decisions that changed my life

5 Decisions That Changed My Life Personally And In Business

This article was last updated on May 12, 2016

I want to give you some context before going over the five major decisions I made that changed my life for the better.

My name is Jordan and in the last three years my life has changed, to say the least.

If you met me three years ago, you’d think I was a recent university graduate, who opted to become a bartender who did some internet thing on the side.

I was an average student, who in university started a company called Cave in my school’s library with a couple of friends. We had no idea what we were doing, and today we by no means have everything figured out.

But here’s what we do have:

  • We went from $0 to $400,000 in yearly revenue in a 24 month timeframe.
  • Five full-time team members (and several part-time)
  • Office locations in Toronto and Fort Lauderdale

The Decisions

Below are the five decisions that I attribute a lot of my personal and business success to. I’ve put a bigger principle beside each decision to better help you understand the point I’m making with each point.

5 Decisions That Changed My Life Personally And In Business

I stopped bartending [Go All-In]

In the Summer of 2013 I stopped bartending. For a long time I thought that bartending was allowing me to create a business during the day and earn money in the evenings. In reality, bartending was providing me a certain level of comfort and held me back from going all-in with Cave. I was also beginning to resent it, and I shouldn’t have. But it was hard to see all of my friends working 9-5s, making money, getting ahead, and myself going to clock in at a job that I wasn’t passionate about. In mid-2013, I cut the cord and devoted 100% of myself to Cave for the first time.

One of my co-founders, Michael, left his comfortable 9-5 shortly after I stopped bartending – this was a major turning point.

So there we were with two options, sink or swim. We chose the latter.

Well, being honest, we didn’t really have a choice. Our success was fueled by us being equally embarrassed to fail and motivated to win.

I decided to move to the United States [cut distractions]

In early 2014, we made the decision to open, and centralize our office in Fort Lauderdale, Florida. I applied at the border for a work visa specially designated for those moving to start a company in the US. At the time I had just turned 26, and knew one person in Florida (my Co-founder of the American side of the business). Needless to say, this was a huge decision leaving Canada. I was moving away from family and friends to open a business in a place I had spent a grand total of 30 days in before.

Now, this may seem foolish at first, but I would argue that moving to Florida was one of the most pivotal decisions in my life professionally. With my family and friends thousands of miles away that meant one thing: it was time to get down to work.

If I was going to be far away from friends and family, I better be giving everything I have to developing the business. Not that my family and friends are distractions, but when it’s a Saturday and your friends are in a different city, it makes it a lot easier to head to the office and knock out some work.

*I realize this isn’t for everyone, but it’s for me. My work is my release.

I became a willing student [learn from others]

I think I read two or three books throughout all of university. To be frank, I disliked it, a lot. Subsequently, I received average grades in university because I was only willing to put in average effort.

Today, professionally, the story couldn’t be more the opposite. Around two years ago I made the decision to start reading both business and fiction books. I figure if I can get one nugget out of a business leader’s book that forms my life, it’s well worth the five hours of reading and the $14.99. This constant commitment to learning has bled over into Cave’s culture. We have a company reading list and all team members are allowed four hours a week of professional development on company time – where reading is heavily encouraged.

I surrounded myself with people who want success as much as me [teamwork/support]

I vocalize my goals to my friends, I speak freely and ask for criticism, support, etc. However, some people aren’t critical, they’re cynical. I had people tell me that I was too young to start a company, or moving to the United States wouldn’t work out. I’ve decided to keep my conversations about aspirations away from these naysayers in my life. I want to be very successful, I want to run a multinational company and I want to be around people who believe that I can do it.

I decided that I was going to be successful [belief in yourself]

This is the most important decision I’ve ever made. I was full of self-doubt, worried that I wouldn’t live up to expectation, and that I would end up living a life of “what ifs?”

It was like a revelation, I don’t know, it’s hard to explain. But I realized that someone has to start the next big company, so why not me? This was the start of my outlook shifting. Today, I believe it with everything in my heart that we’ve got a winning team and formula that’s going to make us and more people successful.

I realized we’re good at our jobs, we’re good people, and we work our asses off. This is our formula for success.


I hope you were able to take one valuable thing from this post, and maybe apply the principle to your own life. I try not to write in absolutes, just on what I’ve experienced so far in my entrepreneurial journey. I’m sure I have some bigger decisions ahead of me, but these ones have been pretty big to date.

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