To Top

Life Lessons: Jessica Ainlay


Life Lessons:
Jessica Ainlay

Are you happy at the moment?

The happiest either of us have ever been! It’s a sunny day in Berlin, where we are spending the month. Berlin in the summer has this perfectly relaxed, quiet and yet somehow always on vibe that fits us perfectly. Plus, we know we have New York City, Arizona and South America on the horizon for the next eight months or so.

If you could go back and say anything to your 16-year-old self now – what would it be?

Stop worrying what anyone else thinks and be exactly who you are. All the judgmental ones turn out to be fatter and more boring than you, so stop letting what they think matter – you’ll be more well-traveled, speak more languages and be genuinely happy while they just barely get by. Also, stop being such a know-it-all.

What’s the most important thing you’ve learned this year?

It might sound like a slogan from a well-known athletic shoe company, but just do it. Of course this is something you hear constantly, but this year we are putting into action all of the things we have been wanting to do for ages. We wrote a book on Housesitting called Break Free: The Ultimate Guide to Housesitting and started a podcast, also called Break Free, where we interview women who have broken free to live life on their own terms while traveling the world. In our personal lives we also followed this mantra, when we were traveling through South America but got an offer to housesit in a condo in Brooklyn Heights for two months this spring. We hadn’t planned on it, but we followed our gut and just did it – and had an absolutely amazing time there.

Secondly, money really can’t buy happiness. We live and work with very little cash compared to the point before we broke free and we are ten times happier now.

What do you most want to achieve in the next 12 months?

I’d like the stories we write on, our book and the podcast to reach at least twice as many people as we do now. People were always telling us that they lived vicariously through our adventures, but there is nothing we want more than for other women to know that they can travel – long-term, short-term, solo, with children, and live more inspired lives because of it.


What’s your secret to happiness?

Freedom. Freedom to decide when to go out for coffee, when to pull long hours, when to go for a bike ride at 10 in the morning rather than sit at the computer; freedom to fly to a different country every month or two and work from wherever. Freedom from routine, from climbing a corporate ladder, freedom from massive bills, mortgages and cell phones. In short, the freedom to live life on our own terms is our secret to happiness.

What one ritual or practice keeps you grounded?

The two of us travel full time, so there are not many consistencies outside of the work we do. The scenery is always changing, but the work is the most ritualistic thing we have. Dani tends to cook healthy meals and desserts wherever we travel, and she really enjoys that. I recently started doing yoga, which in addition to the obvious physical benefits has really given me the ability to pause for those five to ten seconds before overreacting, so that I can think clearly through situations that used to get all up in a tizzy.

What’s your biggest regret?

All those tizzies, for one, and not traveling like this sooner. We went on holiday for a few weeks a year, but it never clicked we could do this forever. The only other regret is not having studied software development or web design, two of the highest earning careers that can be done as a location independent professional.

What’s the most important lesson you’ve taught your kid(s)?

We don’t have kids. What bad habit would you most like to change about yourself? Procrastination and how easily we both lose focus. It’s hard to balance work and play when we’re constantly in a new country and our whole website is based around how much exploration we do in new places. But the exploration is just one part of all the work that goes into running, so if we could sit down, open the computer and focus on productivity without being distracted or putting off projects, we could be much more effective on getting the message out.


Aside from motherhood/fatherhood and marriage what are you most proud of in your life?

Well, we are not married (yet!) but have been together for over seven years. Honestly, I think we are both most proud of and the lifestyle that we have been able to create around travel. Now the goal is to spread that message to as many other people as possible.

When were you happiest?

Again, right now. We are living life on our own terms and making a good living doing it. We have never had fewer possessions and yet we are happier than we’ve ever been.

What ten words best describe you?

Positive. Adventurous. Passionate. Curious. Intellectual. Risk-averse. Self-deprecating. Connectors. Foodies. Photographer.

Dani and Jess have been globetrotting since 2010. The girls have gone from reluctant freelancers to avid bloggers who focus on providing detailed information and travel inspiration for women to break free and travel as often as possible. Urbanites, lovers of street art, street food and ocean views, Dani and Jess also are also avid house-sitters, saving thousands of dollars on accommodation while living in beautiful homes around the world. Follow their adventures on twitter @GlbetrotterGrls.


Leave a Reply

Your email address will not be published.

More in Career

Combing the aisles at Target in search of the best deal on Cheerios, it hit Rene Syler like the stench of a dirty diaper on a hot summer’s day. Not only is perfection overrated its utterly impossible! Suddenly empowered, she figuratively donned her cape, scooped up another taco kit for dinner and Good Enough Mother was born.

Copyright © 2017 Good Enough Mother® Designed By ABlackWebDesign