How I Discovered the #1 Contributor to My Happiness Is the Freedom to Control My Time (Lolly Spindler’s Story)

This post is brought to you by some items Lolly finds useful when nomading: a lipstick-sized portable charger and eBags to save space while packing.

This is the latest interview in a series featuring digital nomads talking about their lives and lessons (click here if you want to be interviewed). The goal is to help demystify the process of making money online, wandering the world, and living an unconventional life!

Lolly set out nomading in 2016 and hasn’t looked back. Below she takes us through how she set up her remote life, how she’s finding clients, and her plans for the future of her business. She has great tips for anyone looking to start nomading and especially for solo females!

Thank you for sharing your story with Freedom Is Everything, Lolly!

Key takeaways from Lolly’s interview:

“Nomading has taught me that I can, indeed, continue to be productive while traveling the world. I can get my sh*t done while still learning about and immersing myself in different cultures. I can, essentially, have the best of both worlds: Continue to grow my business and make $$ while doing what I love the most—travel.”

“You only get one life, so spend it the way you want to spend it. Figure out a way to do what you love and/or live a life you can’t complain about, a life that you don’t need a vacation from. Find community around you—there will always be one, you just have to look for it—learn lessons from them, and give back to them. People are what’s most important in life, so prioritize those special relationships.”

“Don’t be afraid to travel alone as a woman. Honestly, my solo travels have been the trips on which I’ve made the most friends and had the most unforgettable experiences. Be open to where your travels take you, trust your gut, and don’t be afraid to simply say no if you’re uncomfortable. Remember—it’s highly unlikely you’ll see most of these people again, and your safety is more important than their feelings of disappointment.”

“My motto is always be applying: to job postings, pitching your contract offerings while a company is looking for someone full-time, telling your current clients you’re open to more opportunities (with them or their network), etc. Even if you have enough work this month, it’s always good to have a few people in the new-work pipeline just in case. You just never know in the life of a freelancer.”

Introduce yourself! 🙂 Who are you? What do you do for work? And what is your nomadic story?

Lolly stands smiling in front of a wall mural painted with tropical vegetation

Hello, future/fellow nomads+location independent people! My name’s Lolly, and I’m from Seal Beach, California, a sleepy beach town situated next to the more well-known Long Beach. I started nomading back in the fall of 2016 when I set out on Remote Year, a year-long program for remote workers to live in a different city every month for a year. After my program concluded in the fall of 2017, I bounced around for another year until I made Mexico City my home. I now use CDMX as my home base (no more living out of a backpack) and travel from here!

What inspired you to start nomading? And how has nomading changed your perspective on life?

I had been working from home for about a year, and after my relationship at the time ended, I thought to myself, ‘Why am I continuing to work from Long Beach when I could be working from anywhere in the world?’ So I pitched working remotely while traveling to the company I was working for, and they told me to go for it. Thankfully, they were super flexible re: working hours, so even though I was in Asia for a time, I was still able to work normal CST hours.

Nomading has taught me that I can, indeed, continue to be productive while traveling the world. I can get my sh*t done while still learning about and immersing myself in different cultures. I can, essentially, have the best of both worlds: Continue to grow my business and make $$ while doing what I love the most—travel.

Nomading has changed my perspective on life because it’s made me realize that you can have it all. You can take control of your life and live how and where you want to live. It’s possible if you’re willing to make the effort and some sacrifices—and trust me, it’s worth it.

Please tell us the detailed story of how you started your freelancing business.

Lolly sits with one leg up on a stone wall in front of lake como on a grey day while wearing a long yellow rain jacket

After writing for two real estate blogs for a year—an industry I knew nothing about when I started—I realized I could write about almost any industry as long as I did the research and got input from the industry expert/point person, so I took the leap and left my full-time job (which made me miserable) and started freelancing. I started with a few local contacts I had in Long Beach at the time, and slowly grew my client list from there. I eventually took on another full-time job for a startup based in Texas, servicing my clients on the side.

Two months into my nomading journey, however, the startup tanked. No notice, nothing—I was in Cambodia without a salary. Thankfully, I had the freelance content marketing business for a little over two years by then and had a couple of clients I was still working with. When the startup went under, I was grateful that I already had everything in place and could simply start to ramp up my freelance business again.

In hindsight, the startup going under was a blessing in disguise; it gave me the freedom to make my own schedule and dedicate as much time as I wanted to work, which allowed me more time to explore the new places I was traveling to.

What advice would you give to someone who’s thinking about nomading?

  1. Bring less stuff. Honestly, you won’t need it, and if you do, it’s likely you can get it where you’re going.
  2. Go with an open mind. Don’t let yourself be boxed in by preconceived notions you have about yourself. Have you previously identified as someone who is afraid of heights? Don’t let that stop you from paragliding over Medellin or taking a hot air balloon ride over Teotihuacan. 
  3. Strike up at least one conversation with a stranger a day. This can be during a bus ride, at a coffee shop, or while waiting at the airport. You never know who you might meet; but also, that conversation might make you almost miss your flight (oops!).

A photo from above shows lolly sitting below a parachute as she flies through the sky in Medellin

As a woman, what should other people who identify similarly (and who haven’t traveled much) know about traveling/nomading?

Don’t be afraid to travel alone as a woman. Honestly, my solo travels have been the trips on which I’ve made the most friends and had the most unforgettable experiences. Be open to where your travels take you, trust your gut, and don’t be afraid to simply say no if you’re uncomfortable. Remember—it’s highly unlikely you’ll see most of these people again, and your safety is more important than their feelings of disappointment.

What are the 2-3 favorite places where you’ve lived/traveled to and why?

Well, I have to put Mexico City first, as it’s my current home and is honestly one of the greatest cities I’ve ever been to. It’s incredibly cosmopolitan, has something for everyone, and is one of the best food cities in the world.

Lolly stands in front of a grand building in Mexico city with scaffolding on the highest part of it

Next would have to be Madrid, which was my home after college from 2010 to 2012. Madrid has a charm about it that’s unmatched; it reels you in and never lets you go. I still try to visit once a year because it will always feel like home.

Lolly sits at a desk working on her computer at the Santiago Bernabeu in Madrid while a grass sports field is off to her right

Third would have to be Lisbon. It’s incredibly liveable, has that old-school European charm, francesinhas, and is a great jumping-off point to explore the lovely little country that is Portugal.

Lolly stands in front of a wooden door in Lisbon where walls on both sides of the door are covered in classic Portuguese blue tiles

What is one of your favorite travel stories/experiences?

It was my first solo trip ever. I was living in Madrid and wanted to check out Berlin, but none of my friends wanted to go with me. So I made the leap and went alone! Honestly, it was one of the best decisions I’ve ever made. After a gallery-hopping Couchsurfing event, the hosts invited us back to the squat where they were living to enjoy a pay-what-you-can vegan meal. From there, another one of the event-goers invited us to a friend’s birthday party, where we stayed up to the wee hours of the morning dancing to newly-discovered music and drinking 40s out of a bathtub. It was one of my favorite nights ever.

Since launching, what has been most effective to acquire/retain clients?

Referrals! Honestly, the majority of my business comes through a referral network, and the majority of that referral network is through old Remote Year connects. Other than that, I use Communo for one-off jobs, and always keep my writing portfolio on Contently updated so that I can send it over to prospective clients in a flash. My motto is always be applying: to job postings, pitching your contract offerings while a company is looking for someone full-time, telling your current clients you’re open to more opportunities (with them or their network), etc. Even if you have enough work this month, it’s always good to have a few people in the new-work pipeline just in case. You just never know in the life of a freelancer.

For someone interested in becoming a freelancer in your field, what’s the best advice you would give? And what books, podcasts, thought leaders, or other learning resources do you recommend?

Lolly stands in a swimming pool that is next to a large and long suspension bridge with tall mountains surrounding the area

I taught myself the world of digital marketing while on the job blog writing for a real estate company. If I can do it, you can too! Especially since there is SO MUCH free educational material out there on the internet. For starters, I recommend Hubspot Academy, which provides great basics and overall tutorials of the industry. If you want some more in-depth SEO resources, check out Moz. For digital content writing in particular, I’m preparing to launch a course+community on just that, so stay tuned!

What digital tools do you use for your work/business?

I am a huge Trello fan. I use it for my own personal to-do list and regularly set up new clients with their own boards to use with their teams. I also am a member of a lot of Slack workspaces and use Asana and other project management tools when my clients need me in there. I also use Buffer to schedule out my client’s social channels, and And.co to manage my freelance contracts.

What scale is your business at today, and what are your future goals?

I saw a post in a freelance writer ladies Facebook group I’m a member of a few years back, and it really inspired me. Here’s what it said (yes, I still have the screenshot):

A screenshot from Lolly spindler that indicates how she grew her business to earning six figures per year

I totally identified with this and immediately set a goal to hit six figures in six years. 2021 will be year 5 of my timeline, and so far, things are looking good. Starting at a mere $18K, I grew my income an additional 10K from 2017 to 2018, 20K from 2018 to 2019, 10K from 2019 to 2020, and am on track to grow it an additional 20-30K from 2020 to 2021.

What is your philosophy on being happy and/or finding meaning/purpose in life? And any recommended resources for people navigating this journey?

Control of my time has probably been the #1 contributor to my overall happiness. The more freedom I have over how I spend my time, the happier I am 🙂

If you only had a few minutes to live, what are the most important life lessons you would share with the world?

Lolly stands with her face painted in white and black and stands in front of a colorful painting of a flower

Hot damn, this question is hard. I guess it would have to be…

You only get one life, so spend it the way you want to spend it. Figure out a way to do what you love and/or live a life you can’t complain about, a life that you don’t need a vacation from. Find community around you—there will always be one, you just have to look for it—learn lessons from them, and give back to them. People are what’s most important in life, so prioritize those special relationships.

What do you travel with that you couldn’t imagine traveling without?

My Tortuga backpack is the best; five years and counting and still going strong. I also always have my lipstick-sized portable charger with me just in case—running out of battery when you just wanna play photographer is the worst. I am also a huge fan of my eBags to save space while packing. For all-around city/workout/outdoor/water shoes, I recommend Tropicfeel sneakers.

How can people learn more about you and your work?

Me: https://www.instagram.com/travelswithlolly/

My work: https://creacontentmarketing.com

 

Lauren Allain
Lauren is a freelance journalist from Seattle. She travels the globe in search of the best grocery stores, bouldering gyms, and snorkeling locations. Her mission at Freedom Is Everything is to help others make the transition into location-independent lifestyles.