LAUNCHING:

Meagan

Drillinger

www.vaerajourneys.com; drillinjourneys.com

@vaerajourneys @drillinjourneys

01.

What is your professional title, purpose or passion?

I began this life as a freelance writer, and since then it has led me to add other hats to my collection. Most recently, I am the founder of Vaera Journeys, which is a retreat company for women looking to start their own location-independent businesses.

03.

What did you want to do when you were a child and what changed?

I have always wanted to be a writer. I remember being in kindergarten and getting lost writing stories for hours. The only thing that made me truly happy was getting lost in words. The business owner part came separately, and snuck up on me. It never actually dawned on me that as a freelancer I was a business owner by nature. It brought me so much joy - much more so than when I had a desk job - that I truly wanted to help other women who thought this lifestyle was impractical or out of reach see that it’s entirely achievable.

05.

What's the best career advice you've ever been given?

There are a few: Mind over matter is definitely a big one. Believing in yourself and taking the risks always result in progress and ultimately success. There will be stumbles along the way, but my dad once said to me, “what’s the worst that can happen? You will never be homeless. So take the leap.” Another is to always pay quarterly taxes. Seriously! If you’re working for yourself remember to always take taxes out of each check you receive and pay quarterly, that way you don’t get slammed in April!

07.

What is the best thing about your current working environment?

That I make my own schedule. I love that I commute to my living room, and that I get to pick and choose where and when I travel. 

09.

Where do you see yourself in five years' time?

Ideally I see myself running more retreats for Vaera. I’d love to have that become a bigger part of my day-to-day. I also would like to see a byline in glossy publications like Travel + Leisure or AFAR.

11.

Tell us more about a charitable organisation or project you think is great.

My sister-in-law has a company called Gifts for Good. It’s a company that is aiming to change the way the world gifts. Every product in her inventory gives back to the world in some way, and has an impact in more than 65 countries. I am so proud of all she has accomplished all before she’s 30 years old. 

13.

What drives you?

The desire to always live on my own terms. For years I worked for someone else. It was a great experience, and I wouldn’t change it for a thing. But I knew when it was time to move on and I have never once looked back. I would not change this freedom for anything, so to keep that privilege is what drives me. 

15.

Any final comments?

Vaera Journeys has been a dream to watch grow. I love when Vaera alum come back to me telling me that they’ve gone off to start their own location-independent businesses, or have started projects with other women they met on the retreats. Creating a network of women who can rely on each other and help each other succeed is so important to me. It’s how I got to do this thing I love to do, and I want to bring the same freedom to any woman who has ever entertained the notion. 

02.

What does a normal day look like for you?

It all depends on whether or not I’m on the road. I try to keep a routine as much as possible, because when you’re working for yourself there are so many uncertainties that it helps to make at least a few things predictable. When I’m not traveling I wake up around 6:30 and start writing. My brain is most active in the morning. I’ll break mid-morning to workout, and then come back home to write, handle emails, and work on the marketing for Vaera Journeys.

04.

What have you achieved that you feel most proud of?

Launching Vaera Journeys has absolutely been a highlight of my career. Having women sign up to learn from our amazing speakers, and to come meet and connect with other inspiring women in beautiful places, continues to leave me speechless. I am so proud of the women who have joined our retreats and have subsequently gone on to launch their own location independent businesses, or have implemented what they learned with us to their existing companies. The proof of concept, for me, has been overwhelming. 

06.

Tell us about a a woman who inspires you

My friend and ‘colleague,’ Joni Sweet. Joni and I met on a press trip in Puerto Rico four years ago. She was just on the verge of launching her freelance career but needed a supportive push to take the plunge. Now she’s officially two years into her full-time freelance career and is absolutely crushing it. She is truly an inspiration at how someone can make the freelance life work. She hustles harder than anyone I know. She advocates for herself. She knows her value. And she is firmly of the belief that there is plenty of room for all women at the top. We help each other succeed in any way that we can, and it’s so refreshing to see someone work hard and do so amazingly well.

08.

What was your biggest failure?

I have a lot of debt — and not from student loans. In my 20s I lived very much outside of my means and I’m paying for it now. The word ‘failure’ rubs me the wrong way. I prefer to think of it as a learning experience that I won’t let myself fall victim to again. Failure is just an opportunity to try another way to see if that works better.

10.

What do you like most about yourself?

I like that I am resilient. This is not an easy lifestyle. It requires a lot of trial and error, a lot of rejection, and a lot of ‘learning experiences.’ I have never chosen the ‘easy path’ with anything. Big risk has always equalled big reward for me, but also big mistakes and big heartbreak along the way. I’ve never let it stop me, though. 

12.

How can we make the world more inclusive and accepting?

Travel. Travel everywhere. Talk to everyone. It’s hard to have prejudices and preconceived notions after you’ve actually spoken to someone about their life and the way that they live. Travel is the best education, and education is what leads us to be more accepting. 

14.

What skills have been key to your journey so far?

A conflicting marriage of discipline and recklessness. I have always known the importance of the hustle and meeting my monthly quotas to, well, survive...but I also take a lot of leaps of faith. I follow my heart, which I think is key to any adventure, but knowing when to reign it in to get sh*t done is a big part of it. I believe in spreadsheets and budgets, but also I believe in saying f*** it and buying that last-minute plane ticket.

FREELANCE WRITER & FOUNDER OF VAERA JOURNEYS

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