top of page
  • Writer's pictureJay Ashcroft

What Should My Career Be? Looking to Your Childhood To Understand What Defines You

a photo of philosophical thoughts for a blog written mindset hacker for small business and being an entrepreneur using your subconscious mind and trusting your gut, how to look back to move forward

A career is a funny thing. What the hell is it? I suppose my definition of a career falls somewhere along the lines of that thing that drives you, gives you a sense of fulfillment, earns you an income and gives you a reason to get out of bed in the morning.


And a career is much different from a job. We’ve all been there. Jumping between jobs, trying the figure out “Gah! What should my career be??”


Some of us figure it out by 18, some by 23, some by 29. Some of us never figure it out. And I say God bless ‘em. As that guy said in the Sunscreen Song, you know the one – “… they’re some of the most interesting people in the world.”


Now, unless you’re some kind of freak who has no internal or external drivers (also God bless you – we could all learn to be a little more accepting) then you’ve likely asked yourself “what should my career be?”


If you’ve already figured out your career – then feel free to go and read something else. But if you haven’t, then listen up – I’ve got a pretty cool concept that’s proven itself to me time and time again.


If you’re needing someone to hold your hand, and walk you through the tough choices of career building, then you can depend on the childhood you. Look back. Be honest with yourself – there really is some truth that lies in your childhood.


When I was between the ages of 21 and 29 – I searched ferociously for my career. I needed it. I was in such a rush to find it too. Ironically, I think the sense of urgency is to blame for the length of my journey in self-discovery.


At the start of that time period, I had no idea – at all. I would lean on Google and the opinions of others – big time. “Maybe I can be a Graphic Designer, maybe I can be an animator. I could be an architect.”


These are all just titles – they mean nothing.


You see, a career is an extension of yourself. We spend a staggering 1/3 of our time working – some of us more, some of us less.


If we’re “working” that much, then shouldn’t that career path be something that resonates with us on every level?


The answer is yes, and astounding yes.


So STOP. Stop Googling, and stop asking others for their advice. Deep within yourself, you know the truth. You know what you’re supposed to do, and God Damn it, you’re going to do it once you’re done reading this.


Look to your childhood, like I did.


Around 25 or so, I started to do this. I had spent the past 3 or 4 years just spinning my tires. Asking around, listening, Googling. To no avail.


You see, my parents had been separated when I was 21, and I became a very angry and confused man boy child. But, by 25 or so, the dust had settled. I was ready to get a move on.


I needed answers! Why am I the way I am? Who even am I? I started to watch old family videos, and I’d ask family members about myself as a kid.


As time went on, I began to notice things. I noticed that I spent a lot of time with my little brother. That me and him were always creating things endlessly. Whether it was building tree forts, or putting trailers on 4 wheelers and loading them up with stuff.


Or playing a game we called “buds”, where we just pushed little toy trucks around and said “hey bud”.


And we loved the cottage. I mean loved being there. As a teenager, I started to take my mother’s camera and snap photos. I would get lost in the process.


Okay – so I have that version of myself on lock. Between the ages of maybe 4 – 14, that’s all I did.


Then we have 15 – 21. I was ultra-hyper creative. I would always be drawing. In school I made 3 or 4 videos for class projects throughout the years. I was masterful at it.


I was great at communications technology class, which was mainly making animations and video editing.


I accelerated in shop class, building shelves and chairs and benches – obtaining 100% on all of my projects.


I liked to read and write and socialize.


In University, when I was arguably still a child – I studied studio art. I loved psychology, art history, architecture, sculpture and black and white film photography.


I loved women and partying and more and more socializing.


And then – I lost it all.


I moved home, I got confused – I became more and more saddened by my reality in life. But we don’t need to sit here through the confusion of 21 – 25. That’s for another day.


So, let’s flash forward again. I’m 25 – and I start to have all of these memories, all of these epiphanies.


By thinking back on my childhood, I was able to connect the dots – I could see the truth, I could see who I was. I could then take an average of all of my experiences and put them together into one, all-encompassing being.


Here’s what I landed on.


I’m a socialite. I love psychology and a good conversation. Family is important to me, but I won’t hesitate to remove someone from my life if they’ve done me wrong a few too many times.


My brother is very important to me – he holds the key to my past and the bridge to my future. I love being outdoors with him, and playing with our big boy toys.


I love to create and build – I feel the need to express myself with cameras and written word, somewhere in the void where digital and analog technologies intersect.


I like to help people and listen to their problems, offering solutions and creating new avenues on which to experience their lives.


I’m an introvert, posing as an extrovert. I see the value in both ways of being and allow myself to move freely between both.


Now, let’s look at what I’ve accomplished, where I’m at now and where I’m heading.


At 29 I move home from Calgary and start to learn how to be a photographer from my mentor. I do that for a year or so, before I decide that I need more.


I’m looking online for photographer jobs. There are none. But, there are videographer jobs. I quickly learn videography and start my own business.


At 30, my dad dies and I move in with my girlfriend, Emma. She prefers the term “partner”. I don’t know why. I prefer “girlfriend”. I also don’t know why.


I continue to build my business and eventually get an office of my own on Ontario St. – I’m now 31.


By 32, going on 33 I’m approaching my first 200k year, and I’ve built a studio for my business. At this time, I start to realize – “is this it?” Oh god, it’s like 25 all over again!


“I’ve missed something! I’ve left my brother behind.” I realize. I immediately get to work to solve this massive problem that I’ve created for myself. How can I be closer to him? How can we be together? For as long as I can remember, Steve has been a pivotal part of my life, as has the cottage.


So I do what any other genius who had just sunk 40k into a brand new photo studio would do – I give it away to move closer to my brother so we can make YouTube videos and start an AirBnb Empire. Ha!


Now – here we are. In the present. Depending on if you’ve been following along or not, I’ll remind you or tell you for the first time that I’ve been recovering from a broken leg since I moved here. And now – things have changed. I’ve really had to look within, and to my childhood for guidance.


This is where I’m at now.


I have 3 brands that I’m working on vigorously. I have Jay Ashcroft, which is my personal brand. This, what you’re reading, is a part of my personal brand. It’s just me and my mind. It’s all of the experiences I’ve had, and the information that I’ve absorbed, distilled down into digestible bits of digital content.


Then I have four32 MEDIA. That’s my photography and videography business. In that model, I’m able to be a chameleon, fitting into whichever box a client needs me to fit into, so that I can help them to grow, expand, learn more about themselves and work with their dream clients.


Finally, I have Ashcroft Bros – the newest pet project. That’s the YouTube channel with my brother Steve – where I’m able to express all of my loves and interests with zero concern for criticism or revision requirements.


It’s been 8 years or so since I started looking back on my childhood to help me connect the dots. I’ve made leaps and bounds. I’ve had realizations and revelations, and I’m only just beginning to live in perfect harmony with my truest self.


In this moment, I’m fulfilled, excited, curious, and I’m making a bit of money with it to boot.


If you’re at all struggling to find your way, please, please – even if it’s painful – look back to your childhood. When we’re kids we’re natural and pure – we don’t take fear of consequences into consideration when we’re choosing how to spend our time. We allow ourselves to just be.


We act naturally and do as we please. We simply play, something that we should continue to do as adults. No matter how long it takes, be patient, love yourself and trust in the process. Have faith.


I hope that you can use some of what I’ve used to find your way.


To Your Success,

Jay Ashcroft      


bottom of page