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Freelancer by Day and Entrepreneur by Night

by Ornella
Freelancer by Day and Entrepreneur by Night

When she’s not running her own company or traveling around the world, Meagan Drillinger is living her best life as a freelancer. This Genius started her writing career at a travel trade agency in NYC and went on to write for major publications like Thrillist, Harper’s Bazaar, Glamour, and Conde Nast. When she’s not home in NYC, she gets to spend half the year traveling to beautiful locations like Mexico, Indonesia, and The Philippines. We interviewed Meagan to get the full scoop on how she built her freelance dynasty. 

How did you become a writer?

I recently stumbled across an elementary school magazine and the bio for my 9-year old self said, “Meagan wants to be a writer.” It’s always been my passion so I followed my dream to journalism school and I developed an interest in writing about travel. I interned at a few travel magazines and landed a job at a travel trade agency after graduation. After about 4 years of staying with them, I decided to take a leap of faith and start freelancing.  

Why did you leave your job to become a freelancer?

There came a point where I realized that there was no more room for me to grow and I needed a new challenge. Thankfully, I made some great connections with other publications and started freelance writing for them. Nothing was holding me back to just go for it and now, 6 years later, I couldn’t imagine myself doing anything else. 

What does a typical day in your life look like?

In New York, a typical day for me looks very structured. I like to block off my day into sections so the first thing I do in the morning is go through some emails, then I write for a few hours, exercise, and write again until about 4 PM. After that’s done I work on Vaera, my travel business for the rest of the evening. For Vaera, my schedule varies but usually, I’m working on marketing initiatives, creating itineraries, or speaking with suppliers. When I’m traveling to Mexico for business, it’s more or less the same schedule but I leave more room in my day to go to the beach. 

Did you always know you wanted to start your own business?

I never saw myself as an entrepreneur but I knew I loved writing and I didn’t want to have a traditional job. One day somebody said to me, “You love what you do. Wouldn’t it be amazing if you could inspire others to do the same?” It was only then that I realized that I could make my love of writing and travel into a business and Vaera was born. It was never a part of my original plan but I’m really happy that it came along.

What gets you excited about freelancing?

It’s the idea that if I want to pack up my bags and go somewhere else tomorrow, I can. If I was chained to a desk, I’d be closed off to so many amazing opportunities and I wouldn’t get to live the flexible lifestyle that I do. Beyond the flexibility and travel, I love the fact that I can write about something new every day. Before, I was stuck to a very niche market but now I write about a variety of topics and every article I write is an opportunity to learn something new.

On the flip side what’s not so great about freelancing? 

It can be unstable and there have been some months where I’m worried about making rent on time. I keep a budget spreadsheet where I calculate how much money I need to earn each month to pay my bills and to live comfortably. Then I add another $300 on top of that as a safety measure and calculate how much to take out for quarterly taxes. The key to living a stress-free life as a freelancer is to prepare your finances ahead of time and be vigilant with your spending. 

What advice can you give to people who want to start freelancing?

The first advice I can offer is to just do it. The more you overthink it the more you’ll psych yourself out. It can feel nervewracking going outside of your comfort zone but if you’ve got the wit and drive to make it work, it will. The second is to make as many professional connections as you can and attend networking events within your space. I once took a blogger that I had admired out for coffee just to pick his brain. Sometime after that, he contacted me and introduced me to some major publications like Thrillist, Time Out, and Harper’s Bazaar. Making those kinds of connections can take you a long way.

Are there any changes you’d like to see implemented for freelancers?

The biggest issue my freelance friends and I have noticed is that some companies don’t have a streamlined payment process in place and consequently pay their freelancers late. It hurts us financially because we face late fees if we don’t pay our bills on time. For that reason, more freelancers have been charging late fees which have been a shock to some companies but it’s a necessary evil to make our lives easier.

How has your freelance experience been with WorkGenius?

To be completely honest, it’s been amazing. Hyperwallet has been the easiest payment method I’ve used as a freelancer and it saves me the stress of paying my bills on time. The platform itself is functional and has been very easy to work with. I just finished up a content project for Tom’s of Maine and received good feedback so I can’t complain.

Do you see yourself freelancing long term?

I will probably never go back to working full time because the positives outweigh the negatives every time. Every day, I get to pursue my passion and I have fun doing it. I have this fire lit under me to continue building my career and between my business and freelancing, I don’t see myself slowing down anytime soon.

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