• Jennifer

Freedom to Choose: Sea or Sky?

I believe freedom is when you are able to make your own choices within your personal circumstances, and realizing you are only one choice away from a completely different life. Freedom can be felt everyday and should not only be a distant point in the future.

Chris and I chose to resign from our 747 pilot jobs to sail across the world. It was not an easy decision or made on a whim or a based on a split second romantic idea. We carefully considered if we were better off staying in our current situation or making a drastic change in order to follow our dreams. We consulted spreadsheets, drafted pros and con lists, and considered industry predictions. I partially wrote this article while trying to decide what to do, in order to organize my thoughts and figure out what to do.


Timing was an issue since we could only leave Seychelles westbound to Africa by November due to seasonal conditions. Bon Jovi (and sometimes Chris and I on karaoke nights) sing, “It’s my life, it’s now or never, I ain’t going to live forever”. It was becoming now or never, and as time kept ticking, we had to make a decision.


Making your own choice

I had the freedom to make my choice to determine our decision, and that feels super empowering 'Our decision' was two 'my choice’s' put together. One Chris choice + one Jennifer choice = 'our decision'. If other people make important decisions for you and you cannot say no, then you are not free.

Chris had made up his mind already that he wanted to get back on Skylark and sail across the world. He really wanted me to feel the same, but was very clear we shouldn’t make any drastic changes unless wanted it too. When you tag along with plans you don’t believe in, it can lead to regret and resentment if the plan turns out to be a flop. He didn't want the liability of pressuring me into quitting our jobs, and then it turning out to be a bad choice.

Ultimately I was a free to decide what I wanted, and I chose sailing. Whatever happens along the way would be dealt with knowing we both chose this. We will aim to make Skylark a complaint free boat...in between all of the problems along the way of course!

We are all evolving

I previously believed you should continuously work hard in an industry that you trained for until you retire. Career progression and watching my net worth increase were very important to me. Several years ago, a colleague of mine quit just prior to upgrading to Captain, to pursue his passion in another industry. At the time I was very confused by his decision to leave what I perceived to be a great job, and couldn't imagine doing something similar myself. Now, I completely understand and respect the courage it took him to make the decision to go against the standard path and follow his dreams.


The pandemic changed my whole outlook and priorities in life and helped me realize that there are no guarantees. My world is not the same as it was 15 years ago when I finished my PPL and had the initial plan of someday becoming an Air Canada pilot, and it's surely going to be different in 15 years from now. There will be changes in our health, relationships, technology, political policies and probably some black swan events along the way. Very little is permanent and the world is changing faster than ever before.


We are always evolving and are a product of our choices and experiences. It's okay to change your mind from what you previously wanted and believed. If we live in fear of the unknown and making mistakes, then we cannot make the choices that lead us to our goals and dreams. You have the freedom to choose the life you want. My choice to give up flying temporarily to live out a dream has some risks. However, by denying my dream now while in the position to live it, I risk it never happening.


Worrying about what others think

One of the biggest hurdles I faced was stressing about what people would think. Will my parents think I should be working hard and saving for retirement through a profession they worked so hard to help me achieve? Will our friend that recommended us be annoyed that we are leaving the company so soon? Will people think we are derailing our career or lack a solid worth ethic? These toxic thoughts plagued me and initially prevented me from feeling free to choose the life I desired. The reality is that the entire time other people were busy living their lives, I was worrying about things that didn't end up happening. Worrying about what people possibly think can paralyze you from making important choices. These choices add up to who you end up being or not being. Worrying can turn your mind into a prison. I had to 'prison break' myself out from that mindset to discover what I wanted in life and experience the freedom of personal choice.


One friend gave the best advice, "Friends advice (like mine too) always has a bias of personal influences and beliefs, they are influenced by that persons priorities. Advice is a hybrid picture, you take bits from everyone good and bad, pro or con and formulate something. At the end of the day follow your gut and all of your friends will always support you guys 110% whatever the decision". Thanks Will! It helped me realize the reality that we are not all in the same boat, and every life is different. Nobody else has lived the exact life as me, so it’s impossible for them to ever completely understand my life choices, just as I cannot do the same for them. When we all recognize this, it makes it easier to live our best lives and support each other’s journeys. Once I stopped worrying about being misunderstood, I felt the freedom to choose what I needed.


Thankfully our friends, family, colleagues have fully supported us, maybe even more than 110%, even if it’s something they wouldn't desire for themselves. Their love and encouragement was so incredibly meaningful that it made us feel really good about this difficult decision. We are so incredibly grateful for all of the amazing people in our lives and hope we can meet up with as many of them as possible on Skylark during our upcoming journey! Thank you!


Champagne idea's

On our last Q-suite flight departing from Chicago, we came up with an idea over a glass of champagne. A 'champagne idea'. It’s like a 'beer idea' only slightly classier and doesn’t involve regrets. We decided to write why we NEED to do this drastic change and choose to sail across the world. We planned to print them and display them by the nav station so we can remind ourselves why we made this decision, even during the roughest of seas and the worst of maintenance problems (usually the worst problem is the one that is currently occuring).


Maybe the 'champagne idea' was a little fuzzy from the bubbly, since we both completed our assignments differently. Chris wrote a nice letter specifically to me of why he wants to sail across the world with me, and I wrote a statement that you can read below.


Why I need to sail across the ocean - Jennifer

I’m choosing to sail off on a an epic journey across the world.


I wanted to fly and sail. I wanted to “have it all”. Unfortunately with the reality of time constraints, this was not feasible and left us shackled in the proverbial golden handcuffs. I am fortunate to have the luxury to pursue anything, and realize I can’t have everything. I’m grateful to have flown the queen of the skies and visit new cities around the world with great people I never would have got to know otherwise. Now it’s time to go back to the seas for a while and finish what we started.


It’s not going to be all sunsets, cocktails and beaches. There will be squalls both literally and figuratively and life will change in ways I’ve yet to discover. I will evolve and learn incredible lessons along the way through good times and hard times.

I want to sail to beautiful islands I didn’t know existed, explore new cultures, and eat healthy exotic foods. I want to practice meditation, yoga and kindness. Crossing the Indian and Atlantic Ocean will be challenging but will provide intense joy and satisfaction. I want to look back in 20 years and be proud of my decision and the risk I took.


Life is too short to wade around in the shallow. I choose to sail off into the sunset and truly explore both myself and the world. I will find courage to cross deep water into the unknown.




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