Flexibility, Give-and-Take, and Digital Nomadism With John O’Donnell

John O’Donnell is a digital nomad and entrepreneur who has been living and working remotely for the past five years. He is passionate about helping others achieve the same level of freedom and flexibility that he has achieved. In this interview, we discuss the importance of flexibility, give-and-take, and digital nomadism. We also discuss how to make the most of the opportunities that come with being a digital nomad and how to stay motivated and productive while working remotely.

Everything comes with a cost. The cost for freedom? Flexibility.

To John O’Donnell, Talent Acquisition Specialist at Kinsta, freedom’s everything, and flexibility is a price he pays with a smile.

We interviewed him on his experience as a digital nomad neophyte and asked him plenty of questions on his way of working while on the road — and he shared his top four pro tips, too.

Q1: John, what was your first step on your path to nomadism?

I’m from Ireland. I grew up there, and I started my career in sales. Then I wore the consultant hat, recruiting for a number of companies. I then became a Talent Acquisition Specialist and eventually found my way to Kinsta.

Q2. Why was Kinsta a match for you?

Last summer, I knew I needed to join a remote company, but not just any remote company.

My previous employer’s culture and way of working were impressive, and once I got exposed to that, it set the bar for my future expectations.

As I looked for new opportunities, I set out to find a job at a company that really trusted their employees and provided that flexibility, that work-like balance that I was used to — the kind of culture that makes you want to give even more back to your employer. I wanted it to be a company that was striving and had good-quality services as well.

Whereas plenty of organizations claim they’re remote, but then ask you to be bound to a certain country (or even city), Kinsta sets itself apart by walking the walk.

A remote-first company is a rarity (at least, for us Europe-based talent)! At Kinsta, you can work from just about anywhere. We don’t even have an office.

Within a month from my starting date at Kinsta, I went off traveling. Kinsta trusted me to act like a professional. I’ve been at the company for about six months, out of which almost five were spent on the road. How cool is that?

Q3. You joined and almost immediately went on your trip. How did you approach such a delicate conversation with a new employer?

The digital nomad lifestyle was actually something that I’d wanted to experience for a long while. I was originally meant to do this while working for my previous employer, but then things went south because of the economy.

When I started interviewing with Kinsta, I was honest about my intentions from the get-go. Setting expectations helps immensely — it makes things much easier. Ask your questions, find out the information you need, before joining a company and only then finding out you can’t live a life you love.

A man and a woman standing in front of an elephant.
My partner and I had this picture taken while visiting a verified elephant sanctuary, where we got to feed and shower these majestic creatures!

Q4. What’s it like to finally be working… on the road?

It’s unreal. It’s perfect. It’s all that I thought it would be.

I get to drastically change my environment and choose exactly where I work from. Of course, I keep it professional. You can’t dial into a meeting from a waterfall, but getting to pick which cafe to work from is already great.

I usually have all of my calls from my apartment, and those days on which I have lots of admin to do or I don’t have as many meetings, it’ll be more so from different cool locations as much as possible.

Q5. What challenges have you faced so far?

I didn’t realize how hard it was going to be to get into a healthy routine.

Back home, I played sports every week, went to the gym, and ate somewhat healthily.

Now I’m in Asia, where there are endless exquisite dishes I can taste for the very first time. I’ve eaten worms, too! I’ll try any delicacy once. That makes it much harder to get out of holiday mode — when you eat and drink… everything. Throw working and traveling into the mix, and it makes things even harder.

We’re just on the road so much. We’re moving from one environment to the other. Getting into a routine is hard, but I think I’m getting there.

A smiling man standing on a high balcony above a lit city, with his right arm resting on the balcony's glass railing.
I had this picture taken on the 78th floor of the tallest building in Thailand: Mahanakhon Skywalk.

Q6. What’s something you wish you’d known before becoming a digital nomad?

Planning further ahead can be of benefit. As a digital nomad, you’d want to be as flexible as you can and make decisions on a whim but that costs significantly more.

Planning even just three months ahead will save you lots of money on flights and accommodations.

It also ensures that you’re never stranded upon arrival. Some locations are very popular — you don’t want to end up being somewhere without a place to stay, especially not if you’re supposed to be working.

Q7. How has it been working for Kinsta while doing this?

Between the people being fantastic, the company being so flexible and well-organized, our top-tier product, and Kinsta’s culture, I have a hard time imagining working somewhere else and being this happy.

I joined the company, and within the month, I had solid plans to go to Thailand. That speaks volumes about how flexible the culture is.

There’s a learning curve, but it’s so motivating! I’ve only been here for a few months, yet I’ve learned so much more than I would have at most other workplaces in such a short span of time.

Finally, I must add — everyone is so helpful and kind. Being nice is wildly underrated.

Every day, more and more, this company feels like my best-case scenario. I’m not sure what any other company out there could do any better than what Kinsta is doing for its people. That’s not something I’ll ever take for granted.

You can tell by skimming through our Glassdoor reviews. People are really appreciative when an employer respects and values them, and they’ll go above and beyond their duty for an organization deserving of it.

A smiling man in a white baseball cap sitting in a tropical environment, holding a beverage cup in his right hand and touching a brown monkey that's balancing on his left knee with his left hand.
I had to be very careful not to get my Kinsta mug stolen by the furry inhabitants of Monkey Hill, in Phuket Old Town!

Q8. How do you manage your workload together while being so far apart?

I told my manager that I wanted to stick to EMEA hours. That’s the time zone I was recruiting in, and having just had started with Kinsta, I wanted to be in the same time zone as my manager while I got settled.

They’ve been very flexible in that, and Zsofi, my manager, has always said that we can work around that and change it if it’s ever needed.

I usually get started around 2 or 3 p.m. and finish around 10 or 11 p.m. I truly don’t mind, though! You get a lot of sun time in the morning and the early afternoon.

Kinsta’s very flexible, but also, there’s flexibility from my end that comes with that. You can’t ask for something you’re not willing to give — that wouldn’t be fair.

Sometimes we hire in the U.S.A. When that’s the case, it helps to have candidates based on the West Coast. Our time zones clash quite a bit, but there are workarounds.

When setting up interviews, I always send candidates my calendar link. Based on where they’re located, sometimes they can only see time slots at 2, 3, even 4 a.m. I can’t keep my calendar open 24 hours a day, but when that happens, candidates know to reach out to me to schedule ad-hoc meetings. That has happened on numerous occasions.

On most days, I do work continuously from the early afternoon until the evening. Whenever needed, my day’s split. It’s important not to be too rigid when it comes to schedule.

Q9. Do you use any tools to coordinate your efforts with the team?

Slack‘s our team’s favorite tool. It’s pretty good for communicating across different time zones. We also email quite a bit and make good use of Trello boards.

There’s no micromanagement at Kinsta. No need for it when we communicate so well. Our team also has a custom TA tracker. It makes it very easy to stay aligned on priorities and individual contributors’ progress.

Q10. Have you gotten to meet any teammates yet?

Yes — I met my colleague Mohit! We got to know each other a little better. Meeting in real life sparks different conversations, deepens relationships, and facilitates collaboration.

We worked together throughout the day and made the time for a lovely, authentic Thai meal.

Mohit used the unofficial meetup budget to come meet me at the location I was staying. He used it for the travel expenses and also some of the meals and coffees that we got that day.

Two smiling men sitting with laptops at a table in an outdoor rooftop area.
Mohit and I worked together at the rooftop café on Patong Beach.

This was after work when me and Mohit decided to explore parts of Pathong, going for some Authentic Thai food and checking out the bars.

Q11. Any advice for those who are considering living the digital nomad lifestyle?

Definitely do it. It’s invaluable — you’ll get to experience the most beautiful places in the world up close. Who wouldn’t want to do that?

Once you get over the initial fear and go on the trip, you realize how feasible it is and how flexible you can be. You can write your own story, and that includes choosing the backdrop to your professional life.

A bit of advice, I would say, is:

  • Do your research on the area and your accommodation. Very stable Wi-Fi’s a non-negotiable. The overall location cannot be too noisy. The environment should be around like-minded people that are probably working like you. Make sure to do a deep-dive on platforms such as Tripadvisor, where you can check a number of genuine reviews and ratings. I take all important video calls from my apartment – you want to make a good first impression with candidates. This is a way to positively impact the outcome of your interaction. It also helps me minimize distractions.
  • Invest in a good pair of headphones! Good noise canceling is a game-changer, especially if you ever end up working from a cafe’.
  • Thoroughly research visa processes. Some countries offer digital nomad visas – some don’t! Make sure to be on top of each nation’s requirements, as every single one’s different.
  • Invest in exhaustive health and travel insurance. I have digital nomad insurance that covers me in most countries worldwide. Anything can happen, and you don’t want to have to worry about every little thing while on your big, bold adventure.

Here’s a pro tip: You can use this type of lifestyle to save more money. There are so many affordable cities which cost much less than back home, where the cost of living is very high. That’s a huge benefit too, and another way in which you can benefit from this lifestyle.

A man standing at the open door of a yellow Jeep Rubicon with a view of the ocean in the background.
Nai Harn Beach, Phuket.

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Jaspreet Singh Ghuman

Jaspreet Singh Ghuman

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