As a lawyer, I can negotiate tooth-and-nail for my clients. Ironically, I have found that I am often too shy to negotiate with the same degree of vigour when it comes to myself. When I negotiate payments, compensation, settlements for my clients, it’s a matter of fairness, just compensation, and my clients not being exploited to the benefit of someone else. When it comes to myself, it always feels dirty to argue over money. I often feel less ashamed giving something up than arguing over it. It’s paradoxical, but it’s natural. And it’s something to overcome.

If venturing out into the YouTube world has made me appreciate one thing, it’s that no one is going to give you something if you don’t ask for it. No one is going to value your time and talent if you don’t value it yourself. Of course I learned these lessons from law as well. But they were always principles that guided the representation of my clients. There is a difference between knowing something to be true, and actually having experienced it for yourself. It’s one thing to ascribe value to, and demand correlative remuneration for your client. It’s another thing to do it by yourself, for yourself. And it’s something that most people are too shy or embarrassed to do, from negotiating their salary, to taking a shot in the dark at something more outrageous.

Two concrete examples: When we went to France a few years back for the Mont Blanc marathon, there was a race being held the Friday before called the “Vertical Kilometre” – a race that ascended one vertical kilometre over the 3 km course. It was a race that had been booked solid for nine months. And when we arrived in Chamonix, and I saw the course, I knew I had to do it. Whatever it cost, I had to do it. So I asked. And I was told “Monsieur, absolutely no chance, this has been booked for almost a year”. And so I waited ten minutes and then I asked someone else. And they said “No”. And then I asked a third person, and I could tell that they would find a way. I joking said that surely someone must have cancelled – a flight delayed, an injury… Surely someone cancelled. They said they liked my smile, my Quebecois accent, they found a cancellation, and with less than 60 minutes to race-time, I was in for the time of my life.

On another occasion, while passing a daredevil in the streets of Montreal going for a world-record jump from a cherry-picker onto an inflatable crash pad, I asked if I could attach my GoPro to the rail on the cherry-picker while it ascended into the air. They (surprisingly) said yes, and we both ended up with one-of-a-kind, utterly unique video footage of the event.

The point is that you have to ask. The worst thing that can happen is that they say “no”. It can hurt. It can be embarrassing. It can be demoralizing. But that’s the worst thing that can happen.

Actually, worse than that is no response at all. When you get no response at all, you never know if you’re being ignored, if the ask was so stupid that it doesn’t deserve a response, or if they simply never received your ask to begin with. Better than no response is a “no”, because at least you know you were heard, and they had the courtesy to acknowledge your ask. And the best feeling is the “yes”. But if you don’t ask, no one is going to ask for you (unless you have seriously insane helicopter-parents well into adulthood”).

So this week I asked Gary Vaynerchuck and Casey Neistat to read my mom’s book. In truth, I have been bothering these two in particular (people who I greatly admire for their message and content) to check out my content. So far, no response, although I don’t take it personally. But maybe, just maybe, one of my messages will get through and they’ll shoot me a quick “Thanks but no thanks, we’re very busy”. Or maybe, just by the most remotest of maybes, they will say “sure, I’ll check it out”. And from there, a world of possibilities the door to which can only be opened if you give it a knock.

Peace out!