Friends and family joke that I have no shame about asking for what I want, especially when traveling and in other service-related situations. They’re right, and I own it.
I view knowing what you want and asking for it as a positive trait. So many people accept what’s offered to them in life. Life happens to them. They may want more, but they never take action to try to get more. I’m not wired like that. By taking the step of saying what I want and asking for it, I’m increasing the chances of getting the outcome I’m aiming for. I’m also making others aware of my goal or expectation.
I want to be clear that I’m not saying it’s okay to bully people into doing what you want or ask in a negative or nasty way. I don’t believe in that. I try to ask for what I want in a manner and tone that mirror how I would want someone to treat me.
I’ve explained to family and friend that I think about this in terms of risk and reward. In many of these situations, the upside dwarfs the downside. The upside is often a more enjoyable experience or a positive impact on you and those with you. The downside is just hearing no.
Family and friends still joke with me about this. When they do, I remind them of the famous Wayne Gretzky quote: “You miss 100% of the shots you don't take.”