what is the best gamble you have ever made in your life?

6 comments

1. I would say the best gamble I have ever made was investing in myself. I have never been one to shy away from risks, but there is always a calculated element to the risks I take. When it comes to gambling on myself, I invest time and energy into learning new things and taking on new challenges. This has paid off handsomely over the years, both in terms of my personal growth and in terms of tangible results like career advancement and increased earnings.

2. Moving out of my hometown, moving 5 states since, and finally finding a place that’s fantastic to live in (as opposed to just settling for a mediocre place).

3. Going into business. Let’s see how it goes.

4. 3AM quickie with my then girlfriend, now wife, without protection.

   Can’t remember a time when I wasn’t a father.

5. It didn’t pay off right away but it did in the long run. Risking the destruction of a good friendship in the hope that it could be more.

6. I didn’t make just one gamble, I made two.

   In 2014 I quite my day job as an IT Contractor. It was making me suicidal. I quit to do music full time and it was the greatest thing to ever happen to me.

   Fast forward to 2021 and my music career is on hiatus because COVID and I came out as pansexual. I had to burn a lot of bridges because of it, but it was so worth it.