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Why she chose the nomad life and never regretted it
And that proved to be her best life decision
alivewithad
alivewithad is a newsletter for Digital Nomads, sharing real stories and advice from experienced nomads to help you make the most of this lifestyle.
Read Time: 8 Minutes
Hey, Shagufta here! Welcome to the 10th edition of alivewithad.
Now, let me introduce today’s guest!
Lights, Camera, and Action 🥁 👟🧗🏻♀️
Nomad of the Week is Jenni🦘
Let’s hear her story told in her own words!!

Say hi to Jenni!
Hi, I'm Jenni. I've been a digital nomad for about 4.5 years. Originally from New York, I have lived in Chicago, San Francisco, India & now wherever I plan my next destination. I work remotely for startups assisting with legal operations, contract management & general paralegal consulting.
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The Nomad Story
1. How did you start your digital nomad journey?
I work in the technology/start-up space. Since the pandemic, I have been able to work remotely. In 2024, I left a full-time high-growth start-up to go out on my own as a paralegal/legal operations consultant and it's been the best decision I ever made.
2. How do you balance work, travel, and personal time?
Depending on what time zone I'm working from, I utilize the daytime and weekends to explore. Structure your days so you have personal time to step away from your laptop and enjoy the area you are in. It's important to keep that balance.
3. What’s your most memorable travel story?
There are way too many, they are all memorable! Road trip through Oman. It is such a beautiful country and the nicest people! Rounding second is a road trip in Sikkim, I recommend both.
4. What’s your biggest challenge as a digital nomad?
Making sure you have a good internet connection and a dog-friendly place to stay. I travel with my dog.
Explore various cultures with Tiqets
Through the Lens of a Nomad
5. What’s the most affordable country you’ve visited?
India
6. What’s one item you can’t travel without?
My Laptop(s). I currently travel with 3.
7. What’s the quickest way to meet people in a new city?
Go on a tour, co-working spaces, facebook groups.
8. What’s the best travel hack you’ve discovered?
Only book one-way tickets, you never know when you want to leave.
9. How do you find good Wi-Fi while traveling?
I always check in with the local host for speed, if your Airbnb is posting their speed that is always a good sign. Do some internet research on the area you will be staying in to see if there are outages and check if you can purchase data locally.
Know Your Nomad (Rapid Fire)
10. Favorite city?
Oh, I can't... There are just so many amazing places I fell in love with while traveling. I could easily name at least five off the top of my head, and each one is special in its own unique way. ❤️
11. Top bucket list destination?
New Zealand/Cook Islands
12. Best travel season?
Shoulder Season
13. Essential travel gadget(s)?
Portable Charger
14. Favourite way to travel (plane, train, etc.)?
Plane/Train
15. One word to describe nomad life?
Adventure!
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Favorite Digital Nomad Resource/s
16. Please share your go-to app, website, or a resource that helps you stay connected, manage finances, find accommodation, etc.
I use Airbnb for most of my travel, Facebook groups, and IG.
Let’s Wrap Up
17. If you could give one piece of advice to new nomads, what would it be?
If you are traveling solo, be comfortable being alone. Don't doubt yourself, you can do it.
Thank you for reading the 10th edition, I appreciate your support. ❤
I will keep publishing such interesting interviews every Sunday at 11:00 AM sharp. To not miss any edition, subscribe to the newsletter here. 👐
I see you next Sunday, till then keep traveling and conquering the world!
Your well-wisher,
Shagufta
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