Courtney Machi: My thought on Hacker Paradise and being a digital nomad

Hi! I’m Courtney Machi. I’m originally from Pittsburgh, PA and now live in San Francisco.

I’ve worked in product development for quite some time now, and currently I’m Director of Product at Anaplan, an enterprise software company based in SF.

Most of my career has been spent in development, consulting or product roles working with companies who want to build out an analytics strategy.



How long have you been a digital nomad?

I’ve been location independent up until the last 4-5 years, when I decided to make my home in SF. I started my career in consulting where the firm required weekly travel to different companies around the world each week, so they didn’t care where I lived.

Looking back, I don’t think I really took advantage of that freedom. I based myself in various cities around the US but never went international or tried to connect with a community of people living the same lifestyle.

In fact, I didn’t know about the ‘digital nomad’ term until recently. I decided to give the lifestyle another shot when I signed up to spend the summer working in Portugal with Hacker Paradise.


Best and not-so-good experiences as a digital nomad?

The best experiences I have when I’m on the road involve connecting with people from different backgrounds and different parts of the world.

When you meet fellow travelers working on interesting projects, or locals who have stories and viewpoints that you’ve never considered, you grow as a person.

You learn to see things from different angles and find inspiration in ways you weren’t able to in the past. I’m a natural extrovert and I receive my energy from the people around me, so the constant influx of new faces works well (though we all need our alone time).

It can be lonely. When it is, you start to question why you decided to do it in the first place, so you have to remind yourself and stay positive.

It’s also difficult to stay in touch with family and friends if you’re in a different time zone (the difference between Porto and SF is 8 hours).

And last, it’s never fun being sick on the road. I’m sick right now, and all I want is my Dad’s chicken soup!



Did you encounter any safety issues while traveling?

Actually, no. I’ve had moments of feeling unsafe when walking home alone at night, for example, but never any incidents. It’s important to always be aware of your surroundings and use your best judgement in all situations.

For example, if you know your late night walk home will take you through a questionable neighborhood, call an uber or a taxi.


How do you balance traveling and working?

It can be difficult, but the easiest way to find balance is to get into a routine.

For instance, I always join a local gym immediately after I arrive in a new place. That way I can start to structure my day around classes or sessions at the gym.

From there I make sure to go to a co-working space or cafe during the work day and keep my evenings open, just like I would at home. The key for work is to stay in contact with your colleagues who are back home.

Even if you don’t have any meetings scheduled for the day, make it a point to give someone a call and see how things are going. Otherwise, you may start to feel disconnected.


How was your experience with Hacker Paradise? What made you decide to join Hacker Paradise?

Hacker Paradise is great because it provides a strong community for people who want to be digital nomads.

I chose to do it because of that community and I’m really glad I did.

That being said, I find it’s still important for me to take time to myself to wander the city and meet locals, or break into smaller groups of 2-4 to get to know people a little better. Locals are less likely to approach and welcome groups of 15 foreigners.

So, if you don’t like traveling with a large group it may not be for you.



Any advice for aspiring digital nomads?

Join Hacker Paradise! But really, it would be a great first experience with working and traveling remotely. There are a number of people in our group this summer who have never traveled and they’re all really loving it.

Before you go, I’d think about your goals and what you plan to get out of the experience.

This goes back to my point about getting lonely and reminding yourself why you came. Are you looking to experience a new part of the world? Do you want to learn a new skill? Do you want to network with other nomads? Are you challenging yourself to be “homeless” just to see if you can do it, and how it changes your appreciation for your life at home?

Once you decide that, it’ll help you understand where you should go, for how long, in what type of group, what you need to bring, etc. Stick to that goal and ride it out!


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