The Pivot

From Occupational Therapist to “Digital Nomad”

Exploring the freedom and flexibility of career transitions from a clinician’s perspective.

Winnie Tsui
Written byWinnie Tsui
Published on30 May 2024

Winnie Tsui, OT, CHT, CSPO, MBA is an occupational therapist, product leader, and digital nomad. She’s passionate about building good technology, and its ability to create impact at scale and increase access to care. In fact, good tech can reduce a clinicians’ burden, freeing clinicians to provide high value care and exercise more clinical reasoning and skills. She’s grown her career beyond clinic into different industries, geographies, and responsibilities, blending career growth with work/life balance. Below, she details some of her learnings from her time as a digital nomad, product manager, professor, and clinician.

The brick and mortar clinic. The hospital system. The classroom. These are three places that clinicians are very familiar with.

It doesn’t have to be the place you spend your entire career.

I’m a digital nomad. I’m also a clinician, professor, product manager, and tech enthusiast.

The transition wasn’t easy, but your career can be whatever you want it to be — if you build it that way. If you’ve ever wondered what life as a digital nomad could look like (coming from a clinical background), let me show you.

Let’s dive in.

Question 1 — What is a “digital nomad”?
Question 2 — What are some perks and challenges with moving every few months?
Question 3 — How do I stay involved with my clinical community using my clinical expertise?
Question 4 — Technology is so different from healthcare, how did you gain the skills to pivot into tech development?
Question 5 — What resources helped you along your journey?

Question 1 — What is a “digital nomad”?

A digital nomad is someone who works in technology and is able to work fully remotely. During COVID, many technology staff worked remotely and started exploring working from further and further away. All you need is your laptop and tech gear, and you can work anywhere you can imagine. 

For the last 3 years, I have worked primarily in Canada, throughout Europe, and South America. After years of working in clinics, I was able to travel only during my few weeks off a year. The freedom to blend travel with work is a freedom that pivoting to a career in technology has afforded me. The transition has taken years of planning and additional training to manifest into reality. While being a digital nomad is optional, my technology career affords me the privilege of having that choice available.

Question 2 — What are some perks and challenges with moving every few months?

I’ve travelled a lot when I was working full-time. My colleagues felt I worked in order to travel and try out new cuisines. Earlier in my career, I tried travel therapy, and I really loved it. Now I can truly blend my passions, but on a global scale. For example, last year, when I travelled with a digital nomad travel company, Remote Year, to Peru and Argentina. After a marathon of virtual meetings, I had a group of other digital nomads to hang out with at a new beach or go wine tasting for seasonal Malbecs. The travel opportunities are only limited by your work schedule and your interests. I live in NYC for the same international opportunities and cuisines, Broadway shows, top museums, etc. But is NYC enough? I can now enjoy the international wonders IRL (clinically = in situ).

Challenges: As an experienced traveller, I have always packed light, I speak 5 languages, and it’s 2024. The challenges have mostly been solved by technology: Wi-Fi access, smartphones (maps, translations, answers at your fingertips), international no-fee credit cards; travelling is so easy now. The biggest challenge is, what do I do with my NYC apartment and my stuff?

Question 3 — How do I stay involved with my clinical community using my clinical expertise?

Building tech in healthcare has expanded my clinical landscape because you have to deeply understand the space you inhabit to build good tech.

I’ve worked in Ophthalmology (cataract surgery), Kaia Health (physical therapy), and NeuroLutions (stroke therapy & BCI or Brain-Computer Interface). Now at Squegg, I get to build video games and yet still be deeply involved in hand therapy research, evidence-supported clinical practice, and sharing my learning with other clinicians. In 2024–2025, I have submitted to be a speaker at 5 education sessions at AOTA, IFSHT, ASHT. 

I’m never going to totally give up on my clinical side because I continue to teach hand therapy as an adjunct professor, and every year, I guest lecture in OT programs around the world about what it’s like to advocate as an OT in technology and industry.

Question 4 — Technology is so different from healthcare, how did you gain the skills to pivot into tech development?

From clinical to tech, there are many transferable skills. Especially as a product manager where we lead by influence, work with a multidisciplinary team, and when we develop a product (product life cycle), it’s just like a therapy plan of care. The product life cycle is when the product manager has a plan to build a product, set short/long term goals for the team to work towards, try it out with the users to see if the product works. If it doesn’t work, you can iterate on the set goals and adjust the approach to the build until the product has maximised progress on all set goals and is released into the world. 

The product life cycle is familiar to all providers because as a clinician, your patient/client is the product, and the treatment plan is the product life cycle.

The engineers and designers I work with know a lot of medical terms and procedures, so why can’t I learn some of the tools in their toolkits? 

Similar to becoming a clinician, as a product manager, I’ve taken courses and have earned tech certificates that are recognized as standards in the software development world. So people who see these certificates know I can build a lot of different technologies, but I choose to innovate in healthcare. See my list of resources.

Question 5 — What resources helped you along your journey?

Here are a few resources I’ve found that have helped me along my journey:

The digital nomad lifestyle is exciting, but it’s not for everyone. But, if you’re coming from a clinical background, there is a way to do it. You’ll have to upskill beyond direct patient care, but that’s doable. So, if it interests you, go for it. You got this.