Digital Nomad Interview – Dale, remote worker & entrepreneur

What’s it like to travel and work at a day job, while developing your own business as an entrepreneur?

This is my latest interview in the series of interviews with digital nomads.

Dale is originally from New York. She’s been a digital nomad on and off for the past year, but is planning to travel full-time for at least a year at the end of 2020. 

Before she become a digital nomad, she was a full-time college student and briefly lived the “road warrior” consultant lifestyle, before taking her job fully remote.

Dale Digital Nomad

What made you decide you wanted to be a digital nomad?

I was inspired to become a digital nomad one summer during college while I was stuck inside my cubicle at another corporate internship.

I started reading travel blogs and learned about what it meant to become a digital nomad and I was hooked on the idea!

How do you make a living working from anywhere?

I run the travel blog Wander Her Way along with two other monetized niche sites.

In addition to my own business, I also have a day job working as a cybersecurity consultant (which I’m planning to leave at the end of 2020) that allows me to work remotely.

What do you wish you had known before you became a digital nomad?

That it takes time and hard work to build a sustainable business that you can take on the road as a digital nomad.

It’s not always the glamorous “work on the beach with your laptop” lifestyle a lot of people try to sell it as.

Dale in Cartagena

What are the best cities for digital nomads from your experience?

Right now I’m based in New York, which being one of the most expensive cities in the world is not my top recommendation for digital nomads.

My only other experience has been working out of cities in Western Europe (also pricey.) 

I am looking forward to trying out places like Medellin, Kuala Lumpur, and Bali at some point since they are all digital nomad hotspots and offer a high quality of living for a lower cost.

What’s your favourite thing about this lifestyle?

For me, it’s definitely the complete freedom and the ability to make money from something I genuinely enjoy doing.

What has been your biggest challenge?

My biggest challenge has been getting my own business to a place where I feel comfortable leaving my day job to pursue it full-time. 

When making the leap to becoming a digital nomad, I think it’s really important to have everything planned out.

If you like your day job and are able to take it on the road and work from anywhere, that’s great.

But if you want to take the entrepreneur route as a digital nomad, I think it’s important to make sure you have your own business in a sustainable place (even if it takes a couple years) before taking it on the road.

How many hours a day do you work on average? 

Between my day job and my websites, I typically work 8-12 hours a day on weekdays.

When I leave my day job in about six months, I plan to scale that number back to 4-6 hours a day on weekdays just working on my websites.

How do you stay productive while you travel?

The biggest thing I do to stay productive while traveling is schedule half my day for working and half for fun.

If I go out and explore a destination in the morning, I typically head back after lunch and work for the rest of the day until the sun goes down.

I also am willing to spend more on accommodation when I plan to be working and traveling.

I’m the kind of person who can’t concentrate in a busy cafe or crowded coworking space, and I prefer to mostly work from home.

So I’ll spend more money on a nicer Airbnb or hotel that makes working from home comfortable.

What apps do you use and recommend for digital nomads or long term travellers?

While not travel related per se, I highly recommend the Personal Capital app for digital nomads and long term travelers.

It’s a personal finance tracking app that you can integrate with all your bank accounts, credit cards, and investment accounts.

It’s a great way to keep track of spending and income at a glance while you’re on the road.

What are your plans for the future?

I plan to quit my day job in six months at the end of 2020 and work full-time on my websites while traveling long term.

Due to current world events, international travel is uncertain, but I am hoping that by the start of 2021 I’ll be able to head out on my planned adventures.

I am definitely hoping to spend a few months in Central America, followed by a few months in Eastern Europe!

Follow Dale on her blog and on Pinterest.


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