Pillar No. 2: Risk

“I was that girl. The one with the good job that paid well, where my clients loved me and I enjoyed what I did well enough…But what others didn’t see was that as the years went on, I was slowly dying inside. The job was taking so much out of me not just physically but emotionally as well…As much as I wanted to keep loving it, I found myself yearning for something more. I wanted to be my own boss…When I finally launched my own company, friends and family were happy to help get the word out, because they knew how passionate I am about my work. That’s all I could ever have asked for. I still need part time work to help make ends meet. But every client I have the opportunity to work with under my own business is a gift and fulfils my heart on a level I never felt when working for someone else. I am able to schedule my own hours in my studio and only work during those hours which means I get to enjoy time with my family and friends. And I am proud of the work that I do. Has it been easy? Absolutely not. Has it been worth the risk? You bet it has. The work I do now sets my soul on fire, and there is nothing in this world worth more than that.”

This is my friend Dianna and like many others in the modern workforce she yearned to step out to truly live her dream and speak her truth. This quote is a very realistic snapshot of what it is like to do so as it is very taxing and challenging but also very rewarding in the end when things work out. I have been close to her family for quite sometime and while they are lovely people they do lean on the conservative side of taking risk and do not take major decisions like this lightly. I met Dianna through her brother Nick who is one of my closest friends in life. He went on a similar journey beforehand and will be talked about later. But I do have to mention an evening him and I shared together back in the summer of 2007.

There used to be an English style pub in Brantford, ON named The Oxford Circus. This was our consistent meeting place for a pint and some pub grub. After we finished up for the evening I decided the night was still young and was going to head down to OLG Brantford Casino to play some poker. I learned to play in late 2004 and was getting decent playing home games with friends. This was also the year the NHL went on strike and lost a full season so this would occupy a lot of time in my social circle. It was also shown a lot more on the sports channels to fill the void a cancelled hockey season left behind. Myself and a select few others became borderline obsessed with the game and it had become so hot at that point in time that it was interesting to see how far we could go with it.

I started to play when an old girlfriend wanted to find something for us to do and said her friend held games near Laurier University every Monday. I didn’t see the harm playing for small stakes but this is a decision that would snowball to how I live my life till this very day. Even though the relationship wasn’t built to last I’ll never forget being guided to make this decision that shows that nothing truly is a waste of time if you have the right perspective. But on this August night in ’07 I was testing my skills at the casino the very first time. I was there probably under two hours and I managed to pocket $120 of profit. I didn’t even have to play that many hands and for the time being I felt like a genius. It was a watershed moment that proved I could maybe succeed at this in a high pressure situation. Sure, it was low stakes at a local casino but that is a situation that can be overwhelming to many.

Fast forward to 2015 and I win my biggest prize to date in one sitting which was just shy of $2100. This would be at OLG Mohawk Slots near Milton. They used to run poker tournaments on electronic I-Pads with live players. A very cool concept that didn’t last but I would come in with a third place finish a couple of weeks later and to this day would be the best rush I ever went on. I am now building my skills and bankroll in the online world given the current climate we are in but it is still on my bucket list to cash in a major professional tournament and even play in the annual international World Series Of Poker in Las Vegas.

The reason I mention all this is that I feel learning and studying the game of poker can really make a positive impact on your life, as long as you can control yourself and not let it become an addiction. Like learning any other skill poker requires discipline, mental toughness, flexibility and the ability to calculate risk. You can also sharpen your intuition by deductive reasoning and studying other’s body language which are all transferrable skills to everyday life, especially in business. Even though I have enjoyed studying the game of poker and its nuances I never wanted to do it professionally. I believe my joy of the game would become impaired by being around it too much and living with the stress of not always having a guaranteed income. I believe this is why some amateur players on the World Poker Tour have done so well because their whole life doesn’t revolve around playing and studying the game. I look at it as a ‘side-hustle’ to build while I am still working a steady job. Now I would like to introduce Dianna’s brother Nick who built a successful side-hustle that he has lived to cultivate over the past decade…that side hustle being the independent wrestling promotion MCW:

“Starting MCW wasn’t the plan. Initially it was supposed to be a one shot deal. But then I quickly realized that one night just wouldn’t work. I went through the first show and since then it’s like an addiction. As far as risk, I think that each time I announced a show, especially in the building stages, there was always an element of risk. Questions like, will fans come to watch? Will they like the product? But even more than that, especially in the beginning it was a financial risk for me. I think ultimately my love that I gained for promoting and the love I have for professional wrestling itself, it lessened the financial risk of it all because my focus shifted to how to bring more people into the shows and how to keep more eyes on the product. So it was the risk of bringing in better (and sometimes bigger talent) and really hoping that talent connected to our fan base…Ultimately through all the set backs or low crowd numbers and frustrations that come up from making mistakes, (and I make them daily) I have a really good bunch that are behind me so some of those mistakes become bearable and the truth is, the reward of having happy fans and fans that come back show after show, I believe truly outweighs all the risks that arise.”

A one time event is still operating ten years later so that risk paid off in spades. I think Nick and the rest of the people involved since day one will tell you the same thing. One of them being wrestler Rip Impact who ended up marrying Dianna and turning the promotion into a family affair. Rip also made wrestling his main source of income after opening the Hamilton Pro Wrestling Academy while still working independent shows. Dianna as well as their mother are nearly permanent fixtures working the door at these shows. MCW would also turn into a ‘side-hustle’ for myself as well. But first let’s explore what this buzz-word ‘side-hustle’ is all about.

In 2018 I discovered the podcast and books of Chris Guillebeau. He can be described as an author and entrepreneur who also has the unique distinction of someone who has literally visited every single country in the world. He started journalling about it in a blog and turned it into a podcast and a series of books. He found that most people were stuck in dead end jobs and wanted to create a dream that involved them investing in something that could make extra income and maybe become their passion or defining career choice. His work opened my eyes to break out of working in the traditional ‘system’ and showed how these skills can be transferrable to anybody willing to put into the work. Through his work and series of synchronicities I became the main videographer / editor / commentator for MCW. I also host and put together a show on Youtube about the promotion (even though it’s currently on a break) and I feel more opportunities may become available once wrestling shows are allowed to run again. Nick would love to promote, Dianna would focus all her energy on her event-planning company, and I would all love to shoot wrestling shows and interviews and make a living doing it but we all understand that we need to work other jobs to help make ends meet.

Up until recently this simple concept of having a sustainable job was a difficult one for me to grasp. I have in fact lost count of the amount of jobs I’ve had throughout my life. A Jack of all trades and a master of none, you could say. However this process has always been able to help me land on my feet when I needed it during the most uncertain times. While this may look a bit unstable and irresponsible I was always guided by the philosophy that in the big picture I will not settle for less. I have lost count with the amount of people I have encountered at these various jobs who have decided for themselves that their current gig was it for them. I’ve seen that this attitude leads to frustration, cynicism, possible substance abuse and just all around toxic energy. Sadly most of these people don’t realize how actually free they really are to decide their future. In the western world there just aren’t enough Chris Guillebeau’s and too many of those who have decided to remain stuck. Job security is an illusion especially in this pandemic economy. By not partaking in any risk surrounding your job or career you are still playing a risky game as you never quite know when it will be taken from you. This is a big reason why I pulled off my biggest professional risk in 2016.

In the summer of 2010 I began working at the warehouse of Gordon Food Service in Milton, ON. I had spent the last couple of years washing dishes, driving a catering van and stock receiving food orders, all with a college diploma no less. This was work I had to take before my daughter was born and this would lead me on the path to GFS. Remember, it’s all connected. While I thoroughly did not enjoy most of my time there this job would make a real ‘man’ out of me and increase my work ethic. I also made some friends that I still consider near and dear to this day. However in the spring of 2014 I wondered if I really wanted to continue working there. I was going through a separation and was gaining a new lease on life. I felt like this ran its course and that something else was calling my name. Once again through some crazy synchronicities I decided I wanted in the music business, specifically in the fields of artist management or concert promotion. Through the recommendation of a good friend I was directed to The Harris Institute in downtown Toronto.

Long story short I would get accepted to Harris in the spring of 2016 and be attending in July for a one year program. In order to attend I would be walking away from a job where I had seniority, trust from management, benefits, and a steady routine. Also in the summer of 2015 I would gain custody of my daughter which is something I was not expecting to happen. This would mean that I couldn’t move closer to the school which was my original plan. After those proceedings came to a close in Feb. 2016 I took a solo vacation to Cuba and while on the beach I constructed a plan to pull this off despite the newfound obstacles in my path. To the amazement at the power of the universe the stars aligned and I did it. Even graduated from the program barely sneaking onto the Honours list. Did going to and graduating from Harris get me to the great career path I envisioned? It did not. In fact things went a little sideways for a couple of years but that will be explored more in the next Pillar. I met some really cool people (like Mik and Jonah) and learned a skill set that would help me deliver Unexplained Inc. as well as this blog. So I have zero regrets of going there when I did to do what I did even though it was a bit of a rough ride after the fact.

Which leads me to one more point I would like to explore before concluding this Pillar. I touched upon the toxicity of people in the workplace feeling stuck and constantly taking it out on themselves and others but there is another aspect that needs exploration. That is the concept of dependency. Yes, we all need to feel safe and life is so much better when you feel those you are working for have your back. This is not always the case unfortunately as I have been in several work-related situations where I not only felt abandoned by my given employer but also felt endangered. In the most extreme situations I knew I had to get out even if it meant taking a pay cut or working at a less than stellar job for a while. In the current state of our economy building multiple revenue streams is slowly becoming a ‘must’ instead of a ‘maybe’ as a means for survival.

I am really hoping that while this deficit increases to unheard of levels more and more people will take the time and energy to start some kind of an entrepreneurial revolution. Business is going through a major shift and I believe more people will put in an effort to buy more locally sourced products and help small businesses. I work in the shipping department of a successful e-commerce company who has seen record profits during this crazy time. If you have the hustle and the drive money can be made during this time especially if you offer products or services that can help people out during all of this. The silver lining of the pandemic may prove to be that self-made products, services and businesses may experience a renaissance period due to having to make adjustments to the current environment. But in order to do that you have to realize that every decision in life has an assessment of risk. Even if you choose to stand pat in this area of your life you are in fact putting risk into play because your power lies in the hands of a company or an employer. Your employer, your government, your bank are only going to do so much for you at the best of times. Wake up and realize your inner power and realize that calculated risk is not a bad thing at all. Just roll up your sleeves and accept the consequences that come with it. You never know, you may surprise yourself by how far embracing risk will take you…it’s certainly worked for me as I work my day job, produce content for MCW, play poker and eventually plan to monetize this blog and podcast when more people jump on board.

But before I finish I want to share one more quote from Ian. I only met Ian in the fall of 2019 and within minutes we hit it off and he already felt like an old friend. Ian is an aspiring filmmaker and knows a thing or two about risking it all to get his projects out to the world. He’s a little crazy too and I mean that in the nicest way possible as to me he is the embodiment of someone who will go to great lengths to risk it all for their passion. It can be summed up in his quote below:

“I need risks in my Life. Physical risks and emotional risks. I grew up wide eyed with constant curiosity running through me. That curiosity would lead me into many encounters where I was challenged with something and my fear of uncertainty would lead me not to take that risk. I saw the reward it could have brought me lost in my mind, and it drove me crazy. I began to realize to do what I wanted to do I needed to risk my pride, my fear, my emotions, and finally start DOING instead of just thinking and not ACTING…Risks brought me to a competitive level of hockey I’d have not gone into had I listened to my insecurity and not risked a try out. Taking risks brought into the world Of professional wrestling and then more risk taking into hardcore wrestling for many years. More recently in my filmmaking career I have returned and re trained for in ring work on a feature film which I am Also producing and directing from a production company I had founded and am growing. Again NONE of that would have been without taking risks into places and feelings I would have not otherwise accessed. I would not be who I am today and had the success’s I have have had without following my Heart and my passion and taking risks.”

Recommended Reading:
Born For This by Chris Guillebeau
Chris has written so many great books on these types of subjects but this one from 2016 is a personal favourite. There are many examples of people like Ian and Dianna who went all-in on their ideas that connected to their life purpose. Also people like Nick and myself who still work full time but build up their side-hustles. This book is a blueprint to build the professional life of your dreams, whatever that may be. I also guarantee you’ll find something that suits your wants and needs. Especially love the chapter on crafting the ‘Prison Break’….a must read for anybody willing to take the professional plunge into cultivating their dream life.

What I need to work on: Yes…I’ve talked a big game but I still don’t feel I’ve fully tapped into the potential of risk. Whether its cultivating new relationships or going all-in on certain ideas I still get gripped by doubt and the path of least resistance. I spend too much time in the ‘analysis paralysis’ stage but more of this will be talked about in the upcoming third Pillar.

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