Mindset Hacks: 3 Lessons I learned Driving Across The Country With $500
- Jay Ashcroft
- Jun 23
- 6 min read
Updated: Jul 6
When I was 26 years old I drove out West with a savings of $500. Now, obviously that $500 wasn’t going to get me out there - but by the time I came back home, I had $5,000 in the bank, a $30,000 truck in my name and the perspective I needed to start a career as a photographer.
If you’re hesitating to start something, or to take an action that feels scary, just jump in - because I promise you it works out, and I want to share a story to illustrate this point.
Being in your early to mid twenties is a strange thing. You’re forced to decide what you’re supposed to do for the rest of your life, and it feels like an insurmountable amount of pressure.
I was a normal enough kid. I received endless amounts of unconditional love from my family, and I was given every opportunity to fulfill my potential from a young age. So one would think that I had it all figured out right away.
However, this was not the case. With some introspection, I feel it’s appropriate to blame the plumes of pot smoke that were always circling my head. When you’re a musician, this is just how it is.
Me and that crew, we looked to the greats like The Beatles, The Rolling Stones, The Chili Peppers - and we did what they did. This meant lots of weed, lots of beers and a pack a day of cigarettes.
But when our ignorance inevitably led to a collective implosion, and a bombshell of an ending to a lackluster music career - we all went our separate ways and faced the struggle of young adulthood alone.
I found myself delving into my other skillsets, one of which was building. I loved building, and I was good at it - but after multiple failed attempts at developing some sort of career in the construction industry, I was at a loss.
After some thought and a lot of sleepless nights, I decided to drive out West. I didn’t know why, and I didn’t even know if I would make it out there in my scrap pile on wheels.
I had managed to save up about $5,000 for my trip - but hit a wall when I had to put $4,500 of that into mechanical issues with my truck to even make it down the first leg of the highway.
This didn’t stop me though - I fixed that truck up, and I hit the road. With $500 in the bank… I’m in Canada, so to give a brief geography lesson, to get to where I was headed I had to leave from Ontario, drive through Manitoba, through Saskatchewan and arrive in Alberta. The original plan was to push all the way through to British Columbia, but that wouldn’t end up happening.
By the time I got to Saskatchewan, I was sitting in a parking lot, shaded by the one tree I could find - waiting for my father to put money in my bank account. Was this selfish? Yes. But, was it necessary? Yes. I knew it would come up when I left. I had no real skills I could use to make money on the road, so I knew I would have to lean on my dad.
So this is lesson #1: just ask for help. It takes a couple of ingredients to do this. First you need to drop your ego, and second you need to be honest with yourself about who would be willing to help you. My father wasn’t independently wealthy (his words), so asking him to borrow some money didn’t come without some hesitancy - but I did it anyway. I told him I would pay him back with interest as soon as I got out West and found a job.
Part of the job finding idea was to drive all the way out to British Columbia and to get a gig building boats with my older brother’s high school buddy. This did not happen. When I arrived at my cousin’s house in Alberta, this guy had ghosted me. In this moment, I learned a valuable lesson.
People will offer you help and opportunities, but a lot of the time they’re just talking. The impression I got in this instance was that he didn’t think I would actually do it. This was obviously a let down. I was landlocked in Alberta, with no plan and no money.
Luckily my cousin opened her door to me, in exchange for helping her with her toddler - but something had to be done. After looking at job postings online for a couple of days, it took everything in me to not have a full on panic attack.
Right when I was about to give up hope, I had an idea come to me. I remembered this guy named Josh who worked with my older brother and me back home. He told me about this landscaping company that he operated heavy equipment for - and it was in Calgary, where my cousin happened to live.
I called Josh, he gave me a great referral to the owners of the company, and the next week I found myself operating skid steers and excavators for this commercial landscaping company.
This is lesson #2. When your back is up against the wall, your instincts will give you a way out. But here’s the vital takeaway, you need to act on those instincts. I could have been shy or self deprecating, and refused to reach out to Josh - but I made the call, and it made all the difference.
While I was working this job, I still had a sense of adventure brewing inside of me. I wanted to make it all the way to the ocean - and so, I kept attempting to leave. But they valued me as an operator and in my position that had evolved into a site supervisor. They offered me more money.
1 month would go by and I would mention leaving again, and for a second time they offered me more money. This happened 3 times. I was working hard, playing hard, saving up a bunch of money and enjoying life - but there was still this sense of adventure growing and begging to be explored.
One day I was driving to my next site for work, and I had an idea to call an old friend who was a photographer back home. By this point, I had built a photography website and started taking more photos - but something wasn’t clicking.
Before I ever drove out West, I decided I wanted to be a photographer, and now while I was working, moving dirt around and driving dump trucks - I found myself day dreaming about taking photos for a living all day every day.
When I called the old friend and asked him how to be a photographer, he didn’t really give me any advice on the spot - but he did tell me he was building something really cool back home, and to give him a shout if I ever made it back to Ontario.
This was it. This was the answer I was looking for - a plan, a life purpose. After several months, I would tell the landscaping company I was leaving for the final time - but it wasn’t to go stand beside the ocean, it was to go back home and learn how to become a professional photographer from one of the greats.
And this is lesson #3: when you get an instinctual idea to do something, say, get in a crappy vehicle and drive out West - the reason you’re doing it is sometimes buried somewhere beneath the surface. I went out West thinking that I was going to build boats with a stranger I had never met before.
Contrary to my initial plan, I ended my journey right back where I started, with someone who I had known for 15 years, beginning the career I had deep down always wanted to have. This didn’t all come at once. It came with a number of off chance decisions that were made, and it came with an open heart and an open mind.
Something I harp on quite often is that you don’t have to know why or even how, you just need to know what. What is the thing? What do you want to do? It can be anything. If you have an idea, pursue it. Let it lead you where it is trying to lead you.
Along the way, ask for help, trust that when your back is up against a wall, your instincts will show you the way out, and be cognizant of the fact that the real reason you’re pursuing something is usually buried somewhere beneath the surface.
All The Best,
Jay Ashcroft
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