How to Justify an Extended Family Trip

Regular readers of this site will know that our family plans to embark on a months long journey to Europe. For how many months is the question we are trying to answer. When we finalized our decision to leave, we intended to take a pass on the back end of winter in Toronto by leaving in mid-February. Today is the first day of Spring; we are still here.

Against the advice of our realtor, we priced our condo too high. Our love for the downtown unit blinded us to the realities of Toronto’s short term rental market. The apartment generated little interest when we listed it at the beginning of February. We then lowered the rent at the end of the month and generated a little more interest, but nothing solid. This past week, after another reduction, interested renters have been streaming through the place. We have no offers we like as yet, but finding a renter now feels imminent, and by extension, so does our adventure.

I receive a lot of wide eyed expressions when I tell people of our plans, forcing me to describe the idea out loud, in turn making me nervous. Becoming a nomad for several months is not an easy decision for even a solo traveller. For Yashy and I to bring two kids along is stretching the limits of my imagination. However, I’ve now known Yashy for more than 10 years and have learned not to doubt her ideas when it comes to travel.

Yashy, a seasoned traveller from a young age, views this trip as a chance to get away before both our kids start school. I have that outlook as well. Now is the perfect time to put our family routine on hold, but schooling is not the only factor. Yashy has told others that she has been nagging me to take this trip for years and now seems surprised that I have finally relented. I was just waiting for the right opportunity. Now that a conflation of factors have made this trip possible, we are confident that we can make it work. Mainly, we just have to have the right attitude. Here are some of the reasons we are able to get away.

By Considering the Trip to be a Mid Life Retirement (i.e. Having the Right Attitude)

Ever since Yashy and I graduated from Schulich, we have been working hard to pay down our mortgage, save for retirement, and, more recently, contribute money towards our kids’ education. My idea has always been to save enough to take an early retirement. Since we both know that we’ll never want to stop travelling, I have justified the idea, and its cost, as borrowed time from our retirement years. Why not dip into our savings to travel while we are still young and adventurous? Plus, we can enjoy some extended time with the kids before they start school full time.

By Freelancing (ie Becoming Millennials)

For the past couple years, both Yashy and I have been increasing our freelancing activities. When the agency I worked for closed last August, I began to freelance full time. Yashy has already been generating opportunities through this site and so she was confident enough to quit her job in order to pursue more freelance work. Since we both work in Digital Marketing, we are positioned to generate earnings while we are away, and our plan is to make this the focus of our trip. We’ll be creating video and editorial content on our journey, aimed at helping others to discover Europe and providing tips for family travel. We’ve even put together a website, Y Curation, that summarizes our services.

Using our Experience (i.e. Fulfilling our Destiny)

We really haven’t stopped moving since The Little Monkey came into our lives almost 5 and a half years ago. She’s already been to enough countries and cities to start her own travel blog (when she learns to write, of course). Our kids are experienced flyers. While travelling with kids is not an exact science, we have been honing their etiquette skills from the moment they could speak. Both kids actually enjoy the novelty of staying in hotels and trying new foods desserts at restaurants. Knowing the right mix of activities and food to carry helps too. We travel with two tablets, two colouring books, a few small toys, some snacks, and juice bottles. Those are the essentials.

I also realize that this is a chance for me to play a role in the Little Monkey’s education. She will be missing three months of school when we leave. Her current studies in senior kindergarten largely consist of art and crafts and physical activity, but she will be missing valuable math and reading lessons. Before we leave, we’ll be making a quick trip to Indigo to find a few study guides. For a couple hours each day, The Little Monkey and I will be going through educational materials to prepared her for Grade 1 in the Fall.

We still haven’t finalized any details regarding our initial destination and know that we’ll have to act quickly once we have found a tenant. The first few weeks of our trip may be like any other vacation. We’ll hop on a plane to Europe, find a place for a week or two and then start to find adventures as opportunities arrive. I’d like to say that we have a script for this story, but we don’t. It’s a work in progress and we’ll be filling in the pages as we go along.