Storytime: How Trying Cost Me Everything

Category

Life

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Date

April 8, 2025

Do you ever overthink and have anxiety over upcoming decisions in your life.? I remember being 18 years old and thinking I was invincible. Everything and anything was possible and I had little to no doubt in the process. 

I had a huge decision to make—what to do after school. How would I make this massive decision, and would it be right? It was late 2008, and I was at a point where the next choice I made could have a significant effect on the rest of my life. I spent the past year after high school taking a “gap year” (where I worked full-time at Home Hardware), at a building centre in Barrie, Ontario, Canada. 

But time was ticking, and I knew I wanted something more, different, and adventurous. Over the previous year, I had been diving into self-discovery of what I enjoyed and what I didn’t, as well as endless research on Google, trying to see what would suit my needs and life. I also made sure I leveraged people I knew and talked to friends and family about how they made their future decisions and how they got started.

Beyond the little self-doubt I had I came across that piqued my interest a lot. I found a site online about helicopters and learning how to fly. My attention was instantly locked in and I went down the rabbit hole of research, posts, and content online. Shortly after I found a company located in Vancouver, British Columbia. A flight training company called B.C. Helicopters out in Langley. I was all in and then I saw what it would cost me… Around $55,000 for 100 hours and to become a certified Commercial Helicopter Pilot… $55,000 was a huge amount of money I nor my parents had lying around for a short 4-month program. 

But I wasn’t going to let that dim my light and my dreams, so I needed to figure out a way to make it work. With big dreams, the support of my parents, and thanks to TD Bank for my student loan I was set to get started. Keep in mind I was a naive 18-year-old who thought I could do anything. So some debt, helicopters and cross-country travel didn’t sound like much… I remember having a final family gathering and party at my parent's house shortly before leaving. I was about to enter the world of unknowns, adulthood, and fantasy.

For what I knew before, who I knew, and how I thought would all shift. In the spring of 2009, I flew on a one-way flight with my bag packed for a new life. Around 3,300 kilometers away from home I would embark on the flight and journey of a lifetime. The following 4 months were magical. From living on my own (well with a roommate) for the first time in my life, doing my laundry, making pasta nearly every day, biking 5 kilometres to the gym and back several times a week, and flying amongst some of the most beautiful terrain and scenery out there. Needless to say, I was in heaven and truly living life to the fullest. 

As I think back on this moment in time and experience in my life I’m shocked at how I just jumped without much hesitation at all. Getting started has become more and more difficult as I age and weigh out the pros and cons of risk and reward. But in that moment as a young 18-year-old kid, the dream was stronger than the rest of it. And that dream brought me to where I am today. 

Following my training, I had completed all of my 100 flight hours, passed the flight test (on the 2nd attempt…), and was ready to enter the world of careers and work in my newfound industry and passion. Over the next 8 months, I would apply to hundreds of aviation outfits all across Canada. I’d email them, show up on their doorstep, phone them, and do just about anything else to get their attention and into the industry. Yet no matter how much I persisted I would hear the same thing for 8 months straight… No, you’re too young, you don’t have enough experience, and we’re not hiring, check back next year. 

It didn’t matter that I had a license saying I could fly helicopters and could do the thing. None of that mattered because the industry had other plans and I wasn’t part of them. Around that time I’d find myself sitting outside of the apartment I was renting at the time. Alone, exhausted, and defeated. I was now working in another industry I had experience in which was building centres and hardware stores. Even doing that wasn’t enough as I checked my bank account. My credit card and student line of credit were maxed out… My checking account said -$523.14… I was broke… No money to pay rent, bills, or buy food. I felt sick to my stomach. And the weight felt so heavy on my small 19-year-old shoulders. 

I didn’t know what I was going to do next and had no clue how I got here. I began questioning everything and anything I decided to do that led me to this exact point. Would I have been better off not to try at all? Getting started seemed simple at that point in my life yet it would cost me all of this pain, anxiety, stress, and worry. I knew at that moment that I didn’t want to feel like this ever again. And that I needed to figure out an alternative path to my future ASAP. 

From there I’d need to pivot and ask for help. Luckily my parents (and ultimate supporters) took me back and I found myself living back in their basement working my old high school job (yes, back at Home Hardware)... I’d get bombarded by previous employees and co-workers when I was back. “What happened Chris?” “Why aren’t you flying?” and so much more. With each question, it is dug a little deeper that I failed. And it honestly felt horrible. 

But even though helicopters had taken me for a ride (literally and financially), I needed another door of entry, because I knew the one I was knocking on was locked and boarded up. From there I went back to the drawing board and my trustee friend (Google of course). I asked people in the aviation industry what they were doing and why. I knew the road led to helicopters but it might indeed look different than my 18-year-old self previously imagined it. After some careful thought, consideration, and conversations, I decided to go back to school and pursue aircraft maintenance. I’d apply to B.C.I.T. - British Columbia Institute of Technology to become an Aircraft Maintenance Engineer (or someone who works on aircraft). That was going to be my in. The process would consist of taking on another $15,000 worth of debt, moving back out to Vancouver where I’d failed before and getting started all over again. 

This process took some time for me to accept and go for. Finally, I mustered up enough courage and applied. The school required me to take 3 pre-tests to get in. I barely passed 2 of them and failed reading comprehension… Yet another sign telling me to give up. That I wasn’t smart enough. Another hurdle I’d have to accept and get over. I retook the test again and passed. From there I’d commit to 4 years of school. 1.5 years of learning and a 2.5-year apprenticeship. The road was finally looking brighter. I applied myself at every chance I got and ended up graduating from the program with Distinction with an overall average of 91%. Not an easy feat for me. But I did it. 

Following school, I got introduced to a contact from an instructor and received a job right away. I had done it. It was harder, longer, and more expensive than I ever could have imagined. And yet $70,000 of debt later and 3 solid years of setbacks I was working in the industry. 

Every setback has made it a little bit harder to start on the next phase of plans for my life. Getting turned down, failing, and falling short isn’t fun. I’ll be the first one to admit it. Winning and succeeding is so much more enjoyable. Both on paper and as an individual. But I began to learn that without hardships, lessons, and learnings success isn’t possible. How could you possibly know and be grateful for the mountain peak if you were just dropped off at the top with a helicopter? To know the highs you must know the lows too. And although every time to get started is a bit more difficult it’s something I’ve managed to accept, endure, and thrive in. 

So if you’re going through a low and are struggling to see the light, I see you. I know how it feels to be down and out. Waiting for the perfect time to try again. It took me years to understand that today is the best day to try, to do it. And while getting started can often be seen as the hurdle and the thing in your way, it’s the opposite. Getting started is the opportunity. It’s the thing that creates change, results, and impact. 

The time is now to start. Block out the distractions, noise, people, and judgement, and go for it. While it didn’t work out for me for several years, it ultimately led to where I am today and who I am today. 

Chris M Wilson

Chris Wilson is a keynote speaker, CTI coach, and entrepreneur. Through his Hover to Fly framework, he aims to impact the next generation in their careers and lives.

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