One Giant Leap

I just quit my dream job to travel. Whether I am being daring or reckless remains to be seen.

The Backstory

Almost two years ago an amazing job fell into my lap. Among my portfolio of clients, I had done some freelance copywriting for One day I followed up about the prospect of more assignments only to receive the reply, “We’re hiring a copywriter. Are you interested?” Inside of a week I went from being self-employed and not in the market for a job, to having a full-time position at one of Canada’s largest OTAs.

In many respects it is my dream job. I get to sit quietly and write about my favourite subject all day. I am paid a decent salary that I don’t have to chase after anyone to collect, and I seldom work overtime. I am a member of a great team with intelligent, fun people who brighten my days. As the contributing editor of their blog I get to write about whatever wacky shit I like and crack stupid jokes, and they love me for it. Yet something’s missing.

Easter Island
Easter Island – Photo by Nicky Hartnell

In January 2012 my friend Roseitta and I were out for dinner when from left field she tossed out the question “How would you like to go to Easter Island?” with a slightly forced nonchalance, as though she’d been saving this question for the right moment. Unbeknownst to her, when I was about 10 years old I had been mesmerized by the centrefold from my National Geographic World magazine, depicting the moai of Easter Island at twilight with eyes aglow in the moonlight. I had taken it out of the magazine and hung it on my bedroom wall. I can still visualize what it looked like. And so began our conspiracy to tour South America.

The Decision

To make a long story short, although I was originally told that the time off I needed for the trip wouldn’t be an issue, months later it became a very big deal. It boiled down to either cancelling the trip or quitting my job.

I’d like to claim that I saw the light straight away and knew the right path instantly. The truth is that I agonized over it a great deal.

I have had my eye on location independence for some time now. Although I enjoy my job at FlightNetwork, the one thing it lacks, and which has chafed me from the start, is the opportunity to travel and be master of my own schedule again. I have an unhealthy obsession with the amount of vacation days I have left. Previously my plan was to stay at FlightNetwork for another year and replenish my coffers after the trip while building up this blog and my freelancing business to the point where I could begin my career as a digital nomad in early 2014 with a trip to Australia.

weigh scale decision
Weighing the options – Photo by Haven’t the slightest

After much hand-wringing and deliberation I made my choice. Actually, I did know early on in my heart that the trip trumped any job, but I needed to reason my way into giving myself permission to do it. It is not easy to buck the trend and give up a good job while constantly being bombarded with messages about how scarce they are these days. My parents’ generation certainly don’t understand why anyone would turn their back on stable employment in favour of the uncertainty of self-employment (Dad’s advice was to apologize to my boss and wait until I retire to travel.) It took a long time to shake the notion that I am being irresponsible or selfish, and to fathom how my mortgage would continue to get paid despite a two-thirds reduction in household income.

Ultimately I realized that there was only one choice, and that is the path of least regret. Somewhere down the line I might come to regret leaving this great job, and this is by no means the easy choice, but I already know that I would regret passing up this trip. If I did, every time I had a bad day at the office my inner ten-year-old would scream “I gave up Easter Island for THIS?!?!” Eventually it would turn to resentment and before long it would not be my dream job anymore. Besides that, we’d already been planning the trip for months, and even taken some tango lessons. I’d saved mercilessly for the better part of a year, and every time I was tempted to spend money on something I wanted, I would utter the watchword “Easter Island” to myself and go without.

new chapter
A new chapter – Photo by Amanda Breann

A New Chapter

This all went down in August and September. Once I had made my decision I had to bide my time until I tendered my resignation. I knew things would get weird if gave too much notice, and I needed to work until the end of the year to save up some money. I continued to work as hard as ever and contribute ideas as though nothing had changed. I don’t think anyone caught on that my leaving was in the cards. The hardest part of all was not being able to talk about my trip anymore. I’m a very passionate person, and travel is my biggest passion. It was so difficult to keep this under wraps.

Finally, I gave them a month’s notice and the countdown began. Yesterday was my last day on the job. Today is the first day of the rest of my life.


Taking a giant leap - Photo by Dave Scriven
Taking a giant leap – Photo by Dave Scriven


  1. Congratulations! It’s a big jump, but I’m certain you’ll be just fine. I’m glad I get to meet up with you early on in your new adventure! Here’s to the rest of your life!

    1. Thanks Cassie. I’m fairly confident that it will all work out swimmingly, but still can’t help having the occasional “What have I done?!?!” moment. Like the skydiver in the photo, I just have to believe that the chute will open at the right moment, and enjoy the exhiliration of freefall. 😉

  2. THATAWAY, Steph! Trips of a lifetime don’t come along every day and your thought process is probably what mine would be. Can’t wait to live it vicariously through your blogs! AVANTI!!!

    1. Thanks hon. Now that I’m footloose and fancy-free I hope to get to see you more often and plan a trip or two together when the time is right. Living vicariously is good, but living it for real is even better!

  3. Such an inspiring story! It’s funny how the older generation always says to wait until you retire to travel. Who knows what kind of condition I’ll be in by then. I think it would be a bit harder to hike up a mountain or jump out of a plane when I’m 70!

    1. Wow, knowing that I have inspired someone is one of the best compliments I could possibly ever receive. I’m of the same view of retirement. I consider every day as a blessing. Not to be too morbid, but I don’t live my life banking on living to a ripe old age. You never know what hand you will be dealt and I firmly believe in making the most of every day.

      There’s a quote that I use as a guiding principle (but I’m too lazy to look up where it comes from) that says “Dream as though you will live forever. Live as if you will die today”

  4. It’s been great working with you! This trip will be an experience of a lifetime. I’m looking forward to reading about your adventure and seeing your photos/videos.

    1. Hey Rob, it was a blast working with you. I will miss our chats and other nonsense. You are definitely one of the people who brightened my days. I was serious when I insisted that we keep in touch. Glad to know that you will be following my exploits 😉

      P.S. Thanks again for all of your tips and advice on working the kinks out of this site, and of course for lending a sympathetic ear to all of my technological woes.

  5. I’d be lying if I didn’t say I was jealous! Following your dreams is something we should all do – I think your story will make us all look at things just a bit differently this next year! Enjoy your travels!

    1. Thanks Jodie! It’s human nature to get jealous/envious, but I have learned that it’s much better to get inspired instead. If there’s something you really want to do in life, find a way to make it happen! Both jealousy and regret are incredibly wasteful emotions — neither accomplishes a damn thing 😉 Inspiration on the other hand is immensely powerful!

  6. Congrats, Steph! I’m sure you will not regret this! I’m not sure why FlightNetwork thinks that their travel writers don’t need to travel….its a weird concept to me. I know you can mine the net for info, but what if no one travelled independently….would the writers just look at wikis and make stuff up? LOL! Anyway, your decision is a brave one, and I applaud you and Heath for it – it’s great that he is being supportive. As you well know (Antarctica! South Africa!), travel is a wonderful teacher through the experience you gain and the people you meet. Your writing, which I think is what you are meant to do, will be that much better for your experiences. Have a great trip and post lots of pictures and blog entries!

    1. Thanks Sandy! I often think about the speech you gave at our orientation for the summit in South Africa, telling about how your daughters make you walk the talk about fulfilling your dreams, as well as the quote from Helen Keller. Travel is indeed one of the best teachers around!

      BTW, have you stayed in touch with Alejo Contreras Staeding at all? I would love to interview him for the blog, but I don’t have a way of getting in touch with him. Roseitta and I have a free day in Santiago at the end of the trip due to a flight schedule change, so it could be the perfect opportunity. Can’t remember if he’s based in Santiago or Punta Arenas.

    2. You know, I was thinking the same thing Sandy was. I’m surprised you didn’t have location independence while working at FlightNetwork. Just doesn’t make much sense to me – especially since you were blogging for them, right?

      I’ll never understand how corporations think…

      1. You would think so, but they have their own ways of doing things. My departure may have been a wake-up call to them. I sounds like they might offer my successor a much different arrangement.

  7. Wow you are one gutsy lady. What an absolute luxury all I can say is. “Carpe Diem”. Looking forward to seeing the world through your blogs

  8. Good on you Steph! (I am a FB friend of Vikki’s) I gave up my job in my twenties to travel to the UK & Europe from Australia. My father was horrified but my darling mother was delighted. Then, my partner and I gave up our jobs in banking (him)and vocational training (me) in our early forties to travel and write freelance articles. We have never regretted it for a single moment. As a result I am about to publish two books in the UK containing a lot of my partner’s photographs. I am now 60 and so grateful for all the experiences we have had. You are young and have the world at your feet so off you go and enjoy it! You sound really lovely.

    1. Hi Pauline, thanks for visiting my blog. I’m delighted you found me. Your story is so reassuring and an immense encouragement. Good luck with the books!

  9. What a great post Steph! It’s really resonating with me – especially since no one at my work yet knows that Becki and I are leaving in October for extended travel.

    It’s exciting, but kind of lonely in a way. And of course we’re still going back and forth in our minds, wondering if we’re crazy awesome for doing this, or simply crazy 😉

    Congrats on the big decision – your writing is wonderful and I know you’ll do well. Can’t wait to hang out in Dublin!

    1. Thanks Andy. I’m really glad you could relate to my post. I’m so grateful to have the blogging community for support. It makes tough decisions like this a lot easier. When I told Dad about my plans he mumbled something about trying to cheat the system and then asked “Do you know of anyone else doing this?” and I was able to assure him that lots of people live and work this way. It put us both at ease and he seems to have accepted what I am doing.

      I don’t think those doubts will completely dissipate until we’ve been travelling for a while, but I am confident that it will work out for all of us. Thanks for the compliments on my writing. Not that I’m vain, but it’s always helpful to get feedback from readers that I’m on the right track.

      I would love to hang out with you guys in DUB. I was there last spring and loved it, and I think you will too. I have this crazy idea for a project that would involve an extended stay in Ireland, but I have yet to figure out how to make it happen. There’s the small matter of my earning enough dough to get myself there (or securing sponsorship), but by golly I’m determined to go.

  10. The first step’s always the scariest, making the rest so much easier. 🙂 Work can always be found. But sometimes experiences don’t come around again. Congratulations for taking this step. Totally exciting. 🙂

    1. Thanks Debbie! That’s very true, and something that Roseitta and I have often discussed. Who knows what may arise that would preclude us from doing this later on? Now that I have taken the plunge, I think things will start to fall into place. In some ways they already are.

  11. First of all Congratulate you dear and thanks for sharing such a wonderful experience. 🙂 God Bless You!!

  12. As you know I have chosen a different type of travel, one that involves flurries of movement interspersed with months of staying still. I am sure you will have a wonderful time and, above all, will generate wonderful stories. Judging from the number of comments you have already managed to garner, I am sure you will succeed!


  13. Know you are AWESOME. Following your heart and passions in life with joy and the Universe will open up ways unimaginable and more mind blowing than any thing your mind could have visualized. Trust yourself. Happy travels, as I look forward to hearing more on your blog.


  14. well done……REGRET must be avoided. That’s the advice I give my adult children and one I fervently believe. You sound very clever and will always find another job. Will you be posting your experience?

    1. Thanks Trixie! I definitely made the right decision. I have lots more to post about from the trip to South America. I don’t generally post about how things are going from a professional standpoint. When I got back from the trip and word started to get around that I was available, I got a whole bunch of unsolicited job offers. They were tempting, but I stuck to my guns and am making a go of self-employment. The important thing for me right now is to be able to be location independent and only accept work that offers the flexibility required to accommodate that. It’s been a topsy-turvy ride, but I’m cautiously optimistic that it will all work out. I have no shortage of work. It’s just a matter of finding the right mix of jobs. Thanks so much for your encouragement!

  15. Well, I know I am reading this a bit after you wrote it, but GREAT job following your bliss. I quit my job in April 2013, giving a 2 month notice, and moved to Costa Rica with the new job title of Intentionally Unemployed. I agree about the whole secret thing. My wife and I took 1.5 years to sell everything, plan and make the move. The majority of that time our social groups and employers were in the dark…that’s a long, long time to be silent on such a big move and something we were excited about. And I Ramble. Best of luck to you.

    1. Thanks Greg! It’s now been a year, and there have been huge unexpected twists and turns in my journey that have made it very difficult at times, but I still know that I made the right decision. I hope your big leap has gone well. Enjoy your freedom!

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