same time is more exhausting than you think. Also, excessive traveling takes a toll on one’s health. I underestimated how difficult it is to find healthy food on the road and how much discipline is required to keep up with my workout routine while traveling.

I wish I understood the benefit of having a home base and wish I had the knowledge of how to stay healthy while being on the road that I have now.

What do you consider your greatest achievement?

I am most proud of being able to make my own dreams come true. This includes building a brand in the industry, working with high-profile brands, speaking in well-known design and tech conferences, and moving abroad 4 times.

Where would you most like to live and why?

This is a difficult question because the grass is always greener on the other side! Before I moved to Europe in 2015, I thought Europe is where I wanted to live the most. I changed my mind after living in Amsterdam for one year.

My next goal is to live in Australia. Based on several factors, I believe it would be suitable for my lifestyle. I’d also love to explore Australia and New Zealand!

What, according to you, are the most important traits to have to embrace a location independent lifestyle?

The most successful digital nomads I’ve met are resourceful hustlers. Remote work is not new, but many businesses are skeptical about remote work because they don’t think a remote worker is as effective as someone who works at an office.

Generally speaking, remote workers have to overcome this skepticism and work harder to find clients, customers or remote jobs. Therefore, if someone wants to be a digital nomad, they have to prepare to hustle and work harder.

In addition, remote work takes a lot of self-discipline. I learned from my own mistakes that when I changed cities too often and moved too quickly, I lost time on productive work. If a digital nomad wants to be successful, he or she has to learn how to manage their time and communicate effectively.

Jenny will be mentoring on ‘Sustainable Freelance Career: From Finding Clients, Invoicing, Negotiating Contracts to Maintaining Self-Discipline and Hustling While Traveling the World’ on the Re.Now platform. To register your interest, click here.



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