The easiest way to kill someone’s dreams is to question them as if they should have an answer. Ask a lot of questions about hypothetical situations and watch the doubt fill their face. “What will you do if you get sick and can’t pay the bills?” “What is your plan b if it does not work?” “Are you absolutely certain you want to be doing this?”

Sometimes, finally getting yourself to do what you’ve always known deep down you should be doing is hard. Sometimes it feels like everyone is against you. You are trying to coax that higher version of yourself to take centre stage. And there are so many who are asking questions and shining a light on the doubt you have.

But, the truth is no one is certain of anything. I can’t tell you how many times I’ve had people question me about what I would do when I left a job. And, it really scared me. But, sometimes, those people end up losing their “secure” job anyway. No one really knows.

I think I experienced this most when I left the Army. I was so unsure of whether I was doing the right thing that I continued going strong until the last day. I elected to attend PLDC (Primary Leadership Development Course) and the promotions board to get my E5 sargeant stripes even when others I entered with were just waiting to leave. I still wasn’t sure.

I had all my friends and colleagues wanting me to give them my life plan. “What are you going to do for work?” “Are you going to college?” “If you go to college, what will you do afterwards?” And the most I said “I don’t know” the more I doubted whether I was doing the right thing.

And the Army recruiter was just as bad. I still get angry when I think about it sometimes. They just had to put doubt into my head. They just had to hint that maybe I was not doing the right thing and my fear took over. I very nearly stayed in.

On one of the many times I left a full-time contract to pursue Overpass full-time, I got the same treatment. It wasn’t so much that people doubted I could do it (but many did) as much as it was their constant questions about whether I had “thought everything through.”

But sometimes, you don’t need an entire plan. You don’t need to know how to get from A to Z. You just need to focus on A to B first.

And then you leap.

And it’s scary.

And if you can get used to uncertainty, the world is yours.