It was just another day in 2013. 

I’d hit the snooze button three times, checked my phone, and already had four missed calls. 

I felt trapped. I had bills to pay, people relying on me, and dreams to invest in. 

But the truth is, I was over it.

Don’t get me wrong; my career was rewarding and taught me a bunch of skills. But I needed to make a shift. I was living each day over again, like Groundhog Day. 

I’ve changed careers four times in my life. 

Each time was hard and overwhelming because, when you change your career path, there’s so much at stake: your time, income, future, and pride.

It's scary to think you might be making a bad decision because even small changes can make a big difference in where you end up down the road.

But it's only in hindsight that we can zoom out and see how all the dots are connected, what worked and what didn’t.

For me, one of the biggest changes in my career came from a conversation after a chicken bus ride in Guatemala. 

It was only a few simple words that made all the difference, and now I cross these career bridges much more easily.

So, how did I get there from making coffees for $7 an hour during high school?

A series of service jobs turned into an internship, which then got me a graduate role in 2010. At the company I worked for, I got my butt kicked for years - late nights, working weekends, and on call 24/7. 

And I'm so, so, so grateful for it because it gave me a bunch of skills that I use every day.

In that role, I thought I was set and on the outside, other people probably did too. I thought I was on a stable path to financial security.

But after five years, my dreams had evolved. I didn't want to be in services forever; I wanted to experience a real business, something I could call my own. 

The problem was that outside of a few side hustles, I didn't know how to do that.

I was reading a lot of Tony Robbins books at the time, and one thing that really stuck with me was that proximity is power. If I wanted to build a business, I had to go where all the best businesses were being built—the USA.

We packed up all our stuff and said goodbye to out people and bought a one-way ticket to Colombia in 2014 to get some time to refresh, recharge, and find inspiration. 

We had a great time, but each day, I couldn't escape the elephant in the room: I had to get a job in America and change careers.

During this time, I spoke to a lot of people, and the feedback was consistent.

"Andy, you can change geographies, or you can change your careers, but you can't change both at the same time."

If we moved to the US, it would be easiest for me to stay in finance.

It made sense, but I wouldn’t accept it. It meant taking a step back from what I really wanted to do, and I was scared that I'd be in the office a ton with my wife trapped at home.

I’m stubborn. So, I continued knocking on all doors to find a job in technology in the US. 

I had this giant spreadsheet with a list of opportunities. I hammered my credit card with Skype credits for international calls, as video conferencing wasn’t free yet.

And after all that, I was lucky enough to get two offers.

One was in New York, back in finance. That was a safe option. I knew a few people there, would make good money, and I’d know exactly what I was doing. 

That path was clear.

But the other job was working for a tech start-up at a company no one had heard of yet, in a place where we didn't know anyone. Oh, and I had to take a massive pay cut.

We were sorting out our options while travelling in Latin America, and the hostel we were staying in one night had one of those book swaps. 

As luck would have it, there was a poem in one of those books by Robert Frost that I'd come across in high school:

Two roads diverged in a yellow wood,
And sorry I could not travel both
I took the one less travelled by,
And that has made all the difference.

But taking the less-travelled road is scary. 

I wanted to be brave, but I didn’t know if I was. 

Frost only said that path made all the difference; he didn’t guarantee it was an easier road.

One night, we were on a twelve-hour chicken bus that was taking us to Guatemala. 

Reggaeton was blaring through the speakers, and the music was so thumping so hard that even the locals asked the driver to turn it down, but the bus driver said he needed it to stay awake.

We didn’t sleep that night in case the bus driver did.

So the following day, with no sleep and two street tacos, I called one of my mentors in Sydney.

I told him my situation. I'll never forget his reply. He said:

“Andy, zoom out. What do you really want to be doing in 10 years?

Go do that. Don't worry about the money; that will take care of itself.”

He was right. There's no point in delaying tomorrow when you can get started today.

Making the career change to technology was the right move for me, as it opened many more doors. It was the future; finance was the past.

Shortly after, we landed in San Francisco and I got to work at that start-up. The first six months were rough.

I was out of my depth in this new world of tech and had to keep reminding myself that I was going through my Rocky training montage. It'd all be worth it in the end.

But it really hurt my identity. 

I went from being comfortable in a high-paying finance job to being paid almost minimum wage in a new industry that I had to learn everything about. 

After a couple of years, the new setting became normal, and although it hasn't been 10 years yet, so far things have worked out.

In hindsight, it’s easy to see that transition as a no-brainer, but I remember how tough it was going through it. For both of us. 

My journal from that trip has pages and pages of stress, anxiety, and uncertainty around what the future would look like.

But now, whenever I'm facing crossroads in my career, I just remind myself of that conversation:

"Andy, what do you want to be doing in 10 years? Go do that."

Like all things, what worked for me might not work for you, and you should always focus on your unique path. But if you're like me, lost or thinking about making a change, remember:

It’s not about where you've been but where you want to go.

Even if you don't know the destination, direction is far more important.

Action creates information, so getting moving in the direction is where you’ll find the information to grow and the people that can help you on your path.

That’s the road less travelled.

And while you're on that path, remember to focus on your own journey and not compare yourself to others.

I struggled with this for years until a therapist took me down the rabbit hole of figuring out who I should compare myself to.

And if that sounds familiar - check out what I found here.